The German Biodiesel Market Today

inform December 2009 www.aocs.org Volume 20 (12) 737–800

International News on Fats, Oils, and Related Materials

The German biodiesel market today

ALSO INSIDE: The promise of industrial oil crops Distillers’ dried grains with solubles Beijing soybean conference report

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$ECEMBER 6OLUME n

Departments and Information The market situation and 740 Index to Advertisers political framework in 740 Calendar Germany for biodiesel and 742 Letter to the Editor vegetable oil Marketplace: Dieter Bockey analyzes recent regulatory developments and their 753 News & Noteworthy effect on the German biodiesel market. 757 Biofuels News Industrial oil crops—when will they ﬁnally deliver 761 Health & Nutrition on their promise? Denis J. Murphy outlines key targets for the future of industrial oil News crops. 765 Biotechnology News 769 S&D News From abstract to presentation Catherine Watkins walks us through the development of the technical 771 Student Page PROGRAM FOR THE ST !/#3 !NNUAL -EETING %XPO 772 People News/ Campaign for Technology a global success Inside AOCS $ONORS TO THE !/#3 &OUNDATIONS #AMPAIGN FOR 4ECHNOLOGY DROVE 773 In Memoriam one of the most successful campaigns ever undertaken by the &OUNDATION #ATHERINE 7ATKINS REPORTS

Publications: Distillers’ dried grains with solubles (DDGS)— 774 Book Review A key to the fuel ethanol industry 775 Patents Kurt A. Rosentrater examines how DDGS ﬁt into the larger biofuels landscape. 778 Extracts & Distillates A phospholipids primer 782 Classiﬁed Advertising Moghis U. Ahmad offers an overview of various phospholipid applications, from functional foods to pharmaceuticals to cosmetics.

World Soybean Research Conference VIII, Beijing Keshun Liu reports on this conference, which has run every ﬁve years SINCE ITS START IN

AOCS Mission Statement To be a global forum to promote the exchange of ideas, information, and experience, to enhance personal excel- lence, and to provide high standards of quality among those with a professional interest in the science and technology of fats, oils, surfactants, and related materials. inform s )NTERNATIONAL .EWS ON &ATS /ILS and Related Materials )33. )&2-%# n 740 inform December 2009, Vol. 20 (12) Editor-in-Chief Emeritus: James B.M. Rattray Bold type new listing For details on these and other upcoming Calendar meetings, visit www.aocs.org/meetings. Contributing Editors: Rajiv Arora Keshun Liu 7% !RTZ Mark Messina January February Scott Bloomer Robert Moreau %DUARDO $UBINSKY D.J. Murphy January 9–14, 2010. Triglycerides &EBRUARY n .ATIONAL "IODIESEL 7ALTER % &ARR Willem van and Triglyceride-Rich Particles in #ONFERENCE %XPO 'AYLORD 4EXAN 2ESORT Anu Hopia .IEUWENHUYZEN Health and Disease, Keystone Sym- #ONVENTION #ENTER 'RAPEVINE 4EXAS 9 3 6IC (UANG Brent Sørensen posium, Big Sky, Montana, USA. 53! )NFORMATION WWWBIODIESELCONFER- S.P. Kochhar T. Thiagarajan Information: www.keystonesym- ENCEORG Gary List posia.org/meetings/ViewMeetings. cfm?MeetingID=1033. &EBRUARY n .ATIONAL /ILSEED Processors Association Annual Meeting Editorial Advisory Board: *ANUARY n ,AB!UTOMATION 4UCSON !RIZONA 53! )NFORMATION -ICHAEL %SKIN (ANS .IEUWENHUIS Palm Springs Convention Center, Palm www.nopa.org. -ICHAEL (AAS &EREIDOON 3HAHIDI 3PRINGS #ALIFORNIA 53! )NFORMATION Arnis Kuksis Bernard Szuhaj WWWLABAUTOMATIONORG,! &EBRUARY n 'LYCOLIPID 3PHIN- Robert Moreau golipid Biology, Gordon Research Confer- January 24–29, 2010. Adipose ENCE 6ENTURA "EACH -ARRIOTT 6ENTURA Tissue Biology, Keystone Resort, #ALIFORNIA 53! )NFORMATION WWWGRC AOCS Ofﬁcers: Keystone, Colorado, USA. Infor- ORGPROGRAMSASPX YEARPROGRA President )AN 0URTLE #ARGILL -INNEAPOLIS mation: www.keystonesympo- m=glycolipid. Minnesota, USA sia.org/Meetings/ViewMeetings. Vice President * +EITH 'RIME *+' #ONSULTING cfm?MeetingID=1043. February 8–10, 2010. 2010 Packag- Cincinnati, Ohio, USA ing Conference, Aria CityCenter, Secretary 3TEVEN % (ILL +RAFT &OODS *ANUARY n 3OAP AND $ETERGENT Las Vegas, Nevada, USA. Informa- 'LENVIEW )LLINOIS 53! !SSOCIATION !NNUAL -EETING )NDUSTRY tion: www.thepackagingconference. Treasurer 4IMOTHY +EMPER $ESMET "ALLESTRA Convention, The Grande Lakes Orlando, com. .ORTH !MERICA )NC -ARIETTA 'EORGIA USA /RLANDO &LORIDA 53! )NFORMATION WWW CLEANINGCOMMEETINGS &EBRUARY n TH !NNUAL Executive Vice President Jean Wills Hinton, .ATIONAL %THANOL #ONFERENCE #LIMATE !/#3 5RBANA )LLINOIS 53! January 31–February 5, 2010. Prac- of Opportunity, Gaylord Palms Resort tical Short Course on Feeds & Pet #ONVENTION #ENTER /RLANDO &LORIDA AOCS Staff: Food Extrusion, Texas A&M Univer- 53! )NFORMATION WWWNATIONALETHANOL- Area Manager, sity, College Station, Texas, USA. conference.com. 0UBLICATIONS *ACK 7OLOWIEC Information: e-mail: mnriaz@tamu. -ANAGING%DITOR *EREMY#OULTER edu; www.tamu.edu/extrusion. &EBRUARY n !GRICULTURAL !SSOCIATE %DITOR #ATHERINE 7ATKINS /UTLOOK &ORUM #RYSTAL 'ATEWAY -AR- Technical RIOTT (OTEL !RLINGTON 6IRGINIA 53! )NFOR- 0ROJECTS %DITOR -ARGUERITE 4ORREY MATION WWWUSDAGOVOCEFORUM $ESIGN,AYOUT 'RETCHEN 7IESHUBER &EBRUARY n 'RAIN %LEVATOR AND 0ROCESSING 3AFETY '%!03 %XCHANGE #ENTURY )) 0ERFORMING !RTS AND #ONVEN- TION #ENTER 7ICHITA +ANSAS 53! )NFOR- )NDEX TO ADVERTISERS MATION WWWGEAPSCOMEXCHANGE

!GRIBUSINESS 7ATER 4ECHNOLOGY (ARBURG &REUDENBERGER -ASCHINENBAU February 21–26, 2010. Principles !NDERSON )NTERNATIONAL #ORP 'MB( and Practice of Cosmetic Science: !RMSTRONG %NGINEERING !SSOC /IL $RI #ORPORATION OF !MERICA An Interactive Residential Course, #ROWN )RON 7ORKS #OMPANY 2OSKAMP #HAMPION # Wessex Hotel, Bournemouth, United $ESMET "ALLESTRA'ROUP .6 # 3AF4EST $IVISION OF -0"IOMEDICAL # Kingdom. Information: e-mail: ifscc. 'IANAZZA %NGINEERING SRL 3HARPLEX &ILTERS )NDIA 064 ,4$ [email protected]; www.scs.org. 3PRINGER3CIENCE -EDIA"6 uk.

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an extent that made it edible on its own. movable suction pipe to pump stearine off Letter to the Editor It was a four-kettle, multi-vacuum-system the bottom and olein off the top. Ammonia arrangement. He called it the “Wesson refrigeration was applied later to a bank of Process.” First built in the Savannah plant rectangular tanks (cells). Mr. Willhite, of the Southern Cotton Oil Co. (SCOCO), When Wesson joined the SCOCO, it produced the first domestic edible veg- there were three SCOCO plants: Savan- I read your article on Frank Smalley and etable oil, “Wesson Oil.” Barbed wire and nah, Memphis, and New Orleans. All three David Wesson with great interest (see inform guards surrounded the process because were built in the 1800s, post-Civil War, 20:671–672, 2009). I am the ConAgra plant Wesson did not trust that a patent would and engaged in the crushing and process- manager in Memphis, Tennessee (USA), protect his secret. He personally off-scaled ing of cottonseed oil for nonedible pur- where all Wesson Oil and related oil and the dial thermometers in his temperature- poses (such as soap and paint base). There shortening products are manufactured. I sensitive operation and issued operating was still a paint manufacturing operation on started my career in oil processing in 1971 instructions in “degrees Wesson.” As late the site of the Savannah plant in the 1970s. in the Savannah, Georgia (USA), plant as the 1980s, in what was by then the Hunt- Although Wesson and Smalley both lived where David Wesson and Frank Smalley Wesson Co., we still referred to a deodor- in Savannah, they had an active presence worked for many years. Both lived there, izer as a “Wesson Process.” in the Memphis plant I now manage. It thus and Wesson’s home is still standing. I had Winterization was key to produc- follows that they were both in Memphis at the advantage as a young man to be trained ing a clear salad oil and to allowing cot- the founding of the AOCS and that New at the knee, so to speak, by older men who tonseed oil to be used in mayonnaise. The Orleans figured prominently in the annals were steeped in the history of David Wesson company sold mayonnaise makers in the of AOCS meetings. and his work. 1920s (which can still be found on eBay) I am fascinated by the history of our Wesson’s primary contribution to with a recipe etched in the glass. Wesson industry and always enjoy your articles. our industry was deodorization. Although later introduced “Blue Plate” mayonnaise, Keep up the good work. there were some previous crude attempts at one of the first prepared mayonnaises for improving the flavor of cottonseed oil with retail sale. The original winter plant was Rick Brantley steam (so it could be applied as an adulter- still in use in Savannah when I started there. Plant Manager ant to lard), it was David Wesson who first Of course, at first the process was simply ConAgra Foods Inc. combined deaeration, a vacuum vessel, and to store cottonseed oil in large tanks in Memphis, Tennessee, USA sparging steam to refine cottonseed oil to the wintertime (winterization) and use a Subject: ,,Screw presses"

More than just mechanical engineering.

Harburg-Freudenberger considers itself as a partner providing know-how and innovation for economic production solutions in line with market requirements - as an example for press technologies in oilseed processing.

For many decades, Harburg-Freudenberger has been one of the leading providers in the screw press technology field. These high-performance machines are globally deployed for the mechanical oil extraction of oilseeds.

~~ HARBURG FREUDENBERGER ~ powered by commitment harburg-freudenberger.com 744 December 2009 inform in Germany forbiodiesel cates thestarkreduction inthenumberofpublic fillingstations in 2007to2.695MT2008. of biodieselfelloverall by16.9%from3.245MT of biodieselasanadmixture, componentsales into considerationtheincreaseinutilization which equatestoareductionof40.6%.Taking fuel in2007,only1.082MMTweresold2008, 1.821 MMTofbiodieselweremarketedaspure itive development.Inabsolutefigures:Whereas of 739,000MTinsalespurefueloffsetthispos- (MT) to1.613millionmetrictons(MMT),aslump fossil dieselfuelincreasedby190,000metrictons tion ofbiodieselasanadmixturecomponent in in 2008comparisonto2007.Althoughutiliza- sales ofbiodieselandvegetableoilinGermany and ExportControl(BAFA) confirmedthedropin tistics OfficeandFederalofEconomics The finaldetailscompiledbytheFederalSta- Dieter Bockey and political framework This negative salesdevelopment unfortunately alsoindi- The market situation and vegetable oil destag (lower houseofGermanparliament) resolutiontochange target istobeachieved ontime. As aresultoftheGermanBun- tion ofbiodieselandPVO isnecessaryifthisclimateprotection of CO ages atargeted reductionwithinthetransportsectorof30MMT federal government’s nationaldecarbonization strategy envis- sector ofaround9MMTin2007and7.12008. The two fuelscontributed toaCO requirement in2007and10.2%2008. As aconsequence,the consumption—these biofuelsreplaced12.7%ofthefossildiesel ness sectorsisthefact that—measuredagainstoverall dieselfuel a dropof46%. slump insalesfrom772,000MT2007to418,0002008, pure vegetable oil(PVO) sector registered aneven moredramatic biodiesel willalsograduallydisappearfromthepubliceye. The sel fillingstation was animportantpublicrelations multiplier, 2007. This network no longer exists, andgiven thateachbiodie- sion instrumentforalternative fuelthroughoutGermany up to this distribution channelwas byfar themostsignificantprovi- Förderung von Oel-undProteinpflanzen) foraround20years, level. Guidedandsupportedintensively byUFOP(Unionzur was obligedtodiscontinuequalityassuranceatthefillingstation to around250bytheendof2008.Subsequently, the AGQM itätsmanagement Biodiesele.V.) survey, thisfigurehad fallen start of2007accordingtoan AGQM (ArbeitsgemeinschaftQual- offering biodiesel. Whereas around 1,900stationsdidsoatthe Notable fromtheperspective ofthebiodiesel andPVO busi- 2 peryearfrom2020. These figuresshow that the utiliza- 2 reductionwithinthetransport December 2009 inform 745 Biofuels efficiency will be will be efficiency 2 As such, the mediating committee was overruled. Although the tax increase Although the tax increase overruled. was As such, the mediating committee . balance of individual plants to establish the reduction potential. plants to establish the reduction potential. balance of individual 2 reduction quota. How this mandate is to be implemented and monitored remains, and monitored remains, this mandate is to be implemented reduction quota. How 2 The Bundestag in 2008 to reduce the admixture quota from 6.25 to 5.25% resolved In addition, the UFOP has reinforced its position that tax concessions from suppli-In addition, the UFOP has reinforced its In its report on tax concessions, the UFOP recently established that pure biodie- In its report on tax concessions, the UFOP In terms of the Bundestag elections, of significance is the demand encompassed In terms of the Bundestag elections, of significance is the demand encompassed retroactively to January 1, 2009. This will be raised to 6.25% for the period 2010 to This will be raised to 6.25% for the period 2010 to to January 1, 2009. retroactively will be the first European Union (EU) country to introduce 2014. From 2015, Germany a CO ers of petroleum products should specifically benefit the transport sector. In relation to In relation benefit the transport sector. ers of petroleum products should specifically for the promotion of climate protection by the toll structure, the UFOP has also called would Such a move PVO. use biodiesel or reducing tolls for companies that verifiably thereby providing sales for small- and medium-sized facilities, primarily boost regional material and biofuel desired decentralization of raw for the structurally a perspective in buffer Significant for meeting quota mandates is that a certain quantity manufacture. quotas; otherwise a punitive for generating tradable the form of pure fuel is available imposed on incomplete quotas. penalty of around €0.62 per liter may be sel was undercompensated by $0.20 per liter. Moreover, in the case of the decentralized in the case of the decentralized Moreover, undercompensated by $0.20 per liter. sel was an undercompensation of of rapeseed fuel, the UFOP calculation shows manufacturers In 2010, as a result of the Bundestag$0.28 per liter. resolution, at least a halving of pure The level. price remains at its present low fuel sales must be anticipated if the diesel from tax has robbed pure public transport and rail traffic refusal to completely exempt fuel of a further future sales perspective. on biodiesel of $0.03 per liter was reduced retroactively to January 1, 2009, and for the to January 1, 2009, and for the reduced retroactively per liter was on biodiesel of $0.03 the price decline on given ensure competitiveness to not sufficient coming years, this is of the drastic Irrespective and, as a consequence, the diesel markets. the crude oil markets the Bundestag endorsed the of pure biodiesel (B100) and PVO, drop in sales in terms to change biofuel funding. bill government paigned to adjust tax concessions in favor of biodiesel and PVO—to once more provide once more provide and PVO—to of biodiesel concessions in favor paigned to adjust tax the small- and of pure fuel and subsequently marketing for the regional a perspective ultimately pushed through its operators—the federal government medium-sized plant BiofuelsAmendment of the Promotion of on the Draft Law of the Bundestag by way resolution RENEWABLE ENERGY DIRECTIVE (EER)RENEWABLE COMES INTO EFFECT adopted in March 2007 within the scope and climate protection package was The energy minimum 20% reduc- an average This envisages of the German EU Council presidency. a and efficiency, tion of EU greenhouse gas emissions by 2020, a 20% increase in energy A subordinate obligatory mix. within the energy energies 20% proportion of renewable share of at least 10% for the transport energy goal for all member states is a renewable The EER proposal of the EU Commission and council resolution had sector from 2020. ultimately Heated debate in the Parliament by the European Parliament. to be approved would be established as addi- sustainability criteria led to the compromise that verifiable oils for generating elec- the use of vegetable tional requirements, particularly regarding A prerequisite for national funding is the tricity and heat as well as for biofuel production. a determining criterion as regards the competitiveness of biofuel providers. As such, As such, of biofuel providers. the competitiveness a determining criterion as regards should react to this situation as quickly as possible and calculate biofuel manufacturers the CO BUNDESTAG SETS THE WRONG POLICY TAX AGENDA BundesratAlthough the German cam- (upper house of German parliament) vigorously the biofuels policy, a response is even more urgently needed to the question of how the the to the question of how needed more urgently a response is even policy, the biofuels in light of climate can be compensated oil utility of biodiesel and vegetable reduction mandates. protection however, unclear. What is clear is that, from 2015 at the latest, CO What is clear is that, from 2015 unclear. however, within the Bundesrat resolution of June 12, 2009, whereby the immediate creation of of within the Bundesrat resolution of June 12, 2009, whereby the immediate creation is required, with a commensurate, dynamic tax and economic frameworks reliable legal German govern- the new Whether and how situation. adjusted to the market regulation conditions that are appropriately based on the market tax framework ment will provide situation remains to be seen. 746 December 2009 inform of thedirective intonationallaw. The key requirementsofthe Germany isgoingitsown way asregards toitsincorporation SUSTAINABILITY ORDINANCE GERMAN “BIOFUELS”BIOMASS for new plantsthatarebuilt afterJanuary1,2017. to riseaminimumof50%fromJanuary2017,andatleast60% to theemissionsfromfossildieselfuel. This reductionfigurehas reduce greenhousegasemissionsbyatleast35%incomparison provision ofevidence thatbiofuelsandliquidbio-combustibles months toincorporatethedirective intonationallaw. Official Journal gases! The Renewable Energy Directive was publishedinthe raw materialachieves aminimum 50% reductioningreenhouse is onlypossiblewhenthebiodieselproducedusingrespective fuels inrelationtothebalancingoutofgreenhousegasemissions balance ofbiodiesel.” Noteworthy isthefact that“mixing”bio- with arelevant project:“Optimizationofthegreenhousegas commissioned theGermanBiomassResearchCentre(DBFZ) diesel production.Commensuratewiththisobjective, theUFOP of theraw materialandthenthroughtheprocessingstagetobio- are neededthroughoutthelifecycle, beginning withcultivation as afuelincogenerationunit,additionalefforts to closethisgap opportunity toserve asaraw materialforbiodieselproductionor gas reductionlevel. Consequently, toafford rapeseedalong-term diesel madefromrapeseedasregards therequiredgreenhouse Thus, a“CO attheendofJune2009;memberstateshave 18 2 reductiongap”would exist inrelationtobio- EU at thefirststage,agriculturaltrade? tractual conditionsmusttheraw materialvolumes berecorded balance systems.Onequestioninparticularis:underwhatcon- provided alongthesupplychaininformofso-called mass of maintenancethesesustainabilityrequirementshastobe tion viacorrespondingcertificationsystems.Continuousproof laws thatstipulatetheverification ofsustainablebiomassproduc- in therequirementsofEUdirective andtheaforementioned bureaucratic excessiveness. The backgroundofthedebatelies cussion intheagriculturaltraderegarding itspracticality and tions andlimitsconcerningbiomassoriginrequirements: graphs 4to7,whichspecificallyconcernthe verification obliga- biomass sustainabilityordinanceforbiofuelsaresetforthinpara- .Biomasscultivation mustbecarriedoutaccordingtogood 5. Noutilizationofbiomassesgrown inareasthatweredeemed 4. Carbon-richareas,e.g.,moors,wetlands,orpermanently 3. Grasslandencompassingsignificantbiologicaldiversity. 2. Noutilizationofbiomassesgrown inareasdeemedworthy 1. Implementation ofthisordinanceisnow generating dis- professional practice(crosscompliance). turf moorsonJanuary1,2008(referencedate). wooded areas. conserved withinthescopeofinternationalagreements. evident; andareasthatarealreadyconservation areasorare areas inwhichnoclearlyvisiblesignsofhumanactivity are forests andnaturalareascontainingdomestictreespeciesor of high-level natureconservation. These include:primeval December 2009 inform 747 Biofuels Dieter Bockey is withDieter the Promotion for the Union Oilseeds and of Protein Plants Ass., reg. and managing director of the Working Group Quality Management Biodiesel Ass. reg. Contact him via e-mail at [email protected]. limit until June 30, 2010, that is, without verification. In Germany In Germany without verification. June 30, 2010, that is, limit until equating to of rapeseed crops, to 1 million hectares this relates gener- as well as the domestically MMT of rapeseed, around 3.5 onward, From July 1, 2010, for bioethanol production. ated grain a sustainability or 2009 harvest of origin from the either proof the requirements As such, to be presented. certification will have in Sustainability Ordinance only apply stipulated in the Biomass ordinance will present all partici-This full for the 2010 harvest. there is enormous challenges. Moreover, pants in the trade with of these requirements the enforcement much debate regarding it is notable that practically Yet countries. in terms of third-party (which are also the most nations involved all the agricultural United biofuel manufacturers)—the internationally significant Malaysia, and Indonesia—are intensely Argentina, States, Brazil, It is introduction of certification systems. debating the national form of playing field is being created in the apparent that a level biomass cul- for international regulations practically equivalent, would and documentation obligations. Such regulations tivation or impossible to implement in the past due been unthinkable have from Organization Trade World to frequent criticism aimed at the competition in the biomass cultivation unfair the EU as regards evaluation. it is still too early for a conclusive However, sector. Pressure from the relevant trade associations was nonethe- trade associations was Pressure from the relevant The motivation and origin of this debate are one of the are one of the of this debate and origin The motivation less successful in ensuring that the new regulation would not not would regulation less successful in ensuring that the new As such, the ordinance stip- actually apply to the 2009 harvest. purposes without ulates that biomasses can be used for energy reasons that an end-use-related verification is stipulated in the stipulated in the is verification an end-use-related reasons that such for biofuels. Previously, Ordinance Biomass Sustainability of the obligatory within the scope was only required verification resources renewable and cultivating land of fallow setting aside that veri- The agricultural trade rightly demands on such land. bureaucratic involve- little with as effected fication should be of requirements that go beyond by way ment as possible and and Biomass Sustainabil- the directives Yet cross compliance. supplementary requirements within ity Ordinances encompass to be adequately 4 to 7 that have the aforementioned paragraphs raised fears among agri- These requirements have documented. The increase considerably. will culturalists that the bureaucracy is respon- Agriculture and Nutrition (BLE) for Federal Office in contrast to the obli- however, sible for the implementation; is apparent that in relation to land, it gation to set aside fallow focusing on monitoring implementation, the BLE is exclusively Introduction and implementation of the “monitoring systems.” at the first documenta- the corresponding certification systems biodiesel manufac- tion stage and subsequent stages (oil mills, whereas sector, business turers) are incumbent upon the relevant the certification systems and monitor- the BLE merely approves ing posts. Preorder Special! Save 40% off List Price! The For a limited time, preorder The Biodiesel Handbook, 2nd Edition for only $75! Biodieser Mention Promo Code: 09PS234 Handbook 2nd Edilion The Biodiesel Handbook, 2nd Edition Gerhard Knothe, Jurgen Krah I, and Jon Van Gerpen, Editors 2009. Hardbound. ISBN 978-1-893997-62-2. 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The 2nd ed ition of this invaluable handbook • Analytical Methods for Biodiesel • Influence of Biodiesel and Different Petrodiesel updates topics including: converting vegetable • Fuel Properties Fuelson Exhaust Emissions and Health Effects oils, animal fats, and used oils into biodiesel fuel. • Cetane Numbers-Heat of Combustion-Why • Current Status of the Biodiesel Industry The Biodiesel Handbook deliverssolutions to issues Vegetable Oils and Their Derivatives Are • Current Status of Biodiesel in the United States associated with biodiesel feedstocks, production Suitable as a Diesel Fuel • Current Status of Biodiesel in the European issues, quality control, viscosity, stability, • Viscosity of Biodiesel Union applications, emissions, and other environmental • Cold Weather Properties and Performance of • Biodiesel Quality Management: The AGQM impacts, as well as the status of the biodiesel Biodiesel Story industry worldwide. • Oxidative Stability of Biodiesel • Status of Biodiesel in Asia, the Americas, • Literature Overview Australia, and South Africa TENTATIVE CONTENTS INCLUDE • Stability of Biodiesel • Environmental Implications of Biodiesel (life- • Introduction • Biodiesel Lubricity Cycle Assessment) • The History of Vegetable Oil -Based Diesel Fuels • Biodiesel Fuels: Biodegradability, Biological • Potential Production ofBiodiesel • The Basics of Diesel Engines and Diesel Fuels and Chemical Oxygen Demand, and Toxicity • Other Uses of Biodiesel • Biodiesel Production • Soybean Oil Composition for Biodiesel • Other Alternative Diesel Fuels from Vegetable • Basics of the Transesterification Reaction • Exhaust Emissions Oils • Alternate Feedstocks and Technologiesfor • Effect of Biodiesel Fuel on Pollutant Emissions • Glycerol Biodiesel Production from Diesel Engines

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Card number ______Address ______Expiration date ______csc ___ City/State/Province ______Name on Card ______Postal Code/Country ______Signature ______Phone ______0 I prefer to pay by wire transfer (in U.S. dollars). Please send Bank transfer to Busey Bank, 201 W. Main, Urbana, IL 61801, USA, Account #111150-836-1 , Fax ______ABA #071102568. Please reference 09PS234. After you have arranged the wire transferwith yourbank, plea se fax usa copy oft he requestalong with acopy of this Email ______order form. Industrial oils inform December 2009, Vol. 20 (12) 749 )NDUSTRIAL OIL CROPS when will they ﬁnally deliver on their promise? Denis J. Murphy MMT) is used for nonfuel industrial applications as oleochemicals. However, the recent interest in supposedly carbon-neutral crop- Most inform readers are aware of the large number derived biofuels has started to divert significant amounts of vegetable oil feedstocks away from food or oleochemicals and toward of articles over the past few decades that have the large-scale production of biodiesel. highlighted the promise of new types of industrial oils from crop plants. As a researcher in this CONVENTIONAL BREEDING area since the 1970s, I am one of many who have Due to the unusual and exotic nature of many industrially useful fatty acids (FA), conventional breeding approaches have been less regularly pointed out the vast range of possible useful in manipulating the FA profiles of edible oil crops to produce industrial oils that could be obtained from plants. industrial oils. This is because most crop plants do not already Indeed it is now more than 15 years since I edited contain genes allowing them to accumulate such exotic FA and therefore a transgenic (genetically modified) approach is normally a book, optimistically entitled Designer Oil Crops required. (VCH Publishing, Weinheim, Germany, 1994), that One important exception is oleic acid, which can be used as described the brave new world of customized oil either a premium edible oil or a high-grade industrial feedstock.

crops that could be bred or engineered for dozens Existing uses of high-oleic soybean oil include lubricating oils, greases, printing inks, plasticizers, electrical insulation, detergents, of nonfood applications, from polymers to high- soaps, shampoos, and disinfectants. Oleic acid is a major compo- value cosmetics. However, as we approach the nent of all plants and is often abundant in seed and fruit oils, which second decade of the 21st century, only a very means that many plant oils have the potential to act as feedstocks for some of the uses listed above for soybean oil. However, the few of these new oils have achieved any signiﬁ- value of oleate-rich oils as industrial feedstocks is often severely cant commercialization. The purpose of this article limited by the additional presence of oxidation-prone polyunsatu- is to brieﬂy survey the near- to medium-term pros- rates, especially linoleic and _-linolenic acids. These FA reduce the thermal performance and oxidative stability of many plant oils pects for the industrial oil crops sector. and therefore restrict their industrial uses. A major challenge for In 2008, worldwide-traded oil production from crop plants breeders has therefore been to reduce polyunsaturate levels in seed was almost 130 million metric tons (MMT), mostly used as edible oils. vegetable oil. The proportion of plant oils used for nonedible or This challenge has been addressed with considerable success industrial purposes has fluctuated as petroleum and coal feedstocks by breeders in several major oil crops. For example, breeders in the increasingly competed with plant oils as sources of hydrocar- former Soviet Union developed high-oleic (75%) sunflower vari- bon-based products such as polymers, lubricants, fine chemicals, eties. Sunflower and safflower lines are now available with 75% and fuels. Currently, only about 20% of global vegetable oil (25 oleate and <1% _-linolenate. More recently, breeders in the United 750 inform December 2009, Vol. 20 (12)

States and Europe have developed high oleate/low polyunsaturate enzymes/genes required to accumulate a given novel FA are not lines of soybean and rapeseed/canola, which may have potential always predictable. A further problem in obtaining high levels of industrial applications and are now being marketed by major seed novel FA is that in some crop species, such as rapeseed/canola, not companies. By 2004, high-oleic rapeseed/canola was already being all of the novel acyl groups are necessarily channeled to storage planted on about 250,000 hectares (ha) in Canada, which is 5% of lipids. Some of the exotic FA may accumulate instead in mem- the total area of canola cultivation. Some of these new high-oleate brane lipids. This is one reason why some transgenic plants are oils have already been used as biodegradable lubricating fluids: unable to accumulate high levels of novel FA. It is also an impor- Their characteristics include relatively long working lives and low tant reminder of the complexity of metabolic regulation in plants susceptibility to oxidation at high temperatures. and the difficulties of manipulating this process via the insertion Efforts are also under way to produce very high-oleate vari- of one, or a few, transgenes. eties of oil palm. This is especially challenging owing to the slow Although transgenic approaches to oil modification have growth and long generation time of oil palm trees, which take 5–7 mainly focused on the introduction of exotic FA, they have also years to flower and produce oil and 10–15 years to reach full com- been used to downregulate existing genes in order to reduce levels mercial productivity. Over the past decade, several promising lines of unwanted FA. For example, linoleate desaturase genes have of the two oil palm species, Elaeis guineensis and E. oleifera, that been suppressed to reduce levels of _-linolenate in seed oils. This can contain up to 65% oleate in the mesocarp oil have been identi- approach has been used by several companies to complement con- fied in Africa and South America. By using DNA-based molecular ventional breeding programs aimed at developing high-oleate, low- markers, breeders now hope to cross high-oleate lines into existing polyunsaturate oils. The following high-oleate transgenic lines commercial lines; this is unlikely to produce commercial amounts have been developed, but not necessarily commercialized, to date: of high-oleic palm oil, though, until well after 2020. rapeseed/canola with 89% oleate; soybean with 90% oleate; and cottonseed with 78% oleate. TRANSGENIC OIL CROPS In theory, it is possible to express almost any FA in a plant oil CHEMICAL AND BIOTECHNOLOGICAL TRANS- by genetic engineering. However, despite 20 years of intensive FORMATIONS OF BASIC INDUSTRIAL OILS research, most novel FA still only accumulate at relatively low Even relatively homogeneous oils, such as 95% triricinolein, still levels in transgenic species, as shown in Table 1. The main reason often require downstream chemical and/or biotechnological con- is that simply transferring the relevant acyl modification gene into versions to generate specific oleochemical products at the required a plant does not necessarily mean that the corresponding FA will degree of purity. Less pure oils will require even more processing, accumulate at high levels in the storage oil of the recipient plant. and therefore research and development (R&D) into appropriate Indeed, despite more than 20 years of sometimes ingenious efforts technologies will still be necessary, whatever the success of breed- by molecular biologists, yields of novel FA in most transgenic ers in producing new crop-based oils. Downstream conversion and plants remain stubbornly low. diversification transformations sometimes require biotechnological Sometimes novel FA levels can be increased by transfer- procedures such as lipase-catalyzed interesterification or transes- ring additional genes, such as acyltransferases. But the additional terification. Alternatively, they may involve strictly chemical processes such as epoxidation or hydroxylation. After a relatively slow start, novel oils from several new crops information are also becoming industrially available, although not as yet in large quantities. Examples include petroselinic acid from corian- For further reading: der, calendic acid from Calendula officinalis, _-eleostearic acid Q #AHOON %" *- 3HOCKEY #2 $IETRICH 3+ 'IDDA 24 from tung oil, santalbic acid from Santalum album, and verno- -ULLEN AND *- $YER %NGINEERING OILSEEDS FOR SUSTAINABLE PRO- lic acid from Vernonia galamensis. Useful new products include DUCTION OF INDUSTRIAL AND NUTRITIONAL FEEDSTOCKS SOLVING BOTTLE- environmentally friendly industrial fluids and lubricants, insulat- necks in fatty acid ﬂux, Current Biology 10n ing fluids for electric utilities, and additives to asphalt. In addition Q Dyer, J.M., S. Stymne, A.G. Green, and A.S. Carlsson, High-value to modern methods of synthetic organic chemistry, enzymatic and oils from plants, The Plant Journal 54n microbial transformations can be used for the selective function- alization of alkyl chains. Some of the products of such syntheses Q 'UNSTONE &$ *, (ARWOOD AND !* $IJKSTRA EDS The include long-chain di-acids, t-hydroxy FA, and t-unsaturated FA. Lipid Handbook RD EDN 4AYLOR &RANCIS /XFORD 5NITED It is also possible to open up C=C bonds via chemical epoxida- +INGDOM tion to produce such advanced intermediates as polyetherpolyols. Q Metzger, J.O. and U. Bornscheuer, Lipids as renewable Finally, the purification of biologically produced (and therefore RESOURCES CURRENT STATE OF CHEMICAL AND BIOTECHNOLOGICAL enantiomerically pure) FA from oil crops provides the basis for the conversion and diversiﬁcation, Applied Microbiology and Bio- synthesis of high-value nonracemic building blocks in the manu- technology 71n facture of fine chemicals. Q -URPHY $* &UTURE PROSPECTS FOR BIOFUELS Chemistry Today 26n KEY TARGETS FOR FUTURE INDUSTRIAL Q van Beilen, J.B., and Y. Poirier, Prospects for biopolymer pro- OIL CROPS duction in plants, Advances in Biochemical Engineering and Bio- technology 107n One of the prerequisites for the commercial viability of future industrial oil crops is that they should accumulate single FA Industrial oils inform December 2009, Vol. 20 (12) 751

TABLE 1. Selected examples of transgenic plants modiﬁed to produce potential industrial oilsa stimulate further efforts to improve them to supply renew- % FA in % FA in able oleochemicals. donor Recipient recipient Q Use of co-products: The com- b FA Donor species species species species mercial viability of any indus- ,AURIC California bay Rapeseed c trial oil can be considerably increased if co-products of

c the crop are also exploited for Petroselinic Coriander Arabidopsis profit, rather than being an c additional expense for sepa- Ricinoleic Castor bean Arabidopsis d ration and disposal. Examples /( include the protein “cake”

c in oilseeds, which can often 6ERNOLIC Crepis palaestina Arabidopsis be processed to make animal c /( feed. In other crops the vegeta- Crepylinic Crepis alpina Arabidopsis c tive parts of the plant, such as c TRP fibers, stems, and trunks, can be used. c _ %LEOSTEARIC Momordica Soybean Q Management and process- c t t charantia ing of industrial oil crops:To Calendic Calendula ofﬁcinalis Arabidopsis e date there has been relatively little research into the kinds of t t c a management and processing )N THE VAST MAJORITY OF CASES WHICH ARE NOT SHOWN HERE ONLY VERY LOW LEVELS OF NOVEL FATTY systems that will be required acids were produced. for many new industrial oil b&! FATTY ACID c, cis double bond; t, trans double bond; trp, triple bond. crops. Most of these crops have c*AWORSKI * AND %" #AHOON )NDUSTRIAL OILS FROM TRANSGENIC PLANTS Current Opinion in Plant Biology been developed separately on 6n a piecemeal and rather empiri- d"URGAL * * 3HOCKEY # ,U * $YER 4 ,ARSON ) 'RAHAM AND * "ROWSE -ETABOLIC ENGINEERING OF HYDROXY FATTY ACID PRODUCTION IN PLANTS 2C$'!4 DRIVES DRAMATIC INCREASES IN RICINOLEATE LEVELS IN cal basis, with relatively little seed oil, Plant Biotechnology Journal 6n dissemination of useful meth- e#AHOON %" #2 $IETRICH + -EYER (' $AMUDE *- $YER AND !* +INNEY #ONJUGATED FATTY odologies or best practice. acids accumulate to high levels in phospholipids of metabolically engineered soybean and Arabidopsis Among the novel challenges seeds, Phytochemistry 67n that might face the grower and user of completely new crops are differing requirements for species, or very specific FA mixtures, or other lipid-derived feed- the sowing, cultivation, harvesting, oil extraction, and down- stocks (such as polyhydroxyalkanoates) at the highest possible stream processing of such crops. This might entail the pur- yields and purity. This needs to be achieved without compromis- chase or hire of new kinds of equipment on-farm. Cultivation ing other important agronomic characteristics of the crop. It will of the new crops might also affect the management of existing also be necessary to ensure that such industrial crops can be grown, crops being grown on the same farm. harvested, and processed on a large scale without affecting adjacent crops that might be destined for animal feed or for the human FUTURE PROSPECTS food chain. A list of some key targets for developers of industrial For the foreseeable future, oil crops will continue to serve pri- oil crops is given below. marily as sources of edible vegetable oils for a global population Q Tailored oil composition: The chosen FA for a particular end that is projected to rise to more than 9 billion people by 2050. use should make up the vast bulk of the triacylglycerol oil of The recent diversion of plant oils towards the biodiesel sector is a crop, ideally at least 80–90%, in order to reduce downstream likely to be transient as second generation biofuels are developed. costs. This goal has been difficult to achieve due to the genetic In the much longer term, as fossil-derived hydrocarbons inevita- and biochemical complexities underlying storage lipid com- bly become depleted and therefore more expensive, plant oils will position in plants. Further progress here will depend on more gradually begin to replace them in more and more applications. information about the identity of target genes to be selected However, and unlike the picture a few decades ago, it now appears by breeders. that this process will take many decades and the speed of the tran- Q High oil yield: An industrial oil should be accumulated at the sition from petrochemicals to oleochemicals will depend crucially highest possible yields by the crop in question; for example, on factors such as the health of the global economy, progress in simply increasing the proportion of oil in seeds of a crop like R&D into new plant oils, and wider political developments. Exam- meadowfoam from its current low levels of 20% to a value ples of the latter include government policies such as carbon taxes of 30% would result in an increased crop oil yield of 50%, or renewables obligations that might encourage use of plant oils without affecting any other production costs. This could sig- and stimulate a more rapid rate of R&D into industrial plant oils. nificantly increase the market uptake of such minor crops and CONTINUED ON PAGE 800 101st AOCS Annual Meeting & Expo May 16-19, 2010 PHOENIX CONVENTION CENTER Phoenix, Arizona, USA

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PHOTO: BROCK PEOPLES Briefs inform December 2009, Vol. 20 (12) 753

ILSI (International Life Science Insti- News & Noteworthy tute) Europe has released a draft report on 3-MCPD (3-monochloropropane-1,2-diol) esters in food. The report summarizes the ILSI Europe workshop held in February 2009 in Brussels, Belgium, commissioned by the ILSI Europe Process-Related Compounds and Natural Toxins Task Force and Risk Assessment of Chemi- cals in Food Task Force in association with the European Commission and the European Food Safety Authority. The report is available at www.ilsi. org/Europe/Publications/ILSIEurop- eReportMCPDEsters7Se09-1.pdf. A resource page about the issue of chloroesters in foods is available at www. aocs.org/tech/3-mcpd.cfm. QQQ Presentations from an OECD (Organ- isation for Economic Cooperation and Development) workshop held in August 2009 on the sustainability of biobased products are now available at https://www.oecd.org/docum ent/40/0,3343,en_2649_34537_4345 Cognis 7128_1_1_1_1,00.html. The meeting looked at existing national and inter- SDA soy achieves of a Δ15 desaturase with temporal expres- national approaches to assessing the sion similar to the Δ6 desaturase increases the flux of ALA [ -linolenic acid] to SDA. health and environmental impacts of _ GRAS status The Δ15 desaturase also lowers LA levels, proposed new biobased products, thus lowering the substrate pool for GLA including biobased chemicals, biobased Monsanto Co.’s biotech high-stearidonic acid (SDA) soy oil has achieved GRAS production. Compositional data on several plastics, enzymes, biobased materials, (Generally Recognized as Safe) status from lots of SDA soybean oil support the opinion and biofuels. the US Food and Drug Administration. that the phenotype is stable over several QQQ Monsanto (St. Louis, Missouri, USA) generations.” AMC Technical Briefs, a resource pro- made the announcement in November in The fatty acid composition of the vided by the UK’s Royal Society of tandem with Solae LLC (St. Louis, USA), SDA oil is “significantly different” from Chemistry (RSC), covers innovations which will develop and market the oil. conventional soybean oil, Monsanto said. and contemporary technical issues in Solae’s majority owner is DuPont and its SDA soybean oil contains 15 to 30% SDA analytical science. Designed for use minority owner is Bunge Ltd. Bunge also (18:4n-3), which is not present in conven- by analytical practitioners and those has a joint venture with Pioneer Seed, tional soybean oil; 5 to 8% GLA (18:3n-6), commissioning and then using analyti- which is owned by DuPont, to market new which also is not present in conventional cal data, each brief is a one-page docu- biotech-derived soy oils. soybean oil; and slightly higher levels of ment dealing with a single topic. The “The production of SDA in soybean ALA (18:3n-3) and palmitic acid (16:0) briefs are produced by the RSC’s Ana- MON 87769 involves the introduction of than in conventional soybean oil. It also lytical Methods Committee (AMC), two desaturase genes that encode for the contains lower levels of oleic acid (18:1) which has been active in matters of proteins Primula juliae Δ6 desaturase and and linoleic acid (18:2) than those present analytical data quality since the 1930s. Neurospora crassa Δ15 desaturase,” Mon- in conventional soybean oil. Now that the oil has achieved GRAS More than 40 briefs are available, free santo said in its GRAS submission. “Soy- status, it can be used in a long list of foods of charge, at www.rsc.org/amc. beans lack Δ6 desaturase and the minimal requirement for production of SDA in soy- and beverages including baked goods and QQQ beans would be the introduction of a gene baking mixes, breakfast cereals and grains, Cognis Nutrition & Health (Monheim, encoding Δ6 desaturase. However, Δ6 cheeses, dairy product analogs, fats and Germany) announced in October desaturase also may convert LA [linoleic oils, and snack foods, at levels that provide acid] to GLA [a-linolenic acid]. Addition 375 milligrams of the oil per serving. CONTINUED ON PAGE 754 754 inform December 2009, Vol. 20 (12)

2009 that the Ministry of Health of the People’s Republic of China has rec- Research suggests that about 33% of the glycidol esters. Shipments are expected to ognized Tonalin as an approved novel SDA ingested by humans is converted to resume by March 2010. food. This means that Cognis’ brand eicosapentaenoic acid (20:5n-3), a long- of CLA (conjugated linoleic acid) can chain polyunsaturated fatty acid usually be used in functional foods and bev- sourced from fatty cold-water fish such as US BioPreferred erages in the Chinese market. Cognis menhaden. received US Food and Drug Adminis- The new oil is not expected to be com- label program tration GRAS (Generally Recognized mercially available until 2011 or 2012, A notice of proposed rulemaking regarding as Safe) status for Tonalin CLA in July Monsanto said. the US Department of Agriculture’s (USDA) 2008. The company has also applied voluntary labeling program has appeared for novel food approval in Europe and in the Federal Register (74:38295–38317, expects to gain it in 2010. EFSA: Health claims 2009). “When final, the regulation will allow biobased product manufacturers to QQQ The European Food Safety Authority participate in a voluntary labeling program (EFSA) has published its first series of to identify biobased products on retail store opinions on the list of “general function” shelves,” according to USDA. health claims compiled by member states The BioPreferred program was created and the European Commission. Experts on by the Farm Security and Rural Investment EFSA’s Panel on Dietetic Products, Nutri- Act of 2002 (2002 Farm Bill) as a preferred tion, and Allergies (NDA) evaluated the sci- procurement program to increase the pur- entific evidence for more than 500 claims. chase and use of biobased products within The opinions will help inform future deci- the federal government. The Food, Con- sions of the European Commission and servation and Energy Act of 2008 (2008 Member States concerning the authoriza- Farm Bill) expanded the program’s scope tion of health claims. to promote the sale of biobased products in General function claims defined under other sectors. Article 13.1 of the Regulation 1924/2006 BioPreferred comprises two pro- on nutrition and health claims made on grams: a preferred procurement program food include: The role of a nutrient/sub- for federal agencies and a voluntary label- stance in growth, development, and the ing program for the broad-scale marketing functions of the body; psychological and of biobased products. A complete list and behavioral functions; slimming and weight detailed description of each BioPreferred control or reduction of hunger, increase of designated item, and items for future desig- satiety, or the reduction of available energy nation, can be found at www.biopreferred. from the diet. These claims do not include gov. Food-labeling laws in Australia and those related to children’s development or A summary of how the USDA BioPre- New Zealand will soon be under health or disease risk reduction. ferred label differs from other ecolabels is review by an expert panel recruited The full opinion is available online at available at www.betalabservices.com/ by the Australian and New Zealand www.efsa.europa.eu. News/2009/09/usda-biopreferred-program- Food Regulation Ministerial Council. label/. Former Australian health minister Neal Blewett heads the panel. More infor- Kao incurs losses mation is available at www.foodstan- Turkish Lipid Group dards.gov.au/newsroom. on DAG oil halt QQQ Kao Corp. said on October 27, 2009, that it formed In other labeling news, the Smart posted a 6-billion-yen (around $66 million) A group of participants from industry, aca- Choices Program, a US food industry- unaudited loss for April–September 2009. demia, and government have formed the led effort to create front-of-package The company, which is Japan’s Turkish Lipid Group (YABITED), with nutrition labels, voluntarily postponed largest personal care and household prod- Aziz Tekin of the University of Ankara as “active operations” on October 23. ucts company, cited several reasons for the president. The group aims to further scien- This move followed an announce- slide. They included reduced sales of cos- tific research and the fats and oils indus- ment by Food and Drug Administra- metics and chemicals as well as the compa- tries, and to organize meetings. YABITED tion Commissioner Margaret Hamburg ny’s decision in September to temporarily has joined Euro Fed Lipid as an institu- that the agency intends to develop suspend shipments of its 59-item portfolio tional member, Tekin said. standardized criteria on which future of products based on its Econa diacylglyc- Persons and companies interested in front-of-package nutrition labeling will erol (DAG) cooking oil. Shipments were joining the Turkish Lipid Group should be based. Q halted because of the presence of high contact Tekin at [email protected]. levels of a process contaminant known as tr. Q inform December 2009, Vol. 20 (12) 755

agreement in the area of research and QQQ Acquisitions/ development of soy products. “Thanks to A group of scientists, including a number the acquisition, Mona’s production capac- of AOCS members, petitioned the Euro- mergers ity is expected to double to 50 million liters pean Commission (EC) to amend the EC’s annually,” FLEXNEWS said. new omega-3 labeling regulation, saying Kamolkij Group, one of Thailand’s oldest they believe it will confuse consumers. The commodity export groups, plans to con- group vowed to continue the fight in the solidate all of its edible-oil operations Commodities European Parliament, after the EC backed to improve efficiency for future growth, the regulation in October. The new rule the Bangkok Post newspaper said in late CACAO/CHOCOLATE does not discriminate between plant and October 2009. The group’s rice-bran oil marine-sourced omega-3 sources. products under the Chim, Alfa One, and ADM officially opened its new cacao Rizi brands “have performed strongly in processing plant on October 9, 2009, in OLIVE OIL both export and domestic markets, with Kumasi, Ghana. The facility comprises a Cargill and Spain’s Hojiblanca coop- total sales expected to reach 2.5 billion baht bean warehouse, a processing plant, and erative have inaugurated a new oil bot- (about $75 million) this year, up from about a finished goods warehouse that sit on a tling plant at Antequera, near Malaga. The 1 billion baht in 2007,” the report noted. 75,000-square-meter site. The new plant 50:50 joint venture between the companies According to Kamolkij Group Chief Exec- processes cocoa beans into cocoa liquor under the name of Mercaóleo represents an utive Officer Korbsook Iamsuri, five com- for use in chocolate. Construction of the investment of €18 million in the plant itself, panies handling upstream to downstream Kumasi plant started in January 2008, and in addition to the working capital required production will be grouped under a single the facility began processing beans in July to operate at full capacity. The oil bottled entity, Kasisingha Co., which will be 2009. will be sold and distributed to customers by renamed Kasisuree Co. when the process its parent companies. is completed in 2010. CANOLA/RAPESEED OIL QQQ The Canadian government will invest PALM OIL Archer Daniels Midland Co. (ADM; $6.4 million in three projects in efforts to Decatur, Illinois, USA) has acquired five increase the competitiveness of the canola The Malaysian Palm Oil Board (MPOB) oceangoing dry-bulk commodity vessels. industry. One of the programs is the Canola has released a statement on 3-MCPD The five carriers—one Handy, one Handy- Council of Canada’s Grow Canola 2015, (3-monochloropropane-1,2-diol) esters max, a Supermax, and two Panamax ves- which was allotted $1.7 million to build an and glycidol fatty acid esters in foods sels—provide cargo-carrying capacity efficient, up-to-the-minute communication at www.mpob.gov.my/html/issue/issue40. between 36,000 short tons and 67,000 short network for canola growers using web and html. In the statement, MPOB identifies its tons (roughly 33,000 and 61,000 metric social media technology. Another $1.69 research strategies as working with others tons) and will transport all types of grain, million will contribute to the Council’s on a collaboratively tested method, eluci- grain products, and bulk commodities to international promotion efforts about food dation of its formation and mitigation, and and from ports in Europe, South America, use of canola oil under CanolaInfo (www. collaborative work on toxicological studies. Asia, and other parts of the world. Once canolainfo.org). For more information on chloroesters in in operation, the five dry-bulk carriers will foods, see inform 20:200–202, 2009. augment ADM’s transportation network, FISH OIL which also includes 1,700 barges, 58 tow Signatories to the 28th meeting of the Com- boats, 29 line boats, 23,500 railcars, and mission for the Conservation of Antarctic 1,600 trailers, according to the company. Living Resources, which was held in early QQQ November 2009, agreed that krill fishing In other ADM news, the company has could only be increased significantly if the acquired ViaChem Group’s oilseed pro- harvest moves to areas other than Area 48. cessing assets in Olomouc, Czech Repub- Krill fisheries in Area 48 near Antarctica lic. This facility, in the eastern part of the have been under pressure recently because Czech Republic, consists of an oilseed of growing interest in the use of krill oil as a crushing, refining, and biodiesel plant that source of omega-3 fatty acids, phospholip- produces oil and meal for the food, feed, ids, and the antioxidant astaxanthin. Com- and energy markets. panies that produce krill oil such as Israel’s QQQ Enzymotec and Canada’s Neptune Tech- Austrian soy food product maker Mona has nologies & Bioressources Inc. believe acquired Germany’s Sojaland and its pro- that krill are not threatened, noting that the duction facility in Schwerin, according to current annual harvest constitutes less than FLEXNEWS.com. At the same time, Mona 1% of the estimated biomass of krill. For and the German aroma and flavor producer more on krill oil, see inform 18:588–592, Wild concluded a strategic cooperation 2007. 756 inform December 2009, Vol. 20 (12)

SOYBEAN OIL by the railroad industry and the leading US called BL10, was discovered after the team rail destinations for soy. isolated, cultivated, and identified marine Chen Bin, director of China’s Department microalgae from 10 marine habitats around of Industry under the National Develop- Taiwan, according to a report by Taiwan’s ment and Reform Commission, said in Central News Agency. Q October that China would set up a soybean New ventures information release system and improve Cognis (Monheim, Germany) has intro- statistics services “in hopes of guiding duced Lamequick SUN 40, a new whipping the soybean processing industry through concentrate with fewer saturated fats, to the a healthy development.” The country will Interested in European market. The product is based on also decline applications for new soybean sunflower oil and is suitable for cake fill- contributing processing projects or project expansions ings, mousses, Chantilly cream, and other to inform magazine? in principle, in order to curb overcapacity creamy desserts. and avoid blind competition in the industry, Do you have a story that would be Chen told the Asia Pulse Businesswire. perfect for the pages of inform? A new QQQ development in your field that is sure A recent study by the US soybean check- R&D to generate widespread interest? A profile of a colleague or institution? off-funded Soy Transportation Coalition A research team at Taiwan’s National found that “42% of rail movements of soy- Been to a meeting whose hot topics Cheng Kung University in Taipei says it has stirred great debate? inform magazine beans are transported at rates that could be discovered an indigenous alga that is rich in classified as excessive,” according to the is actively seeking the contributions docosahexaenoic acid (DHA), containing of you and your colleagues. Contact United Soybean Board (St. Louis, Mis- 10 times as much of the omega-3 fatty acid souri, USA). The study, titled “Railroad inform’s managing editor at jeremyc@ as existing DHA supplements such as fish aocs.org for more information. Movement of Soybeans and Soy Products,” oil. The indigenous DHA-rich algal strain, also analyzed the volume of soy transported inform December 2009, Vol. 20 (12) 757 Briefs Biofuels News Oxford Catalysts (Oxford, UK) and its US subsidiary Velocys (Plain City, Ohio) won the Best Innovation by an SME (small- and medium-sized enter- prise) Award, presented by ICIS Inno- vation Awards 2009 (www.icis.com/ awards). These awards, sponsored by Dow Corning and CRA International, recognize the resourcefulness of the chemical industry in meeting the needs of its customers, consumers, and the environment. Oxford/Velocys have developed small-scale, high-intensity microchannel reactors to convert bulk waste, including animal-derived waste, crop residues, lignocellulose waste from trees, and municipal solid wastes, into liquid biofuels such as diesel and jet fuel. Microchannel reactors minimize heat and mass transport limitations. QQQ According to Biofuels Digest (October 13, 2009), the US Secretary of Energy, Steven Chu, told attendees of a meeting on alternative energy development, “If it were up to me, I would Relation of M. put every cent into electric cars.” The GENERAL Digest also said less than $20,000 in tuberculosis and American Recovery and Reinvestment US energy research Act funds had been released by the biofuel? Department of Energy (DOE) for bio- projects receive Yeasts and bacteria such as Escherichia coli fuels, whereas the DOE had made loan are known for their abilities to produce bio- guarantees of $1 billion for all-electric funding fuels, especially bioethanol, but Anthony luxury sport cars. The US Department of Energy’s Advanced Sinskey and his research group at the QQQ Research Projects Agency-Energy (ARPA- Massachusetts Institute of Technology A study carried out by P.C. Smith and E) announced funding for 37 research proj- (Cambridge, USA) have been exploring coworkers at the University of Ade- ects on October 26. This is the first round representatives of a lesser-known bacterial laide in Australia proposes that the of projects funded under ARPA-E, which group, Rhodococcus, as possible synthesiz- alkoxylation of the unsaturated frac- is receiving a total of $400 million under ers of biofuel. tion of biodiesel could reduce the the American Recovery and Reinvestment Rhodococcus spp., which are soil- cloud point of the fuel without com- Act. dwelling microorganisms, are related to promising ignition quality or oxidation In announcing the selections, Depart- Mycobacterium tuberculosis, the causative stability, at least at lower concentra- ment of Energy Secretary Steven Chu said, agent for tuberculosis. They are known for tions. Specifically, the study considered “ARPA-E is a crucial part of the new effort their non-fastidious appetites for a wide the butoxylation of butyl biodiesel. by the US to spur the next Industrial Revo- range of sugars and toxic compounds. From The research appeared in Energy & lution in clean energy technologies, creat- these compounds Rhodococcus makes triacylglycerols (TAG), which can be pro- Fuels 23:3798–3803 (2009). ing thousands of new jobs and helping cut carbon pollution.” cessed further into biodiesel. QQQ The strain that Sinskey and colleagues Biodiesel production in India is running Selected projects receiving funding are listed in Table 1 (see page 758). are studying, R. opacus, was originally at 5% or less of its 200,000-metric- isolated from contaminated soil in which tons-per-year capacity. According to Business Standard, a majority of biodie- CONTINUED ON PAGE 758 CONTINUED ON NEXT PAGE 758 inform December 2009, Vol. 20 (12) sel units are not operational most of the year because of the lack of avail- TABLE 1. ARPA-E funded research projectsa ability of jatropha seed and other nonedible oil feedstocks. The total Lead organization Grant Location amount Project description area in India on which jatropha has been planted is estimated at around Agrivida, Inc. $4,565,800 Cell wall-degrading enzymes grown 450,000 hectares; of this, over 70% Medford, Massachusetts within the plant itself that are activated are new plantations and will mature after harvest in the next four years. Biodiesel is not Arizona State University $5,205,706 Cyanobacteria that produce and produced from vegetable oils in India Tempe, Arizona secrete fatty acids for biofuel feedstock for food security reasons. Most pro- using sunlight, water, and CO2 as inputs ducers are using nonedible oilseeds, Ceres, Inc. $4,989,144 Genes that enable energy crops to nonedible oil waste, and animal or fish Thousand Oaks, California produce more biomass using less land fat as feedstock. (and lower-quality land), less water, QQQ and less fertilizer than standard energy The US Department of Energy’s feedstocks National Renewable Energy Labora- E.I. du Pont de Nemours & Co. $9,000,000 Production of biobutanol, an advanced tory (NREL) announced a new website Wilmington, Delaware biofuel, from macroalgae that contains an online directory of Iowa State University $4,373,488 Metabolic engineering and synthetic web-based tools, database searches, Ames, Iowa biology approaches to increase lipid cost calculators, and interactive production, CO2 uptake, and thermal maps—all related to alternative fuels tolerance of algae for the production of and advanced vehicles. Twenty-three biofuels directly from sunlight and CO2 tools, maps, and searches are available Ohio State University $5,000,000 Syngas chemical looping (SCL) to on the Alternative Fuels and Advanced Columbus, Ohio convert biomass or coal into electricity Vehicles Data Center (AFDC) web site while efficiently capturing the CO2 for transportation technologies, the Pennsylvania State University $1,900,067 Catalyst-coated TiO2 nanotube mem- NREL said. Users can find the tools University Park, Pennsylvania branes to convert sunlight, CO , and page on the AFDC under Informa- 2 H2O into CH4 and other hydrocarbon tion Resources at www.afdc.energy. fuels gov/afdc/applications.html. United Technologies Research $2,251,183 Synthetic form of carbonic anhydrase QQQ Center for capturing CO2 from coal plant flue The Indonesian Ministry of Agriculture East Hartford, Connecticut gas streams has indicated that the protein resulting as a co-product in the growth of Univenture, Inc. $5,992,697 A new algae harvesting system that Marysville, Ohio could reduce the energy cost to algae for biofuel by PetroAlgae (Mel- harvest, dewater, and dry algae by bourne, Florida, USA) is suitable for using a novel absorbent moving belt use as a raw material in animal feed in harvester Indonesia. The protein also has been cleared for importation as a raw mate- University of Minnesota $2,200,000 Production of liquid hydrocarbon St. Paul, Minnesota transportation fuels directly from sun- rial to be used as an ingredient for light, water, and CO2 using an artifi- animal feed. cial symbiotic colony of photosynthetic QQQ cyanobacteria and Shewanella, a hydro- The OECD (Organisation for Eco- carbon-producing bacterium nomic Co-operation and Develop- a ARPA-E, US Department of Energy’s Advanced Research Projects Agency-Energy ment) and the Food and Agriculture Organization (FAO) predict that biodiesel production within the European the organisms were breaking down petro- hope is that “once scientists have found Union may reach 4.86 billion gallons leum waste products. These researchers a way to break down cellulosic biomass per year, or 18.4 million kiloliters, by are working to engineer the organism to into simpler sugars, the ability [of the 2018. They also project that 9.1% of produce TAG more efficiently, using waste organisms(s)] to use more than one will the European market will be biodie- streams of carbon as feedstock. They have simplify the production process.” Strains sel by that time, that global biodiesel already created a strain of Rhodococcus that can feed on glycerol have also been consumption will be 11.5 billion gallons, that can use two types of sugars, glucose engineered. that feedstock prices will increase and xylose, at the same time. According to Further down the road, Sinskey and 30%, and that biodiesel prices will MIT’s Technology Review (www.technol- his team hope to engineer the bacteria to rise 17%. Q ogyreview.com/biomedicine/23526/), the aggregate the lipids they produce into lipid inform December 2009, Vol. 20 (12) 759

bodies, which would be easier to recover www.usda.gov/oce/energy; click on Papers would then be processed further into bio- than solubilized lipids. and Reports, then on “Energy Life-Cycle diesel. Their technology could avoid having Sinskey is also known for founding Assessment of Soybean Biodiesel” by A. to harvest algae and dry them, both of Metabolix in the early 1990s, a company Pradhan et al. which are expensive, before using solvent that makes biodegradable plastics. to extract their oil. And solvent extraction is costly, as well as hard to scale up. ALGAE OFAT’s technology can work on algae BIODIESEL in concentrations as low as the ones found in natural waters, 0.1–0.2% by weight, New algal growth although the process is more cost effec- Biodiesel without tive if the concentration can be increased system to 10% or more. waste OriginOil, Inc. has added another method OFAT is seeking to raise about $4 In Amsterdam, the Netherlands, Yellow to its collection of ways to grow and harvest million to build a commercial prototype. Diesel B.V. announced in mid-October algae for use in producing biofuels. The The company plans to sell its technology to that the company has succeeded in produc- Attached Growth System (AGS) uses types algae biofuels makers, instead of growing ing high-quality biodiesel in a continuous of algae that will attach to a surface rotating algae and converting them to fuel. fixed-bed micro plant based on hetero- in and out of the aqueous medium, expos- geneous catalysis. Starting with various ing the algae to sunlight (or artificial light). types of feedstock, including low-quality At harvest time, the algae are scraped off SunEco Energy oils, waste oils, and fats, the process yields as a sludge, greatly decreasing the energy pure biodiesel—with specifications better cost of dewatering during oil extraction. predicts 200,000 than those required by the European norm, The AGS is reminiscent of rotating biolog- gal/acre/yr of algae EN14214—and cosmetics/food grade ical contactors that have been used since glycerol. the 1960s in secondary treatment systems oil All aqueous waste streams, as gener- for municipal wastewater. ated by conventional homogeneous acid/ In fact, the company is proposing that Located in the Imperial Valley of Califor- base catalyst technology, are eliminated. their growth system can be used in waste- nia, SunEco Energy says it can currently With the novel catalyst used in the reac- water treatment plants by configuring the produce at least 33,000 gallons of de- tion and the integrated process design, the reactor surfaces to encourage the growth watered, de-gummed biocrude algal oil per process saves up to 40% of the capital costs of bacteria as well as algae. Better nutrient acre-foot (1.01 million liters/hectare-meter) and 30% of the operating costs compared extraction can be achieved by combining per year from algae grown in its 1,200 acres to a conventional plant. algal and bacterial growth, which is one of of outdoor ponds in Niland, California, The company is presently scaling up the goals of sewage treatment, and at the USA (www.sunecoenergy.com). Company Chief Technology Officer Jim Hardin says the process to pilot-scale. same time CO2 is tied up in biomass that can be used as feedstock for fuel. that the company uses a polyclonal system A demonstration system is now being composed of more than 30 algal species to The energy built at the company’s headquarters in Los achieve this yield, and that heterotrophy has Angeles, California, USA. a part in these high yields. needed to produce The company also claims it can achieve this growth in ponds that are 6–8 feet deep biodiesel Shocking algae (1.8–2.4 m), which would be equivalent Research out of the University of Idaho and to 200,000–260,000 gallons of oil/acre/ Organic Fuels, a Houston, Texas (USA)- year (6.1–8.1 million liters/hectare/year). the US Department of Agriculture shows based biodiesel producer, has entered into that for every unit of fossil energy needed Surface area is the typical basis of compar- a joint venture (JV) with the University of ison of yields in the industry, not volume to produce biodiesel, the return is 4.5 units Texas at Austin’s Center for Electrome- of energy. That is, the energy balance of the (acre-foot), since in conventional systems chanics to use electricity to break open most photosynthesis takes place in the process is 4.5. algal cell walls and release oils contained in Key factors making biodiesel made surface few centimeters. the cells. The concept is somewhat similar Experts have expressed considerable from soybean oil an efficient fuel include to that of OriginOil (see inform 20: 576, (i) new seed varieties and management misgivings regarding these claims because 2009), which is using ultrasound to remove of the depth to which the company claims practices that are enhancing yields, (ii) oil from cells. reduced tillage practices that cut the photosynthesis takes place. The company The JV, called Organic Fuels Algae counters that they are not at liberty to amount of fuel needed to grow soybeans, Technology (OFAT), subjects cell walls to (iii) soybean varieties that have lower need explain these yields in detail because of “electromechanical lysis.” OFAT claims the intellectual property security. for pesticides, and (iv) modern processing process is inexpensive, and estimates that and biodiesel manufacturing plants that use their process would produce oil for about less energy. The report may be obtained at $1.50 per gallon ($0.40 per liter). The oil CONTINUED ON NEXT PAGE 760 inform December 2009, Vol. 20 (12)

to think like and act like farmers, accord- has not been attractive for two reasons: Parallels in ing to Michael Melnick, venture capitalist, high levels of isobutanol would kill the investor in Biolight Harvesting, and presi- organisms producing the alcohol, and the corn and algae dent of Inventure Chemicals (www.eenews. separation of isobutanol from the growth net/public/climatewire/2009/10/07/1). medium is difficult. Gevo solved these production A number of entrepreneurs, though, issues by genetically modifying the organ- In an article by Annie Jia in the October are betting that sooner or later field expe- ism to tolerate butanol, and by separating 7 issue of Environment and Energy Daily rience with algae production will reach a the butanol out as soon as it is produced (www.eenews.net/cw), James Levin, a critical point and that algal oil production with its patented Gevo Integrated Fermen- research biologist with Kent Bioenergy will take off in the same way that corn pro- tation Technology. (San Diego, California, USA) who studies duction did—and these risk-takers want to The process offers the advantage of a algae, said, “Similar to what occurred in be there to see algal oil compete head-to- flexible choice of feedstock; it can use all the Green Revolution, where there were head with petroleum products. typical ethanol feedstocks as well as cellu- advances made both in traditional farming losic biomass. techniques and the adopting of new tech- The additional cost of capital equip- nology to farming, biofuels will probably ETHANOL ment to convert to the biobutanol process follow a similar path.” is projected to be approximately $0.30 per That is, 100 years ago, the typical yield gallon of installed ethanol capacity. Retro- of corn per acre in the United States was Gevo retrofitting fitted facilities will have the flexibility to 30 bushels/acre (1,900 kg/ha). With all produce either ethanol or biobutanol. the study of corn nutrition, and advances for biobutanol Gevo plans to acquire and retrofit as in corn genetics, yields in 2008 averaged Gevo Inc. (Englewood, Colorado, USA) many as five ethanol plants to produce more than 150 bushels per acre, or 9,400 has formed Gevo Development, LLC biobutanol. Q kg/ha. to develop a number of biorefineries to Most of the yield predictions and cost produce biobutanol. The plan is to retro- figures for algal oil production published fit existing ethanol plants, based on Gevo’s so far (e.g., see story on SunEco Energy, proprietary technology, to produce biobu- inform 20:759–760, 2009) have been devel- tanol. This higher alcohol can be blended Published something oped in the laboratory, where one does directly with gasoline and also can be used not have to deal with or can control wide to make renewable hydrocarbons, jet and lately? swings in temperature, out-competition diesel fuel, chemical intermediates, and We would like to begin listing recent by windborne algal-contaminant species, biobased plastics. publications of our student members, excessive light, and predation by invasive A primary component in Gevo’s tech- including dissertations. Please send animals. nology is its genetically modified bio- complete citations to inform Associ- The crux of making algal oil produc- catalyst, that is, a strain of yeast that can ate Editor Catherine Watkins (cwat- tion competitive lies in growing algae “in produce isobutanol rather than ethanol. In [email protected]). the field.” That is, entrepreneurs will have the past, yeast production of isobutanol inform December 2009, Vol. 20 (12) 761 Briefs Health & Nutrition Work led by Dennis Hsieh of the China Medical University in Taiwan may cause regulatory agencies to reex- amine the tolerable daily intake (TDI) for melamine. Hsieh and colleagues calculated a TDI of 0.0081 mg/kg of body weight per day, as compared with the World Health Organization’s TDIs of 0.5 and 0.2 mg/kg of body weight per day. (The second WHO value is a result of increasing the safety factor values in the calculation.) Melamine, an industrial chemical, is an adulter- ant used to create economic value for food ingredients by seeming to increase protein content (see inform 20:563–565, 2009). QQQ A soy supplement (SE5-OH) containing S-equol—an isoflavandiol metabolized from the soy isoflavone daidzein— improved menopausal symptoms, including significantly reducing hot flash frequency by nearly 59%, according to a study in Japanese women. The study was delivered in an oral presentation at the North American Meno- pause Society’s 20th annual meeting of liver cancer occurrence by 60 times, and (Sept. 30–Oct. 3, 2009; San Diego, Aflatoxin trigger toxin-related cancer causes up to 10% of all California, USA). A second oral pre- deaths in those nations. sentation reported peer-reviewed data found “It’s shocking how profoundly these that documented for the first time the Jennifer Fitzenberger molds can affect public health,” says Tsai, pharmacokinetics, or absorption and UCI molecular biology and biochemistry, distribution in the body, in menopausal University of California Irvine chemistry, and pharmaceutical sciences women of S-equol when taken as a associate professor and lead author of a supplement using SE5-OH contain- (UCI; USA) scientist Sheryl Tsai study that appeared in Nature (461:1139– ing S-equol. For more on equol, see and colleagues have discovered 1143, 2009). inform 19:718–721, 2008). Aflatoxin can colonize and con- what triggers aflatoxin to form taminate nuts and grains before harvest QQQ or during storage. The US Food & Drug Which is better for the prevention of on nuts and grains, which could Administration considers it an unavoidable coronary heart disease (CHD): eating lead to methods of limiting its food contaminant but sets maximum allow- as many as 17 small meals each day production. able limits. or feasting on one large meal a day? Aflatoxin, which is produced by mold, The toxin wreaks havoc on a cancer- A recent review article by Surabhi can cause liver cancer if consumed in large preventing gene in humans called p53. Bhutani and Krista A. Varady of the quantities. Without p53 protecting the body, aflatoxin Department of Kinesiology and Nutri- Because of lax or nonexistent regu- can compromise immunity, interfere with tion at the University of Illinois at lation, 4.5 billion people in developing metabolism, and cause severe malnutrition Chicago (USA) concludes that nibbling countries are chronically exposed to vast and cancer. may be the better option, although amounts of aflatoxin—often hundreds of Tsai, graduate student Tyler Korman, there were only eight randomized, times higher than safe levels. In places and undergraduate Oliver Kamari-Bidkor- controlled, crossover studies available such as China, Vietnam, and South Africa, peh, along with Johns Hopkins University for review. The study appeared in Nutri- the combination of aflatoxin and hepatitis researchers, found that a protein called PT tion Reviews (67:591–598, 2009). Q B virus exposure increases the likelihood is critical for aflatoxin to form in fungi. 762 inform December 2009, Vol. 20 (12)

Previously, scientists did not know what “Scientists and health authorities are prompted the toxin’s growth. Omega-3s and increasingly persuaded that the intake of “The protein PT is the key to making fish—even in small amounts—will protect the poison,” Tsai says. “With this knowl- heart failure against the risk of fatal myocardial infarc- edge, perhaps we could kill the PT with The news release headline was definite: tion,” said Marianne Geleinjse (Wagenin- drugs, inhibiting the mold’s ability to make “No Major Role for Fish in the Prevention gen University, the Netherlands) in a news aflatoxin.” of Heart Failure, Study Suggests.” With release. Geleinjse was the correspond- Destroying the mold—rather than just interest high among consumers for infor- ing author on the study, which was led by the PT—is the traditional method of decon- mation about omega-3 fatty acids, the story S. Coosje Dijkstra, also of Wageningen. tamination, but it is expensive, costing hun- made the rounds quickly. In fact, by early “However, there is no strong evidence that dreds of millions of dollars worldwide. November 2009, 9,960 websites and blogs eating fish will protect against heart failure. “This finding will lead to an increased had broadcast the “news” about the study, One study has suggested that this might be understanding of how aflatoxin causes liver which appeared in the European Journal of so, but we could not confirm it in our cohort cancer in humans,” says Frank Meyskens, Heart Failure (11:922–928, 2009). study of older Dutch people.” Daniel G. Aldrich Jr. Endowed Chair and A closer look at the study results, Harry Rice, who is director of regula- director of UCI’s Chao Family Comprehen- however, suggests the jury is still out on tory and scientific affairs for GOED (Global sive Cancer Center. “It should allow for the omega-3 fatty acids and congestive heart Organization for EPA and DHA Omega 3; development of inhibitors and, hopefully, failure. First, although large, the study was Salt Lake City, Utah, USA) questions that a new chemoprevention approach to this observational, involving men and women conclusion. He points out that the study deadly cancer.” over the age of 55 living in a suburb of Geleinjse alludes to (Journal of the Ameri- Aflatoxin belongs to a class of organic Rotterdam. The analysis comprised 5,299 can College of Cardiology 45:2015–2021, compounds called polyketides. “Because subjects (41% men, with a mean age 67.5 2005), which was led by Dariush Mozaf- polyketides provide the building blocks for years) who were free from heart failure farian of the Harvard Medical School, is both carcinogens and some of our most sig- and for whom dietary data were available. not mentioned in the actual 2009 study by nificant drugs, the importance of this study During 11.4 years of follow-up, 669 sub- Dijkstra and colleagues. cannot be overemphasized,” says Christo- jects developed heart failure. Their habitual “The Mozaffarian study was the first pher Hughes, UCI molecular biology and diet had been assessed at baseline (in a self- to examine the relationship between fish biochemistry professor and chair. reported checklist and by expert interview); intake (EPA + DHA) and risk of heart “This discovery provides insight into subjects were specifically asked to indicate failure. Findings from that study support the mechanism of carcinogen production the frequency, amount, and kind of fish they a role for fish intake (EPA + DHA) in the as well as an Achilles’ heel that can be tar- had eaten, either as a hot meal, on a sand- prevention of heart failure,” Rice wrote in geted by new generations of inhibitors. The wich, or between meals. an e-mail. basic understanding of polyketide synthesis Results found that the dietary intake Further, fish intake (EPA + DHA) that this work provides will be invaluable of fish was not significantly related to likely was too low in the 2009 study to in the design of new polyketide-derived heart failure incidence. This relative risk demonstrate a benefit for the prevention of drugs.” was measured according to five levels of heart failure. “In fact, the level of EPA + The National Institutes of Health, the fish consumption as reflected in intake of DHA in four of the five quintiles was below Pew Charitable Trusts, the U.S. Department two long-chain omega-3 polyunsaturated what has previously been reported to have of Energy, and the Damon Runyon Cancer fatty acids (eicosapentaenoic acid [EPA] a benefit,” he wrote (see Table 1). Research Foundation supported the study. and docosahexaenoic acid [DHA]), both For more on this issue, see the online of which have been shown to exert some report on a recent Heart Failure Society of Jennifer Fitzenberger is a member of the Com- cardiovascular benefit via anti-inflamma- America meeting at www.natap.org/2009/ munications Department staff at the Univer- tory mechanisms, anti-arrhythmic effects, newsUpdates/101709_05.htm. sity of California Irvine. and/or a reduction in serum triglycerides, blood pressure, and resting heart rate. Oleocanthal and TABLE 1. Comparison of EPA + DHA intake levels (milligrams/day) by quintilea Alzheimer’s disease Mozaffarian et al., 2005 Dijkstra et al., 2009 Oleocanthal, a naturally occurring com- Q1 19 14 pound found in extra virgin olive oil, alters the structure of neurotoxic proteins Q2 83 42 believed to contribute to the debilitating Q3 261 89 effects of Alzheimer’s disease according to a recent study. This structural change Q4 474 161 apparently impedes the proteins’ ability to Q5 1064 313 damage brain nerve cells. aMozafarian et al., Journal of the American College of Cardiology 45:2015–2021 (2005); Dijkstra et “The findings may help identify effec- al., European Journal of Heart Failure (11:922–928, 2009). Abbreviations: EPA, eicosapentaenoic tive [preventive] measures and lead to acid; DHA, docosahexaenoic acid; Q, quintile. improved therapeutics in the fight against inform December 2009, Vol. 20 (12) 763

Alzheimer’s disease,” said study co-leader Paul A.S. Breslin, a sensory psychobiologist at the Monell Center, Philadelphia, Penn- sylvania, USA. Known as ADDLs (amyloid-derived diffusible ligands), these highly toxic proteins bind within the neural synapses of the brains of Alzheimer’s patients and are believed to directly disrupt nerve cell function, eventually leading to memory loss, cell death, and global disruption of brain function. (Synapses are specialized junc- tions that allow one nerve cell to send information to another.) “Binding of ADDLs to nerve cell synapses is thought to be a crucial first step in the initiation of Alzheimer’s disease. Oleo- canthal alters ADDL structure in a way that deters their binding to synapses,” said William L. Klein, who co-led the research with Breslin. “Translational studies are needed to link these laboratory findings to clinical interventions.” Klein is professor of neurobiology and physiology and a member of the Cognitive Neurology and Alzheimer’s Disease Center at Northwestern University, Evanston, Illinois, USA. Klein and his colleagues identified ADDLs in 1998, leading to a major shift in thinking about the causes, progression, and treatment of Alzheimer’s disease. Also known as `-amyloid oligomers, ADDLs are structurally different from the amyloid plaques that accumulate in brains of Alzheimer’s patients. Reporting on a series of in vitro studies, the team of researchers found that incubation with oleocanthal changed the structure of ADDLs by increasing the proteins’ size. Knowing that oleocanthal changed ADDL size, the researchers next examined whether oleocanthal affected the ability of ADDLs to bind to synapses of cultured hippocampal neurons. The hip- pocampus, a part of the brain intimately involved in learning and memory, is one of the first areas affected by Alzheimer’s disease. Measuring ADDL binding with and without oleocanthal, they discovered that small amounts of oleocanthal effectively reduced binding of ADDLs to hippocampal synapses. Additional studies revealed that oleocanthal can protect synapses from structural damage caused by ADDLs. An unexpected finding was that oleocanthal makes ADDLs into stronger targets for antibodies. This action establishes an opportunity for creating more effective immunotherapy treatments, which use antibodies to bind to and attack ADDLs. Breslin commented on the implications of the findings. “If antibody treatment of Alzheimer’s is enhanced by oleocanthal, the collective antitoxic and immunological effects of this compound may lead to a successful treatment for an incurable disease. Only clinical trials will tell for sure.” In earlier work at Monell, Breslin and co-workers used the sensory properties of extra virgin olive oil to identify oleocanthal based on a oral irritation quality similar to ibuprofen. Oleocanthal and ibuprofen also have similar anti-inflammatory properties, and ibuprofen—like extra virgin olive oils presumably rich in oleocanthal—is associated with a decreased risk of Alzheimer’s when used regularly. Future studies to identify more precisely how oleocanthal changes ADDL structure may increase understanding of the pharmacological actions of oleocanthal, ibuprofen, and structurally related plant compounds. Such pharmacological insights could provide discovery pathways related to disease prevention and treatment. The study appeared in Toxicology and Applied Pharmacology (240:189–197, 2009). Q r~ ~ ~ MEMBERSHIP APPLICATION 101NF ;: e ..: Street Address: 2710 S. Boulder Drive, Urbana, IL 61802-6996 USA. 0 · Mail Address: P. O . Box 171 90, Urbana, IL 61803-7190 USA. N 4. ..:::m ""'"" •1-217-359-23«, "'" • 1-217-351-8091' Em•;I, m~be"htpO•ocm• Web' www.•ocw• 0 Dr. 0 Mr. 0 Ms. 0 Mrs. 0 Prof. Please print or type. All applicants must sign the Code of Ethics. Last Name/Family Name______First Name ______Middle Initial ______Firm/Institution ______

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I hereby subscribe to the above Code of Ethics. Signature of Applicant ------inform December 2009, Vol. 20 (12) 765 Briefs Biotechnology News A report on pesticide use and genetically engineered (GE) crops claims that GE corn, soybeans, and cotton have increased the use of weed-killing herbi- cides by 383 million pounds (about 174 million kilograms) in the United States for the 13-year period from 1996 to 2008. The report, entitled “Impacts of Genetically Engineered Crops on Pes- ticide Use in the United States: The First Thirteen Years,” was released November 17 by The Organic Center, the Union for Concerned Scientists, and the Center for Food Safety. Sharon Bomer Lauritsen, executive vice president, food and agriculture for the Biotechnology Industry Organization (BIO), issued a statement in response: “. . .Biotech crop varieties have dramatically reduced farmers’ reliance on pesticide applications. Since 1997, the use of pesticides on global biotech crop acreage has been reduced by 790 million pounds, an 8.8% reduction. “Decades of documented evidence demonstrate that agricultural Report finds reduce crop yields. Farmers who plant such biotechnology is a safe and beneficial crops are supposed to plant a refuge of conventional corn in, adjacent to, or near the technology that contributes to both environmental GE crop. That refuge is designed to reduce environmental and economic sustain- the risk that pests that survive the toxin will ability. Many experts agree that agricul- noncompliance on breed with each other and produce resis- tural biotechnology has an important GE crops tant offspring. Resistant offspring not only role to play in helping to feed and fuel would reduce yields of the Bt crops but a growing world. In the future, biotech- In November, the Center for Science in could also threaten organic or conventional nology’s benefits will only improve.” the Public Interest (CSPI; Washington, farmers who use natural Bt-based pesticides For more on the report, visit DC, USA) released a report that main- on non-GE crops. http://truefoodnow.files.wordpress. tained “[o]ne out of every four farmers Depending on the location of the crop com/2009/11/13years2009-fullre- who plants genetically engineered (GE) and the pests targeted by the strain of corn, port-11-16-09.pdf. corn is failing to comply with at least one farmers have varying requirements speci- QQQ important insect-resistance management fying the size of the refuge and its distance Three oil palm genomes have been requirement.” The report argued that this from the GE crop. According to industry sequenced and assembled, accord- noncompliance would increase the likeli- surveys submitted to EPA in 2008, ing to a consortium that includes the hood that pesticide-resistant insects will r PG HSPXFST QMBOUJOH DPSO Malaysian Palm Oil Board (MPOB) and threaten both biotech crops and some borer-protected crops met the size of their nonbiotech neighbors. With the Orion Genomics of St. Louis, Missouri, requirement; 88% met the distance report’s release, CSPI called on the Envi- USA. The work aims to find ways to requirement. ronmental Protection Agency (EPA) to not increase yield, protect against disease, r PG HSPXFST QMBOUJOH SPPUXPSN renew registrations of the GE corn varieties protected crops met the size require- and strengthen plants against environ- unless compliance rates improve. ment; 63%, the distance requirement. mental stress. The three genomes The report found that, in 2008, 57% r PG GBSNFST HSPXJOH TUBDLFE WBSJFU- came from two oil palm species: Elaeis of the US corn acreage was planted with ies of GE corn—corn protected against oleifera, which originates in South corn spliced with genes from the Bacillus both corn borer and rootworm—met America, and E. guineensis, which is thuringiensis bacterium (Bt). Those crops the size requirement and 66% met the native to Africa. produce natural toxins that kill corn root- distance requirement. CONTINUED ON NEXT PAGE worms and corn borers, which otherwise The report found that those compliance 766 inform December 2009, Vol. 20 (12) The consortium also included MOgene and The Genome Center at Washington University, both in St. Louis, as well as South Korea’s Mac- rates are down from 2003 to 2005, when oil content in seeds.” rogen and Adelaide, Australia-based compliance rates often topped 90%. “The worldwide license applies to GeneWorks. MPOB, Orion, and Although compliance assessments made development of Wrinked1 in canola and MOgene also announced plans to study on the farm tend to show higher compli- soybean for the life of the patents, approx- the epigenetic makeup of oil palm in ance rates than the surveys, those rates also imately 20 years,” Herlache said, but not 2010 in an effort to improve yields, decreased in the last three years, accord- oil-producing plants such as sunflower, saf- according to the Cleantech Group ing to CSPI. flower, peanut, and palm. In lieu of the EPA not re-registering “Beyond the application in seeds as consultancy. the existing varieties of Bt corn until com- currently licensed by BASF Plant Science, QQQ panies demonstrate better compliance, the we believe that MSU can use this transcrip- Monsanto Co. (St. Louis, Missouri, CSPI asked the EPA to levy “severe fines tion factor to convert a starch storage organ USA) has completed US regulatory or seed sales restrictions” if noncompliance into an oil storage organ in plants such as submissions in support of the Vistive rates remain high. rutabaga,” Benning said. “Moreover, we III soybean trait. The company expects To view the report, visit http://cspinet. are confident that we can use Wrinkled1 to that this second-generation product org/new/pdf/complacencyonthefarm.pdf. produce oil in straw of different grasses to will be available for farmers to plant enhance their energy density.” by the “middle of the next decade,” according to a spokesperson. To Plant oil increase stability and extend fry life International of the Vistive III soy oil, the fatty acid enhancement congress yields profile of the bean was changed as Technology that could enhance plants’ seed follows: oleic acid (18:1) increased oil content for food and animal feed appli- fats and oils from 24% to 75%, linoleic acid (18:2) cations has been licensed to BASF Plant decreased from 52% to 15%, and lino- Science under an exclusive commercial research lenic acid (18:3) decreased from 8% to agreement with Michigan State University The 9th International Congress on Plant less than 3%, the spokesperson said. (MSU), East Lansing, USA. Molecular Biology was held at the end QQQ Following a long-term collaboration, of October in St. Louis, Missouri (USA). Bayer CropScience (Monheim am a plant gene that regulates oil accumula- Abstracts from the presentations include: Rhein, Germany) announced in tion in plant seed was licensed to BASF October that it had sequenced the Plant Science by MSU Technologies, Mich- PROTEOMICS ANALYSIS OF entire genome of rapeseed/canola igan State’s technology transfer office. (Brassica napus) and its constituent The gene is a transcription factor that pro- SEED FILLING IN OILSEED genomes present in B. rapa and B. oler- duces a protein, dubbed Wrinkled1, that CROPS—CURRENT STATUS acea. Rapeseed/canola is the second- was isolated in the laboratory of Chris- AND FUTURE GOALS largest oilseed crop after soybeans, toph Benning, professor of biochemistry Author/Presenter: Jay Thelen, University accounting for approximately 15% of and molecular biology. It is being licensed of Missouri world production. The Bayer Crop- by the plant biotechnology company for further development of enhanced soybean Oilseeds are important renewable Science sequencing project was a col- and canola varieties. sources of protein and oil, which are pro- laboration with several parties: The “The technology can be used in the duced primarily during the maturation Beijing Genomics Institute-Shenzhen development of new oil crops that have this or seed-filling phase of embryo develop- (BGI-Shenzhen, China) provided Bayer transcription factor turned up to produce ment. To characterize this developmen- with a high-density, fully assembled, more oil in their seeds, and farmers can tal process at the proteome level, my lab and annotated sequence of a B. rapa earn a bonus,” MSU Technologies technol- employed high-resolution two-dimensional and a B. oleracea line. Complemen- ogy manager Thomas Herlache said. “This gel electrophoresis (2-DE) coupled with tary genome sequence data sets of an can improve production of vegetable oil in mass spectrometry to quantitatively profile elite proprietary Bayer CropScience B. general, but also the oil used for biofuels.” and identify over 500 proteins expressed napus parental line were provided by The transcription factor can be used to during seed filling in diverse crop oilseeds Keygene N.V. (the Netherlands) and turn gene expression up or down, like a tap including soybean, canola, and castor. As the University of Queensland (Aus- on a faucet, he said. It was discovered in an ‘omics approach, proteomics does not tralia). Q Benning’s lab as a mutation causing wrin- require a sequenced genome or the devel- kled seeds of the Arabidopsis plant. opment of analytical tools such as microar- “Photosynthesis produces sugars,” said rays thus enabling global investigations of Benning. “The Wrinkled1 protein controls nearly any crop. The principal objective of the conversion of sugars into fatty acids and these studies was to quantitatively compare thereby affects carbon partitioning between protein expression in developing seed that carbohydrates and lipids. Enhancing this differs in oil/protein ratio and photosyn- process is a viable strategy to increase the thetic capacity. I will present some of the inform December 2009, Vol. 20 (12) 767

findings from these studies and illustrate the metabolic flux maps of three different seeds is presented with the study of meta- features of the Oilseed Proteomics web soybean genotypes with varying protein bolic flux for two different mutants with database (www.oilseedproteomics.mis- contents to investigate the changes in the severely impaired oil accumulation. souri.edu) that was developed to ware- pathway interactions. The BC3-128 gen- house these datasets. I will also present otype, a back-crossed line created from CONSTRAINT-BASED FLUX results on global, 2-DE-based phospho- a high-protein line (High PI) and Evans, VARIABILITY ANALYSIS OF proteomic screens and propose alternative produced more protein than Evans and less approaches to 2-DE for in-depth, quantita- than High PI. The temperature studies and DEVELOPING OILSEED RAPE tive proteomics. genotype studies have enabled the devel- SEED STORAGE COMPOUND opment of hypotheses of important meta- FLUX CARTOGRAPHY IN bolic nodes in protein/oil partitioning. The TRADEOFFS OIL SEEDS—ANALYSIS OF integration of the flux and transcript data Authors: Jordan Hay; Jorg Schwender; from the genotype study is under way to Presenter: Jordan Hay METABOLIC ROADBLOCKS better understand the underlying physiol- Oil stored in the embryo of oilseed Authors: Vidya Iyer, Matt Studham, Ling ogy of these isolines and thus identify pos- rape (Brassica napus) is a promising Li, Eve Wurtele, Mark Westgate, Julie sible targets for genetic manipulations for renewable energy source. However, the Dickerson, all Iowa State University; Pre- influencing higher protein or oil yields. efficient conversion of nutrients taken senter: Jacqueline Shanks up by the developing embryo into oil is The inverse relationship between the PRIMARY CARBON limited by starch and protein synthesis. protein and oil yields in soybeans presents How carbon and nitrogen are partitioned a conundrum for developing high-protein METABOLISM AND STORAGE into these biomass components is not well or high-oil seeds. Our research group uses SYNTHESIS IN DEVELOPING understood. We have modeled stoichiomet- metabolic flux analysis to provide clues to OIL SEEDS ric and thermodynamic constraints on the this riddle. Metabolic flux maps provide central metabolic network of developing a quantitative depiction of carbon flow Author/Presenter: Jorg Schwender, Brassica seeds according to the literature. through competing metabolic pathways, Brookhaven National Laboratory The full model contains 435 reactions, and thus providing: analysis of substrate utili- In developing seeds the transformation lumping of reactions into 50 summary reac- zation and product formation; flexibility or of maternal carbon supplies to storage prod- tions reduces the total number to 283. In the rigidity of carbon flow at network nodes; ucts is mediated by the primary (central) reduced model, there are 143 metabolites, the rate of a given enzymatic reaction in carbon metabolism reaction network. The 11 compartments, and 9 transport/exchange vivo; and inferred availability of NADPH or biosynthesis of different storage prod- interfaces. By using linear programming ATP. Thus, metabolic fluxes are an impor- ucts has different requirements for the (flux balance analysis), we quantify the fea- tant physiological characteristic comple- intermediates and cofactors provided by sible range (variability) of each flux of the mentary to levels of transcripts, proteins, central metabolism. Central metabolism reduced network as a function of each of and metabolites and can help to identify is a highly connected network and the use three storage compound tradeoffs (starch/ metabolic roadblocks. Our group has devel- of metabolic flux analysis has revealed in protein, TAG/protein, TAG/starch, where oped a comprehensive generic mathemati- part unexpected functionality, for example TAG = triacylglycerols), various nutritional cal tool (NMR2Flux) for 13C metabolic flux the bypass of glycolysis by RubisCO in cases of carbon (heterotrophic and photo- analysis in plant systems (Sriram, G., et al., developing seeds of Brassica napus. To heterotrophic) and nitrogen (organic and Plant Physiol. 136:3043–3057, 2004). 13C understand how carbon allocation into inorganic), and different objectives (e.g., metabolic flux analysis, with isotope detec- oil, protein, and other storage compounds minimize all uptake or only sugar uptake); tion via two-dimensional HSQC (1H, 13C is regulated, the study of in vivo pathway and we describe metabolic pathway usage heteronuclear single quantum correlated usage in developing embryos of the oil crop patterns involved with storage metabolism. spectroscopy) NMR (nuclear magnetic B. napus by metabolic flux analysis in par- Relatively large flux variability is charac- resonance) of metabolites (proteinogenic allel with the determination of enzyme and teristic of biomass compositions with a amino acids and starch), quantifies intrac- metabolite levels is presented. This allows high TAG proportion. Some simulated ellular metabolic fluxes for medium-sized one to determine flexible adjustment of tradeoffs reveal discontinuities (piecewise reaction networks, as well as tests the con- metabolism to different nutritional condi- linear phases) in the biomass composition- sistency of the network topology operat- tions and identifies rigid behavior of key dependence of flux variability and shadow ing for the given physiological conditions. metabolic branch points, which can be prices, indicating how shifting biomass We have charted metabolic flux maps for further explored by enzyme kinetic models. between biomass components may involve soybean (Glycine max) in response to two Since most extractable enzyme activi- readjustments in the pattern of metabolic parameters: temperature and genotype. ties are in large surplus relative to the flux network usage. In addition, the model lends The dominant effect of early development capacity required to sustain the observed support for the coupling of biomass forma- temperature on several nodes in central in vivo fluxes, the biochemical architec- tion to biosynthetically produced pyrophos- carbon metabolism in Glycine max Evans ture and regulation of central metabolism is phate by predicting the activity of various was evident from flux map data (Iyer, V.Y., expected to play an important role in carbon pyrophosphate-metabolizing enzymes. et al., Plant Cell Environ. 31:506–517, partitioning. Further insights into central For more on the congress, visit www. 2008). More recently, we have examined metabolism during storage synthesis in oil ipmb2009.org. Q ~Springer springer.com• the language of science

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Contact Doreen Berning at the AOCS to become a member and order your subscription. AOCS, P.O. Box 17190, Urbana, IL 61803-7190 USA 1> Phone:+ 1-217-693-4813 1> Fax:+1-2 17-693-4857 1> Email: [email protected] 1> Web: www.aocs.org 014166x inform December 2009, Vol. 20 (12) 769 Briefs S&D News Genencor, a division of Danisco, has introduced PuraFast™ HS protease. PuraFast is a performance ingredient for laundry detergent aimed at improving cleaning performance in shorter-cycle and lower-temperature washes. QQQ At the end of September 2009, Admin- istrator Lisa Jackson of the US Envi- ronmental Protection Agency (EPA) announced core principles that outline the Obama Administration’s goals for legislative reform of the country’s chemical management law, the 1976 Toxic Substances Control Act. Jackson also announced plans for a major effort to strengthen EPA’s current chemical management program and increase the pace of the agency’s efforts to address chemicals that pose a risk to the public. The core principles are available online at www.epa.gov/oppt/existingchemi- cals/pubs/principles.html. QQQ Many US consumers are likely to purchase eco-friendly products across many industries, including 74% in health To join them by becoming a poster pre- and beauty and 59% in apparel, accord- Montreux 2010 senter, visit www.aocs.org/meetings/ ing to a report by Grail Research, a montreux/. To stay current on conference consultancy based in Cambridge, Mas- promises history details, follow Montreaux2010 at www. sachusetts, USA. The report, entitled For more than 30 years, the AOCS World twitter.com/Montreux2010. “The Green Revolution,” also ﬁnds Conference on Detergents has created a sin- that price is the main reason some gular opportunity for participants to share consumers do not buy green products, knowledge, to network, and to conduct European home and followed by a lack of choices, and the business. lack of availability. The complete report The seventh confer- fabric care market is available at http://grailresearch. ence in the series will The chemicals industry was particularly com/About_Us/FeaturedResearch. be held October 4–7, hard hit by the economic recession, as aspx?aid=90. 2010, at the Mon- reflected in the closure of numerous man- treux Music & QQQ ufacturing plants, laying off of personnel, Unilever has taken viral marketing to Convention Center and bankruptcies of some major players. in Montreux, Switzer- a new level, according to The New York However, the market for specialty ingredi- land. There, history will be Times. The Anglo-Dutch consumer ents in home and fabric care formulations made when, for the first time, remains dynamic, fueled by consumers’ products giant is paying about 20 New the chief executive officers of the three top desire to minimize risks from bacteria and York City street musicians and college detergent-manufacturing companies— germs and to reduce the time and effort bands a reported $1,000 each to help P&G, Henkel, and Unilever—will give required for household chores. Or so says market Unilever’s Axe Instinct deodor- their unique perspectives on the industry, market research firm Frost & Sullivan in its ant. For that sum, the lucky buskers along with their strategies for the future. new report entitled Strategic Analysis of the will put up signs, give out samples, and The speakers, who are all invited, will Home and Fabric Care Specialty Ingredi- sing “Look Good in Leather,” which is examine “New Strategies in a Dynamic ents Markets in Europe. featured in the deodorant’s TV cam- Global Economy” and include top-level The home and fabric care specialty paign. Q executives offering significant insights ingredients market generated €615.8 from both inside and outside the industry. million in revenues in 2008, according to 770 inform December 2009, Vol. 20 (12)

the report, which estimates revenues will “When combined with plant shutdowns, to support oneself.” Sustainability is also reach €706.2 million in 2015. The segments recently introduced legislative frameworks strongly associated with environmental covered in the report include specialty that increase costs (such as REACH), concerns, whereby consumers are being surfactants, functional polymers, fabric and the ongoing economic uncertainty, challenged to develop and express an “eco- enhancers, active ingredients, and rheol- it becomes clear that the suppliers to the consciousness” in their daily habits and ogy modifiers in home and fabric care, as home and fabric care industry are facing a purchases. But using “eco-conscious” or well as hard-surface cleaners, car interior challenging environment.” “green” as synonymous with sustainabil- and upholstery cleaners, fabric care, furni- Strategic acquisitions, focus on key ity unduly limits the frame of reference, ture, shoe and leather polishes, and dish- market segments, promotion of product dif- according to the reports; these older terms washing products. ferentiation, and green innovation are criti- fail to acknowledge the variety of social, “The advent of the ‘green’ con- cal in overcoming market challenges and economic, and environmental issues that sumer who prefers natural products that addressing evolving market and consumer real-world individuals believe to be impor- are derived from renewable or recycled needs. However, only market participants tant to sustaining themselves, their commu- sources, have an environmentally friendly with strong cash flows can complete stra- nities, and society at large. profile in terms of toxicity, and are safe to tegic acquisitions. Within the personal care market, per- use is the catalytic driving force,” notes “Some of the leading chemicals com- sonal health and wellness concerns remain Frost & Sullivan Industry Analyst Leoni- panies have opted for strategic acquisi- the most important motivation for purchas- das Dokos. “The growing demand for more tions continuing the consolidation trend, ing sustainable products. On the other hand, efficient and technically novel chemicals to while others have focused on strategic alli- household cleaning products with a focus assist in daily home and fabric care tasks ances,” says Dokos. “However, the key to on sustainability have only recently begun has rejuvenated this mature market as pro- growth remains innovation and addressing to enter the US mainstream. Formerly, ducers focus on addressing the evolving the needs of the ‘green’ consumer without the act of cleaning was a form of “germ demands of consumers.” compromising the technical performance warfare” and entailed a combative relation- Specialty ingredients with an improved of products.” ship between consumers and their environ- environmental profile are driving the market Strategic Analysis of the Home and ment. “Recently, however, more consumers and influencing demand. At the same time, Fabric Care Specialty Ingredients Markets talk about the idea of working with nature, there is a push in the form of European in Europe is part of the Chemicals & Mate- not against it, to naturally restore balance Directives, with regulators increasingly rials Growth Partnership Services program, to their home environments,” the report on insisting on reduced toxicity and enhanced which also includes research in the follow- household cleaners notes. biodegradation of such products. ing markets: U.S. Polymers in Personal In response to the current economic Increasing consumption in emerg- Care Market (2008), U.S. Emulsifiers in downturn, many consumers have modi- ing European markets will further assist in Personal Care Market (2008), European fied their purchasing behaviors in relation the growth of home and fabric care spe- Markets for Actives Ingredients in Skin to sustainable products. Nonetheless, the cialty ingredients, whereas in the developed Care (2008), and European Vitamins in Per- report argues that tradeoffs and cutbacks markets of Western Europe, green products sonal Care Markets (2008). For more infor- are less likely for product categories that and innovation are crucial. Also important mation about the report, e-mail Monika consumers view as essential to their quality to growth is the fact that companies active Kwiecinska, Corporate Communications, of life, with food at the top of that list, and in the market are focusing on reducing at [email protected]. including personal care and household the average product development time as cleaners. product life cycles shorten. The consumers and sustainability four- However, sustaining capital and Consumers and report series draws on an online survey of resource investment in research and devel- 1,856 US adult consumers conducted in opment in order to maintain healthy pipe- sustainability September 2008 by The Hartman Group, lines of innovative products, while at the US market research firms Packaged Facts as well as qualitative research on sustain- same time controlling the cost, will be the and The Hartman Group have published a ability in three markets (Seattle, Washing- key challenge for suppliers to this market. series of reports tracking current consumer ton; Dallas, Texas; and Columbus, Ohio) Moreover, the current economic crisis is attitudes and shopping behaviors in rela- during August 2008. For more information, eating into consumer products demand, par- tion to “sustainable” consumer packaged visit www.packagedfacts.com. ticularly in Europe and the United States, goods. The four reports in the just-com- temporarily highlighting consumer price pleted series on consumers and sustainabil- consciousness. ity are on food and beverage, personal care, Unilever: “In 2008 the chemicals sector was the household cleaners, and over-the-counter only one among the top 15 sectors in the medications and supplements. Sara Lee and world showing an investment decrease in Not surprisingly, sustainability means JohnsonDiversey research and development of 1.3%, while different things to different people. Asked the household goods sector experienced to identify what the term means to them, Anglo-Dutch consumer products giant a decrease in research and development consumers most frequently respond “the Unilever announced in early October that investment of 6.1%,” explains Dokos. ability to last over time” and “the ability it had made a binding offer to acquire the Student Page inform December 2009, Vol. 20 (12) 771

personal care business of the Sara Lee Corp. for €1.275 billion (almost $1.8 billion) in cash. The transaction is subject to regula- Meet Bena-Marie Lue tory approval and consultation with Euro- pean employee works councils. Unilever will add skin-cleansing and deodorant brands such as Sanex, Radox, 2009 AOCS Honored Student Bena-Marie and Duschdas to its portfolio of products Lue has pursued her interests in lipids as it builds on its operations in Western across three countries. She started out in Europe and Asia. food science and agricultural chemistry In an interview with The Wall Street at McGill University (Montréal, Canada), Journal (WSJ), Sara Lee (Downers Grove, where she completed a B.Sc. in 1999. Illinois, USA) CEO Brenda Barnes said she During her undergraduate career she found expects the deal will probably close “more applied science—exemplified in enzyme to the latter part of 2010” and said proceeds applications, lipid technology, and bioac- will allow the company to continue growing tive compounds—interested her much more its core food and beverage businesses and than pure science. to repurchase stock. Barnes also told the Lue had her first experience working WSJ that Sara Lee has received “signifi- in Europe at a summer job at the University cant interest in the remainder of its house- of Ulster in Ireland while she was still an hold business and is continuing to pursue undergraduate. After completing her B.Sc., sale options for the unit, which includes air she returned to Europe and completed two care, shoe care, insecticides, and non-Euro- internships in Denmark before returning pean cleaning brands.” to Canada and McGill, where she earned In other Unilever news, the company a master’s degree under Selim Kermasha announced in late October that it will reduce on the esterification and transesterifica- its equity interest in JohnsonDiversey from tion reactions of phenolic compounds with 33% to 4%. This transaction follows on long-chain fatty alcohols or triacylglycerols in organic solvents. from the original 2002 sale of Unilever’s Pursuing her interest in practical problems, Lue returned to Europe, where she worked institutional and industrial cleaning busi- for almost two years at the University of Copenhagen (Denmark). Ultimately she moved ness to Johnson Wax Professional. to the University of Aarhus (Denmark) to work toward a Ph.D. under the supervision of At the same time, JohnsonDiversey Xuebing Xu. Her work has involved the use of “green” solvents (i.e., room-tempera- announced that Clayton, Dubillier & Rice, ture ionic liquids: RTIL) as media for lipase-catalyzed synthesis of bioactive flavonoid Inc. (CD&R) will take a 46% equity interest esters. as part of a broader recapitalization trans- The decision to study flavonoids was made in part because they are present in a number action. In addition, JohnsonDiversey will of foods and are known for their antioxidative, anticarcinogenic, and antimicrobial prop- continue to sell and distribute certain Uni- erties. Lue’s work was based on the hypothesis that incorporating lipidic moieties onto lever products into the professional com- flavonoid structures might enhance their solubility and miscibility and “enhance the uses mercial cleaning and hygiene market. of these bioactives as antioxidants in food systems.” The transaction, which is conditional As to her choice of RTIL, Lue explained that they are viewed as “environmentally on JohnsonDiversey and CD&R complet- friendly alternative to traditional solvents,” in part because of their “thermal stability, low ing debt financing and receiving regulatory vapor pressure, and adjustable solubilities.” To develop an efficient system for the acyla- approvals, was expected to close before the tion of flavonoids with long-chain fatty acids, she first used a quantum chemical model end of 2009. Q to calculate such parameters as solubilities and activity coefficients across a range of solvents to select ones that might be used in the reaction. The solvents tentatively identified as promising were then examined to optimize the reactions she carried out. Lue consid-

ered parameters such as aw (water activity), reaction time, temperature, substrate concentration, molar ratio, and enzyme efficiency in the acylation reaction of the flavonoids rutin information and esculin with palmitic acid. Lue found that lipase activity was profoundly affected by the choice of RTIL used in Did you know that inform provides news the reaction (the anion in particular) and was attributable to interactions between RTIL updates on the AOCS home page at www. and the protein structure of the enzyme. aocs.org? As well as alerts on Twitter at Lue expected to defend her dissertation in November. With that out of the way, www.twitter.com/theAOCS? she is looking for a position in applied research and development, either in industry or academia. Food has both a professional and a personal importance to Lue. She enjoys baking desserts and decorating cakes. She also is a social dancer, and plays squash and badmin- ton. Another avocation is travel—last year she traveled to China and visited Hanzhou, near Shanghai. With her thesis finished, she has a “long-term project: to continue to improve my Danish language skills since I’m now living in Denmark.” Q 772 inform December 2009, Vol. 20 (12) People News/ Inside AOCS From abstract to presentation

Catherine Watkins

Whether you have been presenting at AOCS Annual Meet- ings & Expos (AM&E) for years or are just beginning your career, knowing more about the process of AOCS’ technical program development can only help your results. Previous annual meeting articles have described how division members and interested parties discuss possible session topics at roundtable meetings held at the AM&E. Attending a roundtable meeting is the best way to get involved in program planning. If you cannot attend the one, The Phoenix Convention Center is one of the however, simply contact your division chairperson using the contact information in your top 20 convention venues in the United States. AOCS directory. Photo credit: Jill Richards. Once the call for papers is announced, online submission of declarations of intent begins. Although only the presentation title, authors, affiliations, and keywords are required initially, providing a full abstract is to your advantage. Why that is so will become apparent in a moment. In search of better Along with key information about your presentation, you are asked to identify your abstracts two primary interest areas. Once your submission is complete, it is immediately available Effective abstracts are more than online for review by the session chairs of your No. 1 interest area. They pick and choose just summaries of the four major among submissions, making your chances of acceptance greater if you have provided an abstract. sections of a scientific paper. An If the session chairs of your first interest area do not choose your submission, it is next abstract that draws peers to the referred to the chairs of sessions in the second interest area. If it has still not been picked presentation exhibits the following after that review, you may be offered the opportunity to convert your presentation to a characteristics: poster. There are distinct advantages to poster presentations: They are visible throughout Q Each paragraph is well developed most of the meeting, and there is a dedicated viewing time during which you can talk with in addition to being “unified, interested parties. coherent, concise, and able to Co-chairing sessions is an excellent way for student members to gain visibility and stand alone,” suggests an article experience. The precise nature of a student co-chair’s duties are up to the primary chair- at http://leo.stcloudstate.edu/ person, but duties often include taking house counts, doing introductions, helping speak- bizwrite/abstracts.html. ers load their presentations, and handling the speaker timer. Students interested in learning Q It uses an introduction/body/con- more about this opportunity should contact Donna Elbon at [email protected]. clusion structure that “presents Jim Kenar, who has led the AOCS Annual Meeting Program Committee since 2002, the article, paper, or report’s finds the entire annual meeting program development process to be highly effective. “Every purpose, results, conclusions, and year at the annual meeting, the program committee comes together for a brief but intense recommendations in that order,” session to develop the framework of the next year’s technical program. The exchange of the article continues. ideas, the sometimes heated discussions, and the interactions among the division repre- Q It provides logical connec- sentatives are always fascinating to observe as the technical sessions come together. tions between the elements “As a past division representative and now chairperson of the technical program com- included. mittee for the past few years, it has been exciting for me to have had the opportunity to work closely with division representatives, guide the workings of the program committee, Q It adds nothing that is not already and to watch how the technical program has developed over the years,” he concluded. in the paper or presentation. You, too, can become involved in meeting program development. It is just one of the Q It is accessible to a broad audi- many opportunities AOCS provides for you to become a leader. ence.

Catherine Watkins is associate editor of inform and can be reached at cwatkins@aocs. org. Inside AOCS In Memoriam

William L. Porter, who spent over 50 years conduct- Furman becomes president, ing research with what is now known as the US Army CEO of Ventura Foods Natick Research, Devel- opment, and Engineering In October, the Ventura Foods Members Committee Center (NRDEC) in Natick, announced the retirement of Richard Mazer as president Massachusetts, died on May and chief executive officer (CEO) of Ventura Foods, LLC 26, 2009, at the age of 91. (Brea, California, USA). He was succeeded by Christopher Furman in these two positions on November 9. Furman joins Born in Philadelphia, Pennsylvania, USA, and Ventura Foods from PepsiCo, Inc. (Purchase, New York, reared in Galveston, Texas, USA, Porter received USA), where he had 20 years of experience in a series of leadership roles. his undergraduate education in a pre-med program Ventura Foods is a joint venture between CHS Inc. (St. Paul, Minnesota, at Oberlin College (Ohio, USA). During World USA), an energy grains and foods company, and Mitsui & Co., Ltd. (Tokyo, Japan). War II he served with the US Army Air Corps Ventura processes a range of private-label and branded foods, such as LouAna in England in air trafﬁc control, emerging as a Oils; ClassicGourmet dressings, sauces, and bases; SmartBalance Buttery Spread; Captain. His growing awareness of unmet envi- Hidden Valley salad dressings; Dean’s Dairy Dip; and Marie’s salad dressings. ronmental needs led him to complete an MS in geography at the University of Chicago in 1951 and then a Ph.D. at Harvard University in 1962 New COO at Dean Foods in plant biochemistry. Joseph Scalzo was promoted to the position of chief operating officer (COO) for Porter’s research with NRDEC explored the Dean Foods (Dallas, Texas, USA) on November 1. Before his promotion, he was shelf stability of military foods under adverse con- president and CEO of Dean Foods’ WhiteWave-Morningstar group. In his new role, ditions. To this end, he published in both Lipids Scalzo will oversee all of Dean Foods’ operating businesses, including Fresh Dairy and Journal of the American Oil Chemists’ Society (as Direct, WhiteWave, Morningstar, and Alpro, as well as key strategic functions well as other journals) on the effects of temper- including worldwide supply chain, research and development, and innovation. ature and ventilation on stored foods, packaging With Scalzo’s promotion, Blaine McPeak, president of Horizon® and Silk®, effects, oxidation of fatty acids, and pro-oxidants was promoted to president, WhiteWave Foods, in Broomfield, Colorado. Blaine and antioxidants. He continued his research at will lead Horizon, Silk Soymilk, International Delight®, and Land O’Lakes® cul- NRDEC well past his nominal retirement, and a tured and liquid dairy products. This includes overseeing all functions, including paper that he co-authored (JAOCS 83:697-705, marketing, research and development, supply chain, finance, and sales. 2006) on Maillard browning and antioxidants received the ADM Protein and Co-Products Divi- sion Award at the 2007 AOCS Annual Meeting Solix Biofuels appoints new leaders & Expo (AM&E). Located in Fort Collins, Colorado, USA, Solix Biofuels announced that three new In an oft-cited paper that appeared in the officers joined the company in September. Peter Lammers is now the company’s Journal of Agricultural and Food Chemistry (37:615– vice president of biotechnology. He had previously been the cultivation track lead 624, 1989), Porter and coworkers Edward Black for the US Department of Energy’s Algal Biofuels Roadmap. He brings to the and Anne Drolet presented what they called The company considerable expertise in large-scale cultivation and will oversee the Polar Paradox: “Nonpolar antioxidants function company’s efforts in algal growth and biochemical optimizations. best in polar lipid emulsions and membranes Joanna Money is vice president of business development. She has 20 years while polar antioxidants are relatively more effec- of experience in the biotechnology industry in corporate and business development tive on nonpolar lipids.” That concept was fruit- and strategy development. fully explored for years afterward, as Porter Joel Butler is now chief technology officer for Solix, and Bryan Willson recounted in a presentation to the AOCS Lipid continues as the company’s chief technology strategist. Oxidation and Quality Division at the AOCS AM&E in 1999. Porter was a man of many interests. In addi- National Medal of Science to Venter tion to his work as a scientist, he was an avid On October 7, President Barack Obama presented the National Medal of Science environmentalist and outdoorsman who enjoyed to nine researchers for their outstanding contributions to science and engineering. hiking, camping, skiing, kayaking, and tennis. For One of the recipients was J. Craig Venter, who was recognized for his dedication many years he commuted to work by bicycle. to the advancement of the science of genomics, his contributions to the understand- Porter enjoyed music and singing, and had a gift ing of its implications for society, and his commitment to the clear communication for reciting poetry, frequently surprising others of information to the scientific community, the public, and policymakers. by his recall and choice of just the right poem Venter is well known for his publication of the first draft human genome in for a given moment. 2000. More recently, his company, Synthetic Genomics Inc. (SGI; La Jolla, Cali- He joined AOCS in 1964. He was also active fornia, USA) has been using genetic and genomic techniques to devise ways to in the Natick chapter of Sigma Xi. acquire biofuel from algae. SGI and ExxonMobil jointly announced a five-year research and development agreement in July (inform 20:577, 2009) for the creation Porter is survived by his wife, Nancy of next-generation biofuels from algae. ExxonMobil may contribute as much as Amstutz, and two sisters, Eleanor Porter and $600 million to the effort. Ruth Martin. Q 774 inform December 2009, Vol. 20 (12)

images of wine labels are Book Review well represented throughout this book, adding another Wine Wise: Your Complete Guide to Understanding, dimension to the reader’s Selecting, and Enjoying Wine learning experience. This Steven Kolpan, Brian H. Smith, and Michael A. Weiss, organizational pattern is The Culinary Institute of America, 2008 repeated throughout the book for both major world John Wiley & Sons, Inc., 368 pages , regions and under-explored ISBN: 978-0-471-77064-0, $29.95. regions such as Canada, Austria, Greece, and New Bradley Beam York State. Another positive attribute of Wine Wise is its The appreciation for wine often starts simply; snobbery-free, consumer- either you like it or you do not. Sooner or later, oriented tone, specifically though, a wine comes along, changes everything, in the sections pertaining to wine and food matching, ordering wine in restaurants, and introductory wine tasting. While the section on and you have been hit by the bug. Simple quafﬁng wine sensory evaluation could be more comprehensive, it contains will no longer satisfy your thirst. You require more enough information for those beginning the journey through the world of wine, and some practical tasting exercises applicable to information. novice and intermediate wine enthusiasts alike. It even includes As the popularity of wine continues to grow, so does the an extensive list of recommended bargain wines. Typically, these amount of information available to help new wine consumers lists force the authors’ tastes upon the reader, but Kolpan, Smith, enhance their tasting experiences. Introductory books are designed and Weiss show remarkable, and much appreciated, restraint. No to give the reader just enough information to begin their indepen- flowery descriptions, scores, or even vintages are present; simply dent wine tasting experiences and explorations. Intermediate wine regions, producers, and varietals that have proven reliable based education texts are more specialized, focusing on specific wine- on the authors’ experiences. related themes, including wine tasting and food pairing, grape and While this book should satisfy novice and intermediate wine wine production, wine geography, and consumer guides. Wine- drinkers interested in expanding their knowledge of wine regions, themed art books offer beautiful pictures and labels but little useful those searching for more information on sensory analysis train- information to add depth to consumers’ appreciation of wine. ing techniques or the impact of vineyard management and wine There are many valuable books fitting each of these categories, processing on wine sensory characteristics likely will be disap- but what appears to be lacking is something a bit more comprehen- pointed. The very short sections on grape and wine production sive, with greater detail on a variety of wine-related subjects. As the provide enough information and scattered vocabulary to adequately title plainly states, Wine Wise: Your Complete Guide to Understand- arm the novice for a first wine-tasting party, but not quite enough to ing, Selecting, and Enjoying Wine intends to fill this niche. While add significant depth to the overall appreciation of such a complex not as complete as it claims, this book does a great job of bridg- beverage. ing the gap between general material for the novice and detailed information for the passionate wine consumer. It provides basic Bradley Beam is the Illinois state enology specialist at the Univer- consumer information on a wide variety of topics while offering sity of Illinois in Urbana-Champaign (USA). He teaches an introduc- enough reference material to earn a space in an enthusiast’s library. tory course on wine processing and sensory analysis and has been The book’s style is simple, direct, and organized, making it a useful involved in grape and wine research, industry support, and educa- reference tool. Additionally, the language is friendly enough for tion since 1999. beginners, and the images and illustrations are attractive enough for home display. The real strength of the book is its ability to tell the story of regions from all over the world and the wines they produce. We are looking for additional book reviewers, including reviewers It accomplishes this task well by providing a matrix of informa- from outside North America. If you are interested in reviewing tion, including relevant history and culture, terroir (geography, one or more books, please send an email to the book review topography, geology, and climate), important grape varieties, deci- editor (William Artz) at [email protected] and indicate your phering labels, and important subregions whenever applicable. For subject area of interest. An email request for the review with example, Chapter 9, entitled “Andiamo: Italy,” begins by discussing information about the text is sent to each reviewer, before any the drastic changes in quality that have occurred in Italian wines book is mailed out for review. Reviews are generally expected over the past few years, followed by a thorough list and description three to four months later. After review submission, the books of the common grape varieties grown in the country. It then helps belong to the reviewer. AOCS provides a general review guide- decipher the complexities of an Italian wine label, and subsequently line, available to each reviewer upon request. delves into the major subregions of Italy in great detail. Maps and Publications inform December 2009, Vol. 20 (12) 775

from various known fabrics or materials capable of absorbing and Patents retaining a substantial quantity of the surfactant. During use, as the surfactant is dissipated, the image changes in appearance thereby indicating the quantity of surfactant remaining on the substrate. In Published Patents a preferred embodiment of the invention, the method and article of the present invention are effective for encouraging and making washing enjoyable for children and include the use of an epidermal Production of a reﬁnery feedstock surfactant, such as soap, detergent, or other active ingredient. from soaps produced during a chemical pulping process Catalyst for partial oxidation and Logan, M., et al., Bluekey Energy Inc., US7540889B2, June 2, preparation method thereof 2009 Kang, J.-H., et al., LG Chemical Ltd., US7544633B2, June 9, The process for preparing a refinery feedstock from black 2009 liquor soap comprising adding excess alcohol (preferably meth- The present invention relates to a catalyst for partial oxidation anol) to black liquor soap. Acid is then added to the mixture to and a preparation method thereof, more particularly to a prepara- drop the pH of the mixture to approximately 2 to convert carboxy- tion method of a complex metal oxide catalyst that shows high late salt of fatty and resin acids to the free fatty and resin acids. In activity for conversion of propylene or isobutylene, maintains good the reaction process, the free fatty and resin acids react with the selectivity for such unsaturated aldehydes as acrolein or methacro- alcohol, with the aid of the acid catalyst, to yield the desired ester lein, and improves production yield of such unsaturated carboxylic products. The resulting feedstock can be distilled or refined to yield acid as acrylic acid or methacrylic acid through stable process by sterols and related alcohols, biodiesel, and other fuels. using a drying control chemical additive. Catalytic cracking process for the Rubber composition for tire tread production of diesel from vegetable and pneumatic tire comprising the oils same Pinho, A., et al., Petróleo Brasileiro SA, US7540952B2, June 2, Nakazono, T., and S. Sakamoto, Sumitomo Rubber Industries, 2009 US7544731B2, June 9, 2009 The present invention relates to a thermocatalytic process to The present invention provides a rubber composition for a tire produce diesel oil from vegetable oils, in refineries that have two tread that can prepare a tire having improved grip properties under or more fluid catalytic cracking (FCC) reactors. At least one reactor conditions of a high temperature, and a pneumatic tire compris- processes heavy petroleum or residue in conventional operation ing the same. The present invention relates to the rubber compo- conditions while at least one reactor processes vegetable oils in sition for a tire tread containing more than 5 parts by weight of a proper operation conditions to produce diesel oil. This process basic antioxidant based on 100 parts by weight of the diene rubber employs the same catalyst employed in the FCC process, which components, wherein a metallic compound is a metallic compound processes conventional feedstocks simultaneously. This process comprising (i) a metallic salt of an organic carboxylic acid or (ii) an transforms high heat content raw materials into fuel hydrocarbons. inorganic metallic salt and an acid, and the pneumatic tire having It may improve efficiency for the obtainment of highly pure prod- a tire tread comprising the same. ucts and may not yield glycerin, one by-product of the transesterification process. The diesel oil produced by said process may have superior qualities and/or a cetane number higher than 40. Catalyst-free process for the Once cracking conditions occur at lower temperatures, it may form a less-oxidized product, which is consequently purer than those manufacture of a fatty acid ester obtained by existent technology. oil polyol Kazemizadeh, M., Arkema Inc., US7544763B2, June 9, 2009 Method and article for applying The present invention relates to a manufacturing process for producing a polyol from a fatty acid ester in situ. The process does and monitoring a surfactant not use any added organic or inorganic acid catalyst. The polyol Copland, D., et al., Spencerhall Inc., US7544409B2, June 9, produced by the process is essentially free of any cation or anion. 2009 The fatty acid ester oil epoxidation and hydroxylation reactions can The present invention is directed to a method and an article occur progressively in the same reactor for essentially a one-pot for performing the method of monitoring a surfactant. A preferred reaction. The polyol produced by the process is essentially free of embodiment of the invention, an article comprises a substrate any cation or anion. The polyol can be used to produce polyure- having an image and a surfactant thereon. The substrate is formed thanes having improved properties. 776 inform December 2009, Vol. 20 (12)

acids and a C1–C8 aliphatic alcohol under conditions suitable for Methods and systems for alkyl esterification. ester production Parnas, R., et al., University of Connecticut, US7544830B2, June Electro-optic displays, and 9, 2009 Liquid biomass is combined with an alcohol to form a com- materials for use therein bined liquid stream, introducing the combined liquid stream to Fazel, S., et al., E Ink Corp., US7551346B2, June 23, 2009 a first transesterification reactor between a liquid glycerol outlet An electro-optic display comprises a layer of solid electro- and a liquid alkyl ester outlet, reacting the liquid biomass and the optic material; a backplane comprising at least one electrode; and alcohol to form liquid glycerol and liquid alkyl ester, and removing an adhesive layer disposed between the layer of electro-optic mate- a liquid alkyl ester stream from an upper portion of the first trans- rial and the backplane and adhesively securing the layer of electro- esterification reactor. The combined liquid stream flows upward optic material to the backplane, the adhesive layer comprising a through the reactor at a rate that is less than a settling velocity of thermally activated cross-linking agent comprising an epoxidized the liquid glycerol. vegetable oil fatty acid or an epoxidized ester of such a fatty acid. The cross-linking agent reduces void growth when the display is Solid drawing material subjected to temperature changes. Seki, K., and J. Sin, Buncho Corp., US7547355B2, June 16, 2009 Enzymatic production of peracids A solid drawing material containing a gel-forming substance using perhydrolytic enzymes of an alkali metal salt or an ammonium salt of an aliphatic carboxylic acid having 8 to 36 carbon atoms, an alkoxylated nitrogen- Dicosimo, R., et al., DuPont, US7550420B2, June 23, 2009 containing compound, a reduced starch saccharide, and a coloring A process is provided to produce a concentrated aqueous agent. The solid drawing material, which is in the form of a stick, peracid solution in situ using at least one enzyme having perhy- features a large strength, a small drawing resistance, is less subject drolase activity in the presence of hydrogen peroxide (at a con- to be collapsed or broken, produces little shavings while drawing, centration of at least 500 mM) under neutral to acidic reaction makes it possible to favorably form a drawing even on smooth sur- conditions from suitable carboxylic acid esters (including glycer- faces such as windowpanes, and of which the traces after drawing ides) and/or amides substrates. The concentrated peracid solution can be easily wiped out with a wet cloth. produced is sufficient for use in a variety of disinfection and/or bleaching applications. Particulate creamer comprising fat Starch-vegetable oil graft and food compositions comprising copolymers and their bioﬁber said creamer composites, and a process for their Flöter, E., et al., Unilever Bestfoods North America, US7547458B2, June 16, 2009 manufacture Particulate compositions comprising 10–90 wt% of a matrix Narayan, R., et al., Michigan State University, US7553919B2, June material and 10–90 wt% of triglycerides of fatty acids, wherein 30, 2009 of said triglycerides the amount of H3 (triglyceride of 3 saturated A new starch–vegetable oil graft copolymer, wherein the veg- fatty acids of 16 or more carbon atoms) and H2U (triglyceride of 2 etable oil has been reacted onto the starch backbone using thermal saturated fatty acids of 16 or more carbon atoms and 1 cis-unsatu- or free radical initiators, has been produced in a twin-screw co- rated fatty acid) taken together is at least 55 wt% based on the total rotating extruder. The starch–vegetable oil graft copolymer can amount of triglycerides, wherein the compositions are preferably further be reinforced with biofiber in the presence of an optional low in triglycerides of transunsaturated fatty acids, for use as, for modifier such as maleic anhydride by reactive extrusion process- example, a creamer and/or whitener. The invention also relates to ing to form composites suitable to be injection-molded into biode- a process for preparing such particulates and food products con- gradable articles. taining such creamer. Biofuel and process for making Method for esteriﬁcation of free biofuels fatty acids in triglycerides Morris, M.A., Bio-Alternative, LLC, US7553982B1, June 30, Banavali, R., and G. Pierce, Rohm & Haas, US7550614B2, June 2009 23, 2009 A method of producing biodiesel from a source of triglycer- A method for esterification of free fatty acids in triglycerides. The source of triglycerides is reacted with a blended alcohol ides, with C1–C8 aliphatic alcohols. The method uses an acidic ion composition in the presence of a catalyst to form a mixture of exchange resin as a catalyst. The catalyst is contacted with a reac- at least one fatty acid alcohol ester and glycerin. The fatty acid tion mixture containing a triglyceride having at least 1% free fatty alcohol ester is then separated from the glycerin and is purified to Publications inform December 2009, Vol. 20 (12) 777

produce a biofuel. The blended alcohol composition comprises at least one lower alcohol, a ketone, and ethyl acetate. The use of the Non-dairy whippable food product blended alcohol composition allows the esterification process to Joseph, J., et al., Rich Products Corp., US7563470B2, July 21, proceed under ambient temperature and pressure conditions within 2009 a relatively short reaction time. The present invention provides a nondairy whippable food product that comprises an oil-in-water emulsion. This product is pourable at refrigeration as well as room temperature, making it Pendant fatty acid imaging agents easily whippable. The product comprises at least 30% triglyceride Babich, J., Molecular Insight Pharmaceuticals, Inc., US7556794B2, fats, emulsifiers comprising polysorbate 60 and polysorbate 80, July 7, 2009 stabilizers, and proteins such that the whipped confection has a The disclosure provides pendant fatty acid compounds for use smooth and nongreasy texture, nonwaxy mouth feel and pleasur- in diagnostic imaging (particularly the cardiovascular system), as able organoleptic characteristics. well as kits comprising the same. The disclosure also provides for a method administering an imaging agent with a high specificity for the myocardium. Method for the separation of phospholipids from phospholipid- Flame retardant containing materials Iio, M., et al., Yazaki Corp., US7563395B2, July 21, 2009 Abril, J., et al., Martek Biosciences Corp., US7566570B2, July A flame retardant is provided that has excellent dispersibility 28, 2009 in resin ingredients and can give flame-retardant resin moldings Methods are disclosed for extracting and separating polar excellent flame retardancy and mechanical properties. The flame lipids, including phospholipids, from materials containing oil, retardant comprises magnesium hydroxide particles; a higher fatty polar lipid, protein, ash, and/or carbohydrate, such as egg yolks acid, preferably stearic acid, bonded to part of the surface of the and other phospholipid-containing materials. In particular, methods magnesium hydroxide particles; and a silicone oil, having reactiv- for extracting phospholipids from phospholipid-containing mate- ity, bonded to that surface part of the magnesium hydroxide par- rials through the use of an aliphatic alcohol and control of tem- ticles that does not have the higher fatty acid bonded thereto. perature are disclosed. Using these methods, phospholipids in the aqueous liquid fraction will be efficiently separated and will pre- cipitate readily, and can be subjected to separation for improved Green biodiesel purity. Matson, J., and D. Kannan, Penn State Research Foundation, US7563915B2, July 21, 2009 Methods for improved manufacture of green biodiesel focus Bonded foam product on the selection and use of one or more solid metallic oxide base catalyst(s) selected from the group consisting of calcium oxide manufactured with vegetable oil

(CaO), calcium aluminum oxide (CaO-Al2O3), calcium titanate polyol and method for (CaTiO ), barium titanate (BaTiO ), magnesium aluminum oxide 3 3 manufacturing (MgO-Al2O3), zinc oxide (ZnO), copper (II) oxide (CuO), nickel oxide (NiO), manganese oxide (MnO), titanium oxide (TiO), vana- Gilder, S., L&P Property Management Co., US7566406B2, July dium oxide (VO), cobalt oxide (CoO), iron oxide (FeO), chromite 28, 2009

(FeCr2O4), hydrotalcite [Mg6Al2(CO3)(OH)16·4(H2O)], magnetite A bonded foam product manufactured with a vegetable oil

(Fe3O4), magnesium silicate, and calcium silicate. polyol is herein disclosed. The pre-polymer for use as a binder in the manufacture of a bonded foam product comprises an isocyanate and a vegetable oil polyol, wherein the pre-polymer is substantially Oil ﬁltration process free of any petrochemical polyol. In another aspect, the invention is Oberlin, T., et al., Oberlin Filter Co., US7566468B1, July 28, method for making a bonded foam product, the method comprising 2009 coating a plurality of foam pieces with a pre-polymer, the pre-poly- A process of continuous, on-line active filtration of cooking oil mer comprising an isocyanate and a vegetable oil polyol, wherein during food processing in a vat to remove free fatty acids and other the pre-polymer is substantially free of any petrochemical polyol, undesirable impurities includes moving oil from the vat to a treat- compressing the foam pieces into a foam log of a desired density, ment tank; adding an amount of adsorbent to the oil in the treat- and steaming the foam log to cure the pre-polymer. If desired, a ment tank; mixing the oil and the adsorbent in the treatment tank process oil may be added to the pre-polymer to modify the viscos- for a time to allow substantially all of the free fatty acid adsorp- ity of the pre-polymer. tion of the process to occur in the tank; drawing treated oil from the treatment tank and moving it to a flatbed pressure filter; filter- ing the treated oil through the filter to remove the impurity-laden Patent information is compiled by Scott Bloomer, adsorbent therefrom; returning the filtered oil to the vat; and con- a registered US patent agent with Archer Daniels ducting the foregoing steps at a rate such that a volume of oil sub- Midland Co., Decatur, Illinois, USA. Contact him stantially equal to the volume of the vat is filtered each hour. at [email protected]. 778 inform December 2009, Vol. 20 (12)

In this work 44 fatty acids, which were changes during processing. A PCA dis- Extracts & analyzed as methyl esters by GC–MS (gas criminated between cultivars and, within chromatography–mass spectrometry) in the same cultivar, among the raw materi- scan mode, were determined in genetically als from the rest of the treatments. Using modified corn and soybean seeds. Their fatty acid and triacylglycerol compositions, Distillates relative concentrations were compared predictive DA discriminated between culti- with those of isogenic lines grown in the vars (100% correct), but high discriminant same conditions. Studied compounds com- capacity among processing steps (95% Analysis of phytosterols in prised saturated and unsaturated fatty acids, correct assignation and 87% in cross-vali- including cis/trans isomers and minor fatty dation) was achieved only with fatty acids. extra-virgin olive oil by nano- acids. A classical Soxhlet extraction and an A hierarchical clustering analysis success- liquid chromatography accelerated solvent extraction were assayed fully grouped cultivars and processing steps to extract the fatty compounds from seeds, according to overall olive oil composition Rocco, A., and S. Fanali, J. Chromatogr. A and the GC separation was carried out on and quality. 1216:7173–7178, 2009. a biscyanopropylpolysiloxane chromato- In this work the applicability of nano- graphic column. Soxhlet extraction was liquid chromatography (nano-LC) was eval- Effect of minor oil constituents selected as the most convenient and applied uated for the determination of phytosterols to compare the samples. Specific com- on soy oil conjugated linoleic in extra virgin olive oil samples. These compounds that could denote the origin of the acid production pounds represent a minor part of lipids in crop were observed, but for some sample vegetable oils, but their quantification can Tokle, T., et al., J. Agric. Food Chem. pairs, significant differences were found in be useful to establish oil origin and to reveal 57:8989–8997, 2009. relation to the percentage of certain acids; intentional adulterations. The analysis of Conjugated linoleic acid (CLA) is the highest differences for major acids were five main sterols, specifically brassicasterol, produced by photoisomerization of soy 4.1% in corn and 4.8% in soybean. The stigmasterol, campesterol, cholesterol, and oil linoleic acid. Yields increase with the concentrations of long-chain acids such as `-sitosterol, was performed in a laboratory- degree of oil refining, but the effect of spe- 24:0, 26:0, and 28:0 were higher in some assembled nano-LC system coupled with a cific minor oil components is not known. isogenic lines, whereas the concentrations UV (ultraviolet) detector. The separation Therefore, the objectives were to determine of short-chain acids such as 6:0, 8:0, 9:0, of all compounds was obtained in about the effect of each soy oil minor component 10:0, and 12:0 were higher in their trans- 20 min by using a capillary column packed on CLA yields and oxidative stability after genic counterparts. with a C18-RP (sub 2-μm particles) station- processing, to determine the effect of soy ary phase for 15 cm. Methanol only was oil minor constituent interactions on CLA used as mobile phase. The simple method Inﬂuence of ripe table olive yields and oxidative stability, and to deter- developed and optimized was validated in processing on oil mine how soy oil Magnesol adsorption pre- terms of repeatability, linearity, limit of characteristics and treatment affects CLA yields. Soy oils with detection, and limit of quantification (0.78 varying levels of peroxides, tocopherols, and 1.56 μg/mL, respectively) achieving composition as determined by phospholipids, free fatty acids (FFA), and good results. After this, it was applied to chemometrics lutein were each irradiated by ultraviolet the determination of phytosterols in extra light; and the CLA content and oxidative López-López, A., et al., J. Agric. Food virgin olive oil samples. Isolation of phytos- stability were determined. A peroxide value Chem. 57:8973–8981, 2009. terols was obtained by solid-phase extrac- of above 0.8 greatly decreased CLA yields, The changes in ripe olive fat produced tion, after saponification and liquid–liquid as did a phospholipids content above 500 by processing were studied according to extraction of the unsaponified fraction with ppm. Tocopherols enhanced CLA produc- cultivars using the general linear model, diethyl ether. Recovery tests were per- tion at low levels and reduced yields at high principal component analysis (PCA), pre- formed and values between 90 and 103%, concentrations, whereas lutein and FFA dictive discriminant analysis (DA), and with RSD (relative standard deviation) had little effect. High CLA yields corre- hierarchical clustering. Acidity, perox- within 5%, were obtained. Moreover, the sponded with a lower oil oxidative stability. ide value, K , and ΔK increased during nano-LC system was coupled with a mass 270 The interactions between the minor com- storage. Acidity also increased after steril- spectrometer for an accurate identification ponents showed similar trends as seen in ization, whereas K decreased after dark- of phytosterols. 270 the single-component study. These findings ening; K showed a progressive decrease 232 were supported by observations that Mag- during processing. Fatty acids (except 17:0, Proﬁle and relative nesol adsorption removed large quantities 18:0, and 24:0), triacylglycerols (except of phospholipids and peroxides from soy concentrations of fatty acids in PLLn, OOLn+PoOL, PLL+PoPoO, SOO, oil and greatly increased CLA yields but corn and soybean seeds from and POS+SLS [where P = palmitic, L = reduced the oxidative stability. Minor com- linoleic, Ln = linolenic, O = oleic, Po = transgenic and isogenic crops ponents, particularly peroxides and phos- palmitoleic, and S = stearic]), polar com- pholipids, need to be removed from the oil Jiménez, J.J., et al., J. Chromatogr. A pounds, diacylglycerol, and monoacylglyc- to optimize CLA yields. 1216:7288–7295, 2009. erols also suffered statistically significant Publications inform December 2009, Vol. 20 (12) 779

Oxidation of cholesterol and in lipids extracted from biological samples earth metals Ca + Mg. Such parameters can affects accurate measurement of endoge- be achieved by appropriate partial refin- `-sitosterol and prevention by nous LPA in biological samples. We report ing of oil by degumming. In this article, natural antioxidants for the first time the artificial conversion three common ethanolamines, monoetha- Xu, G., et al., J. Agric. Food Chem. of LPC and lysophosphatidylserine to LPA nolamine (MEA), diethanolamine (DEA), 57:9284–9292, 2009. at the ion source of electrospray ionization and triethanolamine (TEA), were used as Consumption of cholesterol oxida- tandem mass spectrometry (ESI-MS/MS). degumming agents for removing nonhy- tion products (COP) is a growing health To avoid the interference of LPC with the dratable phospholipids from crude rapeseed concern, but little is known about the intake quantification of LPA, a method based on and sunflower oils. Among the studied eth- of `-sitosterol oxidation products (SOP). high-performance liquid chromatographic anolamines, MEA is the most effective for The present study was performed (i) to separation of LPA from LPC has been the removal of phosphorus. After degum- compare the oxidative stability of choles- developed. ming with MEA (0.5 wt%), the phosphorus terol with that of `-sitosterol; (ii) to inves- content in rapeseed oil was reduced from tigate the oxidative pattern of cholesterol Biodiesel preparation in a batch 445 to 3.5 ppm, and from 163 to 2.2 ppm and `-sitosterol in lard, corn oil, and olive emulsification reactor in sunflower oil. After oil treatment with oil; and (iii) to examine the effectiveness of MEA (1.0 wt%), the residual content of green tea catechins (GTC), _-tocopherol, Hájek, M., et al., Eur. J. Lipid Sci. Technol. Ca and Mg decreased from 136 to 4.2 ppm and quercetin in prevention of cholesterol 111:979–984, 2009. and from 55.4 to 1.1 ppm in rapeseed oil. and `-sitosterol oxidation compared with The transesterification of vegetable In sunflower oil, the values of Ca and Mg butylated hydroxytoluene (BHT). Results oils (rapeseed oil was used here) by low decreased from 23.9 to 1.5 ppm and from showed both cholesterol and `-sitosterol molecular weight alcohol is the most used 24.6 to 1.0 ppm. The acid value of the oils were thermally unstable with 75% of cho- method of biodiesel production. Since also decreased after degumming with etha- lesterol and `-sitosterol being oxidized at the reaction proceeds at the alcohol-oil nolamines. The advantage of this oil treat- 180°C for 2 h. The oxidation behavior of interface, it is necessary to create a large ment process is that it takes place at ambient `-sitosterol was similar to that of choles- interphase surface area using a special temperature, resulting in lower production terol in terms of oxidative rate and oxida- emulsifying attachment. We studied how costs and simpler technology. tion products. The major COP produced the conditions (e.g., independent vari- were 7-ketocholesterol, 7_-hydroxy- ables: molar ratio alcohol to oil, amount Distribution of monomeric, cholesterol, 7`-hydroxycholesterol, of catalyst used, KOH, time and tempera- dimeric, and polymeric 5,6_-epoxycholesterol, and 5,6`-epoxy- ture of reaction, intensity of stirring, revo- cholesterol, whereas the major SOP were lution of emulsifying attachment) affected products of stigmasterol during 7-ketositosterol, 7_-hydroxysitosterol, the quality and quantity (dependent vari- thermo-oxidation 7 -hydroxysitosterol, 5,6 -epoxysitosterol, ables) of the ester phase, i.e., the biodiesel. ` _ Lampi, A.-M., et al., Eur. J. Lipid Sci. and 5,6 -epoxysitosterol. Under the same The amount of used catalyst was calculated ` Technol. 111:1027–1034, 2009. experimental conditions, both cholesterol with respect to the content of free fatty acid When plant sterols are oxidized at and -sitosterol were oxidized more slowly in the oil. The statistical system of Plack- ` moderate temperatures (≤100°C), products in corn oil, lard, and olive oil, attributable ett-Burman was used for experiment plan- mainly derive from hydroperoxides, but at to the unsaponified antioxidants present in ning. The relationship between independent temperatures close to 200°C, thermal reac- these fat and oils. GTC, -tocopherol, and and dependent variables was determined _ tions such as dehydration and condensation quercetin were more effective than BHT in and described by multidimensional linear become important. Although sterols are preventing the oxidation of cholesterol and regression. Various statistical tests (princi- often subjected to frying conditions, very `-sitosterol. pal component analysis, correlation matrix) were also performed. little is known of their thermal reactions. In this study, stigmasterol was thermo- Measurement of endogenous oxidized at 180°C, and the formation of lysophosphatidic acid by ESI- Ethanolamines used for dimers and polymers and the amounts of MS/MS in plasma samples degumming of rapeseed and monomers were measured by high-per- sunflower oils as diesel fuels formance size-exclusion chromatography. requires pre-separation of The products were further characterized by lysophosphatidylcholine Zufarov. O., et al., Eur. J. Lipid Sci. Technol. polarity using solid-phase extraction frac- 111:985–992, 2009. tionation. During heating, the amounts of Zhao, Z., and Y. Xu, J. Chromatogr. B Pure vegetable oils can be used as monomers decreased at a steady rate, and 877:3739–3742, 2009. alternative fuel for standard unmodified those of dimers and polymers increased. The levels of lysophosphatidic acid diesel engines, provided the oil viscosity After 3 hr of heating, 21% of the mate- (LPA) or lysophosphatidylcholine (LPC) has been lowered by heating before they rial existed in higher-molecular-weight in plasma have been shown to be markers enter the fuel injection system. In its role products. The amount of polar monomers for several human diseases, including as diesel fuel, a vegetable oil has to have, increased especially during the first hour, cancers. Here we show that the presence among other parameters, a low acidity and demonstrating the formation of oxides and of LPC or other lysophospholipids (LPL) low contents of phosphorus and the alkali their further reactions, whereas that of mid- 780 inform December 2009, Vol. 20 (12) polar monomers decreased constantly, indi- AOCS Journals Q Increased in vitro and in vivo digestibil- cating losses of stigmasterol. Polar dimers ity of soy proteins by chemical modi- contributed to approximately 60% of the fication of disulfide bonds, Wang, H., dimers, and polar polymers to approxi- R.J. Faris, T. Wang, M.E. Spurlock, and mately 78% of the polymers, which sug- N. Gabler gests that in most higher-molecular-weight Q Conversion of methyl oleate to products at least one of the sterol moieties branched-chain hydroxy fatty acid was oxidized. This study showed that a derivatives, Dailey, O.D., N.T. Prevost, significant proportion of thermo-oxidation and G.D. Strahan products are not polar monomeric oxides which are commonly analyzed as oxidation Q Clickable lipids: Azido and alkynyl fatty products. acids and triacylglycerols, Zerkowski, J.A., A. Nuñez, G.D. Strahan, and Methods for the analysis of D.K.Y. Solaiman Q Liquid–liquid extraction of butanol from oxylipins in plants dilute aqueous solutions using soybean- Göbel, C., and I. Feussner, Phytochemistry derived biodiesel, Adhami, L., B. Griggs, 70:1485–1503, 2009 P. Himebrook, and K. Taconi Plant oxylipins comprise a highly Q Response surface analysis and model- diverse and complex class of molecules ing of flaxseed oil yield in supercritical that are derived from lipid oxidation. The carbon dioxide, Özkal, S.G. initial oxidation of unsaturated fatty acids Q Influence of vertical centrifugation on may either occur by enzymatic or chemi- extra virgin olive oil quality, Masella, cal reactions. A large variety of oxylipin Journal of the American Oil P., A. Parenti, P. Spugnoli, and L. classes are generated by an array of alterna- Chemists’ Society (November) Calamai tive reactions further converting hydroper- oxy fatty acids. The structural diversity Q Ratios of regioisomers of triacylglyc- of oxylipins is further increased by their erols containing dihydroxy fatty acids occurrence either as free fatty acid deriva- in castor oil by mass spectrometry, tives or as esters in complex lipids. Lipid Lin, J.-T. peroxidation is common to all biological Q Nutrition labeling: Rapid determina- systems, appearing in developmentally reg- tion of total trans fats by using internal ulated processes and as a response to envi- reflection infrared spectroscopy and a ronmental changes. The oxylipins formed second derivative procedure, Mossoba, may perform various biological roles; some M.M., A. Seiler, J.K.G. Kramer, V. of them have signaling functions. To elu- Milosevic, M. Milosevic, H. Azizian, cidate the roles of oxylipins in a given and H. Steinhart biological context, comprehensive ana- Q Further lipid profiling of the oil from lytical assays are available for determin- the mophane caterpillar, Imbrasia belina, ing the oxylipin profiles of plant tissues. Yeboah, S.O., and Y.C. Mitei This review summarizes indirect methods Q Stability profile of fatty acids in yak (Bos to estimate the general peroxidation state of grunniens) kidney fat during the initial a sample and more sophisticated techniques stages of autoxidation, Zhang, H., Q. for the identification, structure determination, and quantification of oxylipins. Wang, and E. Fan Q Lipid-soluble extracts as the main source of anticancer activity in ginseng Mechanisms of aqueous and ginseng marc, Lee, S.D., G. Yoo, H.J. Lipids (November) extraction of soybean oil Chae, M.-J. In, N.-S. Oh, Y.K. Hwang, Q Conjugated linoleic acid induces Campbell, K.A., and C.E. Glatz, J. Agric. W.I. Hwang, and D.C. Kim uncoupling protein 1 in white adipose Food Chem. 57:10904–10912, 2009. Q Antioxidant activity of phytochemicals tissue of ob/ob mice, Wendel, A.A., Aqueous extraction processing (AEP) from distillers dried grain oil, Winkler- A. Purushotham, L.-F. Liu, and M.A. of soy is a promising green alternative to Moser, J.K., and S.F. Vaughn Belury hexane extraction processing. To improve Q Changes in quality indices, phenolic Q Conjugated linoleic acid isomers, t10c12 AEP oil yields, experiments were conducted content, and antioxidant activity of fla- and c9t11, are differentially incorpo- to probe the mechanisms of oil release. vored olive oils during storage, Baiano, rated into adipose tissue and skele- Microscopy of extruded soy before and A., C. Terracone, G. Gambacorta, and tal muscle in humans, Goedecke, J.H., after extraction with and without protease E. La Notte Publications inform December 2009, Vol. 20 (12) 781

D.E. Rae, C.M. Smuts, E.V. Lambert, indicated that unextracted oil is sequestered trans-9,cis-11 CLA and cis-10,trans-12 and M. O’Shea in an insoluble matrix of denatured protein CLA, and cis-9,trans-11 CLA had cross- Q Hepatic expression of long-chain acyl- and is released by proteolytic digestion of validated coefficients of determinations this matrix. In flour from flake, unextracted 2 CoA synthetase 3 is upregulated in (R v) of 0.97, 0.98, 0.97, 0.98, 0.97, and hyperlipidemic hamsters, Wu, M., H. oil is contained as intact oil bodies in undis- 0.99 and corresponding root-mean-square Liu, W. Chen, Y. Fujimoto, and J. Liu rupted cells, or as coalesced oil droplets too error of validation (RMSEV) of 1.14, 0.69, large to pass out of the disrupted cellular Q The effect of linseed on intramuscular 0.27, 0.07, 0.14, and 0.07% CLA, respec- matrix. Our results suggest that emulsifi- fat content and adipogenesis-related tively. The ATR−FTIR technique is a rapid cation is an important extraction mecha- genes in skeletal muscle of pigs, Luo, and less expensive method for determining nism that reduces the size of these droplets H.-F., H.-K. Wei, F.-R. Huang, Z. Zhou, CLA isomers in linoleic acid photo-isomer- and increases yield. Protease and sodium ized soy oil than GC−FID. S.-W. Jiang, and J. Peng dodecyl sulfate were both successful in Q Cocoa butter and safﬂower oil elicit dif- increasing extraction yields. We propose ferent effects on hepatic gene expres- that this is because they disrupt a viscoelas- Microbial production of sion and lipid metabolism in rats, tic protein film at the droplet interface, conjugated fatty acids Gustavsson, C., P. Parini, J. Ostojic, facilitating droplet disruption. An extrac- Kishino, S., et al., Lipid Technol. 21:177– L. Cheung, J. Hu, F. Zadjali, F. Tahir, tion model based on oil droplet coalescence 181, 2009. K. Brismar, G. Norstedt, and P. Tol- and the formation of a viscoelastic film was Conjugated fatty acids have attracted let-Egnell able to fit kinetic extraction data well. much attention as a novel type of biolog- Q Differential expression of lipid metab- ically beneficial functional lipid. Some olism-related genes in porcine muscle Measurement of conjugated isomers of conjugated linoleic acid (CLA) tissue leading to different intramuscu- linoleic acid (CLA) in CLA-rich reduce carcinogenesis, atherosclerosis, and lar fat deposition, Zhao, S.M., L.J. Ren, soy oil by attenuated total body fat. In considering the use of CLA L. Chen, X. Zhang, M.L. Cheng, W.Z. for medicinal and nutraceutical purposes, Li, Y.Y. Zhang, and S.Z. Gao reﬂectance−Fourier transform a safe isomer-selective process of produc- Q Long-chain ceramide produced in infrared spectroscopy tion is required. The introduction of bio- response to N-hexanoylsphingosine (ATR−FTIR) logical reactions for CLA production could does not induce apoptosis in CHP-100 be an answer. We screened microbial reac- Kadamne, J.V., et al., J. Agric. Food Chem. cells, Mancinetti, A., S. Di Bartolomeo, tions useful for CLA production and found 57:10483–10488, 2009. and A. Spinedi several unique reactions in microorganisms. Conjugated linoleic acid (CLA) Q Analysis of phospholipids in rat brain Lactic acid bacteria produced CLA from isomers in oils are currently measured using liquid chromatography–mass linoleic acid. The CLA, which was obtained as fatty acid methyl esters by a gas spectrometry, Norris, C., B. Fong, A. as the free fatty acid form, comprised a chromatography−flame ionization detec- MacGibbon, and P. McJarrow mixture of cis-9,trans-11-octadecadienoic tor (GC−FID) technique, which requires Q Quantitative determination of geranyl acid (18:2) and trans-9,trans-11-18:2. approximately 2 h to complete the analy- Furthermore, lactic acid bacteria trans- diphosphate levels in cultured human sis. Hence, we aim to develop a method to formed ricinoleic acid [12-hydroxy-cis- cells, Holstein, S.A., H. Tong, C.H. rapidly determine CLA isomers in CLA- 9-octadecenoic acid (18:1)] to CLA (a Kuder, and R.J. Hohl rich soy oil. Soy oil with 0.38−25.11% Q Simple determination of deoxy- total CLA was obtained by photo-isomer- mixture of cis-9,trans-11-18:2 and trans- cholic and ursodeoxycholic acids ization of 96 soy oil samples for 24 h. A 9,trans-11-18:2). Castor oil, rich in the tri- by phenolphthalein-`-cyclodextrin sample was withdrawn at 30 min intervals acylglycerol form of ricinoleic acid, was inclusion complex, Cadena, P.G., E.C. with repeated processing using a second also found to act as a substrate for CLA Oliveira, A.N. Araújo, M.C.B.S.M. Mon- batch of oil. Six replicates of GC−FID fatty production by lactic acid bacteria with tenegro, M.C.B. Pimentel, J.L. Lima acid analysis were conducted for each oil the aid of lipase-catalyzed triacylglyc- Filho, and V.L. Silva sample. The oil samples were scanned using erol hydrolysis. Filamentous fungi trans- formed trans-vaccenic acid (trans-11-18:1) Q Erratum to: Effect of bilayer phos- attenuated total reflectance−Fourier trans- pholipid composition and curvature form infrared spectroscopy (ATR−FTIR), to cis-9,trans-11-18:2 by Δ9 desaturation. This CLA was obtained as a triacylglyc- on ligand transfer by the _-tocopherol and the spectra were collected. Calibra- erol. In addition, lactic acid bacteria pro- transfer protein, Zhang, W.X., G. tion models were developed using partial duced conjugated trienoic fatty acids from Frahm, S. Morley, D. Manor, and J. least-squares (PLS-1) regression using _- and a-linolenic acid. The trienoic fatty Atkinson Unscrambler software. Models were validated using a full cross-validation tech- acids produced from _-linolenic acid were nique and tested using samples that were cis-9,trans-11,cis-15-octadecatrienoic acid not included in the calibration sample (18:3) and trans-9,trans-11,cis-15-18:3. set. Measured and predicted total CLA, Those produced from a-linolenic acid were trans,trans-CLA isomers, total mono- cis-6,cis-9,trans-11-18:3 and cis-6,trans- trans-CLA isomers, trans-10,cis-12 CLA, 9,trans-11-18:3. 782 inform December 2009, Vol. 20 (12)

The use of alternative lipid be quantitatively analyzed via HPLC- 2.4% wt/wt low-melting (LM) lecithin, and CAD except for some volatile lipids such 1.4% wt/wt Tween 60 or 1.4% wt/wt Tween resources for bioenergy as common fatty acid methyl esters and 80] and a cosurfactant (0.6% taurodeoxy- Zyaykina, N., et al., Lipid Technol. 21:182– short-chain free fatty acids (

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Meeting and Exposition, San Fran- sia.org/Meetings/ViewMeetings. cisco, California, USA. Information: May cfm?MeetingID=1024 . http://portal.acs.org/portal/acs/corg/ May 3–6, 2010. BIO [Biotechnol- content?_nfpb=true&_pageLabel=PP_ June 15–17, 2009. International Probiotic ogy Industry Organization] Inter- TRANSITIONMAIN&node_ Conference 2010, Kosice, Slovakia. Infor- national Convention, McCormick id=2060&use_sec=false&sec_url_ mation: www.probiotic-conference.net. Place, Chicago, Illinois, USA. Infor- var=region1&__uuid=b706dc39-e14f- mation: http://convention.bio.org. 4c5f-ba72-080d986957c1. June 17–18, 2010. CosmeticBusiness 2010, M.O.C. (Münchener Order May 13–15, 2010. International Sympo- March 23–26, 2010. 22nd International Center), Munich, Germany. Infor- sium on Microbial Lipids: From Genomics Trade Fair and Analytica Conference mation: www.cosmetic-business. to Lipidomics, Vienna, Austria. Informa- (“Analytica”), New Munich Trade Fair com/en/tradefair/kontakt.php. tion: www.eurofedlipid.org/meetings/ Centre, Munich, Germany. Information: vienna2010. www.analytica.de. June 19–24, 2010. HPLC 2010: 35th International Symposium on High May 16–19, 2010. 101st AOCS Annual March 23–26, 2010. Advancements in Food Performance Liquid Phase Separa- Meeting and Expo, Phoenix Convention Safety Education: Trends, Tools and Tech- tions and Related Techniques, The Center, Phoenix, Arizona, USA. Informa- nologies (sponsored by the US Depart- Hynes Convention Center, Boston, tion: phone: +1-217-359-2344; fax: +1-217- ment of Agriculture and the National Massachusetts, USA. Information: 351-8091; e-mail: [email protected]; Science Foundation), Hyatt Regency www.casss.org/displayconvention. http://Annual_Mtg.aocs.org. Atlanta, Atlanta, Georgia, USA. Informa- cfm?conventionnbr=6136. tion: e-mail: [email protected]; www. May 16–20, 2010. STLE [Society of Tribo- fsis.usda.gov/Atlanta2010. June 20–25, 2010. Lipoprotein Metab- logists and Lubrication Engineers] 2010 olism, Gordon Research Confer- Annual Meeting, Bally’s Hotel & Casino, March 24–25, 2010. Wellness 10, Inter- ence, Waterville Valley Resort, Las Vegas, Nevada, USA. Information: Continental Chicago O’Hare, Rosemont, Waterville Valley, New Hampshire, www.stle.org. Illinois, USA. Information: www.ift.org/ USA. Information: www.gordonre- cms/?pid=1001994. searchconferences.org/programs. May 29–June 2, 2010. 9th ISSFAL Con- aspx?year=2010&program=lipopro. gress, Maastricht, Netherlands. Informa- tion: www.issfal.org.uk/meetings.html. April June 23–24, 2010. Symposium on Breeding for Disease Resistance, April 14–15, 2010. CED 40 Annual Meeting June Krasnodar, Russian Federation. [Comité Español de la Detergencia, Ten- Information: www.isa.cetiom.fr/ sioactivos y Aﬁnes], Barcelona, Spain. event.htm. June 1–4, 2010. AchemAsia, 8th Information: www.cedmeeting.com. International Exhibition, Congress June 27–30, 2010. World Congress on Chemical Engineering and Bio- April 24–28. 2010. Lipid Interac- on Industrial Biotechnology and Bio- technology, Beijing, P.R. China. Infor- tions in Physiology and Disease: processing, Washington, DC, USA. mation: www.achemasia.de. American Society for Biochemis- Information: www.bio.org/events. try and Molecular Biology Annual June 3–4, 2010. Third European Meeting, Anaheim Convention June 27–July 2, 2010. Tribology, Gordon Workshop on Lipid Mediators, Center, Anaheim, California, USA. Research Conference, Colby College, Pasteur Institute, Paris, France. Information: www.asbmb.org/ Waterville, Maine, USA. Information: Information: http://workshop-lipid. Meetings_01/2010mtg/2010mtgint. www.gordonresearchconferences.org/ eu. aspx?id=3158. programs.aspx?year=2010&program=t ribology. Q June 6–11, 2010. Bioactive Lipids: April 25–27, 2010. IMR Conference Food Biochemistry and Diseases, Westin Hydrocolloids, Grand Hyatt Hotel, Berlin, Miyako Kyoto, Kyoto, Japan. Infor- Germany. Information: www.hydrocol- mation: www.keystonesympo- loid.com. 784 inform December 2009, Vol. 20 (12) Campaign for Technology a global success

Catherine Watkins

Donors to the AOCS Foundation’s Campaign for Technology, which ofﬁcially ends on December 31, participated in one of the most successful campaigns ever undertaken by the Foundation. Why? Because of the impact on the global fats and oils community the campaign has had and will continue to have over the coming years. “Updating the technology available to members and nonmembers alike will create new opportunities for networking and information sharing, some of which haven’t even been dreamed up yet,” said Amy Lydic, development manager of the AOCS Foundation. “And it is particularly fitting that we focus on modernizing our information delivery systems as we continue to celebrate the AOCS technology such as RSS feeds, or real-time delivery of new content. centennial.” Currently, there is no way to share late-breaking news stories on Updating technology also fits into the strategic plan developed the home page. Come May, visitors will be able to share content by the AOCS Governing Board. In that plan, the first strategy states, with colleagues with one click and even see what news stories are “AOCS should be the primary source of fats and oils information receiving the most attention. Plans are also in progress to present on the web.” inform in a new and dynamic manner, with embedded multimedia Over the years, visitors to www.aocs.org have come to expect files on occasion. delivery of a range of information, from daily news stories on The AOCS Store is also undergoing an overhaul. The rede- the home page to online purchase of new books and CD-ROMs sign will allow for instant delivery of PDF files as well as helpful from AOCS Press. In May 2010, however, a completely redesigned tips about related resources (both free of charge and for sale). For website will debut. example, buying a book chapter on biodiesel will bring up links to “We not only aim to be the primary source of information information about related materials such as the AOCS method for about fats and oils on the web, we are also making usability our determining biodiesel quality and inform Biodiesel Supplements. No. 1 priority for the new site,” Lydic noted. Another exciting development involves the Lipid Library To that end, campaign funds have allowed AOCS to contract (www.lipidlibrary.co.uk/), the in-depth online resource created by with a web content management system provider. As part of the AOCS member Bill Christie. Christie has generously donated the redesign project—a massive one, given that the current site houses site, which provides a wealth of information on lipid chemistry, more than 2,000 pages of content—every page presently posted is biology, and analysis, to AOCS. He will continue to serve as edi- being rewritten. tor-in-chief of the site content for several years and will oversee Beyond reader-friendly writing, the content management the editorial board, which will function under the umbrella of the system will allow for the use of sophisticated information-sharing AOCS Publications Steering Committee. (Interested in serving on the editorial board? If so, email Christie at billchristie@blueyon- der.co.uk.) A further website upgrade will be the addition of listservs. information Although automatic mailing lists that broadcast emails to everyone on the list are not new, the upgraded AOCS website will allow for Three ways your Campaign for Technology donation has made organized discussions on topics yet to be determined. The addition the global fats and oils community more competitive: will create a new way to build community, exchange information, Q AOCS @ Work podcasts—www.aocs.org/news/archive_ and solve problems. story.cfm?arch=1&id=1045 “None of this would have been possible without our generous Q Online membership renewal—www.aocs.org/member/login. donors. We are very grateful,” said Lydic. cfm Q AOCS Connect—http://aocsconnect.ning.com/ Catherine Watkins is associate editor of inform and can be reached at [email protected]. Thank you for being part of our 1OOth anniversary celebration. Our members play a major role in our growth, success, and longevity. We look forward to serving you and the industry for another 100 years.

Special Thanks to our Centennial Advisory Committee: Philip Bollheimer Michael Boyer Robert Hastert Howard Knapp Richard Wilson Karl Zilch And to George Willhite, Historian Our Strength Lies in our Found

The AOCS Foundation Ag Processing, Inc. (AGP) Thomas Foglia gratefully acknowledges Casimir Akoh Frito-Lay, Inc. AOCS Administration Staff Fuji Vegetable Oil, Inc. the fallowing individuals, AOCS Advertising & Sales Dept. Genencor, a Danisco Division universities, and companies AOCS Membership Dept. Graham Corporation far their contributions in AOCS Technical Dept. Timothy Gum 2009* to the Campaign Anderson International Corp. Michael Haas Archer Daniels Midland (ADM) Connie Hilson far Technology, Annual Archer Daniels Midland Erlend H vattum Fund, the Honored Student Foundation Innolabtec GmbH Program, and the Silent Naomichi Baba Interstate Commodities Corp. Auction. Thank you also to Mike Boyer Toshihiro Itoh ] . Thomas Brenna Kalsec Inc. the many donors who made Roy Carr K-State Alumni Association a gift while renewing their Richard Cantrill Howard Knapp membership. David Casilio Kim B. Koch Gloria Cook Kraft Foods Inc. CPM Roskamp Champion Vera Lebovics Daniels Plant Food, Inc. Gary List (As of November 9. 2009) Richard Della Porta Doug Lopshire *For a complete Albert J. Dijkstra M&W Contractors, Inc. list of donors to Mark Empie Alejandro G. Marangoni the Campaign for Technology, visit David Firestone Dave McCall h ttp://www.aocs.org/found/et echdonors.cfm.

NEW this year! The AOCS Foundation kicked off the Corporate Century Club. Funds raised through the Corporate Century Club will be unrestricted and used to advance the AOCS Mission through development of new products and services beneficial to our members and non-members alike.

Church & Dwight Co Inc.

~PORATE If you'd like to see your company's name on this list, visit http://www.aocs.org/found/corp_cent_club.cfm for more information ~ and to make your gift. Lead the way and be a part ofit! ati on!

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For information, please contact Amy Lydic, Development Manager by e-mail at [email protected]; by phone at +1 217-693-4807; or by mail at AOCS Founda tion, 2710 S. Boulder Drive, Urbana, IL 61802, USA. The Official Methods and Recommended Practices of the AOCS have long been regarded as the standard publication for analytical methods critical to processing, trading, utilizing, and evaluating fats, oils, and lipid products.

Did you know that this critical resource is Electronic Access available by site license and online indi If your company or university has several vidual methods? T hese options allow your laboratories that need access to AOCS organization to select methods only appli Methods, there is no need to purchase cable in your laboratory. several copies. Electronic access is now available to meet your needs. A web-based Online Individual Methods library of AOCS Methods is available for The advantages of online delivery include individual use or for multi-user/ multi-site the ability to select methods related to access. Governments and Universities specific analytical areas, the ability to receive special rates. Electronic access is search by definition and scope, as well as automatically updated when there are addi the low individual methods cost. Visit tions or revisions to any of the methods. www.aocs.org/ tech/ onlinemethods for more information. Contact AOCS Technical Services to learn more and find out what package ''' ~::,,::~,, .. , ... ~ best suits your organization. ,,.

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Phone: +1-217-693-4803 Fax:+1-217-351-8091 TECHNICAL ~ E-mail: [email protected] 113 SERVICES ~~Ii.I.ii Processing inform December 2009, Vol. 20 (12) 789 Distillers’ dried grains with solubles (DDGS)—A key to the fuel ethanol industry Kurt A. Rosentrater

Modern societies face many challenges, including growing populations and increasing demands for food, clothing, housing, and consumer goods and for the concomitant raw materials and energy required to produce all of these. Additionally, there is an overwhelming reliance on fossil fuels for energy. Transportation fuel accounted for 28% of all energy consumed in the United States during 2008, 95% of which came from petroleum sources. And domestic production of crude oil was 4.96 FIG. 1. A typical dry-grind corn-to-ethanol manufacturing plant. million barrels per day, whereas imports were 9.76 million barrels per day (nearly two-thirds of the studies include Kaltschmitt et al. (1997), Kim and Dale (2004), Pimentel and Patzek (2005), Shapouri et al. (2003), and Sheehan total US demand). et al. (2004). Farrell et al. (2006) presented a thorough review Biofuels, which are renewable sources of energy, can help and synthesis of this debate. However, new questions have arisen, meet some of these increasing needs. Potentially, they can be pro- including water consumption and land use change. Answers are duced from a variety of biomass materials, including agricultural now being developed. residues, corn stover, grasses, and legumes. Cur- rently, however, corn grain is the most heavily used feedstock in the United States, because alcohol production from corn is readily accom- plished at a lower cost compared to other biomass substrates. The corn-based fuel ethanol industry is well poised to help extend and augment the nation’s supply of transportation fuels. And, over the last decade, many innovations have occurred in the industry, not only in production processes used and final products produced but also in terms of optimizing raw materials and energy consumed. Due to many advantages, including lower capital and operating costs (including energy inputs), most new ethanol plants are dry grind facilities (Fig. 1), as opposed to the older style wet mills (see also inform 18:658–660, 2007). Questions regarding the energy balance of ethanol, especially about resource and energy inputs and outputs, economics, impacts of manufacture, and the performance of ethanol in vehi- FIG. 2. Trends in production of fuel ethanol and generation of DDGS (distillers dried cles, have led to many Life Cycle Assessment grains with solubles). RFS denotes the mandate due to the Renewable Fuel Standard studies to examine the overall costs and benefits (adapted from Renewable Fuels Association, Washington, DC, 2009; available online of this biofuel. Examples of the more prominent at www.ethanolrfa.org) 790 inform December 2009, Vol. 20 (12)

To help meet the demand for more motor fuel, the number of US ethanol plants has risen rapidly in the past 15 years, as has the quantity of fuel ethanol produced (Fig. 2). As of July 2009, 197 manufacturing plants in the United States have an aggregate production capacity of over 12.7 billion gallons/year (48.1 billion liters/yr). Moreover, 20 plants are currently under construction or are undergoing expansion, all of which will contribute an additional 1.8 billion gallons/yr (6.8 billion liters/yr). As production volume increases, the processing residues (known as distillers grains) will increase in tandem (Fig. 2). PROCESS Briefly, dry grind ethanol manufacturing typically results in three products: ethanol, the primary end product; residual nonfermentable corn kernel components, which are sold as distillers grains; and carbon dioxide. A common rule of thumb is that for each 1 kg of corn processed, approximately 1/3 kg of each of the constituent streams will be produced. Another rule of thumb states that each bushel of corn (~56 lb) will yield nearly 2.9 gallons (~18 lb) of ethanol, 18 lb of distillers grains, and 18 lb of carbon dioxide. The overall production process (Fig. 3) consists of several unit operations. Grinding, cooking, and liquefying release and convert the starch, so that yeast can ferment it into ethanol. After fermentation, the ethanol is separated (via distillation) from the water and nonfermentable residues. Downstream sepa- rations, mixing, and drying are then used to remove water from the solid residues and to produce a variety of co-product streams (distillers grains) that are wet or FIG. 3. Process ﬂow diagram for a typical dry-grind corn-to-ethanol manufacturing plant. CDS, dry, with or without the addition of con- condensed distillers solubles; DWGS, distillers wet grains with solubles; DDGS, distillers dried densed soluble materials. grains with solubles; DWG, distillers wet grains; DDG, distillers dried grains.

TABLE 1. Analysis (% db) of DDGS from South Dakotaa Plant no. Proteinb,c Lipidb,c NDFb,c ADFb,c Starchb,c Ashb,c 1 28.33b (1.25) 10.76a (1.00) 31.84b (4.02) 15.56a (2.29) 11.82a (1.20) 13.27a (3.10) 2 30.65a (1.20) 9.75a (1.05) 39.90a (3.95) 15.21a (3.95) 9.81a (1.52) 12.84a (2.56) 3 28.70a (1.32) 10.98a (0.95) 38.46a (4.01) 17.89a (4.01) 11.59a (1.42) 11.52a (3.05) 4 30.65a (1.23) 9.4b (0.16) 36.73a (1.07) 15.28a (0.49) 9.05b (0.33) 4.13b (0.21) 5 31.78a (0.63) 9.50b (0.41) 38.88a (0.86) 17.24a (1.12) 10.05a (0.65) 4.48b (0.22) aAbbreviations: db, dry basis; DDGS, distillers dried grains with solubles; NDF, neutral detergent fiber; ADF, acid detergent fiber. bMean (standard deviation). cMean values in the same column with different superscript letters show statistically significant differences (_ = 0.05, LSD). Processing inform December 2009, Vol. 20 (12) 791

Carbon dioxide, which arises from fermentation, is generated point and from a livestock feeding perspective. Some of the most during the yeast’s metabolic conversion of sugars into ethanol. This pressing include: by-product can be captured and sold to compressed gas markets, r UIF MBSHF RVBOUJUJFT PG FOFSHZ SFRVJSFE UP SFNPWF XBUFS EVSJOH such as beverage or dry-ice manufacturers. Often, however, location drying, coupled with the high cost of energy itself; and/or logistics make the sales and marketing of this gas econom- r WBSJBCJMJUZ JO OVUSJFOU DPOUFOU RVBMJUZ BOE BTTPDJBUFE RVBMJUZ ically unfeasible. Releasing it to the atmosphere may eventually management programs at each plant; become untenable owing to greenhouse gas emission constraints. r DPTUT BTTPDJBUFE XJUI USBOTQPSUJOH %%(4 UP EJWFSTF BOE EJTUBOU markets; DDGS PROPERTIES AND r JOUFSOBUJPOBM NBSLFUJOH BOE FYQPSU DIBMMFOHFT APPLICATIONS r QSFWFOUJPO PG NZDPUPYJO DPOUBNJOBUJPO r JODPOTJTUFOU QSPEVDU JEFOUJUZ BOE OPNFODMBUVSF Only the starch is converted during the fermentation process; the r MBDL PG TUBOEBSEJ[FE NFUIPEPMPHJFT UP NFBTVSF %%(4 nonfermentable materials consist of corn kernel proteins, fibers, quality; oils, and minerals. These are then used to produce a variety of feed r MBDL PG FEVDBUJPO BOE UFDIOJDBM TVQQPSU GPS UIF JOEVTUSZ materials, the most common of which is distillers dried grains with Poor flowability and material handling behavior are still challenges solubles (DDGS). DDGS are dried to approximately 10% mois- as well. All of these issues ultimately impact the end users—the ture content, to ensure an extended shelf life, and then sold to local livestock producers. The industry is currently working to address livestock producers or shipped via truck or rail to various destina- each of these, and in so doing will increase the value and thus uti- tions throughout the nation, and even globally. Distillers wet grains lization of these co-products. (DWG) are popular with livestock producers near ethanol plants. But because the moisture contents are generally greater than 50 to RECENT PROGRESS 60%, their shelf life is very limited, and shipping economics can be cost prohibitive. The ethanol industry is continually evolving. The modern dry grind Currently, the ethanol industry’s primary outlet for distillers plant is vastly different from a gasohol plant of the 1970s. New grains, most often in the form of DDGS (and, to a lesser degree, in developments, to name only a few, include better enzymes, higher the form of DWG), has been as livestock feed (the other co-prod- starch conversion efficiencies, cold cook technologies, decreased ucts are sold in much lower quantities). As with many food and energy consumption throughout the plant, increased water effi- organic processing wastes, feeding ethanol co-products to animals ciency, and more value streams from both the corn kernel (i.e., is a viable method of utilizing these materials because they contain upstream fractionation) and the resulting distillers grains (i.e., high nutrient levels. DDGS typically contain about 30% protein, downstream fractionation). Additionally, much research has 10% fat, more than 40% neutral detergent fiber, and up to 10% focused on modifying existing processes in order to improve the starch. Composition, however, can vary between plants and even CONTINUED ON PAGE 800 within a single plant over time. For example, Table 1 summarizes composition of DDGS samples collected from five ethanol plants in South Dakota during 2008. More than 80% of DDGS are used in beef and dairy diets, but their inclusion in swine and poultry diets is increasing their con- information sumption as well. Use of DDGS in animal feeds (instead of corn) helps to offset the corn that has been redirected to ethanol produc- For further reading: tion, although this fact is not widely recognized. Over the years, Q Farrell, A.E., R.J. Plevin, B.T. Turner, A.D. Jones, M. O’Hare, numerous research studies have been conducted on co-product use and D.M. Kammen, Ethanol can contribute to energy and envi- in livestock diets. Even so, much work remains to be carried out in ronmental goals, Science 311:506–508 (2006). order to optimize co-product use in animal feeds. Q Kaltschmitt, M., G.A. Reinhardt, and T. Stelzer, Life cycle analy- The co-products are essential to the economic sustainability sis of biofuels under different environmental aspects, Biomass of the fuel ethanol industry. The sale of distillers grains contrib- and Bioenergy 12:121–134 (1997). utes substantially to the economic viability of each ethanol plant Q Kim, S., and B.E. Dale, Cumulative energy and global warming (often between 10 and 40% of a plant’s total revenue). That is why impacts from the production of biomass for biobased prod- these process residues are referred to as “co-products,” instead ucts, Journal of Industrial Ecology 7:147–162 (2004). of “by-products.” Because of the dynamics of the free market Q Pimentel, D., and T. Patzek, Ethanol production using corn, economy, the growing quantity of co-products that will be produced as the industry continues to expand may substantially influ- switchgrass, and wood; biodiesel production using soybean ence the future of the industry. The increased supply of distillers and sunﬂower, Natural Resources Research 14:65–76 (2005). grains may impact potential feed demand and thus sales prices, Q Shapouri, H., J.A. Dufﬁeld, and M. Wang, The energy balance because ethanol co-products compete against other feed materials of corn ethanol revisited, Transactions of the ASAE 46:959– in the marketplace. 968 (2003). Q Sheehan, J., A. Aden, K. Paustian, K. Killian, J. Brenner, M. CONSTRAINTS Walsh, and R. Nelson. Energy and environmental aspects of using corn stover for fuel ethanol, Journal of Industrial Ecology Several key issues are currently associated with the value and utilization of distillers grains, both from the ethanol production stand- 7(3–4):117–146 (2004). Mention Promo Code BOM01209 when ordering to receive discount. Offer expires January 18, 2010 Book of the Month Featuring a Books Plus Product! ~ ~~~~~~~~~~~~~~ Fatty Acids in Health Promotion and Disease Causation Ronald R. Watson, Editor 2009. 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CONTENTS Part 3. Fatty Acids and Health Promotion Part 1. Fatty Acids in Heart Disease • Fatty Acids in Membrane Lipids: Role in Disease Causation · Trans and Other Fatty Acids: Effectson Endothelial Functions and Prevention AOCS •Nutrition and Cardiovascular Disease in American Indiansand • Linoleic Acids and Cancer Cell Functions "Books Plus" Alaska Natives • Effects of Dietary Fatty Acids on Human Microbes: Role in CD-ROMslet · Fish Oils and Stroke Health you access an •Fatty Acids and Cardiac lschemia-reperfusion Injury • Fatty Acids and Lipids in Neurobiology: A BriefOverview entire book in ·Fatty Acids in Corn Oil: Role in Heart Disease Prevention • Fatty Acids in lmmunomodulation: Role in Disease Prevention a lightweight, · Dairy Products: Their Role in the Diet and Effects on and Causation portable, and Cardiovascular Health •Modulation of Cytokine Action by Fatty Acids: Role in Health completely ·Dietary Fatty Acids in Cardiovascular Diseasein Women Part 4. Omega-3 Fatty Acids and Health searchable · Free Fatty Acids: Role in Insulin Resistance, Type 2 Diabetes, ·From ADHD to Alzheimer's: Omega-3 Fatty Acidsand Mental CD-ROM. Of course, and Cardiovascular Disease Health in the AOCS "Books ·Gender Differences in Gene Expression Due to Fatty Acids: · The Importance of the Omega-3 and Omega-6 Ratio: Brain Plus" product the Role in Atherosclerosis and Cardiovascular Disease Biochemistry, Cognition, and Behavior standard book is also •Fatty Acids from Nuts: Cardiometabolic Health Benefits ·The Opposing Effectsof Dietary Omega-3 and trans Fatty included for your Part 2. Trans Fatty Acids in Health Acidson Health: AYin-Yang Effect at the Molecular Level? home, school, or ·Trans Fatty Acids and Cardiometabolic Syndrome • Polyunsaturated Fatty Acids: Effects on Steroid-hormone office use. ·Effects of Fatty Acids Containing atrans Double Bond on Body Bio synthesis Composition • Dietary Fat and Fatty Acids in Exercise and Athletic • Trans and Other Fatty Acids: Role in Diabetic Disease and Health Performance ·Effect of Dietary Long-chain Polyunsaturated Fatty Acidsin • Omega-3 versus Omega-6 Fatty Acid Intake and Immunity Infancy on Both Visual and Neural Development • Omega-3 Long-chain Polyun sa turated Fatty Acids and • Trans Fatty Acids and Oxidative Transformations by Free Obesity Radicals: The Role in Health • Food Sources and Intakes of Omega-3 Fatty Acids • Ruminal Metabolism of Fatty Acids: Modulation of Index Polyunsaturated, Conjugated, and trans Fatty Acids in Meat and Milk ·Fatty Acid Metabolism and Peroxisome Proliferator-activated To order: www.aocs.org/store ·Phone:+ 1-217-693-4803 Receptors (PPARs) Fax:+ 1-217-693-4847 •Email: [email protected] Phospholipids inform December 2009, Vol. 20 (12) 793

A phospholipids primer

Moghis U. Ahmad In the last few years, phospholipids made from marine sources have started to enter the nutritional supplement market. The first Phospholipids are prime building blocks of all life. product of this kind was made from krill, a small crustacean fished from cold Antarctic waters (for more on krill, see inform 18:588– The history of phospholipids begins with the isola- 592, 2007). New phospholipid products entering the nutritional tion from chicken eggs of lecithin, a crude mixture supplement market are now made from the roe of Pacific and Atlan- tic Ocean cold-water fish species. of various phospholipids and other lipids, by the Structurally, phospholipid molecules consist of a hydrophilic French researcher Maurice Gobley around 1847. polar head group and a hydrophobic nonpolar tail (see Fig. 1). The word is derived from “lekithos,” Greek for egg The polar head group contains one or more phosphate groups. The hydrophobic tail is made up of two fatty acyl chains. When yolk. many phospholipid molecules are placed in water, their hydro- In the 1920s, technological advances in Germany made the philic heads tend to “face” into the water and the hydrophobic large-scale production of lecithin from soybeans possible. Lecithin tails are forced to stick together at the surface, forming a bilayer. found applications as a nutritional supplement (i.e., a preparation Most biologically important phospholipids are phosphoglycer- intended to provide nutrients that are missing or not consumed in ides, which contain glycerol joining the head and tail. Examples sufficient quantities in a person’s diet). The same properties that of phosphoglycerides include PC, PS, phosphatidylethanolamine, make phospholipids so important for all life forms make them and phosphatidylinositol. important for food preparation, and today lecithin is widely used in The most abundant phospholipid in cell membranes is PC, the food industry as an emulsifier, a wetting agent for food instan- and therefore it is the most important building block for making tizing, a flow agent for chocolate manufacture, a baking stabi- replacement membrane mass. PC has exceptional emulsifying lizer and pan-release slip agent, a flour improver, and an animal properties, on which the liver draws to produce the digestive bile feed additive. Modern industrial processing of soy lecithin enriches its content of selected phospholipids that form the basis for commercially available nutraceutical phospholipid formulations. Currently, three phospholipids are commercially cost effective for nutritional supplements: phosphatidylserine (PS), phosphatidylcholine (PC), and glycerophosphatidylcholine (GPC). All are safe to consume long-term, while offering valuable proven benefits for health, such as enhancing brain health, protecting liver function, and serving as a source of choline. Egg yolks are the major source of phospholipids used by the pharmaceutical industry for parenteral nutrition, but for nutritional supplements egg phospholipids play no significant role because they have a relatively high cholesterol level and an unfavor- able saturated fatty acid profile. At one time, PS produced from bovine brains was a widely used product in Europe. However, the incidence of bovine spongi- form encephalitis (BSE, or mad cow disease) made this product unusable and challenged researchers to find ways to isolate PS from an alternative source, such as soybean. FIG. 1. Chemical structure of selected phospholipids. 794 inform December 2009, Vol. 20 (12)

fluid. The lining cells of the lung and intestines use PC to make the produce a wide variety of carrier systems that improve the solu- surfactant coatings essential to their gas and fluid exchange func- bility, stability, and delivery of active pharmaceutical ingredients tions, and PC is the predominant building block for the circulat- (API). The carrier system may be micelles, mixed micelles, and ing lipoproteins. liposomes. (Broadly defined, liposomes are lipid bilayers surrounding an aqueous phase.) The emulsifying properties of PC currently FUNCTIONS are being used to produce self-emulsifying drug delivery systems, Phospholipids have many functions in biological systems, includ- microemulsions for oral administration, and emulsions for inject- ing as fuels, as membrane structural elements, as signaling agents, able use. Many new drug molecules that are hardly soluble in any and as surfactants. For example, pulmonary surfactant is a mixture pharmaceutically acceptable solvents can be solubilized in the pres- of lipids (primarily dipalmitoyl PC) and proteins that controls the ence of PC, thus improving the absorption of API. Researchers in surface tension of the fluid lining of the inner lung (the site of gas pre-formulation or generic development make use of PC to modify exchange), allowing rapid expansion and compression of this lining and improve the dissolution profile of their drug, thereby optimiz- during the breathing cycle. Phospholipids are the major lipid con- ing absorption and bioavailability. Also, PC is well known for its stituent in cell membranes, thus maintaining structural integrity ability to reduce the side effects of certain drugs administered via between the cell and its environment and providing boundaries the oral, topical, or injectable route. between compartments within the cell. The application of both synthetic and natural phospholipids in Many intracellular structures also are made from phospholip- liposomes (see Fig. 2) has been extended to a variety of drugs, such ids. These vital phospholipid components are under constant attack as antineoplastic agents, antimicrobial agents, and immunomod- from free radicals, pathogens, and toxins. To repair the structural ulators. Liposomes are microscopic vesicles consisting of one or damage caused by these agents, our body requires a constant supply more membrane-like phospholipid bilayers surrounding an aqueous of phospholipids. The body can synthesize some phospholipids, but medium. The lipid components of liposomes used in pharmaceuti- others must be supplied by the diet. Phospholipids that can only cals are predominantly PC, either synthetic or derived from egg or be obtained through dietary intake are called “essential phospho- soybean lecithins. Due to their biphasic character, liposomes can lipids.” PC is the most important of the essential phospholipids. act as carriers for both lipophilic and hydrophilic drugs. Depend- It can be consumed safely from milligram to gram levels per day ing on their solubility and partitioning characteristics, the drug without adverse effects. molecules are located differently in the liposomal environment. The human body also uses phospholipids as emulsifiers (in Lipophilic drugs are generally entrapped almost completely in the the bile digestive fluid) and as surface-active wetting agents (in the lipid bilayers of liposomes. Hydrophilic drugs may be entrapped lungs, intestines, and kidneys, for example). Additionally, phos- inside the aqueous core of liposomes. pholipids are used to assemble the circulating lipoproteins (low Using liposomes as a drug delivery system for antitumor drugs density lipoprotein [LDL] and high density lipoprotein [HDL]) may lessen the toxicity of encapsulated compounds by altering their that transport fat-soluble nutrients around the body. pharmacokinetics or tissue distribution. The half-life of liposomes in vivo can range from a few minutes to hours depending on their size and the lipid composition. A promising example of liposomal APPLICATIONS OF PHOSPHOLIPIDS delivery system for an antitumor drug has been the use of doxorubi- Pharmaceuticals. PC is an amphiphilic and zwitterionic molecule, cin in liposome-encapsulated form. Doxorubicin, an anthracycline making it a multifunctional ingredient in pharmaceutical prepara- antibiotic, is useful in the treatment of a variety of solid tumors, tions. PC can be used singly or in combination with cholesterol to information

Q Gobley, M., Examen comparatif du jaune d’œufe et de la matiere cerebrale, J. Pharm. Chim. 11:409 (1847). Q Guo, Z., A.F. Vikbjerg, and X. Xu, Enzymatic modiﬁcation of phospholipids for functional applications and human nutrition, Biotechnol. Adv. 23:203–259 (2005). Q Kidd, P.M., Dietary phospholipids as anti-aging nutraceuticals, in Anti-Aging Medical Therapeutics, edited by R.A. Klatz and R. Goldman, Quest Publications, Chicago, Illinois, USA, 2000, pp. 282–300. Q Newsletter, Phospholipid Research Center/Egg Lecithin for FIG. 2. Liposome cross section. The interior of liposomes is ﬁlled Pharmaceutical Applications, Phospholipid Research Center, with water (aqueous core) where water-soluble molecules are encap- Heidelberg, Germany, Vol. 3, May 2008. sulated. Most commonly, water-insoluble compounds are entrapped Q Schneider, M., Phospholipids for functional food, Eur. J. Lipid in phospholipid bilayer. Therefore, liposomes can serve as carriers for Sci. Technol. 103:98–101 (2001). both water-soluble and water-insoluble compounds. In fact, a single liposome can carry both types of molecules. Phospholipids inform December 2009, Vol. 20 (12) 795

TABLE 1. Marketed drugs containing phospholipids mucosa, PC supplied by the oral route has been Products Phospholipids useda Treatment shown to protect from Abelcet® (amphotericin B) DMPC, DMPG Systemic fungal infection gastric lesions and ulcers AmBisome® (amphotericin B) HSPC, DSPG, CHOL Systemic fungal infection induced by stress, malnutrition, and nonsteroi- Doxil® (doxorubicin) HSPC, DSPE-MPEG2000, CHOL Ovarian cancer, AIDS-related dal anti-inflammatory Kaposi’s sarcoma drugs. PC is a source of Myocet® (doxorubicin) Egg-PC, CHOL AIDS-related Kaposi’s sarcoma choline, and choline is an essential nutrient that Visudyne® (verteporﬁn) Egg-PC, DMPC Age-related macular degenera- has been shown to coun- tion; myopia teract and protect against Junovan® (muramyl tripepeptide POPC, DOPS Osteosarcoma liver intoxication. phosphatidylethanolamine) GPC produced from vegetable source DepoCyte® (cytarabine) DOPC, DPPG Lymphomatous meningitis is the only water-solu- DepoDur® (morphine sulfate) DOPC, DPPG, CHOL Pain killer (epidural administra- ble phospholipid and, tion) therefore, it may be used in liquid dietetic formu- las as well as in solid a Abbreviations: DMPC: 1,2-dimyristoyl-sn-glycero-3-phosphocholine; DMPG: 1,2-dimyristoyl-sn-glycero-3-phospho- oral forms like hard glycerol; HSPC: hydrogenated soy phosphatidylcholine; CHOL: cholesterol; DSPE-MPEG2000: N-(carbonyl-meth- capsules. Many health oxypolyethyleneglycol 2000)-1,2-distearoyl-sn-glycero-3-phosphoethanolamine; Egg-PC: egg phosphatidylcholine; benefits from GPC are POPC: 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine; DOPS: 1,2-dioleoyl-sn-glycero-3-phospho-L-serine; DPPG: 1,2-dipalmitoyl-sn-glycerol-3-phosphoglycerol; DSPG: 1,2-distearoyl-sn-glycerol-3-phosphoglycerol; DOPC: known, such as its func- 1,2-dioleyol-sn-glycero-3-phosphocholine. tion as a precursor in the synthesis of PC and choline and its ability to lymphoma, and leukemia. Liposomes also have been used as car- stimulate the synthesis and release of the neurotransmitter acetyl- riers of amphotericin B in the treatment of mycotic infections such choline and the secretion of the human growth hormone. as histoplasmosis, cryptococcosis, and candidiasis. Cosmetics. As components of cell membranes, phospholipids The US demand for drug delivery systems using phospho- are important constituents of human skin cells. Their natural occur- lipids is projected to increase more than 10% annually, reaching rence in the skin decreases toward the outer tissues, allowing these about $130 billion in 2012. The advantages of accurate targeting tissues to become more rigid and crystalline and to form an effec- in the treatment of cancer and other debilitating diseases can lead tive barrier against environmental influences. to the development of less toxic, more cost-effective drug delivery Phospholipids are perfect base substances for cosmetic prod- systems. Such reduced toxicity benefits would broaden the usage of ucts. Phospholipids meet the following requirements: (i) They liposome-encapsulated drugs (see Table 1), especially in the areas support the physiology of the skin; (ii) their chemical features cor- of cancer, neurological disorders, and anti-infective therapy. respond to those of endogenous substances; (iii) in terms of physi- Dietetics. Three phospholipids are commercially cost-effective cal features, they build up the same structure (bilayers) as the skin; for dietetics use: PS, PC, and GPC. PS is a natural brain component, and (iv) they are powerful active agents. PC has long been used in comprising up to 20% of membrane phospholipids in brain cells. cosmetics and cosmeceuticals as a delivery vehicle for active ingre- Due to its prevalence in brain tissues, most researchers have con- dients such as vitamins A and E, coenzyme Q10, whitening agents, centrated their work on identifying the effects of PS on brain func- and anti-inflammatory ingredients. PC improves chemical stabil- tion. PS positively influences the synthesis of the neurotransmitter ity, uptake and efficacy of actives, and because of its high water- acetylcholine and restores its release back to a normal level in aged binding capacity, is an efficient external moisturizer to help keep people. As a result, PS from vegetable sources (lecithin) produces the skin supple, firm, and healthy. PC containing unsaturated fatty beneficial effects in neuronal transmission and may improve age- acids may be rich in so-called essential fatty acids (EFA). Some related memory deficiencies. PS has been demonstrated to influence EFA cannot be synthesized by human cells and need to be supplied the ratio of cholesterol and phospholipids in brain cell membranes, via the oral or topical route. EFA deficiency in humans is often thereby ensuring sufficient membrane fluidity. associated with skin aging and can lead to a dry, scaly appearance PC acts as a biosurfactant in human lipid metabolism. It is and a loss of elasticity and barrier integrity. Thus, PC is an impor- responsible for nutrient absorption from food by functioning as a tant tool for the external supply of EFA to aging skin or for persons natural emulsifier for ingested lipids. PC interacts with lipoprotein suffering from malnutrition, acne, and other diseases affecting the in the blood; it binds specifically to HDL, thereby increasing their skin lipid metabolism. surface and transport capacity for free cholesterol. Also, PC acti- Molecules of PC containing saturated fatty acids are more vates an enzyme (LCAT: lecithin:cholesterol-acyltransferase) that crystalline and less flexible than molecules of PC containing catalyzes the conversion of free cholesterol to cholesteryl linoleate, unsaturated fatty acids and are beneficial in cosmetics for their which is easier to metabolize and, as result, less prone to stick to CONTINUED ON PAGE 800 arterial walls. Being an essential constituent of the human gastric Welcome New Members Your Global Fats and Oils Connection

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Robert B. Ainscow, Jl Technologies Keri Kwong, Health Canada Asima Shahzadi, University of Alberta Ramez Alhazzaa, University of Tasmania Stearns la Seur, IV, Texas Womens Megha Sharma, Texas Womans University Emad S. M. Ameen, Intl Islamic University Ann H. Shaw, Louisiana State University University Malaysia Wanda L. Ledford, Ampro Laboratories Carter M. Silvernail, Ecolab Inc James R. Bell, Cargill Inc Inc David B. Smith, Louis Dreyfus Natasha Berry, Ryerson University Qingruisi E. Li, University of Illinois Agricultural Industries David Bressler, University of Alberta Ning Luo, Biobased Technologies LLC Xiuxhi (Susan) Sun, Kansas State Ri chard Chapas, Battelle Nicholas J. Magazine, Louisiana State University Xue Chen, University of Alberta University Loon Yee Tan, Integrated Fortune Sdn Bhd Kasturi S. Chitre, Texas Womans University Elizabeth H. Malola, Rose-Hulman Inst of Patti E. Tanner, Stratas Foods Adebola T. Coker, Mississippi State Technology Michael C. Thiede, Cargi ll Inc University Sunil 0. Manaktala, Kumar Metal Industries Patricia Tometich, UNl-NABL Center Donna Dean-Zavala, Blue Diamond Vinia 0. M arquez, Quality First Tu Tran, Ryerson University Growers International Inc Cristina Trombetta, M erloni Progetti SpA Arthur H. DJang, Sante International Inc Sergio I. Martinez Moneagudo, University Ike Ukwu, Alpha Medical Systems Inc Brett Doney, Great Falls Development of Alberta Pierre Verdellet, Bunge Europe Authority Priyanka Mathur, Texas Womens Jeff 0. Vidanes, Blue Diamond Growers Nancy C. Easterbrook, Air Products & University Rossana Villa Rojas, Universidad de Las Chemicals Inc Lana C. A. M azzone, Univ Federal Do Ameri cas Puebla Susan Ehrlich, W R Grace & Co Rio Grande Do Sul Robert E. Ward, Utah State University loannis Falagas, Soya Hellas SA D. Julian M cClements, University of Rona ld R. Watson, University of Arizona David Feder, Polytechnic Institute of NYU Massachusetts Carol M. White, Archer Daniels Midland Shrey Garg, University of Minnesota Kathleen M. Morlok, Land O ' Lakes Co Adel H. R. Ghabour, Richardson Oilseed Ali Abdalgadir Mustafa, Univerisit Putra R. Terry Williams, Ventura Foods LLC Processing Malaysia Meizhen Xie, Oklahoma State University John R. Graves, Lumen Renewable Fuels Muhammad A. Naqvi, Ryerson University Young-Keun Yeo, Kyungpook National LLC Todd Nelmark, O xiteno USA LLC University Michael (Scott) Greer, University of Peter Q. Nguyen, Barleans Organic O ils Huaixia Yin, Louisiana State University Alberta Stephen M. O 'Connor, Clariant Corp Hamid Zaman ian, Kesht Va Sanate Renuka T. Gupta, Ryerson University Conor J. O'Hara, CUNO Inc Golbahare Sepahan Gunduz Guzel, Aarhus University David Olander, Corto O live Jinwei Zhang, Newcastle University Maan Hayyan, University of M alaya Ann Owens Merlo, Dow AgroSciences Ying Z hang, University of Alberta Melanie Heckman, University of Illinois Graham Paarman, Paarman Foods Zul llham B. Zulkiflee Lubes, Kyoto Lam (Ricky) Sze Ho, University of Andriene A. Patterson University Saskatchewan Daniel P. Pfister, Iowa State University Mohamed Ali Hourieh, University of David Pink, St Francis Xavier University To become a member of the AOCS, com Aleppo Mamata Pradhan, Ryerson University plete, sign, and fax back the membership Chia-Ping Hsu, Martek Bioscience Corp Susa n K. Raatz, USDA Human Nutrition application in this issue or contact us. Mo Jiang, University of Illinois Research Ctr Tamaratina Jombai, Louisiana State Moumita Ray, Ryerson University AOCS University Meghan Reynolds, UNl-NABL Center Barb Semeraro Ashita Kapoor, M cGill University Hayley J. Rutherford, University of Area Manager, Membership Namrata Karki, Louisiana State University Saskatchewan Phone: + 1-217-693-4804 Jegannathan Kenthorai Raman, University Eric M. Salm, University of Illinois E-mail: [email protected] of Malaysia Sabah Lanny Sapei, Ryerson University Website: www.aocs.org Godlisten G. Kombe, University of Dar Es Gabriela M. Sekosan, Bunge North Sa laam America

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Keshun Liu cooperation on soybean science and technology. A Continuing Committee consisting of representatives from different regions of the world offers guidance to the conference planners as they The 8th World Soybean Research Conference develop each event. Previous meetings focused mostly on breeding and production. Since the sixth meeting, however, there has been (WSRC) was held on August 10–15, 2009. The 2,176 more coverage on processing, utilization, and global trade. participants from 38 countries set a new atten- The Chinese Academy of Agricultural Sciences (CAAS) and dance record for the conference. The meeting Crop Science Society of China hosted this year’s conference. Primary organizers included the Institute of Crop Science and included 19 plenary talks, 329 symposia presen- CAAS; co-organizers included a number of national soybean tations, 34 forum presentations, and 693 posters. associations. The conference also received support from the These presentations covered all aspects of the Ministries of Agriculture and of Science and Technology, the People’s Republic of China; and a few other institutions or soybean value chain, including germplasm, breed- associations. Corporations sponsoring the conference included ing, molecular biology, biotechnology, physiology, Shengfeng Technology Co., Vitasoy, Monsanto, Bayer Crop cultivation, field management, crop protection, Science, Jouyang Co., Dalian Commodity Exchange, American Soybean Association International Marketing/United Soybean storage, processing, utilization, and supply and Board, Pioneer, Syngenta, Wilmar International, Chinese Seed trade. There were soy industry forums and soy Industry, and China-Agri Seed Co. producer forums, as well as more than 40 indus- PLENARY SESSIONS trial exhibitors. The welcoming ceremony on Monday evening was followed by the opening ceremony Tuesday morning, and then a number of plenary BACKGROUND sessions. Additional plenary sessions ran in the early morning WSRC has run every five years since its inception in 1975. The session each day. conference is aimed at promoting international exchanges and In the plenary session on Tuesday morning, Eric A. Kuene- man of the Crop Production and Protection Division, Food and Agricultural Orga- nization, discussed the conference theme, “Developing a global soy blueprint for a safe, secure, and sustainable supply.” He said that agricultural productivity must double by 2050 to meet growing food needs and that soybeans will contribute to satisfying this need. While soybeans are less economi- cally viable as a biofuel feedstock as compared with some

Opening ceremonies for the 8th World Soybean Research Conference (WSRC). 798 inform December 2009, Vol. 20 (12)

other oilseeds, market expansion for soy oil and meal will be driven China has dual benefits, reducing malnutrition for the poor and pre- by strong income growth in developing countries, especially in venting chronic disease for the rich. Also on Thursday, M.C. Fung Asia. At the same time, opportunities exist for expansion of the showed the potential of soy as anticancer drug, and Mark Messina total area devoted to soybean production, particularly in South stated that women who consume soy foods at young ages have pre- America and in the favorable savannahs of Africa. Increased yield, ventive effects on breast cancer in their later lives. though, will be the principal means of meeting future demand. In the area of processing and utilization, strong emphases were In another plenary session on Tuesday, Philippe de Lapérouse of placed on industrial use of soy, soy and aquaculture, modern pro- HighQuest Partners gave a presentation entitled “The U.S. soybean cessing technology, and traditional processing and modernization. industry, production and processing to meet world demand.” He In the session on industrial use of soy held Friday evening, speakers stated that, although the United States continues to be the world’s showed that through modification, soy can be used as a cosmetic largest producer and exporter of soybeans, in recent years the ingredient, plywood glue, industrial lubricant, plastic, and biodie- leading producers in South America, Brazil, and Argentina, have sel. Many of these products have been commercialized success- been steadily gaining, both in terms of production and exports of fully in the United States and Europe. soybeans and soy products. The US soy industry faces challenges In the soy and aquaculture session, several speakers, includ- and opportunities, including ethanol-fueled demand for corn (which ing the author of this report, talked about the reasons for and competes with soybeans for acreage), volatility in the value of the success of using soy proteins to replace fishmeal in raising various US dollar (which affects the competitiveness of US commodities in species of fishes. Clearly, development of plant protein, particu- export markets), rapid consumer adoption of trans-fat-free edible larly soy protein, for fish feed is an emerging issue in the global oils, a dramatic increase in the use of vegetable oils for biodiesel feed industry. production, volatility in dry bulk shipping markets, and continued Modern processing technologies, such as extrusion, hydrolysis growth in world demand for vegetable oils and proteins. of soy protein into peptides, alternative protein extraction methods, and methods for extracting nutraceuticals were well covered, while SOY NUTRITION, PROCESSING, AND modernization of traditional soy foods such as soymilk and tofu UTILIZATION was also discussed. In addition, for the two sessions on processing and value-added utilization of specialty soybeans, various As in the last two conferences, this year’s event included a number types of modified soybeans, obtained through traditional breed- of presentations addressing the areas of processing and utiliza- ing or biotechnology, were discussed. These included soybeans tion, as well as nutrition and health benefits. There were also ses- with modified fatty acid composition, soybeans with modified oli- sions on specialty soybeans and their processing, exemplifying gosaccharides, isoflavones, lipoxygenase-null beans, natto beans, the interaction between quality trait breeding and end use values. and edamame beans. There were three sessions covering the nutritional significance and health benefits of soy. FIELD TRIP, SOCIAL EVENTS, AND AWARDS In the Wednesday plenary session, Susan Ho of the Chinese University of Hong Kong showed the importance to bone health of A field trip on the afternoon of the 13th allowed participants to fortifying soymilk with calcium. In the Thursday plenary session, visit the campus of CAAS and tour the soybean research fields, C.M. Chen emphasized that increased consumption of soy foods in laboratories for molecular genetics and breeding, and facilities for

One of a number of entertaining performances during the WSRC’s Beijing Night. Meeting Report inform December 2009, Vol. 20 (12) 799

germplam storage. The Beijing Night on the evening of 14th was a showcase for Chinese foods and cultures. Participants tasted a variety of delicious food while watching performances that included Shaolin martial arts, magic, acrobatics, Beijing opera, a face-changing show, and traditional Chinese or modern dances. One of the most enjoyable moments of the event came when the audience was invited to dance on stage with the performers. During the closing ceremony on the 15th, WSRC for the first time recognized some meeting attendees with awards. Those recognized included Richard Bernard, a retired ARS soybean breeder, for his contribution in collecting and breeding edible soybeans. For more information on the next conference—which will next be held in Durban, South Africa, in 2013—visit www.wsrc2009. cn/en/index.asp. inform Contributing Editor Keshun Liu is a research chemist with the US Department Agriculture, Agricultural Research Services (Aberdeen, Idaho, USA). Contact him at [email protected]. Attendees visit the exhibit area at WSRC. 800 inform December 2009, Vol. 20 (12)

INDUSTRIAL OIL CROPS (CONTINUED FROM PAGE 751)

Although it is unlikely that there will be a sudden surge in industrial To meet these aspirations, it will be desirable to make use of demand for plant oils over the next few years, it is virtually certain all available plant breeding methods, as well as to continue with that the coming decades will see a gradual but steady increase in efforts to understand the biochemical and cellular processes that the use of oleochemical feedstocks across all sectors. underlie oil accumulation, and related aspects of nonstorage lipid This developmental timescale—measured in decades rather metabolism in plant tissues. As we have learned over the past two than months or years—is ideal for a series of new programs to decades, none of our current breeding or engineering methods are develop improved industrial oil crops using the many new biotech- particularly rapid, but neither is the required timescale for com- nologies now at our disposal. It may take another decade or so to mercializing the new generation of industrial oil crops. By invest- resolve the problem of producing transgenic crops with 70–90% ing relatively modest sums now in applied breeding R&D for new levels of a given FA. Recent progress in this area of research has oil crops and in basic lipid metabolism studies, we could lay the been encouraging, but we still have a long way to go from typical groundwork for the development of sustainable and environmen- current best levels of 25–30%. tally friendly plant-based hydrocarbon feedstocks. Such feedstocks Increasing oil yields will be equally challenging. The best tem- will surely become increasingly needed as fossil carbon resources perate oilseed crops currently yield about 1 metric ton (MT)/ha, become depleted during the rest of the 21st century. but that figure is based on a seed oil content of 40%, which could be increased toward values of 60–70% already found in some nuts. inform Contributing Editor Denis J. Murphy is profes- Oil yields of the major global crop, oil palm, are currently about 4 sor of biotechnology at the University of Glamorgan MT/ha, but trees are available that can yield more than 10 MT/ha. (United Kingdom). He also works as an advisor with If we can increase global oil yields by 50% and improve FA purity the United Nations Food and Agriculture Organization in plant oils, there will be sufficient production to meet demand for and as a consultant in the wider oil corps industry. edible oils and also to sustain a significant growth in price-compet- Contact him at [email protected]. itive feedstocks for a widening range of industrial uses.

DDGS (CONTINUED FROM PAGE 791) quality of co-products. As these process modifications are vali- been rapidly expanding in response to increased demand. This dated and commercially implemented, improvements in the gen- means there will be many opportunities for those involved in erated co-products will be realized, and unique materials (such process and product development to help add value to the process- as high-protein, low-fat, and/or low-fiber distillers grains) will be ing residues—the co-products known as distillers grains. produced as well. Kurt A. Rosentrater is lead scientist, Agricultural and CONCLUSION Bioprocess Engineer, US Department of Agriculture, Ethanol is not the entire solution to our energy needs, but it is a key Agricultural Research Service, North Central Agricultural component to the bigger picture of energy independence. Support Research Laboratory (Brookings, South Dakota, USA). for ethanol has been growing over the years, and the industry has Contact him at [email protected].

A PHOSPHOLIPIDS PRIMER (CONTINUED FROM PAGE 795) stabilizing and regenerating effects on the skin-lipid barrier. PC combination with other active substances, are offering new poten- helps to maintain or restore normal barrier function in dry or sen- tial markets. sitive skin. Further, incorporation of PC containing saturated fatty acids into organic sunscreens improves their water resistance. Moghis Ahmad’s expertise is in synthetic lipid chemistry. Currently he is the vice president of Chemical SUMMARY Technology and Manufacturing at Jina Pharmaceu- Every phospholipid has its own specific application profile. Exten- ticals Inc. (Libertyville, Illinois, USA). He has been sive scientific studies have demonstrated the effects on the human an active member of AOCS for more than 30 years. body that can result from the nutritional action of phospholip- At present he is chairperson of Phospholipid Divi- ids, such as PS as a brain cell nutrient, PC for liver cell regenera- sion and vice president of the International Lecithin tion, soy phospholipids for lipid-reducing effect, and hydrogenated and Phospholipid Society (ILPS). He can be reached at Moghis@ phospholipids as a basis for production of stable liposomes. Further jinapharma.com. tailor-made products produced from natural phospholipids, in . " - . ( ·=- · ·=· J

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