inform November 2009 www.aocs.org Volume 20 (11) 677–736

International News on Fats, Oils, and Related Materials Enhanced oil recovery stages a comeback

ALSO INSIDE: Olive oil quality control Kosher food regulations Rapeseed meal processing C2 inform November 2009, Vol. 20 (11) Genencor4 and you- a partnership of possibilities

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.OVEMBER6OLUME n

On the cover: Harweel enhanced oil recov- ery project in Oman in 2008. Photo courtesy of Shell.  Chemically enhanced Departments oil recovery stages a and Information comeback 680 Index to Advertisers Will enhanced oil recovery disrupt the surfactants market? Catherine Watkins reports. 680 Calendar Kosher food regulations Marketplace:  Joe M. Regenstein guides us through the various aspects of the kosher market, including its dietary laws and their effect on how food 689 News & Noteworthy processing equipment is used. 695 Biofuels News 699 Health & Nutrition Kao suspends DAG oil shipments  Catherine Watkins provides an update on Kao Corp.’s temporary News SUSPENSIONOFSHIPMENTSOF$!'DIACYLGLYCEROL OILPRODUCTS 702 Biotechnology News Making the most of your meeting experience 705 S&D News  )NTHISMONTHSPREVIEWOF!/#3ST!NNUAL-EETING%XPO 707 Student Page !-% #ATHERINE7ATKINSOFFERSTIPSTOENHANCETHE!-% 708 People News/ experience. Inside AOCS Outtakes from the history of AOCS 708 In Memoriam  )NPARTTWOOFASERIES !/#3#ENTENNIAL(ISTORIAN'EORGE7ILLHITE rounds up the stories that failed to make the cut for his yearlong history of AOCS. 719 Classified Advertising 31P NMR spectroscopy on olive oil quality control Publications:  and authentication Photis Dais details a new approach to quality control and 711 Book Review authentication of extra virgin olive oil. 712 Patents 715 Extracts & Distillates Fluidized bed desolventizer for gentle rapeseed  meal processing 4HEFOURTHINAPERIODICSERIES THISARTICLEBY+ARL (EINZ,EIDT ,OTHAR-ÚRL &RANK0UDEL +LAUS7EIGEL AND2EINHARD:ETTLISBASED ONAPRESENTATIONGIVEN7EDNESDAY -AY INTHE0ROCESSING%XHIBITOR 3ESSIONATTHETH!/#3!NNUAL-EETING%XPO AOCS Mission Statement To be a global forum to promote the exchange of ideas, Leptin: A novel target for reducing the risk of information, and experience, to enhance personal excel- lence, and to provide high standards of quality among those  heart disease in obesity with a professional interest in the science and technology 3HERMA:IBADIAND2ONALD2OSS7ATSONEXAMINETHEPOSSIBILITYOF of fats, oils, surfactants, and related materials. leptin-modulator therapeutics in preventing or lessening adverse cardiac remodeling and dysfunction in obese populations. informs)NTERNATIONAL.EWSON&ATS /ILS and Related Materials )33. )&2-%# n 680 inform November 2009, Vol. 20 (11) Editor-in-Chief Emeritus: *AMES"-2ATTRAY Bold type new listing For details on these and other upcoming Calendar meetings, visit www.aocs.org/meetings. 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Catherine Watkins

Nobody knows how much petroleum is left in the ground; estimates range from one trillion to four trillion barrels. Current global produc- tion of petroleum is about 85 million barrels/day (bbl/d), or more than 30 billion bbl/year. OPEC (the Organization of the Petroleum Exporting Coun- tries) expects demand by developing countries to increase global production to 107 million bbl/d by 2030. Here is one more statistic that signals unparalleled opportu- nity for surfactants researchers and manufacturers: Only about 30% of available oil and gas has been extracted from most exist- ing wells. That leaves chemically enhanced oil recovery (CEOR) on the short list of methods available to boost oil production in the secondary and tertiary phases of oil recovery (see sidebar, page 684). Some industry observers are leery of such talk. They remem- ber the research boom in the 1970s and 1980s when the oil crisis pushed up the price of oil and research flourished. They also 682 remember the bust that occurred once oil prices fell. CEOR in the 21st century, however, is significantly different: Custom-made surfactants used at much lower concentrations in tandem with new technology have dramatically changed the outlook. “Shell is quite bullish on surfactant-based CEOR,” Kirk Raney, a senior staff research engineer at Shell International

inform Exploration and Production Inc. in Houston, Texas, USA, explained. “We feel CEOR is a large prize that will maximize

2009 our existing resources and will be an important component of meeting the world’s energy challenge.” Shell is not alone in that belief. Celanese, Rhodia, Tiorco (Stepan’s joint venture with Nalco), Sasol, Oil Chem Technolo- gies, and Surtek are just a few of the participants in the CEOR market anticipating future growth. All of them are bullish about Construction at the Qarn Alam enhanced oil recovery project in CEOR and happy to explain why. Oman in 2008. Photo courtesy of Shell. November Enhanced Oil Recovery

ECONOMICS We also have large branched surfactants available at relatively low cost. In addition, we have developed a process to use sul- The development that most affects the economics of CEOR in fates, as opposed to sulfonates, that can be employed at high the 21st century is the change in the concentration of surfactants temperatures.” used in reservoir flooding. CEOR in the 1970s and 1980s focused The UT scientists are working with Shell, BASF, Harcros on “micellar” flooding with 2–12% surfactant. Now, the surfac- Chemicals, Huntsman, Stepan, and others to commercialize the tant concentrations “are in the range of only 0.1–0.5%,” said Kon many products developed in their laboratory—which points to Wyatt, vice president of engineering at Surtek Inc. in Golden, another difference between the CEOR boom of the 20th century Colorado, USA. As a full-service firm, Surtek has provided engi- and the current boom: “During the first boom,” Pope said, “there neering, laboratory, and operational expertise since 1978 to oil was a complete disconnect between oil companies and chemical companies seeking to improve oil recovery. companies, even when it was the same company.” “The bottom line is that the new surfactant formulations cost in the range of $0.90–$2.75/bbl injected, where a micellar for- mulation would cost $20–$75/bbl injected at today’s chemical OTHER NEW WORK costs,” Wyatt noted in a recent article in The American Oil & Gas Another prominent CEOR researcher is AOCS member and Reporter (52:102–105, 2009). “Establishing a successful CEOR Samuel Rosen Memorial Award-winner Paul Berger, who is vice operation is a long-term commitment, but the rewards can be president and technical director of Oil Chem Technologies, Inc., substantial and long-lived, even at oil prices as low as $20–$25/ in Sugar Land, Texas, USA. The company recently was listed as bbl.” No. 2 on Inc. magazine’s 2009 list of fastest-growing companies in the energy sector, up from No. 6 the previous year. FIRST WAVE OF RESEARCH Oil Chem has been working since 1995 on CEOR and cur- rently has 20 active projects with an annual recovery of up to One longtime CEOR researcher who was involved in the first one million barrels of oil. To date, the company has successfully wave of CEOR research is Gary Pope, a professor in the Depart- injected more than 50 million pounds of surfactants at oilfield ment of Petroleum and Geosystems Engineering and director projects all over the world. In a recently completed Canadian of the Center for Petroleum and Geosystems Engineering at CEOR project, the oilfield went from producing 300 bbl/d to The University of Texas at Austin (UT; USA). Pope, who once producing over 2,000 bbl/d, an increase of more than 600%. worked at Shell, counts among his staff AOCS member and “We are starting to look at very high-molecular-weight glyc- Samuel Rosen Memorial Award-winner Upali Weerasooriya, erides (C –C ) from vegetable oils such as rapeseed, sunflower, who is director of surfactant development for the center. 18 24 safflower, meadowfoam, jatropha, and another I can’t talk about Pope points first to the surfactants used in the 1970s, when petroleum sulfonates were the surfactants of choice. “Now we know what the molecular structures are and how to vary them,” he said. “Those structures can be made at about the same cost, information or even less, than before, mostly at under $2/pound,” he added. Then there are the differences in the scope and speed of Q 4WOPRESENTATIONSFROMTHE!/#3!NNUAL-EETING research. In the old days of CEOR, petroleum companies would %XPOMENTIONEDINTHISARTICLEAREAVAILABLEONLINETO!/#3 put 20 staff members on a pilot study for two years. “At today’s 3URFACTANTSAND$ETERGENTS3$ $IVISIONMEMBERS4HEY cost that would be about $20 million in labor alone at $500,000/ - person/year,” Pope noted. Now, with high-throughput methods ARE0AUL"ERGERAND#HRISTIE,EESTALKONVISCOELASTICSURFAC and a willing graduate student, the same project can be completed TANTSAND#HARLES(AMMONDAND'EOFF2USSELLSPRESENTATION in about three months, he said. ONADJUSTINGOPTIMUMSALINITYOFANIONICMICROEMULSIONSUSED The UT Center currently has separate funding for 16 proj- in enhanced oil recovery. The slides are available at www. ects, including surfactant selection for CEOR at Cairn India’s AOCSORGMEMBERDIVISIONSURFACT4OJOINTHE3$$IVISION large oilfield in Rajasthan. In addition, the group has worked with ORFORHELPACCESSINGTHEPAPERS CONTACT$OREEN"ERNINGAT many companies all over the world. Interest in collaborating with DOREENB AOCSORGOR     683 the Center has accelerated in the last six months, Pope reported. Q A presentation by Gary Pope of the University of Texas at “Once the price of oil hit $50 again [after a low of around $35 in !USTINENTITLEDh/VERVIEWOF#HEMICAL&LOODINGvCANBEFOUND March 2009], interest just exploded,” he said. ATHTTPEORIGGUWYOEDUDOWNLOADS/VERVIEWOF Further changes differentiating CEOR efforts in the 1970s CHEMICAL%/2PDF and 1980s from the present, according to Pope and Weerasooriya, Q "ARNES *2 *03MIT *23MIT 0'3HPAKOFF +(2ANEY include advances in polymer science as well as in oil drilling and M.C. Puerto, Development of Surfactants for Chemical technology, with horizontal well drilling, advanced reservoir &LOODINGAT$IFlCULT2ESERVOIR#ONDITIONS 0APER30%3OCIETY characterization, and 3D seismic exploration now available in OF0ETROLEUM%NGINEERS  -3 PRESENTEDATTHE30% the oil recovery toolkit. $EPARTMENTOF%NERGY)MPROVED/IL2ECOVERY3YMPOSIUM Pope and Weerasooriya also point to breakthroughs in the 4ULSA /KLAHOMA 53! ON!PRILn  UT laboratory within the past year. “We now have an alkaline Q ,EVITT $" !#*ACKSON #(EINSON ,."RITTON 4-ALIK that will work in hard brine,” they said, “allowing us to conduct 6$WARAKANATH AND'!0OPE )DENTIlCATIONAND%VALUATION alkaline-surfactant-polymer flooding without softening the water. OF(IGH 0ERFORMANCE%/23URFACTANTS SPE Reservoir Evalua- tion & Engineering 12n  684

Novemberlow cost. of andat high purity specificity relatively surfactants mentation has allowed researchers to custom-make produced. The advent experi- of high-throughput be can modeled and the surfactant most effective lELDISDIFFERENTANDHASTOBECHARACTERIZEDBEFORE 2009PRESSURE DEPTH SALINITY ANDPERMEABILITY%ACHOIL temperature, reservoir as such factors on depends informfactants modified microorganisms produce can that biosur- genetically atusing looking arealso Researchers PATENT53  ILLUSTRATESTHIS v"ERGERNOTED ASBRANCHEDPETROLEUM DERIVEDPRODUCTSh/UR well equally serve bond adouble with surfactants "ERGERAND,EEHAVEFOUNDTHATNATURALLYDERIVED past, the in choice of feedstock the been has ylene micelles andviscosity eth- microemulsions. Although hydrophobeshighly branched are needed for low- SURFACTANTSHAVEPERFORMEDBESTIN%/2)NGENERAL and gum, To scleroglucan. xanthan anionic date, 0OLYMERSUSEDIN%/2INCLUDEPOLYACRYLAMIDE !-03 ACRYL AMIDO  METHYLPROPANESULFONICACID COPOLYMER flow. increasing thereby viscosity, reduces polymer the and tension interfacial the reduces factant CIALLYINLIMESTONERESERVOIRS vTHEYCONTINUE)NADDITION TH espe- formation, the onto adsorption surfactant of amount the IN3UGAR,AND 4EXAS 53!h4HEALKALIISALSOCLAIMEDTOREDUC TO0AUL"ERGERAND#HRISTIE,EEOF/IL#HEM4ECHNOLOGIES )NC PRODUCESYNERGISTICMIXTURESATTHEOILBRINEINTERFACE vACCOR FORMSURFACTANTShTHATCOMBINEWITHTHEINJECTEDSURFACTANTTO oilto crude the in esters and acids with reacts alkali the that MERMIX ORAPOLYMER ONLYINJECTION#URRENTTHINKINGSUGGESTS #HEMICAL%/2GENERALLYINVOLVESmOODINGARESERVOIRWITH combination,a surfactant-poly- an alkaline-surfactant-polymer rate. flow the improving and it thinning thereby used, be can oil the in dissolve that gases Other well. tion NITROGEN ORCARBONDIOXIDE PUS OILANDMAKESITMOREmUID'ASINJECTIONGENERALLYNATURALGA FAVORABLEFOROILDISPLACEMENT4HEINJECTIONOFSTEAMHEATSTH generate fluid conditions or properties interfacial that are more !LLOFTHESEINVOLVETHEINJECTIONOFmUIDSINTOTHERESERVOIR MAINCATEGORIESTHERMAL CHEMICAL ANDSOLVENTDISPLACEMENT %/2TECHNIQUESˆWHICHSOMETIMESAREALSOREQUIREDIN THEPRIMARYANDSECONDARYPHASESOFRECOVERYˆFALLINTOTHREE well. the of out freely more flow oilto the allow to voir system ENHANCEDOILRECOVERY%/2 TECHNIQUESTHATMODIFYTHERESER involves phase tertiary The it. into orgases water by pumping $EPARTMENTOF%NERGY CONSISTSOFREPRESSURIZINGTHERESERVOIR ERY WHICHCANREMOVEANADDITIONALnACCORDINGTOTHE53 recov- Secondary phase. this in removed is oiltypically available VOIRISHIGHANDOILALLBUTSPURTSOUTOFTHEGROUND!BOUT areblurred. often phases three the separating lines the makeup, chemical and logic TERTIARY"UTBECAUSEEACHRESERVOIRHASITSOWNUNIQUEGEO /ILRECOVERYOCCURSINTHREEPHASESPRIMARY SECONDARY AND primer Oil production The decision about which surfactant to use to surfactant which about decision The areser- in pressure internal when occurs recovery Primary in situ . HESADDITIONALOILTOAPRODUC - courtesy of Shell. Photo 2008. Oman in project recovery oil enhanced Alam Qarn the at Construction ESUR OF DING TO S E E - - - - - in Westlake, Louisiana,USA,involves adjustingtheoptimum AOCS memberCharlesHammond, aresearchassociatebased microemulsions thatcanbeappliedtoCEOR.Researchledby solved solidsandhightemperatures. shale, andforreservoirs having highconcentrationsoftotaldis- surfactants forrecovering oilfromtarsands,heavy oildeposits, CEOR projectsworldwide. The company hasalsodeveloped ny’s presentlineofsurfactants isusedinroughly80%ofcurrent perature inthereservoir system.Berger estimatesthatthecompa- for usedependingonthetypeofoil,pH,water hardness,andtem- the shearisremoved.” become lessviscousundershearbut theirviscosityreturnswhen like micellestoasphericalshape,thisprocessisreversible. They high shear, Berger noted.“Although shearconverts theirworm- zones. Unlike polymers, VS arenotpermanentlydegraded by in thereservoir whilemaintaininghighviscosityinthewater contacting oiltohelpthesweepoutofmicroscopicpores with polymers, VS canprovide someresidualviscositywhen in tightformationswithhightemperaturesandsalinities.Used bility, henoted. They areparticularlyusefulwhenusedalone the reservoir, Berger said. They alsoexhibit highthermalsta- oil, allowing injectionfluidstoflow intooil-bearingportions of fluids tooil-bearingsitesbyreducingviscositiesasthey contact tension tobelow 0.01millinewtons/meter. They divert injection solutions ininjectionfluidsat0.1–1.0wt%,reducinginterfacial that areresistanttohighsalinitiesandtemperatures. tants.’” They arealsousedtomake novel anionicethersulfonates staying insolutionthewater—we callthem‘smartsurfac- “Viscoelastic surfactants actuallyseekouttheoilratherthan salinity andtemperatureswherepolymerswon’t work,” headded. surfactants thatcangive youviscosityinreservoirs withhigh just yet,” saidBerger. “They canbeusedtomake viscoelastic In otherwork, SasolNorth America Inc.isinvestigating Oil Chem Technologies isdeveloping five majorlinesof VS Oil Chem’s viscoelasticsurfactants (VS)formviscoelastic November 2009 inform 685 p- troleum troleum and can be reached inform and oils Natural fats But are the major petroleum companies ready to gamble ready to gamble But are the major petroleum companies by oil companies “There is a tremendous amount of interest There is good reason for oil companies to be cautious about that make molecules more efficient Nonetheless, with new, sold the oil compa- years, we have it has taken “Although Tulsa, Oklahoma,Tulsa, USA, 2008. Shaded April boxes: 19–23, Shell Catherine Watkins is associate editor of of editor associate is Watkins Catherine of most interest to CEOR researchers today are different than than are different of most interest to CEOR researchers today industry,” scale in the detergent those currently produced at large is used to manufacture he added. “Therefore, if current capacity for CEOR, changes to the process will be needed.” surfactants again on CEOR? for CEOR so that when the price of oil in doing the groundwork of sales director Waldman, Tom said ready,” are increases, they Colorado, USA, which pro- of Denver, Tiorco for and marketing is a Tiorco for EOR. vides custom-engineered chemical solutions formed in September 2008 by Stepan Co., a surfac- joint venture located in Northfield, Illinois, USA, and Nalco, tant manufacturer based in Naperville, Illinois. treatment company a water and it is a huge finan- is slow CEOR. “The return on investment oilfield, director, global business noted Bob Krueger, cial risk,” can spend $50 million on flood-pumping company for Stepan. “A equipment and chemicals and not see the first return on invest- days to about five ment for 24 months. By comparison, it takes he added. drill 10,000 feet,” more economic sense than before, CEOR clearly will—slowly industry. surely—alter the surfactants but in place of some nies on the idea that using chemical energy Krueger effect,” a net-net positive can have mechanical energy concluded. at [email protected]. at Enhanced Oil Recovery Oil Enhanced ). [See Fig. 1 for a produc- 16 ) could eventually be as high be as high ) could eventually 28 –C –C 10 14 Different routes to surfactants. Source: Barnes, J.R., Smit, J.P. J.R. Smit, Shpakoff, K.H. P.G. and M.C. Raney, Puerto, Develo “With the ever-growing need for energy, and the high and the high need for energy, the ever-growing “With “Assuming oil prices stay at least at current levels, several several oil prices stay at least at current levels, “Assuming MARKET POTENTIAL use in CEOR is substantial. potential for surfactant The market suggests that annual demand Kirk Raney One analysis by Shell’s for CEOR (C for surfactants volume of hard-to-obtain oil underground, CEOR is inevitable,” CEOR is inevitable,” of hard-to-obtain oil underground, volume tertiary methods there are several Hammond said. “Although that there is great we believe to pursue oil recovery, available is Olefins & Surfactants Sasol In fact, potential for surfactants. structure–property on generating fundamental surfactant working manufacturers will be needed by both surfactant that knowledge continues to grow.” and formulators for CEOR as this market salinity of anionic microemulsions with alcohol ethoxylates. His ethoxylates. His salinity of anionic microemulsions with alcohol Meeting & Expo illus- Annual AOCS presentation at the 2009 propoxylate sulfates trated that the optimum salinity of alcohol ethoxylates and influ-can be shifted by the addition of alcohol of alcohol ethoxylation, the concentration enced by the degree group. the alkyl of alcohol ethoxylate, and the structure of FIG. 1. 1. FIG. ment of Surfactants for Chemical Flooding at presented Difficult at the Society Reservoir of Pe Conditions, SPE-113313-MS, Paper Engineers/Department Energy Recovery Symposium, of Oil Improved surfactants and routes commercial Chemical large surfactant floods are scheduled by the oil industry to occur by the oil industry to occur floods are scheduled surfactant large said. “Each could consume Raney in the 2015–2020 time frame,” per year on the order of 25,000–50,000 metric tons of surfactant of demand would This projected level at full implementation. market. a significant impact on the synthetic surfactant make hydrophobes it is important to note that the surfactant However, tion route flowchart.] as 12.5 million metric tons (MMT)/year. That figure is roughly That figure is roughly as 12.5 million metric tons (MMT)/year. around 6 demand of market total surfactant double the existing MMT/year (predominantly C 686 inform November 2009, Vol. 20 (11) Kosher food regulations

Joe M. Regenstein THE KOSHER MARKET The number of actual consumers of kosher food in the United The kosher dietary laws determine which foods States, that is, those who specifically look for the special kosher are “fit or proper” for consumption by Jewish con- mark found on food products, is estimated to be about 8 to 10 million. Only about one-third of the kosher consumers are Jewish; sumers who observe these laws. The laws come other consumers include Muslims, Seventh-Day Adventists, veg- mainly from the original five books of the Hebrew etarians, people with various types of allergies (particularly dairy, Scriptures. Over the years, the details have been grain, and legume), and general consumers who value the quality of kosher products. interpreted and extended by rabbis (“teachers”) to protect the Jewish people from violating any of THE KOSHER DIETARY LAWS the fundamental laws and to address new issues The kosher dietary laws predominantly deal with three issues, all and technologies. The Jewish laws are referred to in the animal kingdom: r BMMPXFEBOJNBMT collectively as the “halacha.” r QSPIJCJUJPOPGCMPPE Why do Jews follow these dietary laws? Many explanations r QSPIJCJUJPOPGNJYJOHPGNJMLBOENFBU have been given. The following by Rabbi Grunfeld is possibly However, for the week of Passover (in late March or April) the best-written explanation and summarizes the most widely held restrictions on “chometz” (the five prohibited grains), and the ideas about the subject: rabbinical extensions of this prohibition to other plant materials “‘And ye shall be men of a holy calling unto Me, and ye shall (especially corn, rice, and soya), lead to a whole new set of addi- not eat any meat that is torn in the field’ (Exodus 22:30). Holiness tional regulations, focused in this case on the plant kingdom (called or self-sanctification is a moral term; it is identical with . . . moral “kitnyot”). freedom or moral autonomy. Its aim is the complete self-mastery In addition, there is a separate set of laws dealing with grape of man. juice, wine, and alcohol derived from grape products. Basically, “To the superficial observer it seems that men who do not obey these must be handled by Sabbath-observing Jews. However, if the the law are freer than law-abiding men, because they can follow juice is pasteurized (heated, or “mevushal” in Hebrew), then this their own inclinations. In reality, however, such men are subject juice can be handled as an ordinary kosher ingredient. to the most cruel bondage; they are slaves of their own instincts, impulses, and desires. The first step towards emancipation from ALLOWED ANIMALS AND PROHIBITION the tyranny of animal inclinations in man is, therefore, a voluntary OF BLOOD submission to the moral law. The constraint of law is the begin- ning of human freedom. . . . Thus the fundamental idea of Jewish Ruminants with split hoofs, the traditional domestic birds, and fish ethics, holiness, is inseparably connected with the idea of Law; and with fins and removable scales are generally permitted. Pigs, wild the dietary laws occupy a central position in that system of moral birds, sharks, dogfish, catfish, monkfish, and similar species, along discipline which is the basis of all Jewish laws. with all crustacean and molluscan shellfish, are prohibited. Insects, “The three strongest natural instincts in man are the impulses with a few exceptions, are also prohibited. Consequently, carmine of food, sex, and acquisition. Judaism does not aim at the destruc- and cochineal (natural red pigments derived from insects) are not tion of these impulses, but at their control and indeed their sanc- used in normative, mainstream kosher products. tification. It is the law which spiritualizes these instincts and With specific respect to poultry, the traditional domestic birds transfigures them into legitimate joys of life.” (chicken, turkey, squab, duck, and goose) are kosher. Birds in the ratite category (ostrich, emu, and rhea) are definitely not kosher. These and most other birds are prohibited. Furthermore, ruminants and fowl must be slaughtered accord- information ing to Jewish law by a specially trained religious slaughter man. These animals are also subsequently inspected by the rabbis for various defects. In the United States a stricter inspection require- For further reading: ment, mainly with respect to the lungs, has been developed. It is Q 'RUNFELD ) The Jewish Dietary Laws 6OL 4HE3ONCINO referred to as “glatt (smooth) kosher.” This higher standard applies 0RESS ,ONDON 5NITED+INGDOM  PPn mainly to red meats where lung adhesions are a problem and often Q 2IAZ -. AND--#HAUDRY 4HEVALUEOF(ALALFOOD make an animal not kosher (“treife”). In general, a glatt kosher ani- production, inform 15n  mal’s lungs have fewer than three such adhesions. As it is difficult to examine the lungs of poultry, this is not required. Processing inform November 2009, Vol. 20 (11) 687

All equipment, utensils, and the like must be of the proper cat- egory, and anything run through the equipment takes on that status of the equipment. Some kosher supervision agencies do permit such a product run on dairy equipment without any dairy ingredi- ents to be listed as “dairy equipment (DE).” With the DE listing, the consumer can use the product immediately after a meat meal, while a significant wait would be required to use a product with a dairy ingredient. A few products may be marked “meat equipment (ME).” To make the product pareve requires equipment kosheriza- tion (see below). Kosher-observant Jews must wait a fixed time between meat and dairy consumption. Customs vary, but generally the wait after meat before consuming dairy is much longer (3 to 6 h) than the Matzos, or unleavened wait from dairy to meat (0 to 1 h). bread eaten during Passover. PASSOVER During this holiday all products made from the five prohib- The meat and poultry must be further prepared by properly ited grains—wheat, rye, oats, barley, and spelt—cannot be used removing certain veins, arteries, prohibited fats, blood, and the except for the specially supervised production of unleavened bread sciatic nerve. In practical terms, this means that only the front (matzos). In addition, most kosher supervision agencies prohibit quarter cuts of red meat are generally used in Western countries as products derived from corn, rice, legumes, mustard seed, buck- it is often not practical to remove the sciatic nerve. There is no such wheat, and a number of other plants. Ingredients such as corn syrup requirement for poultry, and the entire carcass can be used. and corn starch are also prohibited. To remove the blood, red meat and poultry are then soaked and salted within a specified time period. Furthermore, any materials EQUIPMENT KOSHERING that might be derived from animal sources are generally prohibited There are three basic ways (with variations) to make equipment in kosher food products because of the difficulty of obtaining them kosher and/or to change its status. The procedure depends on the from kosher animals. Thus, many products that might be used in the equipment’s prior production history. After a plant (or a line) has food industry, such as emulsifiers, stabilizers, and surfactants, par- been used to produce kosher pareve products, it can be switched to ticularly those that are fat-derived, need careful rabbinical supervi- either kosher dairy or kosher meat. sion to ensure that no animal-derived ingredients are used. Almost Materials that only have been used cold require a good caustic/ all such materials are also available in a kosher form and usually soap cleaning. However, materials such as ceramics, rubber, earth- are derived from plant oils. enware, and porcelain cannot be koshered. Most food processing equipment is operated at cooking tem- PROHIBITION OF MIXING OF MILK AND MEAT peratures, defined rabinically as above 48.8°C. To kosher cooking “Thou shalt not seeth the kid in its mother’s milk.” equipment, it must be thoroughly cleaned with caustic/soap, left This passage appears three times in Hebrew Scriptures and is idle for 24 h, and then flooded with boiling water in the presence of thus taken as a very serious admonition. The meat side has been a kosher supervisor. For ovens or other equipment that use “fire,” rabbinically extended to include poultry. The dairy side includes kosherization involves heating the metal until it glows in the pres- all milk derivatives. ence of a kosher supervisor. For some foods, the rabbi must “do” To keep meat and milk separate requires that the processing the cooking, which is often accomplished by having a rabbi light and handling of all products that are kosher will fall into one of the pilot light, which is then left on continuously. three categories: For cheese making, the rabbi must add the coagulating agent. r NFBUQSPEVDUT However, if the ingredients are kosher, but a rabbi has not added the r EBJSZQSPEVDUT coagulant, the whey derived from such cheese would be considered r QBSFWF QBSWF PSOFVUSBMQSPEVDUT JF BMMPUIFST kosher as long as it is removed before reaching 48.8°C. All plant products along with eggs, fish, honey, and lac resin (shellac) are pareve. These pareve foods can be used with GELATIN either meat products or dairy products, except that fish cannot be Gelatin is probably the most controversial of all modern kosher mixed directly with meat. Once a pareve product is mixed with ingredients. Gelatin can be derived from pork skin, beef bones, or either meat or dairy products, the product becomes meat or dairy, beef skin and, more recently, from fish skin and scales. Currently respectively. available gelatins, even if called “kosher,” are not acceptable to Some kosher-observant Jews are concerned with the possi- the mainstream kosher supervision organizations. Some are pork ble adulteration of kosher milk with the milk of other animals gelatin-based. Recent gelatin productions from hides of glatt cattle and require that the milk be watched from the time of milking. have been available in limited supply at great expense. “Cholev Yisroel” milk and products derived from milk are required The most lenient Orthodox Rabbinical view holds that gelatin by some of the stricter kosher supervision agencies for all dairy from bones and skin is not a food (flesh). Further, the process- ingredients. ing includes a stage where the product is “unfit” for a man or dog 688 inform November 2009, Vol. 20 (11)

and as such becomes a new entity. Most not be as critical with respect to the kitnyot gelatin desserts with a generic “K” follow prohibition. this ruling. Consumers should not assume that Other rabbis only permit gelatin from kosher markings ensure the absence of beef bones and hides. Still other rabbis will trace amounts of the ingredient to which only accept “India dry bones.” These bones, they are allergic. Currently what is accept- found naturally in India, are aged for over able for kosher may not meet the needs of a year and are “dry as wood.” But none of allergic consumers but does provide some these products are accepted by the “main- useful guidance. stream” kosher supervisions. Joe M. Regenstein is a professor of food BIOTECHNOLOGY science and head of the Cornell Kosher and Rabbis currently accept products made by Halal Food Initiative at Cornell University, simple genetic engineering, for example, Ithaca, New York, USA. He is also a visiting chymosin (rennin). The production condi- professor at the University of Wisconsin–Mad- tions (equipment and ingredients) in the ison and an adjunct faculty member at Kansas fermentors must still be kosher. The rabbis State University (Manhattan, USA). Contact have not yet determined the status of more him by email at [email protected]. complex genetic manipulations.

KOSHER AND ALLERGIES Statement of Ownership, Management, Two important limitations for those with and Circulation (Required by 39 U.S.C. allergies need to be recognized: 3685) r "QSPDFTTPGFRVJQNFOULPTIFSJ[BUJPO is used to convert equipment from one status to another. This is a well-defined religious procedure but may not lead to 100% removal of previous materials run on the equipment. r ,PTIFSMBXEPFTQFSNJUDFSUBJOex post facto [after the fact] errors to be negated. Thus, trace amounts (less than 1/60 by volume under very spe- cific conditions) can be nullified. DE and ME products, although “free” of dairy and meat, respectively, may be problematic. In a few instances where pareve or dairy products contain small amounts of fish (e.g., anchovies in Worcestershire sauce), this ingredient may (or may not) be marked as part of the kosher supervi- sion symbol. For Passover, there is some dispute about “derivatives” of kitnyot materi- als. In general, the proteinaceous part of these materials is not used. Thus, people with allergies to some plants could pur- chase Passover products from supervision agencies that do not permit kitnyot deriva- tives, or if less sensitive, they would know that no proteins (the normal source of an allergen) were used. With respect to equip- ment kosherization, supervising rabbis tend to be very strict about the cleanup of the prohibited grains (wheat, rye, oats, barley, and spelt), so these should come closest to meeting potential allergy concerns, but may Briefs inform November 2009, Vol. 20 (11) 689

3OYBEANANDCORNPRODUCTIONIN"RAZIL News & Noteworthy INISEXPECTEDTODROPAND  RESPECTIVELY ACCORDINGTOTHE "RAZILIAN)NSTITUTEOF'EOGRAPHYAND Statistics. QQQ There has been a slight increase in the concentration of soybean by-product exports in Argentina, according to El Cronista newspaper. Three compa- NIESˆ#ARGILL "UNGE AND !CEITERA'ENERAL$EHEZA ˆREP- RESENTEDOFSOYOILANDMEALSHIP- MENTIN ASCOMPAREDTOTHEIR COMBINEDSHAREINTHEPREVI- ous year. QQQ The latest forecast from the China .ATIONAL'RAINAND/ILS)NFORMATION Center says the country’s edible oil OUTPUTWILLREACHMILLIONMETRIC TONS--4 INTHEnCROP YEAR UPALMOST--4OVERTHEPRE- vious year. QQQ 2APESEEDPRODUCTIONBYTHE%5 IN ISEXPECTEDTOREACHARECORD --4HARVESTEDFROMMILLIONHECT- ares, according to the US Department Kao suspends DAG OF!GRICULTURES%CONOMIC2ESEARCH Get the latest fats and oils news at www. 3ERVICE,ARGER THAN EXPECTEDYIELDS oil shipments AOCSORG,OOKFORTHENEWSHEADLINESAT IN'ERMANYUP METRICTONS THETOPLEFTOFTHEHOMEPAGE9OUCAN ;-4= 0OLANDUP -4 AND Catherine Watkins also follow inform news at www.twitter. &RANCEUP -4 LEDTOTHE COMTHEAOCS On September 16, Kao Corp. suspended increase. shipments in Japan of its 59 diacylglyc- )NCLUDINGCARRYOVERSTOCKSAND erol (DAG) oil-based products, citing IMPORTS THEnTOTALSUPPLY the presence of glycidol esters. Two days Although glycidol (2,3-epoxy-1-pro- OFRAPESEEDIN%UROPEISFORECASTAT later, the Tokyo-based company suspended panol) is listed as “probably carcinogenic --44HE%5RAPESEEDCRUSHWAS shipments of Enova-brand DAG oil in the to humans” by the International Agency for EXPECTEDTOREACHARECORD--4 United States. On September 23, Korean Research on Cancer (IARC), no data exist The increased availability of rapeseed manufacturer CJ [formerly, Cheil Jedang] on the metabolic fate of glycidol fatty acid OILSHOULDLEADTOINDUSTRIALUSEOF Corp. suspended shipments and initiated a esters in the human gut. As a result, IARC --4 WHICHACCOUNTSFORATLEAST voluntary recall of its Litra DAG oil product has classified glycidol (or glycidyl) esters of total domestic use, USDA said. “in light of [Kao’s actions] in Japan.” as “not classifiable as to carcinogenicity to QQQ “We are taking immediate action by humans.” /N3EPTEMBER *APANS-INISTRYOF temporarily halting the sale and shipment The situation is further complicated %CONOMY 4RADE AND)NDUSTRYRELEASED of these products until the amount of fatty by the lack of research on mechanism (it its draft carbon footprint and labeling acid glycidol esters in Econa (called Enova is assumed that glycidol esters are formed during deodorization) and the lack of a vali- methodologies for nonglutinous rice, in North America) and related products can dated method for the detection of glycidol rapeseed oil, and powdered laundry be lowered to levels similar to common esters. detergent. Companies can now market cooking oils,” Kao told inform in a written statement. “While we believe our prod- “The analysis of these process contam- these products by displaying carbon inants has been the subject of discussions footprints if these have been calculated ucts have been and are now safe, we are nevertheless taking this extra precaution at recent technical meetings in Europe and PURSUANTTOTHEDRAFTh3TANDARDSFOR as a way to assure our customers that they Australia,” said Richard Cantrill, director of can continue to enjoy our products with AOCS Technical Services. “As a member/ CONTINUED ON PAGE 691 confidence.” representative at these meetings, AOCS 690 inform November 2009, Vol. 20 (11)

A DAG OIL TIMELINE Oilseed market Q %CONA BRANDDIACYLGLYCEROL$!' COOKINGANDSALADOILISINTRODUCED in Japan by Kao Corp. report Q +AOAND!$-!RCHER$ANIELS-IDLAND#O$ECATUR )LLINOIS 53! FORMAJOINTVENTUREKNOWNAS!$-+AO,,#TOMARKET$!'OILPRODUCTS According to USDA’s September World in the United States. Agricultural Supply and Demand Estimates report, US oilseed ending stocks for 2009– Q +AOAND!$-INTRODUCE%NOVA$!'OILINTHE5NITED3TATES 2010 are projected at 7.3 million metric 4HE#ONSUMERS5NIONOF*APANBEGINSWORKINGTOHAVE&/3(5&OODSFOR tons (MMT), up 0.4 MMT from August 3PECIlED(EALTH5SE STATUSFOR%CONAOILANDOTHERPRODUCTSRETRACTED mostly due to increased soybean stocks. Q 4HE+AO!$-JOINTVENTUREISDISSOLVED ANDTHE53 BASEDENTITYS Soybean production is forecast at NAMEBECOMES+AO(EALTHAND.UTRITION,,#)TASCA )LLINOIS  3.25 billion bushels, up 46 MMT based on Q  higher yields. Other oilseeds are up due to Marchˆ'ERMANYSRISKASSESSMENTAGENCY"F2"UNDESINSTITUTFàR2ISIKOBE- higher peanut and cottonseed production. WERTUNG ANNOUNCESITHASDETECTEDGLYCIDOLESTERSINRElNEDPALM BASED Soybean crush is raised 20 million bushels vegetable fats. due to higher projected soybean meal Juneˆ+AOlNDSTHATITS%CONACOOKINGOILCONTAINSUPTOTIMESTHELEVELOF exports. Higher exports from the United glycidol esters detected in seven common vegetable oils. Using a Deutsche States partly offset a sharp decline in pro- 'ESELLSCHALTFàR&ETTEWISSENSCHAFTMETHOD +AODETERMINESTHATTHEGLYCIDOL jected soybean meal exports for India as ESTERLEVELSINTHESEVENCOMMONVEGETABLEOILSRANGEDFROMnPARTS a reduced soybean crop limits exportable per million. The company does not release a list of which oils it tested. supplies. July and Augustˆ*APANS&OOD3AFETY#OMMISSIONMEETSTODISCUSSTHE Soybean exports are increased 15 issue. million bushels to 1.28 billion reflecting Septemberˆ+AOSTOPSSHIPMENTSOF$!'OILPRODUCTSIN*APANANDTHE increased supplies and lower projected United States. prices. Soybean ending stocks are projected Octoberˆ+AOSURRENDERSITS&/3(5CERTIlCATION at 220 million bushels, up 10 million from last month. Soybean exports for 2008–2009 are projected at a record 1.28 billion bushels, stands ready to help industry and our con- system. “It preys on the insecurities some up 15 million from last month reflecting stituencies develop the analytical tools and people feel about issues like weight or exceptionally strong shipments in the final resources needed to meet this challenge.” health that should be addressed in a more weeks of the marketing year. The increase DAG oil is produced from soy and comprehensive way, not through promo- is offset with lower residual, leaving ending canola oils via enzymatic interesterifica- tion of highly processed products like DAG stocks unchanged at 110 million bushels. tion. Whereas DAG oil consists of roughly oils,” said Yamaura Yasuaki, CUJ secretary Other changes for 2008–2009 include 80% diglycerides in the sn-1,3 configura- general. increased use of soybean oil for biodiesel tion, commonly used cooking and salad oils In the meantime, Kao says it will and reduced soybean meal exports. Season- contain a preponderance of triglycerides continue to work on mitigation: “We are ending soybean oil stocks are projected at a (TAG). Current thinking suggests that dif- working very closely with ADM [Archer record high of 3.1 billion pounds. ferences in the absorption and metabolism Daniels Midland Co. of Decatur, Illinois, The US season-average soybean price of DAG oil result in a reduction of post- USA, which supplies DAG oil to Kao] on range for 2009–2010 is projected at $8.10 meal serum TAG levels and an increase in implementing the processing changes to to $10.10 per bushel, down 30 cents on both overall metabolism, thereby leading to a reduce the level of glycidol esters,” Kao ends of the range. The soybean meal price reduction in the amount of fat stored in the said via e-mail. “We expect these process- is projected at $250 to $310 per short ton, body. ing steps will be completed so we will be down $10 on both ends. The soybean oil DAG oil products in Japan have been able to resume selling and shipping [DAG certified under the FOSHU (Foods for Spe- oil] by the end of March 2010.” cific Health Uses) system and are labeled as Total annual sales for the Econa brand being helpful in controlling body fat depo- are roughly $200 million in Japan, Kao information sition and post-meal blood serum levels. said, and account for 9% of the cooking After the Consumer Affairs Agency said and salad oil market. “Total sales for the Q "F2RECOMMENDATIONONGLYCIDOL on October 8 that it would move to revoke Enova brand in the United States is much ESTERSINFOODSWWWBFRBUNDDE FOSHU status for the Econa product line, less,” a spokesperson wrote. Kao’s share Kao voluntarily stopped using the FOSHU CMINITIAL?EVALUATION?OF?THE? price dropped 2.9% immediately after its label. The company will file a new FOSHU assessment_of_levels_of_glycidol_ announcement on September 16 but later application once it has lowered the level of fatty_acid_esters.pdf glycidol esters through process mitigation, rebounded. Q $'&$EUTSCHE'ESELLSCHALTFàR according to a company news release. &ETTEWISSENSCHAFT'ERMAN3OCIETY The Consumers Union of Japan (CUJ) Catherine Watkins is associate editor of FOR&AT3CIENCE METHODUSEDBY+AO applauded the move, stating that it does not inform and can be reached at cwatkins@ HTTPWWWDGFETTDEMETHODSC? believe that consumers need the FOSHU aocs.org. III? ?E?MCPD?ESTERPDF inform November 2009, Vol. 20 (11) 691

%STABLISHING0RODUCT#ATEGORY2ULESv 0#2 4HERESULTSOFTHECALCULATIONS and the method of labeling must also be approved by the PCR Commit- tee. QQQ The ban on transFATTYACIDS4&! IN THE53CITYOF"ALTIMORE -ARYLAND WENTINTOEFFECTON3EPTEMBER!S of that date, restaurants, delis, baker- price range is unchanged at 32 to 36 cents consumer exposure to pesticides. The work ies, and corner lunch carts could no per pound. looks at a group of pesticides that have LONGERSERVEFOODTHATCONTAINS Global oilseed production for 2009– similar chemical structure and toxic effects GRAMSORMOREOF4&!PERSERVING 2010 is projected at 422.8 MMT, up 0.2 to see if their impact on human health can "ALTIMOREJOINSAGROWINGLISTOFCITIES MMT from last month. Foreign production be assessed collectively rather than just on and municipalities in the United States is down 1.2 MMT to 326.9 MMT. Global an individual basis. that have banned trans INCLUDING.EW soybean production is projected at a record The agency’s Panel on Plant Protec- 9ORK#ITY 0HILADELPHIA "OSTON AND 243.9 MMT, up 1.9 MMT as increased pro- tion Products and Their Residues (PPR) the state of California. duction forecasts for the United States and concluded that it would be necessary to Brazil are partly offset by reductions for reach international consensus on which QQQ China, India, and Canada. Brazil soybean groups of pesticides could be looked at China is working on a new system of production is projected at 62 MMT, up 2 together through a cumulative risk assess- food safety standards that is expected MMT from last month due to an increased ment approach. The Panel specified that in to be more compatible with interna- area projection reflecting favorable soybean order to address uncertainties, the appli- TIONALNORMS ACCORDINGTOTHE8INHUA prices relative to corn. China soybean pro- cation of new cumulative risk assessment .EWS!GENCY)NADDITIONTOTHEIMPLE- duction is reduced 0.4 MMT to 15 MMT methodologies required further work and mentation of the new law, the ministry based on lower yields resulting from that guidance on appropriate methodolo- is also stepping up efforts to establish untimely dry conditions in northeastern gies for exposure assessment was also still an efficient food safety coordination growing areas. India soybean produc- needed. mechanism, improve the health emer- tion is reduced 1 MMT to 9 MMT due to gency response system, and set up a reduced harvested area and lower yields. food safety risk-monitoring and assess- A late start to planting resulted in lower- FDA opens registry ment system. A database is under than-expected area sown. Lower yields are The US Food and Drug Administration construction to facilitate the flow of projected due to a period of dryness in late (FDA) has a new way to head off potential information between different govern- July and early August. Global rapeseed cases of foodborne illness—the Reportable ment agencies involved in food safety production is almost unchanged as lower Food Registry (RFR; http://rfr.fda.gov/)— administration and supervision. production for Canada is offset by higher which food industry officials must use to QQQ production for EU-27. The EU-27 crop ben- alert the FDA quickly, through an elec- #AVITATION4ECHNOLOGIES )NC#4) efited from record yields in France. Other tronic portal, when they find their products ,OS!NGELES #ALIFORNIA 53! ENTERED changes include reduced peanut and cot- might sicken or kill people or animals. The tonseed production for India and increased INTOANAGREEMENTWITH$ESMET"ALL- requirement, a result of legislation, took sunflowerseed production for Kazakhstan. ESTRA'ROUP:AVENTEM "ELGIUM effect with the introduction of the portal. Global oilseed trade for 2009–2010 is TOEVALUATE#4)S.ANO#AVITATION Facilities that manufacture, process, or raised 0.7 MMT to 91.8 MMT. Increased Reactor technology and its potential hold food for consumption in the United soybean imports for China account for benefits to the vegetable oil industry. States now must tell the FDA within 24 most of the change. Global oilseed stocks #4)SNEW'0$SYSTEMCHEMICAL FREE hours if they find a reasonable probabil- are projected higher mainly due to higher 'REEN$ $EGUMMING ISBASEDONITS ity that an article of food will cause severe soybean stocks in China and the United PATENTEDmOW THROUGH.ANO#AVITA- health problems or death to a person or an States, which are only partly offset by animal. TION2EACTORTECHNOLOGYTHAT#4)SAYS lower stocks in Argentina and India. China The reporting requirement applies to promotes the formation, growth, and soybean imports for 2008–2009 are raised all foods and animal feed regulated by the implosive collapse of gas or vapor-filled to a record 39.8 MMT. FDA, except infant formula and dietary bubbles in liquids. The process involves supplements, which are covered by other mixing crude vegetable oil and water regulatory requirements. Some examples and exposing them to high-pressure EFSA’s work on of reasons a food may be reportable include impulses and micro explosions at the pesticides bacterial contamination, allergen mislabel- molecular level, causing the gums to ing, or elevated levels of certain chemical become denser, thus allowing efficient The European Food Safety Authority components. separation and higher oil yields. Q (EFSA) has published the results of con- A guidance document for indus- tinuing work to develop methodologies to try is available at www.fda.gov/ assess the cumulative effects resulting from ReportableFoodRegistry. 692 inform November 2009, Vol. 20 (11)

Glycerol monolaurateALSOKNOWNAS FORALMOSTYEARSINTHE$EMOCRATIC Commodities monolaurin ADERIVATIVEOFCOCONUT 2EPUBLICOF#ONGO)THASAWORKFORCEOF oil, could be used as a microbial agent ABOUT PEOPLEANDPRODUCESPALM in foods, according to researchers led oil from three properties, according to CACAO/CHOCOLATE BY(UI:HANGAT:HEJIANG5NIVERSITYIN 4RI.ORTH A team of food engineers led by Phil Cox China. The scientists combined mono- at the University of Birmingham%DG- laurin with commonly used antimicrobi- BASTON "IRMINGHAM 5+ BELIEVESTHAT als in various concentrations and tested New ventures using tempered cocoa butter emul- it on several bacterial strains and on food )NDIASBhoruka GroupISINVESTING sions CONTAININGUPTOWATERBY components. They found that monolaurin million to build an oilseed crushing facility weight could help reduce the fat content combined with ethylenediamine tetraa- - of chocolate while maintaining its flavor CETICACID%$4! ABINDINGAGENT WAS IN.EW3OUTH7ALES !USTRALIA4HEFACIL and texture. An alternative method being effective against Escherichia coli and Bacil- ITYWILLHAVEANANNUALCAPACITYOF  -4YEAR"HORUKAPLANSTOEXPORTUPTO DEVELOPEDBYTHE"IRMINGHAMTEAMINTRO- lus subtilis but not Staphylococcus aureus. duces water in the form of a water-in-oil The study appeared in the Journal of Food  -4OFREFINEDOILSTO)NDIAAND other Asian countries, according to Bio- cocoa butter emulsion, which comprises Science74-n-   diesel Digest a cocoa butter continuous fat phase in MAGAZINE which an aqueous phase is dispersed. The FISH OIL QQQ Cargill is expanding its animal nutrition team’s study appeared in the Journal of Food Astaxanthin, the carotenoid pigment PRODUCTIONIN2OMANIATHROUGHAMAJOR Engineering95n   that makes krill red and salmon pink, may investment in its feed plant in Sura Mica protect against the development of dia- near the town of Sibiu, the company said, CANOLA/RAPESEED OIL betic kidney disease, according to a study including the construction of a complete- in the Journal of Agricultural and Food Chem- 4HE  METRIC TON PER YEARCANOLA feed production line within the current istryn  2ESEARCHLED crushing facility built by Louis Dreyfus PREMIXFACILITY4HEPROJECTALSOCOMPRISES BY9*+IMOFTHE"USAN7OMENS#OLLEGE Canada and Mitsui Canada near an upgrade to the existing mixing system, in Korea suggests astaxanthin could be 9ORKTON 3ASKATCHEWAN ISEXPECTEDTO the installation of a pelleting line, and the hANEFFECTIVE FUNCTIONALSUPPLEMENTASAN BEGINPRODUCTIONBYMID .OVEMBER addition of a warehouse to store finished ANTIDIABETICPHYTOCHEMICAL vTHEAUTHORS according to www.manitobacooperator. products. The construction process has said. ca. Once it becomes fully operational, already begun and is expected to be com- THEPLANTWILLPRODUCEABOUT -4 PALM OIL PLETEDBYSUMMER OFMEALAND -4OFOILPERYEAR QQQ Construction of the facility began in Sep- Canadian investment firm TriNorth Danisco has expanded its production TEMBER THEREPORTNOTED Capital Inc. says its Feronia subsidiary OFCELLULOSEGUMBY -4)NOTHER QQQ has concluded the purchase from Unilever company news, Danisco’s Genencor Statistics Canada reported in Septem- PLCOFAMAJORITYSTAKEINAN!FRICANPALM unit officially opened its new Grain Pro- ber that Canadian oilseed crushers pro- OILOPERATION&ERONIAHASPURCHASED cessing Applied Innovation Center CESSEDARECORD--4OFCANOLA"Y of Plantations et Huileries du Congo, IN#EDAR2APIDS )OWA 53! ON3EPTEM- CONTRAST PROCESSORSCRUSHEDABOUT--4 OR0(# WHICHHASBEENINOPERATION BER Q IN4HEPROVINCEOF!LBERTACURRENTLY HASTHEMOSTCAPACITY WITH--43AS- KATCHEWANISNEXTWITH--4 FOLLOWED BY-ANITOBAWITH--4/NTARIOHAS ACRUSHINGCAPACITYOFBETWEEN  AND -4/NCETWONEWCRUSH- ing facilities come online in Saskatchewan, that province’s production will rise to as MUCHAS--4YEAR THEOntario Farmer newspaper noted. COCONUT OIL The Maldives government has begun a PROJECTTOREDUCEITSCARBONDIOXIDEEMIS- SIONSUSINGhBIOCHAR vACHARCOALMADE from biowastes such as coconut shells, ACCORDINGTOTHE""#.EWS QQQ ~ r~ ~ ~- MEMBERSHIP APPLICATION l OINF e .: Street Address: 2710 S. Bou lder Drive, Urbana, ll 61802-6996 USA. 0 . Mail Address: P.O. Box 17190, Urbana, IL 61803-7190 USA. N L.ii:::m Ph-., -2"-359"23"; "" .,_,,,_, ,, -8091; Em,;1, -''""''"'oc'"" w,~ w~.•oc • .mg 0 Dr. 0 Mr. 0 Ms. 0 M rs. 0 Prof. Please print or type. All applicants must sign the Code of Ethics. Last Name/Family Name~------First Name ______M iddle Initial ______Firm/lnstitution ------Positionffitle ______

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AOCS: Your international forum for fats, oils, proteins, surfactants, and detergents. This Code has been adopted by the AOCS to define the rules of professional conduct for its members. As a condition of membership, it shall be signed by each applicant. AOCS Code of Ethics • Chemistry and its application by scientists, engineers, and technologists have for their prime objective the advancement of science and benefit of mankind. Accordingly, the Society expects each member: 1) to be familiar with the purpose and objectives of the Society as expressed in its Bylaws; to promote its aim actively; and to strive for self-i mprovement in said member's profession; 2) to present conduct that at all times reflects dignity upon the profession of chemistry and engineering; 3) to use every honorable means to elevate the standards of the profession and extend its sphere of usefulness; 4} to keep inviolate any confidence that may be entrusted to sa id member in such member 's professional capacity; 5) to refuse participation in questionable enterprises and to refuse to engage in any occupation that is contrary to law or the public welfare; 6) to guard against unwarranted insinuations that reflect upon the character or integrity of other chemists and engineers.

I hereby subscribe to the above Code of Ethics. Signature of Appl icant ------seed extraction oleochemicals biodiesel oils and fats refining Briefs inform November 2009, Vol. 20 (11) 695

The Volvo Group and Ford Europe are testing dimethyl ether (DME) as Biofuels News a diesel alternative. Its advantages are that it burns soot-free, produces almost no greenhouse gases on com- bustion, is very energy efficient, and has a high cetane number. BioDME, made by Chemrec AB (Stockhom, Sweden; Deerfield, Illinois, USA), is manufac- tured from black liquor, a waste stream in the wood pulping process. BioDME is claimed to offer as much as 95% reduction of CO2 emissions compared with conventional diesel fuel. QQQ Denmark-based Genencor Interna- tional has expanded its presence in Cedar Rapids, Iowa (USA) by adding to the facility it already has there— for developing enzymes to use in grain processing and laundry products— and opening a new research center. Glenn Nedwin, vice president for tech- nical enzymes for Genencor, told the Des Moines Register, “Our plant is not dedicated to any one product, but since grain processing is so strong in the Midwest, it will take up most of the volume.” Genencor presently employs 114 people in Cedar Rapids, Although no companies located in with growth in staffing expected in GENERAL China appeared in the top 100, The Guard- ian/Cleantech Group acknowledged the the near future. leadership, entrepreneurism, and company- QQQ Promising building in that region that will doubtless In the Philippines, Trans-Asia Oil and lead to China’s inclusion on future lists. Energy Development Corp. dropped cleantech The complete listing may be accessed at its alternative fuels operations as a www.guardian.co.uk/globalcleantech100/ result of problems with its pilot jatro- companies list or http://cleantech.com/news/awards/ pha project. President and Chief Exec- On September 9, The Guardian newspaper globalcleantech100. utive Francisco L. Viray said Trans-Asia (London, United Kingdom) and the Clean- found that jatropha was not easy to tech Group (Boston, Massachusetts, USA) grow: It required huge volumes of released their list of the top 100 of the US fuel standards water to produce a good crop and world’s most promising clean technology did not grow well without cultivation. companies. The final list of 100 was chosen to rise The Philippines Biofuels Act of 2006 by experts from cleantech innovation and New US fuel economy standards intended mandates the preblending of 2% coco venture capital companies in Europe, the to reduce greenhouse gas emissions were methyl ester or coco biodiesel in die- Middle East, Africa, North America, India, announced in mid-September by Secretary sel-fueled vehicles this year. Jatropha and China. About 3,500 companies were of Transportation Ray LaHood and Envi- is one of the two approved feedstocks considered. ronmental Protection Administration (EPA) for biodiesel. Broken down by country, 55 of the top Administrator Lisa Jackson. Domestic QQQ 100 companies are located in the United automakers are to meet a standard of 35.5 Massachusetts’ Clean Energy Biofuels States, 13 in the United Kingdom, and 10 mpg (miles per gallon), or 6.6 km/100 L, by Act of 2008 called for inclusion of 2% in Germany. 2016. This law supersedes a 2007 law that Thirty-seven of the 100 are involved biodiesel within diesel fuel and heating set a nonbinding goal of 35 mpg by 2020. in energy generation. Some of the names in Environmentalists and members of oil by July 1, 2010. Now the administra- the energy generation sector are familiar to the Democratic Party praised the new stan- tion of Governor Deval Patrick is post- readers of inform. They are listed in Table dard, and conservatives condemned it. Rep- poning implementation of those plans 1 (p. 696), along with the product(s) being resentative John Culberson (R-Texas) said, CONTINUED ON NEXT PAGE generated. “Rather than allowing our automakers to 696 inform November 2009, Vol. 20 (11) to 2011, saying it needs further clari- fication from the US Environmental Protection Agency about what type of biofuels will meet new anti-carbon-pol- Table 1. Biofuel-generating companies recognized by The Guardian/Cleanteach Group lution standards. Environmental activ- ists have protested the delay, whereas Company Location Feedstock Product(s) the Massachusetts Petroleum Council Amyris Emeryville, Sugarcane Bioethanol, welcomed it, according to the Boston Biotechnologies California, USA renewable diesel Herald newspaper. BioGasol Ballerup, Denmark Lignocellulose Bioethanol QQQ In Bozeman, Montana, USA, Sustain- Chemrec Stockholm, Black-liquor waste Synthesis gas, able Oils, which produces camelina- Sweden; Deerfield, stream from pulp dimethyl ether based fuels, was awarded a contract Illinois, USA and paper mills in September by the Defense Energy Cobalt Biofuels Mountain View, Corn, non-food Biobutanol Support Center (US Department of California, USA feedstocks Defense) for 40,000 gallons (150,000 Coskata Warrenville, Biomass, Bioethanol liters) of camelina oil-based jet fuel. Illinois, USA agricultural and The fuel will be used to support the US municipal wastes Navy’s certification testing program of alternative fuels. The contract includes Gevo Englewood, Agricultural waste Isobutanol, butanol, an option to supply up to an additional Colorado, USA products renewable alcohol- 150,000 gallons (570,000 liters) of cam- based fuels elina-based jet fuel. Michael Waring, LS9 San Francisco, Sugarcane, Hydrocarbons sales representative for Sustainable California, USA cellulosic biomass Oils, said camelina yields in Montana were 1,000–1,200 lb per acre (1,100– Mascoma Lebanon, New Wood, grasses, Cellulosic ethanol 1,300 kg/ha) in 2009. Hampshire, USA nonedible plant parts QQQ Solazyme Inc. (San Francisco, Califor- Sapphire Energy San Diego, Algae Biodiesel, jet fuel nia, USA) agreed in late September California, USA to provide the US Navy with 1,500 Solazyme San Francisco, Algae, discarded Algal oil gallons (5,700 liters) of algae-derived California, USA plant material jet fuel for testing and certification. This contract follows on a separate Zeachem Lakewood, Cellulosic biomass Bioethanol contract, signed in early September, to Colorado, USA provide 20,000 gallons (76,000 liters) of algae-derived fuel for use in Navy compete and build cars that consumers ships. The ship fuel contract is worth want, they’re forced to build fleets that New technology to about $8.5 million, according to Jon- meet the air quality standards of Califor- concentrate algae? athan Wolfson, the company’s chief nia.” (California was first to promulgate a executive and co-founder; and the jet standard of 35.5 mpg.) Economical methods to separate algae fuel contract is about $200,000. The new requirements are estimated to from water on an industrial scale are not cost automakers $1,300 per vehicle. But the QQQ yet plentiful, but the Palo Alto Research National Highway Traffic and Safety Com- The Environmental Law Institute Center (PARC; California, USA) is devel- mission (NHTSC) and EPA predict the new announced in mid-September that oping new technology that may hasten the standards will save drivers $3,000 in fuel advent of algal fuel. Michael Kanellos, of during the period 2002–2008 the US costs during the lifetime of a model 2016 GreenTechMedia.com, describes PARC’s federal government provided substan- vehicle. Implementation of the standard solution as spiral technology. He explained tially larger subsidies to fossil fuels than is also estimated to conserve 1.8 billion further: “A set of spirals—essentially chan- to renewables. Fossil fuels benefited barrels of oil and reduce greenhouse gas nels that get water to swirl in a way that from about $72 billion during that emissions by 950 million metric tons. mimics how it flows down drains, discharge period; $70.2 billion went to tradi- The new standards will take effect flumes and log rides—can potentially be tional sources, such as coal and oil, once the administration drafts specific rules used to separate algae from water with very and $2.3 billion to carbon capture for the new regulations by March 30, 2010 little external energy. Much of the energy, and storage. Renewable fuels received (so as to meet the deadline for the 2012 in fact, comes from the force of the moving only $29 billion. Of that amount, $16.8 model year). Standards are to be phased in water itself.” billion went to corn-based ethanol. For between 2012 and 2016, with increases in Meng Lean, the principal scientist of further information see www.eli.org/ fuel efficiency by 5% to occur each year, the PARC project, indicated the technique pressdetail.cfm?ID=205. Q according to a joint statement from the could recover 95% of the algae, with very NHTSC and the EPA. little energy usage. inform November 2009, Vol. 20 (11) 697

by the potential for gelling associated with allows for temperature control. With See- higher contents of biodiesel during the cold O-Two’s technology, a two-acre (0.8 ha) months. plant could produce 6,000 tons (5,400 The truckers also object to the lack of a metric tons) of algae and consume more mandate requiring fuel pumps to be labeled than 13,000 tons (12,000 metric tons) of with the biodiesel content of the fuel, and carbon dioxide. to the fact that the $0.14/liter subsidy See-O-Two says it is already has an will be paid by biodiesel consumers, not operating installation in conjunction with producers. an unnamed power company in Austria. The province of British Columbia is The company had $200,000 in revenue in expected to enforce its own B2 requirement the past year and is projecting $14 million by January 1, 2010, and the entire nation by in 2011. 2012. BIODIESEL Biodiesel enhances Manitoba US farm income The United Soybean Board (USB) mandates biodiesel announced from its St. Louis, Missouri (USA) office that a recently completed So far, PARC has assembled a proto- The province of Manitoba has become the study showed US soybean farmers received type that can cycle 1,000 liters per minute. first in Canada to require that oil compa- an additional $2.5 billion in net returns in It is now seeking funding from oil compa- nies add biodiesel to their diesel fuel. As the past four years as a consequence of nies and the US Department of Energy to of November 1, an average of 2% of all demand for biodiesel made from soybean scale up the prototype. diesel fuel must be biodiesel (B2). Accord- oil. Viewed another way, this added $0.25 PARC is a spin-off of the Xerox Cor- ing to the Winnipeg Free Press newspaper, in support per bushel ($9.20 per metric ton) poration and earns money from licensing Manitoba Energy Minister Jim Rondeau to the price of soybeans. and royalties. The mathematics of concen- said, “We will be going to a 5% blend The study was undertaken to quantify trating algae by moving a water/algae sus- eventually.” how much soybean farmers benefit from the pension through a spiral originated with Rondeau also indicated that oil compa- checkoff they pay to the USB for promoting Xerox research into methods of water nies can be somewhat flexible in how they the soybean production industry. Accord- purification. achieve the 2% average. For instance, they ing to a statement released by the USB on Further information is available at can blend as much as 5% biodiesel in the September 9, the study asserts that “the www.greentechmedia.com/articles/read/ warmer months, with lower blends in the biodiesel industry has essentially created parcs-solution-for-algae-fuel-going-down- winter. a new floor for soybean oil prices” because the-drain/. Manitoba intends to stimulate its bio- the price of petroleum diesel “has such a diesel industry by offering biodiesel pro- large influence on the price of biodiesel and ducers a $0.14/liter subsidy for five years. soybean oil.” See-O-Two The subsidy takes the place of the former The study also found that the increased tax exemption for biodiesel. demand for soybean oil resulted in an mitigates CO , Speedway International, a licensed 2 increased supply of soybean meal and a biodiesel producer in Winnipeg, has the grows algae consequent drop of $19 per ton ($21/metric capacity to supply the province’s entire ton [MT]) in meal prices, to $45/ton ($50/ Vienna, Austria-based See-O-Two says it needs for biodiesel, which calculates out MT). This decrease benefits the animal has developed an industrial-scale system to as 20 million to 22 million liters annually. agriculture industry. grow and use microalgae to mitigate CO2 Manitoba truckers expressed dismay emissions. In turn, the algae can be con- over the plan, saying it disproportionately verted into biomass to produce biofuels and affects their industry. According to Today’s bioplastics. Trucking (www.todaystrucking.com, Sep- Iowa railroad tests Chief Executive Officer Joachim Grill tember 14), fuel companies will need to biodiesel says the productivity of the company’s pro- provide only a provincial “pool average” of prietary technology is three to six times B2. However, customer demand can deter- The Iowa Interstate Railroad Ltd. (IAIS) higher than that of competing systems, mine what the actual blend at the pump is. based in Cedar Rapids, USA, has been and at a cost about 20% under that of The website contends, “[S]ome custom- testing B10 (10% biodiesel + 90% petrod- competitors. ers with buying power can demand zero B iesel) and B20 biodiesel blends in its loco- According to Cleantech.com, Grill said content, leaving the supplier no choice but motives since the second quarter of 2009. the company’s multi-stage growth process to deliver blends higher than B2 in other Biodiesel is being supplied by Renew- takes place in a closed pond system, which regions.” Truckers are especially worried able Energy Group (REG; Ames, Iowa), 698 inform November 2009, Vol. 20 (11)

a nationwide biodiesel producer and mar- period in 2008, according to Chicago- company in the United States. It recycles keter. As part of the study, REG, IAIS, based Vantage Oleochemicals (formerly used restaurant cooking oil and by-prod- and Kansas University (Lawrence, USA) Uniqema Chemicals), and 17% over histor- ucts from meat processing industries into are measuring wear and tear on movable ical monthly norms. Vantage expects glyc- useable products such as tallow, feed-grade engine parts, horsepower ratings, and emis- erol consumption to continue lower for the fats, meat and bone meal, and hides. sions. REG’s vice president of customer second half of 2009, but only by 5–7%. Valero Energy Corporation is a and service technical, Myron Danzer, Dave Elsenbast, the vice president Fortune 500 company that owns and oper- said, “We hope this biodiesel blend dem- of biodiesel producer Renewable Energy ates 16 oil refineries throughout the United onstration will serve as the tipping point Group (Ames, Iowa, USA), also anticipates States, Canada, and the Caribbean. It also for the rail industry’s use of renewable that glycerin is at or near the bottom of the has approximately 5,800 retail and branded fuels. We expect to find reduced diesel demand cycle and predicts somewhat better wholesale outlets in the same areas selling particulate matter and carbon emissions as demand for the rest of 2009. gasoline, diesel, and renewable fuels, well as improved lubricity with the use of Production of glycerin has fallen as well as seven bioethanol plants in the biodiesel.” in the United States because of the 50% Midwest (see inform 20:422, 2009). decline in biodiesel production, according to Vantage’s product manager for glycerin, Kinder Morgan Deborah Baldwin. Oleochemical produc- ETHANOL tion, with its by-product glycerin, is also ships B2 by pipeline down about 20% for 2009. In September, Kinder Morgan Energy Glycerin demand is expected to COOL fuel Partners, L.P. (Houston, Texas, USA) increase, in part because a new industry to Growth Energy, a group committed to announced it had started commercial trans- convert glycerin into propylene glycol is growing the US economy through cleaner, portation of blended B2 fuel (2% biodie- gaining strength. (Propylene glycol, which greener energy, is appealing for a new sel + 98% petrodiesel) through its 115-mile is widely used in foods, cosmetics, and approach to ethanol. In a presentation at (185 km) pipeline that runs from Portland de-icing fluids, is traditionally made from the 2009 Farm Progress Show, held in early to Eugene, Oregon, USA. Following receipt petroleum-derived feedstocks.) September in Decatur, Illinois, USA, retired of B2 at both its Portland and Eugene US Army General Wesley Clark, now co- facilities, extensive tests showed that the chairman of Growth Energy, called for the samples met specifications. Kinder Mor- RENEWABLE federal government to require a national gan’s Oregon line is one of only a few pipe- standard of country of origin labeling lines in the United States able to transport DIESEL (COOL) for fuel. This would be similar to blended biodiesel on a regular basis, as this COOL requirements already in place for pipeline does not transport jet fuel, thereby Darling, Valero to common consumer items, including fruits eliminating the potential for “trailback” of and vegetables, meats, cars, and coffee. product into subsequent jet fuel batches. build diesel facility The goal is to help create consumer The first commercial batch of approxi- awareness of the costs and national security mately 100,000 barrels of B2 was created Valero Energy Corp. (San Antonio, Texas, implications of the nation’s dependence on using a newly installed blending system to USA) and Darling International Inc. (Irving, foreign oil. inject B99 into ultra low sulfur diesel at Texas) are forming a joint venture (JV) to Clark said, “The American people the company’s Willbridge terminal in Port- build a facility capable of producing over deserve to know the truth about the hidden land. Other area terminals are expected to 10,000 barrels/day, or 135 million gallons costs of oil: The neighborhood filling be able to deliver B2 to the Kinder Morgan (510 millions liters) per year, of renewable station doesn’t pump neighborhood gas—it pipeline. diesel on a site adjacent to Valero’s St. pumps a product of foreign origin that costs Charles refinery near Norco, Louisiana. consumers and taxpayers billions of dollars Glycerin demand Proposed feedstocks for the fuel are every year.” principally waste grease—primarily animal Tom Buis, chief executive office of predicted to rise fats and used cooking oil supplied by Dar- Growth Energy, added, “Country of origin ling—and potentially other feedstocks that labeling for fuel will let consumers know According to Purchasing magazine, the become economically and commercially if they are pumping a domestic-made world economic recession that started over viable. fuel, like ethanol, or fuel from a foreign a year ago caused demand for glycerin to The companies are seeking a loan source.” fall sharply, but the magazine predicts a rise guarantee for the proposed JV from the US According to the US Energy Infor- in glycerin prices in the next few months as Department of Energy under the Energy mation Administration, Canada was the a response to tighter supplies and stronger Policy Act of 2005, which provides financ- leading exporter of oil to the United States demand. ing guarantees for projects that involve in 2008, followed by Saudi Arabia, Mexico, US Census Bureau data indicate renewable energy. and Venezuela. average monthly consumption of glycerin Darling International (www.darlingii. For further information link to www. during the first half of 2009 in the United com) says it is the largest publicly traded, GrowthEnergy.org and www.LabelMyFuel. States was down almost 12% over the same food-processing by-products recycling com. Q Briefs inform November 2009, Vol. 20 (11) 699

Add Boma the rhinoceros and his rhino-sized case of dry skin to the list of sufferers and maladies helped by Health & Nutrition fish oil and omega-3 fatty acids. Boma, who lives at Zoo Atlanta (Georgia, USA), had a severe case of dry and ulcerated skin. Having read that horses with similar conditions were helped by dietary supplementation with fish oil, his zookeepers felt they had nothing to lose. The word is that Boma very much likes the human-grade fish oil donated by a supplement maker. More to the point, it appears that his skin problem is clearing up. QQQ A review article in Nutrition & Metabo- lism (doi:10.1186/1743-7075-6-36) by Sailas Benjamin and Friedrich Spener evaluates the health benefits of con- jugated linoleic acids (CLA), a group of positional and geometric isomers of linoleic acid predominantly found in milk, milk products, meat, and meat products of ruminants. The authors look at the hundreds of studies high- lighting “that CLA, apart from the classical nuclear transcription factor- mediated mechanism of action, appear to exhibit a number of interdependent molecular signaling pathways account- ing for their reported health benefits. Can an antifat pill very beginning,” added Motonari Uesugi, Such benefits relate to anti-obesitic, who is now at Kyoto University (Japan). In doing so, fatostatin influences many anticarcinogenic, anti-atherogenic, be far away? of the genes involved in fat production antidiabetagenic, immunomodula- A small molecule earlier found to have and in various aspects of metabolic syn- tory, apoptotic, and osteosynthetic both antifat and anticancer effects works drome—a collection of risk factors includ- effects,” they conclude. The article as a literal turnoff for fat-making genes, ing obesity, high cholesterol, and insulin is available free of charge at http:// according to results of a study in Chemistry resistance—simultaneously. www.nutritionandmetabolism.com/ and Biology (16:882–892, 2009). Dubbed Studies in cell culture showed that content/6/1/36. “fatostatin” by its discoverers, the molecule fatostatin significantly lowers the activity QQQ is more formally known as 125B11. of 63 genes, including 34 directly associ- Another review article, this one by The chemical blocks a well-known ated with fatty acid or cholesterol synthe- Breanne M. Anderson and David master controller of fat synthesis, the tran- sis. Many of those were known to be under W.L. Ma of the University of Guelph scription factor known as SREBP (sterol the control of SREBP. in Ontario, Canada, tries to answer regulatory element binding protein). In More detailed analysis reveals that the question, “Are all omega-3 poly- mice that are genetically prone to obesity, fatostatin blocks SREBP by preventing unsaturated fatty acids created equal?” the blocking of SREBP causes the animals it from becoming active and entering the The authors attempt “to assess our to become leaner. It also lowers the amount nucleus, where it would otherwise switch current understanding of the differen- of fat in their livers, along with their blood on the fat-making program. It operates by tial effects of ALA (_-linolenic acid), sugar and cholesterol levels. binding another protein (called SCAP, or EPA (eicosapentaenoic acid), and DHA “We are frankly very excited about it,” [sterol regulatory element binding protein] (docosahexaenoic acid) on cancer, said Salih Wakil of Baylor College of Medi- cleavage-activating protein), which serves as SREBP’s escort into the nucleus. insulin resistance, and cardiovascular cine (Waco, Texas, USA), who led the study. Obese mice injected with fatostatin disease.” The article appeared in Lipids “It goes to the origin of [fat synthesis]— all the way back to gene expression.” show noticeable reductions in their weight in Health and Disease (doi:10.1186/1476- Unlike cholesterol-lowering statins in use despite little difference in their eating 511X-8-33), an open access journal. today, which block a single enzyme in the habits, the researchers report. After four The complete text is available at pathway, the chemical “hits fat from the weeks of treatment, the animals weighed http://www.lipidworld.com/content/ pdf/1476-511X-8-33.pdf. Q 700 inform November 2009, Vol. 20 (11)

12% less and had 70% lower blood sugar levels. They also exhibited a significant decrease in low-density lipoprotein choles- terol of approximately 35%, and a lesser decrease in high-density lipoprotein cho- lesterol of approximately 22%. The con- centration of fatty acids in their blood was actually higher, a sign of the greater demand for fat to burn. Whereas the livers of the obese mice were heavy and pale with fat, treated animals’ livers were more than 30% lighter and were a healthy-looking red. Although less obvious, the SREBP-blocking ability might also explain the molecule’s earlier reported effects against prostate cancer cells in culture since cells require fatty acids and cholesterol to build their cell membranes and continue growing. Fatostatin is not the first molecule to scientists show that a 200 mg dose of DHA act on SREBP, according to the researchers, per day is enough to affect biochemical Soy and fish oil and but it appears to do so in a somewhat dif- ferent way than those described previously. markers that reliably predict cardiovascu- cell proliferation Many steps remain, but Wakil and Uesugi lar problems, such as those related to aging, “Isoflavonoids and fish oil may be protec- are optimistic that fatostatin could prove to atherosclerosis, and diabetes. The study is tive against colorectal cancer, but the evi- be useful clinically in the context of obesity, the first to identify how much DHA is nec- dence in relation to breast cancer risk is and perhaps in cardiovascular disease and essary to promote optimal heart health, ambiguous,” the authors of a new study diabetes as well. “[We hope that] down the according to a news release from FASEB. write. road, fatostatin or a derivative of fatostatin “This study shows that regularly con- “In the present study, we have inves- may be helpful,” said Wakil, who has been suming small amounts of DHA is likely to tigated the impact of soya-derived isofla- studying the enzymes involved in fat syn- improve the health status of people, espe- vonoids and omega-3 fatty acids from fish thesis ever since he discovered them in the cially in regard to cardiovascular function,” oil, both individually and in combination, late 1950s. “It could have a broad impact said Michel Lagarde of the Université de on apoptosis (programmed cell death), cell on the key diseases [from which] we all Lyon, who co-authored the study. proliferation, and estrogen receptor (ER) suffer.” To determine the optimal dose of expression in the colon and mammary gland Fatostatin or its analogs may also serve DHA, Lagarde and colleagues examined the of the rat. Female rats were fed diets high in as tools for gaining further insights into the effects of increasing doses of DHA on 12 omega-3 fatty acids (80 g/kg diet) or soya regulation of SREBP and fat metabolism, healthy male volunteers between the ages protein (765 mg/kg diet isoflavones) for two Uesugi said. Uesugi discovered the mol- of 53 and 65. These men consumed doses weeks, and then killed before the removal ecule, reportedly by screening a library of of DHA at 200, 400, 800, and 1600 mg/day of the colon and mammary glands,” they an estimated 10,000 compounds. for two weeks for each dose amount, with DHA being the only omega-3 fatty acid in continue. “Cell proliferation and apoptosis were their diet. Blood and urine samples were quantified morphologically in whole crypts Just-right DHA collected before and after each dose and and terminal end buds. The expressions of at eight weeks after DHA supplementa- ER-_ and ER-` were measured in colon dose? tion stopped. The researchers then exam- tissue scrapes and the mammary gland. ined these samples for biochemical markers Based on a small study, a team of French Fish oil significantly increased apopto- indicating the effects of each dose on the scientists say they have elucidated the daily sis and decreased mitosis in both tissues, volunteers. amount of DHA (docosahexaenoic acid) an effect associated with a decrease in the “Now that we have a very good idea that is “just right” for preventing cardio- expressions of ER-_ and ER-`. Soya had about how much DHA is just right, the next vascular disease in healthy men. (DHA, no effect on apoptosis in either tissue, but a long-chain polyunsaturated fatty acid step is to try it out in an expanded clinical reduced mitosis in the colon (P < 0.001) found in cold-water fish and some algae trial that involves many more people,” said while increasing it in the mammary gland appears to reduce the risk of a number of Gerald Weissmann, editor-in-chief of The (P = 0.001). The changes in proliferation disease including heart disease and macular FASEB Journal. “Until then, I’ll stick with were associated with contrasting changes degeneration.) tasty foods that contain DHA, like fish, in the ER expression such that fish oil sig- In a study appearing in The FASEB rather than getting a quick fatty-acid fix at nificantly decreased both ER-` and ER-_, Journal (23:2909–2916, 2009), the the local vitamin store.” while soya increased ER-_ and decreased inform November 2009, Vol. 20 (11) 701

ER-`,” write Elisabeth Lund of the Institute of Food Research in Colney, Norwich, UK, and colleagues. The researchers concluded: “The results may provide a novel mechanism by which omega-3 fatty acids could reduce cancer risk, but the interpretation of the results in relation to soya consumption and breast cancer risk requires further investigation.” The study appeared in the British Journal of Nutrition (102:29– 36, 2009). Flaxseed and cholesterol Consuming whole flaxseed, but not flaxseed oil, may help lower cholesterol levels, according to a study led by Xu Lin of the Chinese Academy of Sciences in Shanghai and published in the American Journal of Clinical Nutrition (90:288–297, 2009). Lin and colleagues examined results from 28 studies involving more than 1,500 men and women to try to clarify the impact whole flaxseed and its derivatives have on cholesterol levels. Average whole flaxseed or flaxseed oil intake was about one tablespoon (15 mL) daily. The findings link whole flaxseed with reductions in total cholesterol and LDL (low-density lipoprotein)-cholesterol. Total and LDL-cholesterol reductions with whole flaxseed intake were stronger in women, particularly postmenopausal women, than men, and in people with higher cholesterol concentrations at the outset. Whole flaxseed, however, did not appear to alter levels of triglycer- ides or HDL (high-density lipoprotein)-cholesterol significantly. The researchers also saw declines in total and LDL-choles- terol, but not HDL-cholesterol or triglycerides, associated with taking supplements of flaxseed lignans (about 430 mg on average), but no reductions associated with flaxseed oil supplements. The investigators suggest, based on their findings, that eating whole flaxseed may be a “worthwhile dietary approach” for preventing high cholesterol. They call for further large-scale investigations to assess the impact that flaxseed and flaxseed compounds have among men and women at risk for heart disease. Eat soy: live long, and prosper A new study links daidzein, one of the primary isoflavones found in soy, and longevity. Led by Laura Ions, researchers at Newcastle University (New- castle upon Tyne, England) suggest that the long lives experienced by inhabitants of Okinawa Island in Japan may be due as much to their consumption of soy foods as to their low-energy diet. (Caloric restriction has been found to extend lifespan in a number of species.) The scientists point out the structural similarity of resveratrol (the bioactive polyphenol found in red grapes and wine) and iso- flavones, suggesting that both may activate a protein called sirtuin1 (Sirt1) that has previously been linked to the regulation of aging and longevity. “The concentration of daidzein that elicited [the Sirt1] response (100 millimolar) exceeds achievable plasma concentrations but is not unrealistic with respect to local intestinal concentrations fol- lowing consumption of isoflavone-rich foods or isoflavone supple- ments,” the researchers write. The study appeared in Nutrition Bulletin (34:303–308, 2009). Q inform November 2009, Vol. 20 (11) 702 Briefs Biotechnology News In September the Associated Press reported that a San Francisco judge had rejected government approval of a genetically modified (GM) “Roundup Ready” sugar beet. US District Judge Jeffrey White asserted that the US Department of Agriculture’s (USDA) Animal and Plant Health Inspection Service had not taken a “hard look” at the possibility that these GM sugar beets would affect non-GM crops in the area. “The potential elimination of farmers’ choice to grow nongeneti- cally engineered crops, or consumers’ choice to eat nongenetically engi- neered food ... has a significant effect on the human environment,” White wrote in his ruling. He has ordered that an “environmental impact state- ment examining the issue” be gener- ated. QQQ A 43-page study released by the Union of Concerned Scientists (UCS; Cam- bridge, Massachusetts, USA) main- Weberich Fernando tains that, since the inception of GM crops, no significant increases in crop yields can be attributed to them. This DuPont, Monsanto motives; but at the end of the day it is up finding stands in direct opposition to to us as plant breeders to do everything we possibly can to help ensure no individual findings from other studies produced weigh in on yield goes hungry,” said Niebur. by various GM seed companies. The His comments echoed those presented report argues that substantial increases imperative at the 2009 Farm Progress Show, held in crop yields have been a result not During the World Seed Conference held earlier that month in Decatur, Illinois, USA. of genetic modification, but of changes in September in Rome, DuPont’s William There, seed companies stressed the need to in farming practices, agriculture in S. Niebur identified the need to increase address issues of food security accompany- general, and the overall trend toward food production as a “moral imperative.” ing a ballooning population. According to higher yields in all of food production. Vice president of DuPont Crop Genetics the United Nations’ Food and Agriculture The study, led by Doug Gurian-Sher- Research & Development, he told the con- Organization, agricultural output will need man in the UCS Food and Environ- ference that sustainably increasing produc- to double by the year 2050 in order to feed a ment Program, is a compilation of tivity requires a comprehensive approach to global population of more than 9 billion. published, peer-reviewed, and scien- plant breeding, including: At Farm Progress, representatives of tifically accepted studies done since r CSFFEJOH TQFDJGJDBMMZ GPS MPDBM DuPont business Pioneer Hi-Bred focused the early 1990s and is available for environments; on the theme of “Right Product, Right free at www.ucsusa.org/assets/docu- r VTJOHNPMFDVMBSNBSLFSTGPSHFOF Acre” to address increasing demands on ments/food_and_agriculture/failure- selection; yield. They acknowledged that this increas- to-yield.pdf. r EFWFMPQJOHQMBOUTXJUINPSFSFTJTUBODF ing demand is compounded by the effects to diseases and insects and with toler- of global warming, especially its effect on QQQ ance to herbicides; Agricultural products company available arable land. They suggested that, r JNQSPWJOHESPVHIUUPMFSBODF OVUSJFOU regardless of its cause, the real-life conse- Makhteshim-Agan (Tel Aviv, Israel) use, and nutritional content; quences for seed developers and growers announced in September it had formed r BOENBLJOHQMBOUTCFUUFSBCMFUPXJUI- cannot be ignored. a strategic development alliance and is stand environmental stresses such as Monsanto addressed similar issues at investing $37 million over the next five cold, frost, and saline soils. the Farm Progress Show through its Yields years in Cibus Global (San Diego, Cali- “We know some will want to debate of Tomorrow tour, which took place on a CONTINUED ON NEXT PAGE methods and processes, the science, or our triangle-shaped plot that highlighted yield inform November 2009, Vol. 20 (11) 703

fornia, USA). Under the joint devel- advances from decade to decade and rein- allows them to discover the best planting opment partnership, Cibus will use its forced Monsanto’s own goal: to double populations for a specific hybrid or variety. proprietary technology (which offers yields by 2030. They believe that this data, combined with an alternative approach to inserting The preliminary tour included dem- technology from soil variability mapping foreign genes to create GM crops) onstrations of a genome sequencer. The from Earth Map Solutions and processed to develop new plant traits in five genome sequencer allows researchers to by unique predictive modeling software, unidentified crops for the European look at the plant at the molecular level and creates know-how that allows producers market. As part of the related agree- determine which characteristics cause a to establish yield goals, select the right ment, Makhteshim-Agan will make its particular plant to perform the way it does hybrids, and determine the right plant pop- investments based on Cibus’ progress, (i.e., higher yield, improved disease resis- ulations to help maximize yield potential. and gradually acquire a 50.1% stake. tance, etc.). They then take this knowledge The 2010 Farm Progress Show is Cibus describes its technology, known and apply it to breeding and the integra- scheduled to be held August 31–Septem- as Rapid Trait Development System, or tion of biotech traits—all without ever ber 2 in Boone, Iowa, USA. RTDS, as a “smart-breeding technol- having to grow a plant in the ground. With ogy” that introduces desirable genetic the genome sequencer, Monsanto says that traits in a plant by using directed muta- researchers are able to learn in 10 days what EFSA opinions it used to take them 10 years of research to genesis, a process that takes advantage discover. on GM rapeseed, of mechanisms of gene repair. Q The centerpiece of the tour—the onsite plot—reinforced what Monsanto calls the maize “tripod of biotechnology, breeding, and In late September the European Food agronomic practices as the tools to dou- Safety Authority (EFSA) released opin- animal study showed that the tested mate- bling yields.” The plot tracked soybean ions on a Bayer CropScience application rial of oilseed rape Ms8 × Rf3 was nutrition- yields and varieties back to the 1950s and for renewal of the authorization for mar- ally equivalent to its non-GM counterpart. corn yields and varieties back to 1930s. As keting of existing products produced from In addition, bioinformatic studies using evidence that yield in crops such as corn genetically modified (GM) oilseed rape updated databases confirmed that no rel- and soybeans can be doubled by 2030, the (Ms8, Rf3, and Ms8 × Rf3), as well as her- evant similarities exist between the newly tour pointed out progress already made: bicide-tolerant and insect-resistant GM expressed proteins and known allergens or The average yield for corn in the United maize (Bt11×GA21) for food and feed uses. toxic proteins.” States in 1930 was 25 bushels per acre Their opinion on the oilseed rape applica- In the opinion on the GM maize appli- (1,600 kg/ha). Currently, it is approaching tion read in part: cation, submitted by Syngenta, EFSA 160 bushels per acre (10,000 kg/ha). “In 2005 the EFSA GMO [GM Organ- stated: The plot tour concluded with an isms] Panel had issued a scientific opinion “The safety assessment identified emphasis on biotechnology traits now in the on the safety of glufosinate-tolerant oilseed no concerns regarding potential toxicity pipeline, including Monsanto’s Genuity™ rape Ms8 × Rf3 derived from parental lines and allergenicity of maize Bt11×GA21. family of traits. In soybeans, attendees Ms8 and Rf3 for import and processing for A feeding study on broiler chickens con- saw dicamba-tolerant and insect-resistant feed and industrial uses. In delivering the firmed the nutritional equivalence of this products. present opinion, the EFSA GMO Panel GM maize to its non-GM maize counterpart The tour wrapped up with a look at considered the information provided in the and conventional maize. Considering the agronomic practices. Monsanto reported on application EFSA-GMO-RX-MS8-RF3 as intended uses of maize Bt11×GA21, which research they are conducting with the Gen- well as additional information submitted excludes cultivation within the European eration V planter, currently at the center by the applicant. The new data included Union, no scientific assessment of potential of their prescriptive planting recommen- molecular and bioinformatic analyses and environmental effects associated with culti- dations. Monsanto believes that this tool a 42-day feeding study on chickens. The vation of maize Bt11×GA21 was required. In case of accidental release of viable maize Bt11×GA21 grains into the environment during transportation and processing, there are no indications of increased likelihood of establishment or survival of feral maize plants, except in the presence of glufosi- nate-ammonium- and/or glyphosate-based herbicides.” RISK-ASSESSMENT CONFERENCE In related news, EFSA held a two-day con- ference in mid-September to debate GMO risk assessment. The conference brought together risk assessors from EU (European 704 inform November 2009, Vol. 20 (11)

Union) member states, risk managers, and She also expressed criticism of some of rapid expansion of the fuel ethanol market, representatives from stakeholders includ- EFSA’s scientific opinions on GMO. particularly in the United States) and the ing industry, consumer, and environmental Presenting the views of EU farmers, successful launch of several enzyme-con- groups from the EU and beyond. COPA-COGECA’s Director of Commodi- taining pharmaceuticals. With the world in EFSA Executive Director Catherine ties and Trade, Arnaud Petit, said farmers an economic downturn in 2009, however, Geslain-Lanéelle opened the conference wanted to preserve the option of choosing the market for enzymes has become much by reaffirming EFSA’s role as a provider between GM, conventional, and organic more challenging, and growth going of independent scientific advice on GMO. farming. (COPA is the Committee of Pro- forward will moderate significantly. “EFSA is neither pro-GMO nor anti-GMO,” fessional Agricultural Organisations, and Through 2013 world enzyme demand she said. She acknowledged that there exists COGECA is the General Confederation will average annual increases of 6.3%, led a significant divergence of opinion among of Agricultural Cooperatives in the Euro- by pharmaceutical and biocatalyst enzymes, various actors in the field of GMO in the pean Union. The biotechnology industry, both of which will be less susceptible to the EU. “We are here not only to inform but represented by Willy De Greef of Europa- effects of lowered global economic activ- also to listen and learn. We want to get as Bio (the European Association for Bioin- ity. Diagnostics enzyme demand will also wide a range of views and experiences as dustries), asked for the existing experiences fare well due to expanded access to medical possible,” she said. of the safe use of GM crops to be taken care in developing countries, and the advent The first day’s presentations came into consideration in EU risk assessment of health care reform in the United States. from members of EFSA’s GMO Panel and and called for a clearer distinction between With pharmaceutical companies having dif- the GMO Unit, who discussed the legal risk research and risk assessment. ficulty bringing new small-molecule drugs framework for GMO in the EU, as well as to market, biotechnology will continue some of EFSA’s updated guidelines on the to gain in importance, helping to sustain risk assessment of GM plants, developed in Report examines demand for research and biotechnology the context of mandates from the European enzymes. Commission (EC). world enzymes Among the industrial enzyme markets, Presenters examined environmen- animal feed and ethanol production will tal risk assessment (ERA) of GM plants market both achieve above-average advances, as a complex issue whose ongoing devel- In September, business research company while the food and beverage market will opments have prompted updates in EFSA The Freedonia Group (Cleveland, Ohio, grow at a slower, but healthy pace. Animal guidelines. GMO Panel members Salva- USA) released the report World Enzymes feed enzymes will achieve their fastest tore Arpaia and Jeremy Sweet presented to 2013. The 392-page report examines a growth in developing markets where rising two of the main topics related to the new wide range of topics in relation to enzymes, per capita incomes will continue to increase ERA guidelines: including chapters on global economic con- demand for meat in those markets’ local r UIFBTTFTTNFOUPGFGGFDUTPOOPOUBSHFU ditions; outlook overviews for a variety of diets. Food and beverage enzyme demand organisms; and sectors (world manufacturing, food and growth will moderate to a below-average r UIFBTTFTTNFOUPGMPOHUFSNFOWJSPO- beverage, chemicals, cleaning products, pace through 2013, reflecting the chal- mental impacts. pharmaceuticals, and animal feed); and a lenging environment in North America and Andreas Heissenberger of Austria’s seven-part analysis of key enzyme technol- Western Europe. Similarly, growth in clean- Environment Agency presented Austria’s ogies. The Executive Summary includes the ing product and other industrial markets scientific view on ERA. He concluded that following findings: will also be below average. while Austria endorses EFSA’s case-by-case The world market for enzymes is The fastest growth will be in smaller- approach, it believes the ERA is based on expected to recover from a difficult 2009 volume enzymes such as phytases and insufficient data, and he provided a detailed to reach $7 billion in 2013. Continued some specialty pharmaceutical enzymes view on how it could be improved. EFSA strong demand for specialty enzymes as for treating lysosomal storage disorders. will consider inputs from the EC, member well as above-average growth in the animal Polymerases and nucleases will also have states, and stakeholders when finalizing its feed and ethanol production markets will very strong growth due to the strength of updated guidelines. drive advances. From a regional perspec- the diagnostic and the research and biotech- EFSA’s stated aim with the new tive, the developed economies of North nology markets. Carbohydrases and lipases guidelines is to “strengthen and stream- America and Western Europe will achieve will be just above average, while proteases line” GMO risk assessment processes, healthy gains, while the fastest growth will will trail the other types reflecting their while also “increasing their efficiency and continue to come from the more rapidly greater use in industrial enzyme markets. transparency.” developing economies of the Asia and the A large number of companies compete in The conference’s second day included Africa/Mideast regions; Latin America; and the world enzyme market, with six pro- presentations by representatives from Eastern Europe. ducers—Novozymes, Danisco, Genzyme, “stakeholder organizations.” Helen Holder World enzyme demand increased at a Roche, Allergan, and DSM—accounting from Friends of the Earth acknowledged nearly double-digit pace from 2003 to 2008, for 70% of total enzyme sales in 2008. in her presentation that there had been helped in large part by the rapid increase in For more information about pur- improvements in EFSA’s risk assessment world energy prices (which made enzyme- chasing the report, visit www.freedo- work but reported some outstanding con- related processes and products more cost niagroup.com/DocumentDetails. cerns of her organization regarding ERA. effective and facilitated the legislation of a aspx?DocumentId=466960. Q Briefs inform November 2009, Vol. 20 (11) 705

A brief reminder: Free online access to the Journal of Surfactants and Deter- S&D News gents (JSD) is available from now until the end of November at http://www. springerlink.com/content/1097–3958. JSD is published quarterly by AOCS Press and Springer Business+Media. QQQ According to Chemical News & Intel- ligence (CNI), Japanese chemical pro- ducer Kaneka Corp. is now selling surfactin sodium salt. The product is an anionic lipopeptide biosurfactant produced by microorganisms. Kaneka acquired the intellectual property for the manufacture of surfactin from Japa- nese chemical maker Showa Denko in June for an undisclosed sum, the CNI report said. QQQ The trademark LAUNDERALL has been issued to 200 Kelsey Associates, LLC, of New Rochelle, New York, USA, by the US Patent and Trademark Office. The goods for which registra- tion was sought are “automatic dish- washing detergents, detergent soap, dishwashing detergents, laundry deter- gent, soaps, and detergents.” QQQ Cognis Corp. (Monheim, Germany) efficiency and thus possess the largest has been recognized by the US Envi- Designing greener potential to contribute to global warming. ronmental Protection Agency (EPA) They found that molecules containing for “developing innovative chemistry consumer products several fluorine atoms tend to be strong and technologies that further pollu- NASA (US National Space and Aeronau- greenhouse gases, compared to molecules tion prevention and other environmen- tics Administration) scientists are reporting containing chlorine and/or hydrogen. They tal goals.” Cognis’ cationic surfactant, results of work that screens molecules and found for the first time that molecules con- Dehyquart® L 80, was selected to predicts how certain materials will contrib- taining several fluorine atoms bonded to the receive the EPA’s Pollution Prevention ute to global warming. same carbon increase their radiative effi- (P2) Recognition Award. The surfac- In the study, which was led by Timothy ciency in a nonlinear fashion. “It is hoped tant can be used in fabric conditioners, Lee of NASA’s Ames Research Center in that the results from this study will be used cheater wax (a concentrated drying Sunnyvale, California, the researchers in the design of more environmentally friendly materials,” the study notes. aid) formulation for car care, dust mop note that carbon dioxide is the main green- The study is scheduled for the Novem- treatments, and other antistatic appli- house gas, which traps heat near Earth’s surface like the panes of glass in a green- ber 12 issue of Journal of Physical Chemis- cations, according to Cognis. It is avail- house. However, other gases have the same try A (DOI: 10.1021/jp905097g). Download able only in the United States. effect, and in fact are even more efficient the complete text of the article at http:// QQQ greenhouse gases than carbon dioxide. pubs.acs.org/stoken/presspac/presspac/ Croda Europe was scheduled to close Scientists know that the molecules in full/10.1021/jp905097g?cookieSet=1. its fatty acid plant in Bromborough, gases differ in their ability to contribute to Merseyside, UK, at the end of Sep- global warming. But they know little about tember, ICIS Chemical Business reports. the hows and whys—the molecular basis of Fragrance The ICIS account continues: “The plant those differences. produces tallow-based stearic and oleic Lee and colleagues analyzed more ingredients to be acid and has a capacity of 80,000– than a dozen molecules involved in global 90,000 metric tons (MT)/year. In warming to find out which chemical and listed recent years, output had been limited physical properties are most important The Consumer Specialty Products Asso- to 30,000–50,000 MT/year, approxi- in determining their inherent radiative ciation (CSPA), the Canadian Consumer mately 8–9% of the European market, according to a market source.” Q 706 inform November 2009, Vol. 20 (11)

Specialty Products Association (CCSPA), The paper was presented by Luis Mad- comprises a plasticizer, wherein the plas- and The Soap and Detergent Association rigal and highlighted the development of ticizer is selected from the group consist- (SDA) “welcome with enthusiasm plans novel surfactants, allowing coating formu- ing of glycerol, ethylene glycol, diethylene by the International Fragrance Association lators to more easily comply with exist- glycol, triethylene glycol, 2-methyl-1,3- (IFRA) to become more transparent about ing and upcoming EU (European Union) propanediol, sorbitol, methanol, diglycerol, the fragrance ingredients used in consumer environmental regulations. It described 1,4-butanediol, urea, and mixtures thereof, products.” Dow’s development of a new surfactant and wherein the liquid detergent composi- IFRA announced in August that it will exhibiting equivalent or better dispers- tion further comprises a viscosity modifier, publish a list of fragrance ingredients used ing properties than traditional alkylphenol preferably a hydrogenated castor oil. by industry customers by December 31, ethoxylate-based products. The paper also 2009. The list will be posted on the IFRA demonstrated how the use of high-through- Lavatory freshening and website, www.ifraorg.org. put formulation and testing allowed the cleaning system and method The IFRA initiative “enhances the exploration of a wide formulation space CSPA, CCSPA, and SDA Consumer for the evaluation of new additives for Moodycliffe, T.I., and J.J. Veltman, Product Ingredient Communication Ini- coatings. S.C. Johnson & Son Inc., July 21, 2009, tiative, in which manufacturers of clean- The SLF Congress is organized by US7563755 ing products, air care products, automotive SLF, the Federation of Scandinavian Paint A lavatory freshening and/or cleaning care products, and polishes and floor main- and Varnish Technologies, and NMLF, the system comprises a dispenser for dispens- tenance products will voluntarily disclose Norwegian Society for Paint and Varnish ing liquid composition from under the rim ingredients in these products by January 1, Technology. For more information, visit of a lavatory bowl. The dispenser is in the 2010,” the groups said. www.slfcongress2009.com. form of a reservoir arranged for suspen- sion from the rim of a lavatory bowl, and the reservoir contains the liquid composi- Clariant to build S&D patents tion. The liquid composition comprises a combination of anionic and nonionic sur- new ethoxylation Floor cleaning and care factants having a total concentration equal to substantially 7.6 wt%, a thickening agent unit compositions comprising two having a concentration of 0.4 wt%, and a Swiss specialty chemical company Clari- nonionic surfactants perfume having a concentration of 6.0 ant announced it will build an ethoxylation Rogmann, K.-H., et al., Ecolab Inc., July wt%. plant in Dayabay, situated south of Guang- 21, 2009, US7563759 zhou in China. The plant will be operational Aqueous floor cleaning and/or care Laundry detergent composition in early 2011 and will enable Clariant to composition, containing, based on the Boutique, J.-P., et al., The Procter & Gamble meet increasing demand from the Chinese total composition, at least 3% by weight of Co., July 16, 2009, WO2009/087525 and wider Asian markets. a nonionic surfactant. The invention relates to a laundry The new plant primarily will serve detergent composition comprising a glyco- domestic customers for a broad range of Detergent compositions syl hydrolase and a benefit agent containing applications, including crop protection, Gardner, R.R., et al., The Procter & Gamble delivery particles, compositions compris- construction, industrial and home care, Co., July 22, 2009, WO2009/087515 ing said particles, and processes for making metal working, textile, and paper. The plant Disclosed are detergent compositions and using the aforementioned particles and will also supply important export markets containing Tiron (1,2-dihydroxybenzene- compositions. across Asia. 3,5-disulfonic acid), which do not have or The 80,000-square-meter plant will do not develop the reddish color associated Rapid low-foam wetting agents have an annual capacity of close to 50,000 with the Tiron/ferric iron chelate. Methods Steinbrenner, U., et al., BASF Aktienge- metric tons, the company said. It is part of for reducing the intensity of red color in a sellschaft, July 14, 2009, US7560494 Clariant’s $100 million investment program Tiron-containing detergent composition are The present invention relates to the in China. also disclosed. use of surfactants based on a C8 alcohol, propylene oxide, and ethylene oxide as a Novel surfactants Water-soluble, liquid-containing wetting agent for hydrophobic polymer sur- pouch faces, and to a wetting agent comprising surfactants and a C alcohol. described Kouvroukoglou, S., et al., The Procter & 8 Dow Coating Materials, a business unit of Gamble Co., July 21, 2009, US 7563757 Detergent builder Zeolite-A The Dow Chemical Co., reports via Busi- The invention relates to a water-sol- nessWire.com on a paper presented at the uble pouch that contains a liquid deter- preparation process 19th Annual SLF Congress in Sandefjord, gent composition, wherein the pouch is a Jasra, R.V., et al., Council of Scientific and Norway, entitled “Next-Generation Sur- water-soluble film, the film material com- Industrial Research, India, and National factants for Environmental Regulations in prising a polyvinyl alcohol, and wherein Mineral Development Corp., July 14, 2009, Architectural Applications.” the liquid detergent composition also US7560093 Student Page inform November 2009, Vol. 20 (11) 707

The invention provides a process for the preparation of detergent builder Zeo- lite-A from Kimberlite tailings generated as solid waste during diamond mining. Meet Eric Hodgman The process comprises reacting an acid- treated Kimberlite tailing with alkali solu- tion to obtain sodium silicate and reacting it “I successfully defended my master’s thesis with an alkaline aluminum source at room last week and I had [filling out the student temperature and crystallizing at higher profile] on my checklist for things to catch temperature to obtain Zeolite-A. The up on,” wrote Eric Hodgman, who was at product is useful as a builder in detergent that point an M.S. candidate under AOCS formulations. member Bernie Tao at Purdue University (West Lafayette, Indiana, USA). As of Sep- Polymer modifying method tember 2009, Hodgman began work on his McKnight, S.H., and R.E. Jensen, US Ph.D. in the Chemical and Biological Engi- Army, July 14, 2009, US7560520 neering Department at Northwestern Uni- Methods and systems for modifying versity (Evanston, Illinois, USA). a polymer are disclosed. A matrix is gen- He remembers how he first became erally provided having a surface thereof, interested in science: “My first memories wherein the matrix comprises a plurality of of science were seventh-grade biology class hyperbranched polymers. The plurality of when we first learned cell biology. That is hyperbranched polymers can be chemically when I realized that this is something I will bound to a plurality of surfactants in order be interested in for the rest of my life,” he to modify the surface and produce a poly- said. meric material thereof. The surface is tai- As a student growing up in the US state of Minnesota, Hodgman’s favorite subjects lored with a plurality of functional groups were math and science. “I have a strong passion for understanding how life works,” he that self-assemble and are deliverable to the says, “which is why I decided to become a biological engineer. During the course of my surface of the solution, including interfaces education I learned more about lipids and hydrophobic materials and became fascinated thereof, thereby permitting a high-density with how something like that can exist in an aqueous world. Now I am using my knowl- assembly of functional groups to operate in edge to produce large amounts of lipids within biological systems, combining my passion concert with one another in order to gener- for understanding how lipids are produced in vivo and using my engineering background ate a modified surface thereof. to make beneficial materials.” Hodgman’s work at Purdue concerned biodiesel. “The success of the biodiesel indus- Coating composition with a dis- try depends significantly on finding additional sources of oil as well as a profitable use persion of fine particles for industrial glycerol, which constitutes 10% by mass of the total products in biodiesel manufacture,” he noted. Rather than purifying industrial glycerol—which is expensive— Ghyzel, P.J., Eastman Kodak, July 9, 2009, Hodgman proposed the novel alternative solution of using fermentation to convert glyc- WO2009/085136 erol waste back into lipids for additional biodiesel production. The patent involves a coating compo- “During fermentation, glycerol can be used as a feedstock for the oleaginous yeast, sition [that] comprises a dispersion of fine Y.[arrowia] lipolytica, and be converted back into oil for additional biodiesel production,” particles of silica having a particle size of he explained. “Y. lipolytica is known to grow exceptionally well on industrial glycerol, less than 300 nm, hydrophilic hydroxy- store large amounts of lipids, and is relatively easy to manipulate genetically,” he said. containing polymer, a first nonionic sur- Through metabolic engineering, Hodgman and his team looked to increase the rate of factant comprising an alcohol containing glycerol consumption in the cell and in effect increase the rate of lipid storage. This was perfluoroalkyl repeat units and ethylene accomplished by overexpressing glycerol 3-phosphate dehydrogenase, a key enzyme in oxide repeat units, and a second nonionic glycerol metabolism. surfactant selected from the group consist- Now that he is at Northwestern, Hodgman is undergoing the matching process for ing of nonfluorine-containing surfactants a new advisor to determine what his next research endeavors will be. After receiving his that comprise a hydrophobic moiety and Ph.D., he wants either to apply for an academic position or to work in the food and bever- a hydrophilic moiety comprising hydroxy age or pharmaceutical industries. groups.

Ink composition comprise a hydrophilic component, a lipo- Liquid enzyme composition Kim, D.-H., et al., LG Chem Ltd., July 2, philic component, and a fluorine com- Simonsen, O., et al., Novozymes, August 2009, WO2009/082143 ponent; and one or more second fluorine 6, 2009, WO2009/095425 The invention involves an ink compo- surfactants that comprise a fluorine com- The invention provides a liquid detergent sition for roll printing, which comprises ponent, and any one of a hydrophilic com- composition comprising a surfactant, a serine one or more first fluorine surfactants that ponent and a lipophilic component. protease, and a serine protease inhibitor. Q 708 inform November 2009, Vol. 20 (11) In Memoriam People News/ Nicholas J. Spare AOCS member Dr. Nicholas Spare passed away unexpectedly on July 8, 2009, in Cincinnati, Ohio, USA, at the Inside AOCS age of 52. Spare was born in England, and Technology Award 2009 last month. He received a B.S. in chemistry from the Hamilton to receive was recognized as a distinguished scientist University of Sheffield in 1977. He then and technologist and for his achievements came to the United States and earned award in fats and oils chemistry. a Ph.D. from the University of South- The Avanti Award in Lipids will be pre- He delivered a plenary lecture, “Impact ern California (USC; Los Angeles) in sented to James A. Hamilton by the of trans Fat Nutrition Labeling on the US 1985. Biophysical Society for his “innovative Edible Oil Industry,” at the 7th Euro Fed contributions in the Lipid Congress, held in Graz, Austria, application of NMR October 18–21, and was awarded a certifi- [nuclear magnetic cate recognizing his career. resonance] methods to phospholipids and fatty acids,” Seambiotic which includes the first application of appoints new CEO natural abundance In Ashkelon, Israel, Seambiotic Ltd. 13C-labeled lipids to appointed Daniel Chinn to be chief exec- plasma lipoproteins and novel strategies utive officer (CEO) of the company in using 13C-labeled lipids to study interac- mid-September. He replaces founder and tions of lipids with proteins and phospho- previous CEO Amnon Bechar, who has lipid membranes. been appointed to a new role as chief oper- Hamilton has been with the Boston ating officer. Chinn brings to Seambiotic University School of Medicine for 30 years. his experience in law and venture capital. In his career as a chemist, he He is director of the Cardiovascular Center Seambiotic was founded in 2003 to worked for Fluorochem Inc. (Azusa, for High-Field NMR and Spectroscopy. grow and process marine microalgae for the California) and ISOTET LLC (Dalton, The award will be presented at the biofuel and nutraceutical industries. Seam- Georgia, USA). At the time of his Society’s 54th Annual Meeting on Febru- biotic has been conducting pilot studies death, he was a research and devel- ary 22, 2010, in San Francisco, California, involving growing algae in raceway ponds opment chemist with Pilot Chemical USA. adjacent to the Israeli Electric Corporation Company in Cincinnati, working with Hamilton serves as associate editor for power station near Ashkelon. CO2 emitted surfactants in general and specializing the AOCS journal Lipids. He is an associate by the plant is fed to the algae, providing in alkylation, sulfonation, and formu- editor as well for Journal of Lipid Research an essential nutrient at a reduced cost. lation of sulfates and sulfonates. and has also served as an associate editor His interests outside of work for Obesity. included playing the guitar, collecting Bryan Willson stamps, playing darts, and supporting Euro Fed Lipid recognized USC athletics. Spare is survived by his wife, Eliz- award presented to Colorado State University (CSU; Fort abeth Gretter Spare, and their son, Collins, USA) honored Professor Bryan Ethan. List Willson at the end of August with the Maurice L. Albertson Medal in Sustain- Jan Pettersen Gary List, recently retired from the able Development, which is sponsored National Center for by Village Earth, a nonprofit organization AOCS has received word that Dr. Jan Agricultural Uti- dedicated to promoting sustainable com- Pettersen of Bergen, Norway, died lization Research munity-based development. He has been in June 2009. He was born in 1946, (US Department of with CSU Engines and Energy Conversion and had been an AOCS member since Agriculture, Agri- Laboratory for the past 18 years. Scientific 1981. cultural Research American magazine recognized Willson in Pettersen had an active research Service, Peoria, Illi- June 2009 as one of the 10 most influen- nois) received the tial persons in the United States in assur- European Lipid ing that the benefits of new technologies Inside AOCS 709 career, publishing in Lipids, the Journal and knowledge will accrue to humanity. His Beachy appointed of the American Oil Chemists’ Society, and work in developing two-stroke engine ret- rofits to reduce air pollution was cited. an AOCS monograph, as well as Euro- In 2006, Willson co-founded Solix head of NIFA pean journals devoted to lipids and Biofuels (Fort Collins) to commercial- US President Barack Obama appointed to foods. Areas of research included ize technology to produce oil from algae Roger N. Beachy, the founding presi- analysis of fatty acid isomers, oxida- and convert it to biodiesel. Solix recently dent of the Donald Danforth Plant Science tive stability of fats in tissue materi- expanded, establishing the Coyote Gulch Center in St. Louis, Missouri, USA, to be als such as fish meal, antioxidants as Demonstration Facility on a four-acre site the first Director of the National Institute protectants for fish products, and fish on the Southern Ute Indian Reservation of Food and Agriculture (NIFA). He joined products in general. (inform 20:576, 2009). the agency on October 5. According to the At the time of his death, he was formal agreement, Beachy will be “on loan” senior scientist with Nofima Ingre- to NIFA. In conjunction with this new posi- dients (formerly, Fiskeriforskning) in New sales manager tion, Beachy will become vice chairman Bergen, and he was developing a rehy- of the Center’s Board of Trustees. Philip dratable infant food based on herring for EPAX North Needleman will serve as interim president milt and white maize (corn). Intentions America during the search for Beachy’s successor. are for this powder to be used to as The mission of NIFA, an agency of the a food for malnourished children in Marine omega-3 fatty acid supplier EPAX US Department of Agriculture, is to stimu- poor areas of the world. AS (Aalesund, Norway) has expanded its late and fund the research and technologi- sales presence in North America in response cal innovations that will enhance and make Donald L. Smith to increased demand for its products. The American agriculture more productive and company has hired André Markussen environmentally sustainable while ensuring AOCS member Donald L. Smith, of as an additional sales manager for the the economic viability of agriculture and Leawood, Kansas, USA, and Naples, continent. production. A growing program in compet- Florida, USA died on July 12, 2009, at Markussen brings experience in sales itive research grants will be a hallmark of his Kansas home at the age of 78. and marketing in the pharmaceutical area the new agency. Q Smith was born in St. Joseph, Mis- to his position with EPAX. He is based in souri, grew up on a farm in Rosendale, the EPAX AS sales and marketing office in Missouri, and received his bachelor’s Lysaker/Oslo, Norway. degree from the University of Missouri- Columbia in 1953. After serving in the US Air Force as an intelligence officer, he worked for Quaker Oats Company in St. Joseph and in Sherman, Texas; Making the most of your meeting Lauhoff Grain Company in Danville, experience Illinois; and Archer Daniels Midland (Kansas City, Kansas, and Lincoln, Catherine Watkins Nebraska). He switched careers in 1978, joining Christopher and Long Recruit- Did you know that AOCS offers an itinerary builder for registrants for ment, Kansas City division, and estab- the Annual Meeting & Expo (AM&E)? And resources for job hunters? lished their agribusiness division. Eight As well as ample ways to be involved in technical program devel- years later, Smith founded his own opment? recruiting business, Smith Brown & Jones. He had expertise in soybean Even if you answered “yes” to all three questions, read on for a dozen tried-and- operations, grain milling, and grain true tips for making the most of your AOCS AM&E experience. Some may be obvious storage. He was a member of the Pin- (wear comfortable shoes and do not, whatever you do, try to break in a pair of new shoes while hiking the Expo floor). Others involve new technology (how to use AOCS Connect nacle Society, which recognizes the top to—what else?—connect with your peers both before and after the meeting). All of the 75 recruiters in the nation. tips, however, stress that a bit of planning on your part can increase how much you enjoy Smith was preceded in death by and profit from attending the AM&E, May 16–19, 2010, in Phoenix, Arizona, USA. his wife of 49 years, Sally. He is sur- vived by two children and two grand- ITINERARY BUILDER children. Q Use the itinerary builder function of our online abstract manager to preview and print selected abstracts. You can also preview poster presentations. (Please note: The itinerary builder will be available to attendees starting in April.) 710 inform November 2009, Vol. 20 (11)

Tip No. 1: Choose at least two sessions for every time slot. AT A GLANCE That way, if you go to one and the room is full or the topic is not of 101st AOCS Annual Meeting & Expo interest, you can head immediately to your second choice without May 16–19, 2010 scrabbling around for the printed program. Phoenix Convention Center, Phoenix, Arizona, USA Tip No. 2: Try to attend a few sessions outside your area or Online submission of declarations of intent at http:// specialty. AnnualMeeting.aocs.org ended on October 5, 2009; the THE LAB deadline for abstract submissions is January 11, 2010. This year The Lab will be your one-stop place for all things cyber including e-mail stations and JOBTARGET access. One-on-one, hands-on training will also be available, so make sure you visit the Nomination and Election Committee meeting. Attend a division AOCS Pavilion within the Expo Hall—The Lab will be located in roundtable closest to your interest area—a commitment of only the Pavilion. 60–90 minutes—and take an active hand in setting the topics for the following year’s meeting. AOCS CONNECT Why stop there, though? Look through the program and decide Luddites can scoff all they want, but AOCS Connect truly is the best to sample several committee meetings and division or section lun- way to network with AOCS members and nonmembers both before cheons and dinners. You may end up, a few short years from now, and after the meeting. Adoption of social networking applications on the podium receiving a society award. by science and industry may be slow, but it is the simplest way to Tip No. 6: Do not hold back from introducing yourself to post discussion items, identify must-meet members and potential anyone and everyone of interest. AOCS is renowned for its warmth customers or vendors, and schedule meetings. And it most defi- and inclusiveness. Even the brightest lights of the fats and oils com- nitely is the wave of the future. If you have not already signed up, munity will be happy to talk with you. visit http://aocsconnect.ning.com/ today. Be an early adopter and help build this important resource. EXPO HALL Tip No. 3: Because networking in person is one of the great Do not rush through the exhibits. A little pre-planning can go a benefits of the meeting, bring 50–60 business cards and keep them long way toward making the time spent as effective as possible. at hand. (Putting a few behind your name badge in its plastic holder Visit the Virtual Expo at www.aocs.org/meetings/vexpo/ before will keep them readily available at all times.) the meeting to look for opportunities. Visit it after the meeting to Tip No. 4: This time, listen to that little voice in your head look up contact information for exhibitors. Use AOCS Connect telling you to make a note on the back of each card you take from (http://aocsconnect.ning.com/) to schedule meetings with exhibi- others detailing what they wanted or where and how you met them. tors of interest. Once on the Expo floor, please thank our exhibi- Or am I the only one who keeps thinking I will remember every- tors for supporting AOCS and the fats and oils industries during thing when I return to the office, only to end up at my desk after- difficult times. ward staring in puzzlement at my stack of cards minus helpful Tip No. 7: Be sure to schedule some personal time, too, so notes? you can recharge yourself mentally and physically. Tip No. 5: Speaking of name badges, be sure to remove your Tip No. 8: Go ahead and pick up all the handouts you want; badge before walking back to the hotel. Nothing shouts “good can- you can ship them back to yourself by using the hotel concierge or didate for a robbery” louder than identifying yourself to all and the convention center’s business center. sundry as a visiting conventioneer likely to have a pocketful of travelers’ checks. ALL-PURPOSE TIPS Tip No. 9: Bring packets of tree nuts for easy protein pick-me-ups. AOCS PRESS BOOKSTORE A fistful constitutes one serving. This is the place where you can hold the latest books (and the clas- Tip No. 10: Consider arriving a day early or staying a day sics) in your hands and spend some time with the tables of con- after the meeting if your schedule allows. (Remember that the tents and indexes. And if the thought of toting books back and forth awe-inspiring Grand Canyon is only a four-and-a-half-hour drive sounds exhausting, remember that many AOCS titles are available away.) in “Books Plus CD-ROM” format. You can also custom-build your Tip No. 11: If you do not have the time to arrive early or stay library by purchasing individual chapters. late, sign up for the city tour offered on the opening Sunday of each Be sure to visit the AOCS online store after the AM&E; the annual meeting. You will find information about it with the meeting new AOCS website and online store should be unveiled by the end information at http://AnnualMeeting/aocs.org. Also check out the of May. Our aim is to make it easy for our online visitors to find optional guest tours for the chance to do something unique while everything they want and need with a minimum of fuss. in Phoenix. Tip No. 12: In addition to AOCS Connect, take advantage of PROGRAM DEVELOPMENT all cyber networking opportunities—check out theAOCS on Twitter Few things are as satisfying as helping to develop the AOCS techni- (www.twitter.com) and Facebook (www.facebook.com). cal program. Think of it: You can become an industry leader simply by getting involved. All committee meetings are open to everyone Catherine Watkins is associate editor of inform and can be reached (members and nonmembers alike) with the single exception of the at [email protected]. Publications inform November 2009, Vol. 20 (11) 711

polysaccharides. The Book Review content in the soybean and the methods for structure Soybeans: Chemistry, Production, Processing, determination are covered. and Utilization The in vitro and in vivo fer- L.A. Johnson, P.J. White, and R. Galloway (eds.) mentation characteristics AOCS Press, 2008, 842 pages of several soybean oligo- saccharides, including for- ISBN 978-1-893997-64-6 mation of short-chain fatty acid production, are dis- cussed. Finally, the chapter Isabel N. Wagara concludes with a short dis- cussion on applications of Soybeans: Chemistry, Production, Processing, and soybean oligosaccharides Utilization is written for researchers, students, and in functional foods. Chapter 10 emphasizes industry practitioners who deal with soybeans and the minor constituents of soy by-products. It is a comprehensive, well-writ- soybeans, which comprise ten text, with numerous citations up to the year three main groups: lipid- based components, protein-based components, and a third con- 2007. The book begins with the history of soy from sisting of phenolics, saponins, and phytates. The chapter highlights domestication to various food applications. As its the compositional changes of the minor constituents during seed title suggests, the book is divided into four broad maturation and processing. The compositional modifications of soybean constituents through plant breeding and genetic engineer- subject areas: chemistry, production, processing, ing are discussed and numerous recent citations are included. and utilization. The introductory chapter starts The next three chapters are devoted to soybean oil processing, with a description of the movement of soybean starting with oil seed extraction. Chapter 12 is on soybean crude oil purification and includes degumming, deodorization, and the han- agriculture from the Far East to other continents. dling of finished oil. Chapter 13 describes the various techniques Chapters 2–6 discuss breeding and soybean genetics, post- and processes used for soybean oil modification for increased sta- harvest management, soybean pests and diseases, quality mea- bility and functionality, such as hydrogenation, interesterification, surements, and the economics of soybean production. Breeding crystallization, and fractionation. approaches for the improvement of important traits are outlined. Chapters 14 and 15 focus on human food applications of soy- Key soybean pests and diseases and their effects on yield, seed, beans and include products such as soymilk, tofu, soybean sprouts, and grain quality are discussed in detail, with a brief discussion of and soy nuggets. Soybean oil is discussed in chapter 15, including control measures. Mycotoxins are discussed briefly. soy oil for deep fat frying, margarines, and shortening. Chapter 7 describes in detail the fatty acid composition of Nonfood applications are given prominence in chapters 16 and soybeans, soy triacylglycerols (TAG), and the minor oil constitu- 17. Chapter 16 focuses on bioenergy applications such as biodie- ents, such as phytosterols and sphingolipids. This chapter’s great- sel production, while chapter 17 is devoted to other applications, est strength is the discussion of the fatty acid biosynthesis in the such as wood adhesives. stroma of the plastids, ending with TAG biosynthesis in the endo- Chapters 19 and 20 discuss the importance of soy in animal and plasmic reticulum. It contains information on selected structures of human nutrition. Soy applications in poultry, swine, and cattle pro- lipid components, such as sphingolipids and phytosterols. Sterols duction with nutrition and economic implications are discussed and and human health, and the effects of lipoxygenase on food quality, specific examples are included. Chapter 19 is devoted to the effects are covered briefly. The references provide a good list for those of soybean protein processing on nutrition and has useful informa- interested in the chemistry and biochemistry of soybean lipids. tion for all involved in soybean product development. Chapter 20 However, a more accurate chapter title would have been “soybean emphasizes human nutrition with respect to both soybean oil and lipids” to better reflect the emphasis. soy proteins. The text ends with a chapter on soybean production Chapter 8 is devoted entirely to soybean proteins, with detailed in Brazil and Asia that provides an overview of basic issues such coverage of the two major proteins, glycinin and `-conglyinin. as production, transportation, and trade. The molecular weights of the various subunit peptides, the thermal behaviors of the proteins and their flavor-binding capacity, and Isabel N. Wagara is a senior lecturer in the Department of Biological implications concerning food formulations are presented. A brief Sciences at Egerton University, Kenya, with 17 years of teaching and section is devoted to the lipoxygenase, trypsin inhibitors, and bio- research experience with emphasis on the common bean (Phaseo- active properties associated with soy proteins. lus vulgaris L.). She has a M.S. and Ph.D. in plant pathology from The next chapter is on the two main soy carbohydrate groups, Nairobi University, and a B.S. in botany and zoology from Egerton nonstructural carbohydrates (such as low-molecular-weight sugars University. She can be reached at [email protected]. and oligosaccharides and storage polysaccharides), and storage 712 inform November 2009, Vol. 20 (11)

enable containment of coating liquid such as a chocolate coating. Patents The chocolate coating is recovered and thereby reused as a subse- quent topping for the filled ice cream cone. Published Patents Methods and devices for detecting Removing solution for pancreatic lipase Huth, S., and M. Strong-Townsend, IDEXX Laboratories Inc., photosensitive composition April 7, 2009, US7514255B2 Kaneda, M., Showa Denko KK, March 31, 2009, US7510815B2 A method and device for determining pancreatic lipase in an A removing solution for photosensitive composition for animal blood sample. In one aspect, the device includes a com- removal of colored pigment-containing photosensitive composi- partmentalized container for storing and reacting the reagents for tions, comprising at least one solvent selected from the group con- use in the assay. In another aspect, the device include a multilayer sisting of alkylene glycol monoalkyl ether carboxylic acid esters, device having a spreading layer and reagents layers with dried alkoxycarboxylic acid esters, and alicyclic ketones; at least one reagents for detecting pancreatic lipase. The device also includes a solvent selected from the group consisting of linear amides, cyclic system for the optical determination of a color change in the reac- amides, sulfur-containing compounds, and cyclic esters; and if tion mixture. The method includes the use of the device to detect desired an aromatic hydrocarbon having nine or more carbon atoms. pancreatic lipase in samples. The removing solution for photosensitive composition exhibits excellent photosensitive composition-removing performance. Production of biodiesel using Cyclosporin galenic forms* expanded gas solvents Ginosar, D., et al., Battelle Energy Alliance LLC, April 7, 2009, Cavanak, T., and U. Posanski, Novartis AG, March 31, 2009, US7514575B2 US7511014B2 A method of producing an alkyl ester. The method comprises Pharmaceutical compositions comprising a cyclosporin as providing an alcohol and a triglyceride or fatty acid. An expanding active ingredient, a fatty acid triglyceride, a glycerol fatty acid gas is dissolved into the alcohol to form a gas-expanded solvent. partial ester or propylene glycol or sorbitol complete or partial The alcohol is reacted with the triglyceride or fatty acid in a single ester, preferably, and a tenside [surfactant] having an HLB [hydro- phase to produce the alkyl ester. The expanding gas may be a non- philic-lipophilic balance] of at least 10. polar expanding gas, such as carbon dioxide, methane, ethane, [*galenic: a medicine prepared from plants, according to a fixed propane, butane, pentane, ethylene, propylene, butylene, pentene, recipe, as opposed to drugs of known chemical composition] isomers thereof, and mixtures thereof, which is dissolved into the alcohol. The gas-expanded solvent may be maintained at a tem- Creatine-fatty acids perature below, at, or above a critical temperature of the expand- ing gas and at a pressure below, at, or above a critical pressure of Chaudhuri, S., et al., Multi Formulations Ltd., March 31, 2009, the expanding gas. US7511164B2 The present invention describes compounds produced from a creatine molecule and a fatty acid molecule. The compounds being Oils with heterogenous chain in the form of creatine-fatty acid compounds being bound by an anhydride linkage, or mixtures thereof made by reacting creatine lengths or derivatives thereof with an appropriate fatty acid previously Kodali, D., and S. Nivens, Cargill Inc., April 7, 2009, reacted with a thionyl halide. The administration of such molecules US7514394B2 provides supplemental creatine with enhanced bioavailability and Oils containing a triacylglycerol polyol ester and a nonglyc- the additional benefits conferred by the specific fatty acid. erol polyol ester are described, as well as methods of making such oils. Methods for improving lubrication properties of a vegetable Method, apparatus, and system for oil also are described. coating food items Process for the separation of alkyl Mangé, C., and J. Vandemark, Nestec SA, April 7, 2009, US7513213B2 branched fatty acids from a fatty A method, apparatus, and system for coating food items such as coating empty ice cream cones subsequently containing ice acid mixture cream. A liquid recovery apparatus is used in the method, appa- Tanzi, S., et al., Unichema Chemie BV, April 7, 2009, ratus, and system and is fashioned in a tray-like manner to form a US7514576B2

slideway that includes a bottom section with openings that have A process for the separation of alkyl branched C12 to C24 collars along with opposing sidewalls and endwalls that together fatty acids from a fatty acid mixture comprising linear and alkyl Publications inform November 2009, Vol. 20 (11) 713

branched C12 to C24 fatty acids comprises (i) optionally hydrogenat- whipping performance. The complex mixtures of triglycerides are ing the fatty acid mixture, (ii) cooling the mixture to form crystals, preferably obtained via interesterification. and (iii) separating the alkyl branched C12 to C24 fatty acids from the mixture by dry fractionation. Triglyceride fat Floeter, E., Unilever Bestfoods North America, April 28, 2009, Stabilizing vegetable oils and US7524524B2 methods of making same A fat suited as fat phase for the manufacture of low-fat spreads that are stable at elevated ambient temperatures which fat com- Higgins, N., and J. Stults, Bunge Oils Inc., April 14, 2009, prises a mixture of triglycerides, in which 2.5 to 5.5 wt% of the US7518006B2 triglycerides are HHH triglycerides, 25 to 65 wt%, preferably 25 to A method for modifying ethylenic unsaturation in a triglyceride. 55 wt% of the HHH triglycerides are monoacid triglycerides, and One or more unsaturated fatty acyl moieties present in the triglyc- the remaining HHH triglycerides are composed of mixed fatty acid eride are substituted with a lactone or ketone moiety via metal ion- residues, 1.5 to 5 wt% of the triglycerides are HHM and HMH tri- mediated reaction. The resulting reaction products are useful, for glycerides, at least 85 wt% of the fatty acid residues H in HHM and example, as formulations for lubricants, hydraulic fluids, dielectric HMH are palmitic acid residues, where H denotes saturated fatty fluids, and intermediates for polymer synthesis. acid residues having chain lengths greater than 15 carbon atoms and M denotes saturated fatty acid residues having chain lengths Liquid vegetable unsaturated of either 12 or 14 carbon atoms. Such fat phase can be obtained by incorporating in a triglyceride oil a fat A and a fat B where the fat alcohol and process for producing A and the fat B together amount to 6–15 wt% of the fat and the A/B weight ratio is in the range 1:9 to 4:6, characterized in that of fat A the same at least 50 wt% of the triglycerides are fully saturated; at least 80 Nakaoka, H., and M. Mototani, New Japan Chemical Co. Ltd., wt% of the constituting saturated fatty acid residues have a chain April 14, 2009, US7518022B2 length of 16 carbon atoms (P) or 18 carbon atoms (S), the ratio P:S The invention is directed to liquid vegetable unsaturated being in the range 75:25–25:75, up to 5 wt% of the saturated fatty alcohol mixture having an iodine value of 88 to 100 and a cloud acid residues have a chain length of 12 or 14 carbon atoms and in point less than 7°C, the unsaturated alcohol mixture being pre- that of fat B, at least 20 wt%, preferably at least 25 wt% of the tri- pared by reduction of a vegetable unsaturated fatty acid mixture glycerides consist of HHM and HMH triglycerides. and/or an alkyl ester thereof in the presence of a zinc-type catalyst having a copper content of 30 ppm or less, the vegetable unsatu- rated fatty acid mixture being prepared from at least one vegeta- Process for the production of ble oil selected from the group consisting of palm oil, coconut oil, biodiesel in continuous mode and palm kernel oil. The invention also concerns a liquid vegetable unsaturated alcohol mixture having an iodine value of 88 to 100, a without catalysts cloud point less than 7°C or lower and a conjugated diene content Dall’agnol, A., et al., Intecnial S/A, April 28, 2009, of 1 wt% or less. US7524982B2 A continuous, noncatalytic process for producing biodiesel Dithiocarbamyl -hydroxy fatty from vegetable oils and ethanol or methanol includes pumping a ` mixture of vegetable alcohol through a pump toward a tube-shaped acid esters as additives for reactor, wherein the mixture is submitted to high pressure and tem- perature, where the resulting product is nonreacted alcohol, glyc- lubricants and fuels erin, and a mixture of esters (biodiesel), which is directed to the Rowland, R., Chemtura Corp., April 21, 2009, US7521401B2 reservoir at the reactor outlet where an upper phase of alcohol is Fuels, especially hydrocarbon fuels, and lubricants, especially redirected through an alcohol return pipe to the pump inlet, and the lubricating oils, contain dithiocarbamyl `-hydroxy fatty acid esters, intermediate phase, biodiesel, and the lower phase (mostly glyc- a class of anticorrosion, antiwear, antifatigue, and extreme-pres- erin) are led to the separation reservoir or decantation tank, where sure additives that are derived from epoxidized fatty acid esters. the alcohol is removed through the alcohol return pipe, being bio- The additives exhibit synergistic antiwear activity in combination diesel and glycerin the final products, which are then collected for with phosphorus-containing additives. the end to which they were aimed. Oil in water emulsion Non-emulsion based oil simulant Lansbergen, G., and T. Stam, Unilever Bestfoods North America, Hanson, F., et al., University of Utah Research Foundation, May April 28, 2009, US7524523B2 5, 2009, US7528097B2 Nondairy creams that comprise a mixture of triglyceride com- A composition and method for a non-emulsion crude oil sim- positions, having a large variety in fatty acid and triglyceride com- ulant containing biodegradable oil and a terpene are disclosed and positions contained in the mix, show improved storage stability and described. Biodegradable oils such as canola oil, cottonseed oil, 714 inform November 2009, Vol. 20 (11)

and soybean oil can be particularly beneficial for use in connec- tion with these oil simulants. Terpenes such as d-limonene can be Selective hydrogenation process included to provide oil simulant compositions that exhibit good oil using layered catalyst composition simulant properties. Additives such as photochromic dyes, food dyes, food-grade antioxidants, microorganisms, and nutrients and preparation of said catalyst can also be used. These non-emulsion based oil simulants can be Gajda, G., UOP LLC, May 19, 2009, US7534737B2 readily tailored and adjusted to approximate relevant properties of A selective hydrogenation process and a layered catalyst com- a specific target fluid for use in assessing oil spill response, contain- position for use in the selective hydrogenation process are dis- ment, clean-up of equipment, percolation, and/or spill behavior. closed. The process is useful for the selective hydrogenation of diolefins having from about 8 to about 19 carbon atoms per mol- Method for recovering unreacted ecule to monoolefins. alcohol from biodiesel product Method of producing dicarboxylic streams by flash purification acids Fleisher, C., Orbitek Inc., May 12, 2009, US7531688B2 A method for making fatty acid esters by reacting triglyc- Ngo, H., and T. Foglia, US Department of Agriculture, May 19, erides with an excess of alcohol in a pressurized environment, 2009, US7534917B1 where the unreacted alcohol component is separated from the reac- A method of producing dicarboxylic acids (e.g., _ t dicar- tion product by flash purification techniques. In this manner, the boxylic acids) by reacting a compound having a terminal COOH pressure of the product stream is significantly reduced to vaporize (e.g., unsaturated fatty acid such as oleic acid) and containing at unreacted alcohol, which is then condensed for later reuse. The least one carbon-carbon double bond with a second-generation invention provides a cost-effective and convenient mechanism to Grubbs catalyst in the absence of solvent to produce dicarboxylic simultaneously recycle excess alcohol and to purify ester product acids. The method is conducted in an inert atmosphere (e.g., argon, and/or glycerol product streams. nitrogen). The process also works well with mixed unsaturated fatty acids obtained from soybean, rapeseed, tall, and linseed oils. Method of enhancing reproductive Method for producing a biobased function of mammals by feeding of carpet material conjugated linoleic acids Kurth, T., et al., Urethane Soy Systems Co. Inc., May 26, 2009, Bauman, D., et al., Cornell Research Foundation Inc., May 12, US7537665B2 2009, US7531574B2 The present invention includes a method for making a biobased This invention provides methods for improving reproduc- carpet material by providing tufts, a backing, a pre-coat, and a tive performance of lactating dairy cows and other mammals. The backing material wherein the pre-coat includes the reaction product method in the case of cows comprises feeding to the cows a compo- of a pre-coat A-side having a pre-coat isocyanate and a pre-coat sition comprising conjugated linoleic acids (CLA), cis-9, trans-11 B-side and the backing material includes the reaction product of a and trans-10, cis-12. When these CLA are fed daily to dairy cows backing material A-side having an isocyanate and a backing mate- starting at or prior to calving, and continued after parturition, an rial B-side. The pre-coat B-side and the backing material B-side improvement in reproductive performance is observed. may include a polyol derived from petroleum; a vegetable oil, cross-linker, and a catalyst; or a transesterified polyol. Direct epoxidation process using improved catalyst composition Transesterification process for Grey, R., Lyondell Chemical Technology LP, May 12, 2009, production of (meth)acrylate ester US7531675B1 monomers Catalysts useful for the direct epoxidation of olefins are dis- closed. The catalysts comprise a noble metal, lead, bismuth, and a Benderly, A., et al., Rohm and Haas Co., May 5, 2009, titanium or vanadium zeolite. The noble metal, lead, and bismuth US7528278B2 may be supported on the titanium or vanadium zeolite. The cata- This invention utilizes a mixed salt transesterification cata- lyst may also be a mixture comprising the titanium or vanadium lyst in a transesterification process for the production of esters of zeolite and a supported catalyst comprising the noble metal, lead, alkyl(meth)acrylate monomers. bismuth, and a carrier. The invention includes a process for pro- ducing an epoxide comprising reacting an olefin, hydrogen, and Patent information is compiled by Scott Bloomer, oxygen in the presence of the catalyst. The process results in sig- a registered US patent agent with Archer Daniels nificantly reduced alkane by-product formed by the hydrogenation Midland Co., Decatur, Illinois, USA. Contact him of olefin. at [email protected]. Publications inform November 2009, Vol. 20 (11) 715

(190°C) in a domestic fryer. The technique first centrifugation. These data show that Extracts & used is 1H NMR (nuclear magnetic reso- the pH-shift protein isolation technique can nance) spectroscopy. The degradation rate be used to process herring with elevated of linoleic acyl groups is determined in dioxin and PCB levels and thereby increase this process, as well as the proportions of the usage possibilities of such fish. Distillates monounsaturated groups and of saturated plus modified acyl groups, and the iodine Kinetic studies of lipid oxidation values. Intermediate oxidation compounds induced by hemoglobin An inverse relationship having hydroperoxide groups and conju- gated dienic systems were not detected; measured by consumption of between plasma n-3 fatty acids however, some secondary oxidation com- dissolved oxygen in a liposome and C-reactive protein in pounds such as aldehydes were generated model system healthy individuals very early, among them, the genotoxic and cytotoxic 4-hydroxy-trans-2-alkenals. Both Carvajal, A.K., et al., J. Agric. Food Chem. Micallef, M.A., et al., Eur. J. Clin. Nutr. concentrations of each kind of aldehyde at 57:7826–7833, 2009. 63:1154–1156, 2009. different heating times and changes in their The effect of hemoglobin (Hb) and High sensitivity C-reactive protein (hs- concentration were also determined. Simul- lipid concentration, pH, temperature, and CRP) is a marker of low-grade sustained taneously, the level of oil degradation cor- different antioxidants on heme-mediated inflammation. Omega-3 (n-3) fatty acids responding to a content of 25% of polar lipid oxidation of liposomes from marine have anti-inflammatory properties and are compounds measured by Viscofrit test phospholipids was studied. The rate of lipid associated with reduced cardiovascular was analyzed as a function of the 1H NMR oxidation was measured by consumption disease (CVD) risk. The aim of this study spectra derived data. of dissolved oxygen. Heme-mediated lipid was to investigate whether plasma n-3 fatty oxidation at different Hb and lipid concen- acid concentration is related to hs-CRP trations was modeled by Michaelis−Menten concentration. A total of 124 free-living Removal of lipids, dioxins, and kinetics. The maximum rate (Vmax) for the adults were divided into tertiles of plasma polychlorinated biphenyls reaction with cod and bovine Hb as a pro- hs-CRP (<1.0, 1.0–3.0, and >3.0 mg/L). during production of protein oxidant was 66.2 ± 3.4 and 56.6 ± 3.4 μM/ Body composition and anthropometric isolates from Baltic herring min, respectively. The Michaelis−Menten measurements were recorded. hs-CRP was constant (Km) for the reaction with cod and analyzed using immunoassays, and fatty (Clupea harengus) using bovine Hb was 0.67 ± 0.09 and 1.2 ± 0.2 acids were measured by gas chromatog- pH-shift processes μM, respectively. V for the relationship raphy. Plasma hs-CRP concentration was max Marmon, S.K., et al., J. Agric. Food Chem. between the oxygen uptake rate and lipid negatively correlated with total n-3 fatty 57:7819–7825, 2009 concentration was 43.2 ± 1.5 μM/min, while acids (P = 0.05), eicosapentaenoic acid the K was 0.93 ± 0.14 mg/mL. The effect Dioxins and polychlorinated biphe- m (EPA; P = 0.002), and docosapentaenoic nyls (PCBs) are toxic, lipophilic, and per- of temperature followed Arrhenius kinetics, acid (DPA; P = 0.01). The highest hs-CRP sistent substances that impose a serious and there was no significant difference in tertile (>3.0 mg/L) had significantly lower health threat. A major risk of exposure activation energy between cod and bovine concentrations of total n-3 fatty acids, EPA, to these toxic substances is consumption Hb. The rate of lipid oxidation induced by and DPA when compared with the other ter- of fish from polluted waters, such as the bovine Hb was highest around pH 6. Ethyl- tiles (P < 0.05). This study provides evi- Baltic Sea. The aim of this study was to enediamine tetraacetic acid (EDTA) had no dence that in healthy individuals, plasma investigate whether pH-shift processing of significant effect on heme-mediated lipid n-3 fatty acid concentration is inversely Baltic herring with elevated toxicity levels oxidation, but _-tocopherol and astaxan- related to hs-CRP concentration, a surro- could be used to produce a protein isolate thin worked well as antioxidants. Kinetic gate marker of CVD risk. with low fat content and, thereby, reduced differences were found between iron and dioxin and PCB levels. Both acid (pH 2.7) Hb as pro-oxidants, and the efficacy of the Contribution to further and alkaline (pH 11.2) pH-shift processing antioxidants depended on the pro-oxidant understanding of the evolution were investigated and resulted in efficient in the system. of sunflower oil submitted to reduction of fat, dioxin, and PCB levels. A reduction of 70−80% per amount of protein Near-infrared (NIR) prediction frying temperature in a was determined for all of these parame- of trans-fatty acids in ground domestic fryer: Study by 1H ters. The amounts, and thus the removal, 2 cereal foods nuclear magnetic resonance of lipids and dioxins (R = 0.952) as well as lipids and PCBs (R2 = 0.996) were highly Kim, Y., and S.E. Kays, J. Agric. Food Guillén, M.D., and P.S. Uriarte, J. Agric. correlated (p < 0.01). A mass balance of the Chem. 57:8187–8193, 2009. Food Chem. 57:7790–7799, 2009. alkaline pH-shift process showed that most Near-infrared (NIR) reflectance spec- A study is made of the evolution of the of the fat and pollutants were found in the troscopy was evaluated as a rapid method composition of sunflower oil kept over pro- floating fat emulsion layer of the first cen- for prediction of trans-fatty acid content in longed periods of time at high temperature trifugation, followed by the pellet of the ground cereal products without the need for 716 inform November 2009, Vol. 20 (11) oil extraction. NIR spectra (400−2498 nm) AOCS Journals Q Fatty acid composition, oxidative sta- of ground cereal products were obtained bility, and radical scavenging activity of with a dispersive NIR spectrometer and vegetable oil blends with coconut oil, correlated to trans- and cis-fatty acid Bhatnagar, A.S., P.K. Prasanth Kumar, J. content determined by a modification of Hemavathy, and A.G. Gopala Krishna AOAC Method 996.01. Partial least-squares Q Effects of adhesive application methods regression and Marten’s uncertainty test on performance of a soy-based adhesive were applied to calculate models for pre- in oriented strandboard, Schwarzkopf, diction of trans-fatty acids using spectral M., J. Huang, and K. Li regions affected by lipid absorption. The best model (n = 84) for trans-fat predic- Q Production of fatty acid methyl esters tion used the 700−2498 nm region and sec- via the in situ transesterification of ond-derivative processing of spectra. When soybean oil in carbon dioxide-expanded used to predict test samples (n = 27), the methanol, Wyatt, V.T., and M.J. Haas model had an RPD of 4.8 with a standard Q Fatty acid composition of Baccaurea error of performance of 0.70% (range of courtallensis Muell. Arg seed oil: An 0.05−11.74%) and r2 of 0.97. Optimum endemic species of Western Ghats, models for cis-fatty acids were developed Journal of the American Oil India, Mohan, S. with the 1100−2498 and 700−2498 nm Chemists’ Society (October) Q Functional properties of soy protein ranges and had an RPD of 4.0. Regression isolates produced from ultrasoni- Q Characteristics of virgin olive oils from coefficients indicated that useful absor- cated defatted soy flakes, Karki, B., the olive zone of Extremadura (Spain), bance for prediction of trans- and cis-fatty B.P. Lamsal, D. Grewell, A.L. Pometto and an approximation to their varietal acids was in the overtone and combination III, J. van Leeuwen, S.K. Khanal, and origin, Casas, J.S., C. De Miguel Gor- regions for lipid absorption. S. Jung dillo, E.O. Bueno, J.M. Expósito, M.F. Q Oil and conjugated linolenic acid con- Lipoproteomics: Using mass Mendoza, T.A. Hierro, L.G. González, tents of seeds from important pome- spectrometry-based and M.M. Cano granate cultivars (Punica granatum Q Investigation of frying oil quality using proteomics to explore the L.) grown in Turkey, Kıralan, M., M. VIS/NIR hyperspectral analysis, Yavari, Gölükcü, and H. Tokgöz assembly, structure, and A.A., M. Hamedi, and S. Haghbin function of lipoproteins Q Rapid profiling of animal-derived fatty acids using fast GC × GC coupled to Hoofnagle, A.N., and J.W. Heinecke, J. time-of-flight mass spectrometry, Chin, Lipid Res. 50:1967–1975, 2009. S.-T., Y.B. Che Man, C.P. Tan, and D.M. Lipoproteins are centrally important in lipid transport, fuel metabolism, and car- Hashim diovascular disease. The prototypic lipo- Q Purification and characterization of a protein has an outer shell of amphipathic radical scavenging peptide from rape- lipids and proteins that solubilize a hydro- seed protein hydrolysates, Zhang, S.B., phobic lipid core. Lipoprotein-associated Z. Wang, S.Y. Xu, and X.F. Gao proteins have classically been viewed as Q Determination of trace nickel in hydro- structural elements and factors important genated cottonseed oil by pressur- in lipid metabolism. Recent mass spectro- ized bomb acid digestion and graphite metric analyses revealthat the protein cargo furnace atomic absorption spectrom- of lipoproteins is much more diverse than etry detection, Liu, J., G. Zhang, Z. Lipids (October) previously appreciated, raising the possibil- Meng, and B. Qiao ity that lipoproteins play previously unsus- Q New bioactive oxylipins formed by non- Q Physicochemical and sensory quality pected roles in host defense mechanisms enzymatic free-radical-catalyzed path- of crude Brazilian pecan nut oil during and inflammation. They further suggest that ways: The phytoprostanes, Durand, T., storage, Oro, T., H.M.A. Bolini, D.B. lipoprotein-associatedproteins can identify V. Bultel-Poncé, A. Guy, S. Berger, M.J. humans at increased risk of cardiovascular Arellano, and J.M. Block Mueller, and J.-M. Galano disease. Here, we summarize recent devel- Q Fatty acid distribution in the seed flour Q Contrasting effects of n-3 and n-6 fatty opments in lipoproteomics, the proteomic of wild Vicia species from southern acids on cyclooxygenase-2 in model analysis of lipoproteins. We also discuss Spain, Pastor-Cavada, E., R. Juan, J.E. systems for arthritis, Hurst, S., S.G. the promises and challenges this powerful Pastor, M. Alaiz, and J. Vioque Rees, P.F. Randerson, B. Caterson, and analytical strategy offersfor expanding our Q Oil and conjugated linolenic acid con- J.L. Harwood understanding of the biology and structures tents of seeds from important pome- Q Ezetimibe inhibits expression of acid of lipoproteins. granate cultivars (Punica granatum sphingomyelinase in liver and intestine, L.) grown in Turkey, Kýralan, M., M. Cheng, Y., F. Liu, J. Wu, Y. Zhang, Å. Gölükcü, and H. Tokgöz Nilsson, and R.-D. Duan Publications inform November 2009, Vol. 20 (11) 717

Q Regulation of HMGCoA reductase fied by a soil release polymer and their Changes in cholesterol activity by policosanol and octacosadi- topographic structure, Hasan, M.M.B., absorption and cholesterol enol, a new synthetic analogue of octa- A. Calvimontes, and V. Dutschk synthesis caused by ezetimibe cosanol, S. Oliaro-Bosso, E.C. Gaudino, Q Mixed micellization and interfacial S. Mantegna, E. Giraudo, C. Meda, F. properties of polyoxyethylene sorbi- and/or simvastatin in men Viola, and G. Cravotto tan esters with cetylpyridinium chlo- Sudhop, T., et al., J. Lipid Res. 50:2117– Q In vitro simultaneous transfer of lipids ride: A tensiometric study, Rehman, 2123, 2009 to HDL in coronary artery disease and N., M.A. Mir, M. Jan, A. Amin, A.A. This study evaluates changes in cho- in statin treatment, Lo Prete, A.C., Dar, and G.M. Rather lesterol balance in hypercholesterolemic C.H. Dina, C.H. Azevedo, C.G. Puk, subjects following treatment with an Q Nanoencapsulation of `-cypermethrin inhibitor of cholesterol absorption or cho- N.H.M. Lopes, W.A. Hueb, and R.C. by complex coacervation in a micro- Maranhão lesterol synthesis or co-administration of emulsion, Zhu, Y., X. An, S. Li, and S. Q Suppression in mevalonate synthesis both agents. This was a randomized, dou- Yu mediates antitumor effects of com- ble-blind, placebo-controlled, four-period Q Some Schiff base surfactants as steel- bined statin and a-tocotrienol treat- crossover study to evaluate the effects of corrosion inhibitors, Aiad, I.A., and ment, Wali, V.B., S.V. Bachawal, and co-administering 10 mg ezetimibe with 20 P.W. Sylvester N.A. Negm mg simvastatin (ezetimibe/simvastatin) on cholesterol absorption and synthesis Q Kinetic study of the prooxidant effect Q Synthesis and evaluation of 4-diethyl relative to either drug alone or placebo in of _-tocopherol. Hydrogen abstraction amino benzaldehyde Schiff base cat- 41 subjects. Each treatment period lasted from lipids by _-tocopheroxyl radical, ionic amphiphiles as corrosion inhibi- tors for carbon steel in different acidic 7 weeks. Ezetimibe and ezetimibe/sim- Ouchi, A., M. Ishikura, K. Konishi, S.-i. vastatin decreased fractional cholesterol media, Negm, N.A., M.F. Zaki, and Nagaoka, and K. Mukai absorption by 65 and 59%, respectively (P Q Changes in oil content of transgenic M.A.I. Salem < 0.001 for both relative to placebo). Sim- soybeans expressing the yeast SLC1 Q Synthesis and properties of novel dou- vastatin did not significantly affect choles- gene, Rao, S.S., and D. Hildebrand ble-tail trisiloxane surfactants, Peng, Z., terol absorption. Ezetimibe and ezetimibe/ Q Total synthesis and antileishmanial C. Lu, and J. Lai simvastatinincreased fecal sterol excretion activity of the natural occurring acet- Q Anionic surfactants synthesised from (corrected for dietary cholesterol), which ylenic fatty acids 6-heptadecynoic acid replenishable phenolic lipids, Bruce, also represents net steady-state cholesterol and 6-icosynoic acid, Carballeira, N.M., I.E., L. Mehta, M.J. Porter, B.K. Stein, synthesis, by 109 and 79%, respectively M.M. Cartagena, C. Fernández Prada, and J.H.P. Tyman (P < 0.001). Ezetimibe, simvastatin, and ezetimibe/simvastatin decreased plasma C. Fernández Rubio, and R. Balaña- Q Synthesis and some properties of fluo- low density lipoprotein (LDL)-cholesterol Fouce rinated cationic surfactants, Mohamed, by 20, 38, and 55%, respectively. The co- Q Simple methods to detect triacyl- M.Z., and A.S. Mohamed glycerol biosynthesis in a yeast-based administered therapy was well tolerated. Q Synthesis and characterization of lauryl The decreases in net cholesterol synthesis recombinant system, Siloto, R.M.P., trimethyl ammonium surfactants with M. Truksa, X. He, T. McKeon, and R.J. andincreased fecal sterol excretion yielded new counteranion types, Xu, B.-c., F. nearly additive reductions in LDL-choles- Weselake Han, J.-h. Shui, and Y.-w. Zhou terol for the co-administration of ezetimibe Q Palm-based nonionic surfactants as and simvastatin emulsifiers for high internal phase emul- sions, Lim, H., A. Kassim, N. Huang, Normal phase liquid and M.A. Yarmo chromatography coupled to Q Synthesis, antimicrobial activity and quadrupole time of flight micellization of gemini anionic surfac- tants in a pure state as well as mixed atmospheric pressure chemical with a conventional nonionic surfac- ionization mass spectrometry tant, F.H. Abd El-Salam for separation, detection, and Q Solubilizing and hydrotropic properties mass spectrometric profiling of of isosorbide monoalkyl- and dimethyl- neutral sphingolipids and ethers, Durand, M., Y. Zhu, V. Molinier, T. Féron, and J.-M. Aubry cholesterol Journal of Surfactants and Q Effect of ionic head group on admi- Farwanah, H., et al., J. Chromatogr. B Detergents (Issue 4) celle formation by polymerizable sur- 877:2976–2982, 2009. factants, Asnachinda, E., S. Khaodhiar, Many lipidomic approaches focus Q Correlation between wettability and and D.A. Sabatini on investigating aspects of sphingolipid cleanability of polyester fabrics modi- metabolism. Special emphasis is put on 718 inform November 2009, Vol. 20 (11) neutral sphingolipids and cholesterol and showed that vitamin E components are Protecting oil during frying: their interaction. Such an interest is attrib- present in all major flour fractions of A comparative study uted to the fact that those lipids are altered wheat, but that the vitamin E content and in a series of serious disorders including composition differed significantly between Aladedunye, F.A., and R. Przybylski, Eur. various sphingolipidoses. High-perfor- fractions. The total content of vitamin E, J. Lipid Sci. Technol. 111:893–901, 2009. mance thin-layer chromatography (HPTLC) calculated as _-tocopherol equivalents, The effect of carbon dioxide blanket- has become a widely used technique for changed from 16.1 mg _-TE/g in wheat ing (CDB) and vacuum frying (VF) on the lipid analysis. However, mass spectromet- grain to 12.2 mg _-TE/g in roller-milled frying performance of regular canola oil ric profiling is irreplaceable for gaining wheat flour. The germ fraction had the was evaluated. For 7 h daily and for 7 days an overview about the various molecular highest content of tocopherols, and the French fries were fried in regular canola oil species within a lipid class. In this work we content of _-tocopherol (195.2 μg/g) was at 185 ± 5°C without and with CDB and in a have developed a sensitive method based on 16 times higher (on average) than in any vacuum fryer. The extent of changes in the gradient normal-phase high-performance other fraction. The content of tocotrienols oil was assessed by analysis of total polar liquid chromatography (HPLC) coupled was distributed more uniformly in the wheat compounds (TPC), anisidine value (AV), to quadrupole time of flight (QTOF) atmo- grain, with the highest content in the bran color component formation, and changes spheric pressure chemical ionization-mass fractions, and the content of `-tocotrienol in composition of fatty acids and tocopher- spectrometry (APCI-MS) in positive mode, was higher than the content of _-tocopherol ols. Frying under CDB reduced the amount which for the first time enables separation, in all milling fractions except the wheat of TPC by 54%, whereas 76% reduction on-line detection, and mass spectrometric germ. The content of `-tocotrienol was was observed during VF compared to stan- profiling of multiple neutral sphingolipids 24.1 μg/g in wheat grain, 25.3–31.0 μg/g dard frying conditions (SFC). Similarly, including ceramide, glucosylceramide, lac- in the bran fractions, and 14.3–21.9 μg/g lower oxidative degradation was observed tosylceramide, globotriaosylceramide, glo- in the fractions of endosperm. Overall, when measured by AV. At the end of the botetraosylceramide, and sphingomyelin, as germ and fine bran fractions represent good frying period, the reduction in unsaturated well as cholesterol within less than 15 min. sources of vitamin E and might be used in fatty acid content was 3.8, 1.9, and 12.7% An important advantage of the presented breadmaking. when frying under CDB, vacuum, and SFC, HPLC/APCI-MS approach is that the sepa- respectively. The rate of tocopherol degra- ration pattern emulates the one obtained by Synchronous fluorescence dation was three and twelve times slower in VF when compared to CDB and SFC, an optimized HPTLC method with a mul- spectroscopy: Tool for tiple-stage development. Thus, the lipid respectively. classes previously separated and quantified monitoring thermally stressed by HPTLC can be easily screened regard- edible oils Continuous measurement of ing their mass spectrometric profiles by Poulli, K.I., J. Agric. Food Chem. 57:8194– HPLC/APCI-MS. In addition, the selected galactolipid hydrolysis by 8201, 2009. ionization conditions enable in-source frag- pancreatic lipolytic enzymes Total synchronous fluorescence spectra mentation providing useful structural infor- are proposed for monitoring edible oils using the pH-stat technique and mation. The methods (HPLC/APCI-MS and during thermal stress. Synchronous flu- the optimized HPTLC) were applied for the a medium chain monogalactosyl orescence spectra obtained at an 80 nm diglyceride as substrate analysis of the mentioned lipids in human wavelength interval combined with prin- fibroblasts. This approach is aimed basi- cipal component analysis are suitable for Amara, S., et al., Biochim. Biophys. Acta cally at investigators who perform studies classification of vegetable oil deteriora- 1791:983–990, 2009. based on genetic modifications or treat- tion. Spectroscopic features in the range Galactolipids are the main lipids from ment with pharmacological agents leading of 300−500 nm have been used for extra plants, and galactolipases play a major role to changes in the biochemical pathways of virgin olive, olive pomace, and sesame oil, in their metabolism. These enzymes have neutral sphingolipids and cholesterol. In and the range of 320−520 nm has been used been, however, poorly studied so far, and addition, it can be of interest for research for corn, soybean, sunflower, and a com- only a few assays have been developed. A on disorders related to impairments of mercial blend of oils. The score in the first specific and continuous galactolipase assay sphingolipid metabolism. two principal components explains 91.1% using synthetic medium-chain monogalac- of the data matrix variance for extra virgin tosyl diacylglycerol (MGDG) as substrate Tocopherol and tocotrienol olive, sesame, and olive pomace oil and was developed using the pH-stat technique content in commercial wheat 89.3% for corn, soybean, sunflower, and the and recombinant human (rHPLRP2) and commercial blend of oils. The objective of guinea pig (rGPLRP2) pancreatic lipase- mill streams this study is to develop a rapid method for related protein 2 as model enzymes. PLRP2 Engelsen, M.M., and Å. Hansen, Cereal the prediction of edible oil quality during are the main enzymes involved in the diges- Chem. 86:499–502, 2009. thermal stress. Spectroscopic changes are tion of galactolipids in the gastrointestinal The content of tocopherols and toco- indicative of oxidative deterioration as tract. Monogalactosyl di-octanoylglycerol trienols, collectively known as vitamin E measured through wet chemistry methods: was mixed with bile salt solutions by soni- (tocols), was determined in fractions of peroxide value, p-anisidine value, TOTOX cation to form a micellar substrate before roller-milled wheat grains. The results value, and radical-scavenging capacity. launching the assay. The nature of the Publications inform November 2009, Vol. 20 (11) 719

bile salt and the bile salt-to-MGDG ratio analysis of TAG molecular species from and 29.0 wt%, respectively. The primary were found to significantly affect the rate complex lipid mixtures of mouse liver and fatty acids found in cress oil were oleic of MGDG hydrolysis by rHPLRP2 and white adipose tissue (WAT) using reversed- (30.6 wt%) and linolenic acids (29.3 wt%), rGPLRP2. The maximum galactolipase phase high resolution liquid chromatog- whereas field pennycress oil was principally activity of both enzymes was recorded raphy (LC) coupled with electrospray composed of erucic (32.8 wt%) and lino- with sodium deoxycholate (NaDC) and ionization (ESI)-quadrupole/time of flight leic (22.4 wt%) acids. Cress oil contained at a NaDC-to-MGDG ratio of 1.33 and at hybrid mass spectrometer (QTOF-MS). high concentrations of a- (1422 ppm) and b- basic pH values (8.0–9.0). The maximum For effective profiling of TAG molecu- (356 ppm) tocopherols, whereas _-tocoph- rates of hydrolysis were obtained using lar species, sensitive two-dimensional erol (714 ppm) was the primary tocopherol a MGDG concentration of 10−2 M, and (2D) maps were constructed and individ- discovered in field pennycress oil. The calcium chloride was found to be not nec- ual structures were correctly identified by overall tocopherol concentrations of cress essary to obtain the maximum of activity. the elution profile and MS/MS. As a result, and field pennycress oils were 1799 and Under these conditions, the maximum turn- TAG including their structural isomers and 851 ppm, respectively. The primary phytos- overs of rGPLRP2 and rHPLRP2 on mixed TAG with odd-numbered acyl carbon chains terols elucidated in cress and field penny- NaDC/MGDG micelles were found to be were separated and detected effectively cress oils were sitosterol and campesterol, 8000 ± 500 and 2800 ± 60 μmol/min/mg on the 2D map as compared with conven- with avenasterol also present in significant (U/mg), respectively. These activities are in tional high-performance LC. Our 2D profil- quantity in cress oil. The total phytosterol the same order of magnitude as the activi- ing method also was useful in searching for concentration in cress oil (14.41 mg/g) ties on triglycerides of lipases, and they are characteristic molecular species globally. was greater than that in field pennycress the highest specific activities ever reported In mouse WAT, novel oxidized TAG, which (8.55 mg/g) oil. Field pennycress oil exhib- for galactolipases. For the sake of com- were mainly formed by hydroperoxidation ited excellent low temperature fluidity, parison, the hydrolysis of mixed bile salt/ of one of their linoleic acyl chains, were whereas cress oil was more stable to oxi- MGDG micelles was also tested using other effectively detected in comparison with dation and over a range of temperatures dis- pancreatic lipolytic enzymes, and only TAG molecular species of mouse liver. played lower kinematic viscosities as well native and recombinant human carboxyl as a higher viscosity index. The acid and ester hydrolases were found to display sig- Composition and physical iodine values of field pennycress oil were nificant but lower activities (240 ± 17 and lower than those for cress oil, but both oils 432 ± 62 U/mg, respectively) on MGDG. properties of cress (Lepidium had excellent lubrication properties. Q sativum L.) and field pennycress Global analysis of (Thlaspi arvense L.) oils triacylglycerols including Moser, B.R., et al., Ind. Crop Prod. 30:199– CLASSIFIED oxidized molecular species by 205, 2009. reverse-phase high resolution The fatty acid profiles and tocoph- erol and phytosterol contents of crude Jedwards International, Inc. LC/ESI-QTOF MS/MS oils of cress (Lepidium sativum L.) and Ikeda, K., et al., J. Chromatogr. B field pennycress (Thlaspi arvense L.) are Suppliers of Bulk Specialty Oils to 877:2639–2647, 2009. reported, along with yields from the cor- the Food, Dietary Supplement and Global analysis of triacylglycerols responding seeds. The physical properties Cosmetic Industries. Leading Sup- (TAG) has become increasingly important of these oils were also determined, which plier of Omega-3 Oils. in studies of abnormalities of lipid metabo- included oxidative stability, kinematic vis- lism in metabolic syndrome. TAG consist of cosity, viscosity index, low-temperature flu- www.bulknaturaloils.com various molecular species, including three idity, specific gravity, acid value, lubricity, tel: 617-472-9300 fatty acyl chains with a large variety of and iodine value. The oil content of dried carbon chain lengths and degrees of unsat- cress and field pennycress seeds was 22.7 uration. Therefore, most previously reported methods have been insuf- ficient in global detection of TAG including their structural isomers and TAG with oxi- dized or odd-num- bered acyl carbon chains. Here we report an effective method for global AOCS Call for Nominations for the 2010-2011 Academic Year

This award was established to honor long-time AOCS member Thomas H. Smouse.

Major Contributors: The purpose of this graduate fellowship is to encourage and support outstand­ ing research by recognizing a graduate student pursuing an advanced degree in American Oil Chemists' Society a field of study consistent with the areas of interest of the AOCS. Primary qual­ American Oil Chemists' Society Foundation ifications include the highest standards of academic excellence and the reason­ Archer Daniels Midland Foundation able expectation that the recipient, upon completion of the degree, will enter into and make significant contributions to a field consistent with the goals and Benefactors: interests of the AOCS. American Fats and Oils Association Mr. and Mrs. Edward Campbell Eligibility requirements Or. Stephen S. Chang The individual must be scholastically outstanding with interests and involvement Fabrica De Jabon la Corona, S.A. DE outside the academic discipline. Age, sex, race, financial need, and religion are c.v. not conditions of eligibility for this award. Specific requirements include the National Institute of Oilseed Products applicant be a graduate student beginning or continuing a course of study lead­ Mrs. Bernetta Smouse ing to an M.S. and/ or Ph.D degree with a preference for Ph.D. candidates. The Mrs. Elizabeth Smouse and children applicant must have an above-average interest and aptitude for research, and the Thomas, Deirdre, and Robert student and m~jor professor must be current members of the AOCS. Unichema North America

Fellowship level: U.S. $15,000. ($10,000 Fellowship, $5,000 for travel and research expenditures related to the student's graduate program)

Application procedure All recommendations for the Smouse Fellowship must be submitted on the offi­ cial application form. This form is available by contacting the AOCS Awards Program, P.O. Box 17190, Urbana, IL 61803-7190 USA. Phone: +1-217-359- 2344, fax: +1-217-351-8091, e-mail: [email protected]. Electronic applications available at www.aocs.org/ member/ awards/.

Completed applications must be returned to the AOCS by February 1, 2010. Applicants will be notified of the outcome of the fellowship competition after Your Global Fats and Oils Connection April 15, 2010. Inside AOCS inform November 2009, Vol. 20 (11) 721 Outtakes from the history of AOCS

Alabama. The tree was either planted by the Indians or else a seed- Editor’s note: To celebrate AOCS’ 100th anniversary, AOCS Cen- ling from one which was, because the trees are growing in a straight tennial Historian George Willhite chronicled its history with a series line near the town site. Fort Toulouse was located there by the of articles in inform. During the research, writing, and revision of French in 1714 and remained under them until the treaty of 1760, those 12 articles—appearing in inform from April 2008 to April when they withdrew their outposts and left the country in the hands 2009—countless anecdotes and interesting facts failed to make of the English.” the final cut each month because of space constraints,. Continu- Many of the past AOCS presidents have miniature replicas of those gavels, made in past years by Dick Baldwin, whose hobbies ing this month, we present the “best of the rest” of his research include lapidary. on the history of AOCS.

LAMAR KISHLAR George Willhite Lamar Kishlar, who served as AOCS president in 1943, H.B. BATTLE was a tinkerer. In 1917, he joined the H.B. Battle is best known within AOCS as the creator of AOCS’ US Navy’s aviation wing at traditional gavel. a time when the Navy flew He was a chemist by trade, but his avocations were history wooden planes with cloth and anthropology. He was a co-founder of the Alabama Anthropo- wings. He and his mates logical Society in 1909. He had opened his independent analytical made the first US Navy laboratory in Montgomery, Alabama, in 1906—three years before aviation training films. He the 1909 meeting of analysts in the Jockey Club in Memphis that developed one of the first led to formation of the Society of Cotton Products Analysts. electric starters used for In 1893, when he was 31, Battle had been named head of the aviation engines. After his North Carolina Agricultural Experiment Station. His father, Kemp military service, he began Battle, was a renowned president of the University of North Car- a career in R&D at Ralston olina, serving from 1876 to 1891. H.B. Battle eventually left to Purina in St. Louis, Mis- found a chemical company, and then became a chemist for South- souri. But it is not his oils ern Cotton Oil Co. He moved to Montgomery, Alabama, in 1903 and fats career I want to talk about. as a chemist with Southern Cotton Oil Co. Kishlar’s son, Lamar Kishlar Jr., was 25 in August 1952 when When Battle was president, AOCS had approximately 275 he was stricken with polio and placed in an iron lung. One night the members. It was during his tenure that AOCS began the quar- son’s iron lung failed at the family home in Webster Groves, Mis- terly Journal of the Oil and Fat Industries, giving AOCS its own souri. Kishlar Sr. said he could not find anyone to repair it. A new journal. iron lung was located, but Kishlar said he decided to learn to be a On May 6, 1924, when Battle turned over the AOCS presi- respiratory technician to be ready for future failures. He studied dency to H.J. Morrison, he also presented AOCS with a handmade textbooks, worked on spares owned by the National Foundation gavel. His comments on the gavel were published in the Journal of for Infantile Paralysis, and built up a supply of spare parts in his Oil and Fat Industries (2:144–145), which notes in part that Ameri- home. He devised—using a portable vacuum cleaner and plastic can Indians were the earliest oil crushers in North America, using tubing from coal miners’ masks—a device that his son could use stones to crack nuts, then boiling the cracked nuts and skimming when not in his commercial portable respirator. oil off the surface. The oil would be used as edible products and Kishlar also answered calls from hospitals and patients also for decoration. referred to him for help—and he never charged anyone a cent for The Indians taught children how to crush nuts, he said, “and that help. a hammer stone was used similar to the one upon this gavel, only oftentimes of a larger size. A. RICHARD BALDWIN “The handle is from the wood of a black walnut tree now growing on the ancient site of Taskigi-town, a settlement of the Dick Baldwin played semi-pro baseball to earn money while he was Upper Creek Nation within a very few miles of Montgomery, in college. He played in the Central Florida league, and told me he 722 inform November 2009, Vol. 20 (11) pitched three days, played JIM LYON third base on others. Jim Lyon, as AOCS execu- Dick Baldwin has been tive director, complemented described as a person who Dick Baldwin’s drive to worked 25 hours a day, improve AOCS. eight days a week. There’s Lyon, as treasurer of no other explanation for the National Council of how he was able to accom- Teachers of English, repre- plish so much as director of sented that group as it sold research for Cargill, devote its leasehold on 508 South untold hours to AOCS, serve Sixth Street in Champaign, on federal agriculture advi- Illinois, to AOCS. When sory committees, and be an AOCS Executive Direc- active volunteer in other pro- tor Carl Hauber declined fessional groups, as well as to move from Chicago to his church. He is a member Champaign, AOCS had to of six honorary societies. He find a new chief staff officer. served as AOCS president in Jim Lyon was hired and 1961 when he was 43, one of the younger persons elected to head came to work in 1971. the organization. When Lyon started with AOCS, there were about 2,700 Dick grew up on a Michigan farm. His wife Eleanor said, members. During his tenure, membership essentially doubled. The “Dick’s father was a very energetic man; it bothered him if he annual budget in 1971 was about $500,000; by the time he retired, couldn’t see everybody at work. I guess a lot of that rubbed off on the budget was at $5 million. Dick.” There were about 10 employees when Lyon took over the staff; Baldwin’s family used to go to Florida every year for Dick’s when he retired in 2002, the staff was more than 40. health, which Dick later decided probably involved allergies, so it AOCS’ first world conference venture began with a plane was somewhat logical that he chose to attend John B. Stetson Uni- ticket to Amsterdam that didn’t cost AOCS a cent. versity in DeLand, Florida. (It was there he met Eleanor, a native The US Soy Protein Council was a key organizer of the of Minnesota. The two transplanted Midwesterners had a common World Soy Protein Conference held in Munich, Germany, in 1973. bond.) Baldwin arranged for AOCS to publish the proceedings. Afterward, There’s not enough time to discuss all that Dick Baldwin did Baldwin and Lyon agreed that AOCS, which realized a surplus to improve AOCS’ publication program, promote short courses in from publishing the proceedings, could have realized a much larger the mid-1940s, and then move AOCS into the international arena surplus if it had been the conference organizer. in the 1970s. The result was the idea for a world conference on oilseed and Among the AOCS programs that Dick fostered were: vegetable oil processing. Baldwin discussed the idea with Cargill r BOOVBMTIPSUDPVSTFTJOUIFQPTUXBST colleagues in the Netherlands, and a plan began to take shape to r JNQSPWFETQFFEPGQVCMJDBUJPOGPSNBOVTDSJQUT have the meeting there. r GPSNBUJPOPGLipids; Lyon had won a free trip to Europe in a drawing during an r JOUSPEVDUJPOPGNPOPHSBQIQSPHSBN association executives’ conference. He used that ticket to fly to r BEWPDBDZGPS"0$4XPSMEDPOGFSFODFQSPHSBNTBOE Amsterdam where he met with Kees Meershoek, the chief staff r NPUJWBUJPOGPSDSFBUJPOPGBOFXTKPVSOBMQSPWJTJPOPGOBNF officer for VERNOF, the Dutch oilseed trade group. The result was of INFORM. a very successful 1976 conference in Amsterdam and several other He’s a doer. And he’ll tell you that he received far more back AOCS-organized meetings in the Netherlands during the next few than he gave to AOCS. decades. “I still think the idea of joining a small scientific organiza- tion and then identifying an area in which you can make impor- tant contributions to its main goals and finally put your shoulder STEPHEN S. CHANG to the wheel and GO is a good approach for a budding scientist to Steve Chang was AOCS president in 1971 when AOCS moved from take.” Chicago’s riverfront to Champaign. During the birth pangs of INFORM, there was a meeting in He was roasted at his first past presidents’ dinner for blowing Champaign at which many staff persons voiced their trepidations half the Society’s reserves to finance the move to a new building about separating JAOCS into a technical journal and a news maga- in Champaign, thus causing the staff to resign (including Execu- zine. Afterward Dick told me, “I don’t need people to tell me why tive Director Carl Hauber). Chang replied that he would prefer to something shouldn’t be done; I need people who can find a way be remembered as the president who introduced “hot pants” to the to do it.” society—a reference to a female honored student’s attire at the If you have to choose one AOCS member to be labeled “Mr. 1971 award presentation. AOCS” for the latter half of he 20th century, Dick Baldwin is the One of my favorite tales is that of Steve and Lucy Chang. obvious choice. Without Dick Baldwin, AOCS would not be the They both came to the United States on the same ship in 1947—but organization it is today. Inside AOCS inform November 2009, Vol. 20 (11) 723

neither knew the other at the Wilson’s wife, Pam, time. The ship had stopped was working at AOCS in Hawaii where one of shortly after the Society Lucy’s uncles lived. Chang moved to Champaign. Rich was among the travelers was a graduate student at who accompanied Lucy the University of Illinois and her uncle on an island with AOCS member Evelyn tour. When they arrived Weber as his senior profes- in the United States, Lucy sor. Jim Lyon offered to let headed to Kansas to study Wilson join AOCS for $5 dentistry; Steve headed for in annual dues if he would Wisconsin to pursue a mas- work to clean up the base- ter’s degree in fats and oils ment at AOCS’ new digs in chemistry. When his mentor Champaign. at Wisconsin unexpectedly Wilson agreed. In 2001, retired, Chang moved to when Wilson received the Kansas to study with Fred Alton E. Bailey Award he Kummerow (whom he later commented that he later would follow to the Univer- found out AOCS’ annual sity of Illinois). There Lucy and Steve began dating. They married student membership dues, lo those many years ago, totaled $5. shortly after Lucy’s graduation from dental school, but she never “I think about that every month when I sign Jim’s paycheck,” practiced dentistry, devoting her life to providing a home for her Wilson said. husband. George Willhite, AOCS’ centennial historian, retired from AOCS in RICH WILSON 2002 after 27 years as a member of its publications staff. He is Rich Wilson’s first contact with AOCS in the early 1970s was as an honorary member of AOCS. He can be contacted via e-mail at a janitor—sort of. [email protected]. ~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 .,. Phone: + 1-217-693-481 3 .,. Fax: + 1-21 7-693-4857 .,. Email: [email protected] .,. Web: www.aocs.org 014166x Analytical inform November 2009, Vol. 20 (11) 725 31P NMR spectroscopy on olive oil quality control and authentication Photis Dais

In the past decade, high-resolution multinuclear (H, C, P) nuclear magnetic resonance (NMR) spec- troscopy has been applied effectively to evalu- SCHEME 1 ate quality of extra virgin olive oil (EVOO) and to authenticate it. NMR spectroscopy has a number analysis. By using the same analytical technique, we were able to of advantages over conventional analytical tech- detect and quantify phenolic compounds in the polar fraction of EVOO (Christophoridou and Dais, 2006). niques, such as shorter analysis time, nondestruc- Phenolic compounds have potent antioxidant activity and con- tion of the analyte (1H, 13C NMR), identification of tribute significantly to the extraordinary stability of olive oil against compounds at a molecular level, and simultaneous oxidation by atmospheric oxygen. Figure 2A shows the portion of the 31P NMR spectrum of the phenolic extract of an EVOO determination of several components in a single sample where the signals of the phosphitylated aromatic hydroxyl experiment. The popularity of NMR spectroscopy groups of the various phenolic compounds appear. Several signals is related to its applicability to different types of are detected on the basis of the 31P NMR chemical shifts of a large number of polyphenol model compounds, which we assigned by food and beverages including wine, beer, fruit using 2D NMR spectroscopy, and by spiking the sample, when juices, tomatoes, coffee, milk, meat, eggs, starch necessary. We were able to detect total hydroxytyrosol and tyrosol; granules and flour, olive fruits and oil, and so on. the phenolic acids vanillic and p-coumaric; homovanillyl alcohol; the lignans pinoresinol, 1-acetoxy pinoresinol, and syringaresinol 31 This article discusses the contribution of P NMR (we are the first to detect the latter in Greek EVOO); and finally spectroscopy to the characterization of EVOO. the flavonoids apigenin and luteolin. Figure 2B presents the other portion of the same 31P NMR OLIVE OIL ANALYSIS BY 31P NMR spectrum, which shows the signals of the phosphitylated aliphatic SPECTROSCOPY 31P NMR spectroscopy has been used intensively in our labora- tory for the quality control and authentication of EVOO, which is obtained by cold pressing of fresh, healthy olive fruits and which has a free acidity ≤ 0.8% in oleic acid. This methodology (Spyros and Dais, 2000) is based on derivatizing labile hydrogen atoms of hydroxyl and carboxyl groups of EVOO constituents with the tagging reagent 2-chloro-4,4,5,5-tetramethyl-1,2,3-dioxaphospho- lane (1) (see Scheme 1) and using 31P chemical shifts to identify the labile centers (compound 2). The phosphorus reagent reacts rapidly (less than 15 min) and quantitatively under mild conditions (within the NMR tube). In the 31P NMR spectrum of the EVOO sample in Figure 1, one can see the signals of the phosphitylated hydroxyl groups of the two diacylglycerol (DG) isomers, 1, 2- and 1,3-, FIG. 1. 202.2 MHz NMR (nuclear magnetic resonance) spectrum total free sterols, and the phosphitylated carboxyl groups of the of a phosphitylated EVOO (extra virgin olive oil) sample in the region free fatty acids. The latter signal allows the determination of free where the signals of diacylglycerols (DGs), total free sterols, and free acidity. The signal at b 145.30 ppm belongs to the phosphitylated fatty acids appear. Phosphitylated cyclohexanol is the internal stan- cyclohexanol, which is used as an internal standard for quantitative dard. 726 inform November 2009, Vol. 20 (11)

hydroxyl groups. In this spectrum, we can identify free hydroxy- not virgin, tend clearly toward the lower right corner of the graph, tyrosol and tyrosol, and homovanillyl alcohol. In addition to poly- as expected. Although this diagram is useful to assess the EVOO phenols we observe the signals of glycerol, maslinic acid, and quality, it does not tell anything about the storage history of EVOO. monoacylglycerols. Finally, several signals denoted by _ and ` It is unable to specify the exact storage time or age reflected on were assigned to free_- and `-d-glucose, which are the hydrolysis the DG concentration. Through a kinetic study of the hydrolysis products of the various glucosides in EVOO. The same analytical of triacylglycerols and the isomerization of DG that occur during technique has been used to determine moisture in EVOO (Hatzakis olive oil storage (at room temperature in light and dark for a total et al., 2008), which is responsible for the creation and persistence storage time of 18 months), we were able to derive a mathematical of the suspended and dispersed material that constitutes the so-called “veiling” of EVOO. Finally, 31P NMR spectroscopy with no derivatiza- tion was used to detect and quantify phospholipids in EVOO (Hatzakis et al., 2008). As phospholipids give a single signal in the spectrum and different phospholipids are characterized by specific resonance frequencies (due to the different chemical structures of phospholipids), separation of the components of the mixture is not neces- sary to analyze it. The main phospholipids found in Greek olive oils were phosphatidylinositol, phosphatidic acid, and lysophosphatidic acid, although very small amounts of other phospholipids were detected as well. QUALITY ASSESSMENT OF EVOO The plot of the ratio D (= 1,2-DG/total DG) vs. total DG in Figure 3 constitutes a map of the quality of olive oil samples including commercial EVOO (CEVOO; Froni- maki et al., 2002). Also, commercial blended olive oils (BOO) and refined and olive-pomace oils were analyzed and plotted in Figure 3. Except for one sample from Zakynthos and two samples from Kolymbari, the EVOO from various regions of Greece in Figure 3 are charac- terized by high D values and low total DG. Therefore, the data points tend to gather at the upper left corner of the plot, indicating that the samples are fresh EVOO. Freshly extracted EVOO are characterized by D values close to 1; the closer the D ratio to unity, the fresher the oil. CEVOO samples are char- acterized by low D values and do not fall at the upper left corner of the plot, indicating that they are of inferior quality probably because of their long shelf life. The tendency of the commercial BOO to gather at the lower right corner of the plot is pronounced. This was expected, since BOO are mix- tures of virgin olive oil and FIG. 2. 202.2 MHz 31P NMR spectrum of the phosphitylated polar fraction of an EVOO sample. (A) refined olive oil. Aromatic region, (B) aliphatic region. A = apigenin, L = luteolin, 1-MGs = 1-monoacylglycerols, 2-MGs = Finally, the refined and the 2-monoacylglycerols, f-hydroxytyrosol = free hydroxytyrosol, f-tyrosol = free tyrosol, _ = _-D-glucopyranose, olive-pomace oils, which are ` = `-D-glucopyranose. Analytical inform November 2009, Vol. 20 (11) 727

parameters obtained by 31P NMR spectroscopy—was an advisable way to detect adulteration in EVOO. Figure 4 shows the very good separation of five edible oils, EVOO, corn, soybean, sunflower, and hazelnut, upon application LDA to their NMR data (Vigli et al., 2003). The empty symbols represent EVOO adulterated with seed oils. Mixtures containing the lowest amount of seed oils in olive oil (5%), denoted by arrows, fall outside the ellipse of the group of EVOO (the ellipse denotes the 95% probability that a certain sample belongs to its own group within the region defined by the ellipse). This graph, and the calculated Mahalanobis distances, clearly shows that this methodology is able to detect adulteration of EVOO with seed oils at concentrations as low as 5%. If one thinks that EVOO should contain 10–20% of seed oil for the adulteration to be profitable, the detection limit of 5% achieved by this meth- odology is very useful, especially for the hazelnut oil. By using the same methodology, detection of EVOO adulteration with refined

FIG. 3. Plot of the ratio D vs. total DGs for EVOO samples from information various regions of Greece, commercial EVOO (CEVOO), commercial blended olive oils (BOO), refined olive oils, and olive-pomace oils. D For further reading: = 1,2-DGs/total DGs). Q Christophoridou, S., and P. Dais, Novel Approach to the Detec- tion and Quantification of Phenolic Compounds in Olive Oil 31 expression relating the age of olive oil to the DG concentration in Based on P Nuclear Magnetic Resonance Spectroscopy, J. terms of the ratio D and free acidity (Spyros et al., 2004). Agric. Food Chem. 54:656–664 (2006). Q Fragaki, G., A. Spyros, G. Siragakis, E. Salivaras, and P. Dais, DETECTION OF EVOO FRAUD Detection of Extra Virgin Olive Oil Adulteration with Lam- pante Olive Oil and Refined Olive Oil Using Nuclear Magnetic NMR data were used in combination with chemometrics to detect Resonance Spectroscopy and Multivariate Statistical Analysis, adulteration of EVOO with seed oils including hazelnut oil, which J. Agric. Food Chem. 53:2810–2816 (2005). has almost the same composition as olive oil, and/or olive oils of lower quality such as refined olive oil. The first step for adultera- Q Fronimaki, P., A. Spyros, S. Christophoridou, and P. Dais, Deter- tion studies was the classification of the various types of edible mination of the Diglyceride Content in Greek Virgin Olive Oils 31 oils. A successful classification based on application of multivar- and Some Commercial Olive Oils by Employing P NMR Spec- iate statistical techniques—such as hierarchical cluster analysis troscopy, J. Agric. Food Chem. 50:2207–2213 (2002). (HCA), and linear discriminate analysis (LDA) on compositional Q Hatzakis, E., A. Koidis, D. Boskou, and P. Dais, Determina- tion of Phospholipids in Olive Oil by 31P NMR Spectroscopy, J. Agric. Food Chem. 56:6232–6240 (2008). Q Spyros, A., and P. Dais, Application of 31P NMR Spectroscopy in Food Analysis. 1. Quantitative Determination of the Mono- and Diglyceride Composition of Olive Oils, J. Agric. Food Chem. 48:802–805 (2000). Q Spyros, A., A. Philippidis, and P. Dais, Kinetics of Diglyceride Formation and Isomerization in Virgin Olive Oils by Employ- ing 31P NMR Spectroscopy. Formulation of a Quantitative Measure to Assess Olive Oil Storage History, J. Agric. Food Chem. 52:157–164 (2004). Q Vigli, G., A. Philippidis, A. Spyros, and P. Dais, Classification of Edible Oils by Employing 31P and 1H NMR Spectroscopy in Combination with Multivariate Statistical Analysis. A Proposal for the Detection of Seed Oil Adulteration in Virgin Olive Oils, J. Agric. Food Chem. 51:5715–5722 (2003). FIG. 4. LDA (linear discriminant analysis) plot; EVOO, hazelnut, corn, Q Petrakis, P.V., A. Agiomyrgianaki, S. Christophoridou, A. Spyros, sunflower, and soybean oils are denoted by crosses and solid symbols. and P. Dais, Geographical Characterization of Greek Virgin Mixtures of EVOO with seed oils are denoted by open symbols. Arrows Olive Oils (cv. Koroneiki) Using 1H and 31P NMR Fingerprinting indicate mixtures of EVOO with 5% wt/wt of seed oils. with Canonical Discriminant Analysis and Classification Binary Trees, J. Agric. Food Chem. 56:3200–3207 (2008). 728 inform November 2009, Vol. 20 (11)

olive oil and/or lampante oil at a concentration as low as 5% is pos- sible (Fragaki et al., 2005). GEOGRAPHICAL AND VARIETAL ORIGIN OF GREEK EVOO False labeling is a serious fraud for olive oil. For this reason, the European Union has established regulations for “Protected Desig- nation of Origin” (PDO) and/or “Protected Geographical Indica- tion” (PGI) products with well-defined quality characteristics. This designation guarantees that the quality of the product is closely linked to its territorial and/or botanical origin. In this respect, we attempted to classify Greek olive oils with respect to their geo- graphical origins (Petrakis et al., 2008). NMR spectroscopy has been used to analyze 131 EVOO samples from different geographi- cal origins in an attempt to identify and match EVOO with the geo- graphical areas where they were produced. Application of canonical discriminant analysis (CDA) to phe- nolics content obtained by 31P NMR and to fatty acid profile mea- sured by 1H NMR provided very good accuracy (~90% correct classification). It identified EVOO samples of the most popular Greek cultivar “koroneiki” that originated from three distinct geographical divisions (Peloponnesus, Crete, and the island of Zakynthos; Fig. 5). The predictability was lower (78%) when the FIG. 6. CDA diagram of the cultivar samples in a 2D discriminant statistical analysis was applied to the level of six different sites space. The axes explain a significantly high percentage of the total within the three divisions. The correct classification reached 92%, variation in the original data (CDA1 = 54.1%, CDA2 = 39.5%). though, when the harvesting period was involved in the statisti- cal analysis. Finally, Figure 6 shows some preliminary results of the vari- etal classification of EVOO, based on certain polyphenols deter- mined by 31P NMR spectroscopy. The 2D CDA diagram of this analysis shows satisfactory classification of the most important Greek cultivars: adramitini, throubolia, koroneiki, and tsounati. The correct classification of the four cultivars was 97%. CONCLUSIONS The 31P NMR methodology presented briefly in this article offers new opportunities for the analysis of edible oils and, in particular, for the quality control and authentication of EVOO. Although this technique is considered to be more expensive than conventional methods of analysis, it has a number of advantages that compen- sate for the rather high cost of an NMR spectrometer. A single run detects in a rapid way all the phosphitylated minor compounds present in the olive oil sample and provides signals whose inten- sities reflect the number of magnetically equivalent phosphorus nuclei. The assignment of the chemical shifts of the various func- tional groups is well documented, thus making this technique very appropriate for the screening of a large number of samples and a valuable tool for quality control and authentication of EVOO.

FIG. 5. CDA (canonical discriminant analysis) plot of the three geo- Photis Dais, who is with the NMR Laboratory, Department of Chem- graphical divisions of Greece. The axes (Root1 = 87.8% and Root2 = istry, University of Crete, Voutes Campus, Greece, can be reached 12.2%) account for the total variability of the measured variables. via email at [email protected]. Olive Oil Chemistry and Technology, 2nd Edition

AOCS MONOGRAPH SERIES ON OILSEEDS, VOLUME 1

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A staple food for thousands of years for the To order: inhabitants of the Mediterranean region, olive oil is www.aocs.org/store now popular among consumers worldwide. Olive oil Phone: +1-217-693-4803 differs from other vegetable oils because it is used Fax: +1-217-693-4847 in its natural form and has unique flavor and other Email : [email protected] characteristics. This updated 2nd Edition of the book Olive Oil is a concise, easily understood text on the Mention Promo Code most important aspects of chemistry, technology, BOM1109 when quality, analysis, and biological importance of olive ordering to receive oil. The topics covered have changed rapidly in recent discount. years, and provide the reader with the background necessary to address more specific problems in the Offer expires future. Readers will benefit from more contributors December 18, 2009 and chapters in this 2nd edition, as well as a glossary.

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PHOTO: BROCK PEOPLES Processing Exhibitor inform November 2009, Vol. 20 (11) 731 Fluidized bed desolventizer for gentle rapeseed meal processing only on the original protein structure, but also on the conditions of Editor’s note: This article is based on a presentation given Wednes- processing steps, which may change this structure (Rapsproteine day, May 6, in the Processing Exhibitor Session at the 100th AOCS in der Humanernährung, 2007). Annual Meeting & Expo, held in Orlando, Florida, USA. Therefore, there are some requirements for the meal from which proteins should be extracted. These are: r MPXPJMDPOUFOU   Karl-Heinz Leidt, Lothar Mörl, Frank Pudel, r QBSUJDMFTJ[F•N Klaus Weigel, and Reinhard Zettl r MPXIFYBOFDPOUFOU QQN  r MPXDPOUFOUTPGVOEFTJSFEDPNQPOFOUT HMVDPTJOPMBUFT QIZUJD acid, phenolics); In a conventional desolventizer/toaster the meal r IJHI1%* QSPUFJOEJTQFSTJCJMJUZJOEFY QSPUFJOEFOBUVSBUJPO is treated under conditions that lead to the dena- minimal thermal damage. turation of the contained proteins. Such proteins DESOLVENTIZING OF SOLVENT-EXTRACTED have lost their techno-functional potential and RAPESEED are not suited for applications other than animal The problem is that these requirements cannot be totally fulfilled feeding. A more gentle meal processing is possi- in conventional oilseed processing. By crushing and extracting ble by using fluidized bed technology. This article rapeseed with solvent, the oil content in the meal is decreased to about 1%. The hexane content of the meal is then reduced by the describes a pilot-scale fluidized bed desolven- desolventizing step of the conventional desolventizer equipment tizer and gives results from test trials with rape- (DTDC: Desolventizing-Toasting-Drying-Cooling) to 300 ppm. seed meal. But by the same process the PDI is also drastically reduced. Rapeseed processing in Germany was doubled from 2003 to CONVENTIONAL DESOLVENTIZER 2008, driven by biodiesel production. The doubling of rapeseed processing led also to the doubling of the rapeseed meal amount. In a conventional desolventizer, especially during the first Most of the available meal is used for animal feeding, but about desolventizing and toasting/stripping steps, temperatures of more 1 million metric tons is exported. Like other oilseeds, rapeseed con- than 100°C exist. The treatment takes between 1 and 2 hours. tains not only oil but also considerable amounts of proteins, which Under these conditions the proteins are damaged and the PDI is are enriched in the meal during processing. Rapeseed proteins have, reduced. up until now, not been produced and utilized on an industrial scale, except in feeding the meal. Rapeseed contains different proteins: the storage proteins cruciferin and napin and the (very difficult to recover) membrane protein oleosin. The nutritional potential of rapeseed proteins is very high, holding a strong potential to fulfill information the United Nation’s Food and Agriculture Organization (FAO) requirements, among others. For further reading: Proteins possess very interesting functional properties. Having Q Rapsproteine in der Humanernährung, Heft 32, UFOP Schriften both hydrophilic and hydrophobic properties, they can stabilize 2007 interfaces and form films. By physical, enzymatic, or chemical Q Vavlitis, A., and E.D, Milligan, Flash Desolventizing, in Proceed- modification, the subunits can be dissociated and the polypeptide ings of the World Conference on Oilseed Technology and Utilization, chains can be unfolded, which improves the interface-stabilizing edited by T.H. Applewhite, AOCS Press, Champaign, Illinois, properties. And they can form networks to build bioplastics. These USA (1993), pp. 286–289. functional properties depend on the original protein structures, as Q De Kock, J., Desolventizing and Meal Quality, presented at the well as their changes during processing steps. Because of these New Trends in Oilseed Crushing and Processing, DGF Sym- functional properties, proteins can be used in various technical posium, Leipzig, Germany, March 13–14, 2007. and nutritional applications. The functional properties depend not 732 inform November 2009, Vol. 20 (11)

is an active surface in the tube of about 6.700 m2 when the flakes are 0.009 inches (0.229 mm) thick. But, if the flakes are only a little bit thicker, this active surface will be drastically lower. Finally, spherical parti- cles lead to a very low active surface. Hexane- wetted rapeseed meal particles have a more nearly spherical shape than that of flat blanks. Therefore a flash desol- ventizer system does not seem to be suitable for gentle desolventizing of rapeseed meal. FIG. 1. Pilot-scale equipment. FLUIDIZED BED In the case of soybean processing, gentle meal desolventiz- DESOLVENTIZING ing can be accomplished with so-called flash desolventizers; the A fluidized bed is a product is white flakes. The flaked meal is discharged into a pipe, quantity of solid parti- in which superheated hexane at about 85°C is circulating at a high FIG. 2. Photograph of fluidized bed cles that are contained velocity. The circulating superheated hexane drives out the hexane unit. in a fluid under such from the meal. The treatment is finished after some seconds. This conditions that the solid/ is possible owing to the very high heat and mass transfer surface fluid mixture behaves like a fluid. In our case, the fluid is fed up of the flakes. In the case described by Vavlitis and Milligan, there from the bottom and distributed by a perforated plate. It leaves CONTINUED ON PAGE 736

FIG. 3. Schemes of the operating regimes for total and partial condensation. inform November 2009, Vol. 20 (11) 733 AOCS Career Services

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Visit our website for more information on the best employment opportunities in the fats and oils industry! Health & Nutrition inform November 2009, Vol. 20 (11) 735 Leptin: A novel target for reducing the risk of heart disease in obesity Sherma Zibadi and Ronald Ross Watson disproportionate accumulation of collagen fibers of heart connec- tive tissue, increases the tissue stiffness and impairs heart relax- In the United States, in the past two decades, dra- ation, resulting in cardiac dysfunction. Since adverse remodeling of heart connective tissue contributes notably to functional and struc- matic increases in obesity have occurred in both tural cardiac abnormalities (causing progressive cardiac dysfunc- children and adults. Using body mass index (BMI; tion), it is critically important to investigate the potential mediators weight in kilograms ÷ height2 in meters) as a sur- of obesity-induced cardiac remodeling as a therapeutic target. rogate measure of fatness in adults, overweight LEPTIN, A TARGET FOR TREATMENT? 2 is defined as a BMI of 25.0 to 29.9 kg/m , while Adipose tissue, once considered simply a lipid storage depot, is obesity is defined as a BMI ≥ 30.0 kg/m2. About now known to be a dynamic organ secreting factors such as leptin, the product of the obese gene. two-thirds of adults in the United States are con- Leptin is one of the most important adipose-derived hormones sidered overweight or obese. Approximately 9 and is well-known for its role in regulating energy intake and million adult Americans are defined as morbidly energy expenditure, including appetite and metabolism. Although a clear mechanistic basis for increased cardiovascular risk in obese obese, according to the American Obesity Asso- individuals is uncertain, leptin is a potential causative (or at least ciation. The morbidly obese population is growing at its fastest rate in comparison with the incidence rate of obesity in previous years. information OBESITY AND INCREASED RISK OF HEART For further reading: DISEASE Q Galinier, M., A. Pathak, J. Roncalli, and P. Massabuau, Obesity Obesity contributes to the onset and/or development of heart and cardiac failure, Archives des Maladies du Coeur et des Vais- disease. The relationship between obesity and cardiovascular seaux 98:39–45, 2005. disease has been unequivocally established both clinically and in Q Schulze, P.C., J. Kratzsch, A. Linke, N. Schoene, V. Adams, S. experimental animal models. Furthermore, obesity is associated Gielen, S. Erbs, S. Moebius-Winkler, and G. Schuler, Elevated with other risk factors of heart disease such as type 2 diabetes, serum levels of leptin and soluble leptin receptor in patients hypertension, and dyslipidemia, which aggravate the cardiovas- with advanced chronic heart failure, European Journal of Heart cular outcome associated with obesity. However, obesity has been Failure 5:33–40, 2003. identified as an independent risk factor for coronary heart disease Q Voller, H., K.J.G. Schmailzl, and B. Bjarnason-Wehrens, Obesity and congestive heart failure. In the United States, obesity alone is and cardiovascular diseases—theoretical background and the cause of 11% of heart failure cases in men and 14% of cases therapeutic consequences, Zeitschrift für Kardiologie 93:503– in women. As the prevalence of obesity continues to rise, obesity 513, 2004. is expected to become an important cause of cardiac failure in the Q Wallace, A.M., A.D. McMahon, C.J. Packard, A. Kelly, J. Shep- coming years. Obesity triggers structural and functional changes in the heart, herd, A. Gaw, and N. Sattar, Plasma leptin and the risk of cardio- defined as maladaptive remodeling, which play a major role in the vascular disease in the West of Scotland Coronary Prevention progression of various heart diseases to heart failure. Major con- Study (WOSCOPS), Circulation 104:3052–3056, 2001. tributors to the obesity-induced maladaptive remodeling process Q Zibadi, S., D.F. Larson, and R.R. Watson, Leptin and obesity: in the heart include alterations in cardiomyocytes (heart muscle Role in cardiac functional and structural changes, in Modern cells) and extracellular matrix (heart connective tissue), result- Dietary Fat Intakes in Disease Promotion, edited by F. De Meester, ing in cardiac hypertrophy (abnormal muscle enlargement of S. Zibadi, and R.R. Watson, Humana Press Inc., Totowa, New heart lower chambers) and fibrosis. Cardiac fibrosis, defined as a Jersey, in press. 736 inform November 2009, Vol. 20 (11)

a contributing) factor for hypertension and heart connective tissue, which was asso- leptin-modulator therapeutics to prevent or atherosclerosis as well as some other car- ciated with increased cardiac collagen, lessen adverse cardiac remodeling and dys- diovascular conditions. The primary stim- and induction of heart stiffness and dys- function in obese populations. ulus leading to elevated plasma leptin function. These data support the essential concentrations is obesity and the concomi- role of leptin in the pathogenesis of cardiac Sherma Zibadi and Ronald tant increased body fat. Even in the absence fibrosis. Ross Watson are affiliated of obesity, heart disease can be associated with both the University of with hyperleptinemia, although to a mark- SUMMARY Arizona’s (Tucson, USA) edly lowered degree. Leptin is emerging as Sarver Heart Center, College a novel mechanistic link between obesity These studies lead us to the conclusion that of Medi- leptin initiates or attenuates the adverse and cardiovascular disease. The heart has cine and been shown to be a site of leptin produc- heart remodeling associated with obesity its College of Public Health. tion and action. Leptin directly affects the and other hyperleptinemic conditions, Zibadi can be reached via growth and proliferation of cardiomyocytes which may in turn contribute to the clinical and attenuates heart contraction. Recently syndrome of heart failure. This will likely e-mail at szibadi@email. we have studied the effect of leptin on provide the basis for future development of arizona.edu.

FLUIDIZED BED DESOLVENTIZER (CONTINUED FROM PAGE 732) the separation chamber at the top. The meal batch operation TABLE 1. Energy requirement is fed in from the top and fluidized by the begins with nitro- fluid. After treatment the distributor plate is gen as fluid in the Total Partial turned and the desolventized meal can be same way as pre- condensation condensation removed from the equipment (Fig. 1). viously described. (kWh/kg) (kWh/kg) The velocity of the fluid must be higher But after leaving Specific than the minimum fluidized bed velocity; the filter the fluid is 0.57 0.20 heat power below that, a fixed bed occurs. At the upper only partially con- end, the velocity has to be lower than the densed. In this way Specific 0.54 0.10 fluctuation velocity; above that, pneumatic the circulating fluid cooling power transport begins. Minimum fluidized bed contains more and Specific velocity and fluctuation velocity depend on more hexane. 0.03 0.028 electric power particle size. Therefore, the operating range of a stable fluidized bed is defined by the RESULTS AND minimum fluidized velocity of the largest DISCUSSION particles and the fluctuation velocity of The results of desolventizing by total con- operated in three shifts. The 2-m plant has the smallest particles. In our case particles densation mode show that, to reach the a maximum capacity of 6,000 MT per year. with a size less than 0.4 mm would begin target hexane value of 300 ppm, a treat- The next development is a continuous plant. to leave the apparatus if the fluid velocity ment time of about 45 min is needed. Then It will consist of three parts: a predesolven- is just high enough that particles of about the water content in the meal is about 2%. tizing step followed by the desolventizing 5 mm can be fluidized. In the case of partial condensation trials, step, realized as a fluidization channel, and In the pilot-scale equipment in the the target hexane value can be reached after a gas exchange step. PPM (Pilot Pflanzenöltechnologie Magde- about 20 min. Partial condensation leads burg) lab (Fig. 2) we investigated two dif- to lower energy requirements, as is shown Frank Pudel is managing director at PPM Pilot ferent operating regimes (Fig. 3). The first in Table 1. Pflanzenöltechnologie Magdeburg e.V., Magde- one, called total condensation, uses nitro- The important parameter of meal burg, Germany. Karl-Heinz Leidt is a PPM gen as fluid. The nitrogen is heated and fed quality is the PDI. It can be shown that the Pilot Pflanzenöltechnologie scientist and can by a blower into the fluidized bed chamber. PDI after fluidized bed desolventizing is in It removes hexane and water from the meal the same (high) range as that achieved by be contacted at [email protected]. and then leaves the apparatus. After filtra- drying by ambient temperature. Lothar Mörl is professor for chemical engineer- tion the fluid is totally condensed. Hexane PPM offers a small-scale batch fluid- ing from the Otto-von-Guericke-Universität and water are separated and the nitrogen is ized bed desolventizing plant. The diam- Magdeburg, Germany. Klaus Weigel is owner- discharged. eter of the fluidized bed chamber is 1 or manager of Dr. Weigel Anlagenbau GmbH, The second one, called partial con- 2 m. The 1-m diameter plant has a capacity Magdeburg, Germany, where Reinhard Zettl densation, uses superheated hexane. The of 1,200 metric tons (MT) per year, if it is is chief engineer. inform NovemberDesmet 2009, Vol. 20 (11) C3 Ballestra Leading technologies for detergent, surfactant and chemical industry

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