DOCSLIB.ORG

(12) United States Patent (10) Patent No.: US 8,709,521 B2 Prakash Et Al

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
(12) United States Patent (10) Patent No.: US 8,709,521 B2 Prakash Et Al USOO8709521B2 (12) United States Patent (10) Patent No.: US 8,709,521 B2 Prakash et al. (45) Date of Patent: Apr. 29, 2014 (54) SWEETENER COMPOSITIONS HAVING FOREIGN PATENT DOCUMENTS ENHANCED SWEETNESS AND IMPROVED EP O131640 A 1, 1985 TEMPORAL AND/OR FLAVOR PROFILES JP 600 19472 A 1, 1985 JP 600 19473. A 1, 1985 (75) Inventors: Indra Prakash, Alpharetta, GA (US); JP O325 1160 11, 1991 Grant E. DuBois, Roswell, GA (US); JP O7143860 6, 1995 JP 08000214. A 9, 1996 George A. King, Atlanta, GA (US); JP O8256725 A 10, 1996 Rafael I. San Miguel, Atlanta, GA (US) JP 10136953 5, 1998 JP 11123069 11, 1999 (73) Assignee: The Coca-Cola Company, Atlanta, GA JP 11346708 A 12/1999 (US) JP 2000270804 A 10, 2000 JP 2006238828 A 9, 2006 JP 2008530017 8, 2008 (*) Notice: Subject to any disclaimer, the term of this JP 2008530O20 8, 2008 patent is extended or adjusted under 35 WO WO9915032. A 4f1999 U.S.C. 154(b) by 684 days. WO WOOOO1253 A 1, 2000 WO WOOO62628 A1 10, 2000 (21) Appl. No.: 12/120,876 WO WO 2006O24587 A 3, 2006 WO WO 2006127935 A1 11, 2006 WO WO 2007061795 A1 5/2007 (22) Filed: May 15, 2008 WO WO 2007084185 A1 7/2007 (65) Prior Publication Data OTHER PUBLICATIONS US 2009/0053378A1 Feb. 26, 2009 Prakash, I. et al. “Development of Rebiana, a Natural, Non-Caloric Sweetener' Food and Chemical Toxicology, 2008, vol. 46, p. S75 S82. Related U.S. Application Data Schiffman et al. “Synergism Among Ternary Mixtures of Fourteen Sweeteners.” Chemical Senses 2000, vol. 25, p. 131-140. (60) Provisional application No. 60/939,549, filed on May 22, 2007. * cited by examiner (51) Int. Cl. Primary Examiner — Leslie Wong A2.3L I/236 (2006.01) (74) Attorney, Agent, or Firm — King & Spalding (52) U.S. Cl. USPC ........................................... 426/548; 426/534 (57) ABSTRACT (58) Field of Classification Search The present invention relates generally to improving the taste USPC .......... 426/534, 535,536,537,538,548, 658 of Sweetener compositions having enhanced Sweetness. In See application file for complete search history. particular, the present invention relates to compositions that can improve the tastes of Sweetness enhanced Sweetener.com (56) References Cited positions including at least one Sweetness enhancer and at least one Sweetener by imparting a more Sugar-like taste or U.S. PATENT DOCUMENTS characteristic. In particular, the compositions and methods 4,627.987 A * 12/1986 Barnett et al. ................ 426,548 provide at least one Sweetness enhancer, at least one Sweet 4,871,570 A 10, 1989 Barnett et al. ener comprising a carbohydrate Sweetener, a natural-high 5.437,880 A 8, 1995 Takaichi et al. potency Sweetener, a synthetic high-potency Sweetener, or a 7,879,376 B2 * 2/2011 Boghani et al. ................... 426.5 2005/0084506 A1* 4/2005 Tachdjian et al. ... ... 424/400 combination thereof, and at least one Sweet taste improving 2006/0045953 A1* 3/2006 Tachdjian et al. ............. 426,534 composition. 2006/02862O2 A1 12/2006 Boghani et al. 2006/0286259 A1 12/2006 Hargreaves 42 Claims, 5 Drawing Sheets U.S. Patent Apr. 29, 2014 Sheet 1 of 5 US 8,709,521 B2 96. 640 320 Fig. 1 U.S. Patent Apr. 29, 2014 Sheet 2 of 5 US 8,709,521 B2 300 88 U.S. Patent Apr. 29, 2014 Sheet 3 of 5 US 8,709,521 B2 240) Fig. 3 U.S. Patent Apr. 29, 2014 Sheet 4 of 5 US 8,709,521 B2 69) 3. 80 5 5 25 3) 35 &O Fig. 4 U.S. Patent Apr. 29, 2014 Sheet 5 of 5 US 8,709,521 B2 US 8,709,521 B2 1. 2 SWEETENER COMPOSITIONS HAVING flavor profile of a Sweetness enhanced Sweetener, and a ENHANCED SWEETNESS AND IMPROVED method for improving the temporal profile and/or flavor pro TEMPORAL AND/OR FLAVOR PROFILES file of a Sweetness enhanced Sweetener. More particularly, this invention encompasses a Sweetener composition having an enhanced Sweetness and more Sugar CROSS-REFERENCE TO RELATED like temporal profile and/or flavor profile comprising (i) at APPLICATIONS least one Sweetness enhancer, (ii) at least one Sweetener com prising a carbohydrate Sweetener, a natural high-potency The present application claims priority under 35 U.S.C. Sweetener, a synthetic high-potency Sweetener, or a combi S119(e) to U.S. Provisional Application No. 60/939,549, filed nation thereof, and (iii) at least one Sweet taste improving on May 22, 2007, the disclosure of which is hereby incorpo 10 composition selected from the group consisting of carbohy rated by reference in its entirety. drates, polyols, amino acids, other Sweet taste improving additives, and combinations thereof. FIELD OF THE INVENTION According to another aspect, this invention encompasses a method for imparting a more Sugar-like temporal profile and/ The present invention relates to Sweeteners having 15 or flavor profile to a sweetness enhanced sweetener by com enhanced Sweetness. More particularly, the present invention bining (i) at least one Sweetness enhancer, (ii) at least one relates to improving the temporal and/or flavor profile of Sweetener comprising a carbohydrate Sweetener, a natural Sweetener compositions having enhanced Sweetness. high-potency Sweetener, a synthetic high-potency Sweetener, or a combination thereof, and (iii) at least one Sweet taste BACKGROUND OF THE INVENTION improving composition selected from the group consisting of carbohydrates, polyols, amino acids, other Sweet taste Although natural caloric Sweetener compositions such as improving additives, and combinations thereof. Sucrose, fructose, and glucose taste good to most consumers, According to still another aspect, this invention encom passes compositions Sweetened with the Sweetness enhanced they are caloric. Therefore, alternative non-caloric or low Sweetener having a more Sugar-like temporal profile and/or caloric Sweeteners have been used widely as Sugar or Sucrose 25 flavor profile comprising (i) a Sweetenable composition, (ii) Substitutes. Many non-caloric or low-caloric Sweeteners, at least one Sweetness enhancer, (iii) at least one Sweetener however, are prohibitively expensive and/or exhibit sweet comprising a carbohydrate Sweetener, a natural high-potency tastes that have different temporal profiles, maximal Sweetener, a synthetic high-potency Sweetener, or a combi responses, flavor profiles, mouthfeels, and/or adaptation nation thereof and (iv) at least one Sweet taste improving behaviors than that of Sugar. 30 composition selected from the group consisting of carbohy For example, the Sweet tastes of natural and synthetic high drates, polyols, amino acids, other Sweet taste improving potency Sweeteners are slower in onset and longer in duration additives, and combinations thereof. According to particular than the Sweet taste produced by Sugar and thus change the embodiments, the Sweetened composition comprises a bev taste balance of a food composition. Because of these differ erage, food, pharmaceutical, nutraceutical, tobacco, oral ences, use of natural and synthetic high-potency Sweeteners 35 hygienic/cosmetic product, or the like. to replace a bulk Sweetener, Such as Sugar, in a food or bev According to still another aspect, this invention encom erage, causes an unbalanced temporal profile and/or flavor passes a method for imparting a more Sugar-like temporal profile. In addition to the difference in temporal profile, high profile and/or flavor profile to sweetened compositions com potency Sweeteners generally exhibit (i) lower maximal prising a Sweetness enhanced Sweetener by combining with a response than Sugar, (ii) off tastes including bitter, metallic, 40 Sweetenable composition (i) at least one Sweetness enhancer, cooling, astringent, licorice-like taste, etc., and/or (iii) Sweet (ii) at least one Sweetener comprising a carbohydrate Sweet ness which diminishes on iterative tasting. ener, a natural high-potency Sweetener, a synthetic high-po Compounds have been identified that are capable of tency Sweetener, or a combination thereof, and (iii) at least enhancing or increasing the perception of sweetness of Sweet one Sweet taste improving composition selected from the 45 group consisting of carbohydrates, polyols, amino acids, eners. By combining these compounds with Sweeteners the other Sweet taste improving additives, and combinations amount of Sweetener needed to obtain a desired degree of thereof. According to particular embodiments, the Sweetened Sweetness may be reduced significantly, thereby reducing the composition comprises a beverage, food, pharmaceutical, calories imparted by natural caloric Sweeteners or reducing nutraceutical, tobacco, oral hygienic/cosmetic product, or the the amounts of low-caloric or non-caloric natural or synthetic like. high-potency sweeteners. It is well known to those skilled in 50 Objects and advantages of the invention will be set forth in the art of food/beverage formulation, however, that changing part in the following description, or may be obvious from the the Sweetener in a composition requires re-balancing of the description, or may be learned through practice of the inven flavor and other taste components (e.g., acidulants). If the tion. Unless otherwise defined, all technical and scientific taste profile of Sweetness enhanced Sweetener compositions terms and abbreviations used herein have the same meaning could be modified to impart specific desired taste character 55 as commonly understood by one of ordinary skill in the art to istics to be more Sugar-like, the type and variety of composi which this invention pertains. Although methods and compo tions that may be prepared with that Sweetness enhanced sitions similar or equivalent to those described herein can be Sweetener may be expanded significantly. Accordingly, it used in the practice of the present invention, Suitable methods may be desirable to selectively modify the taste characteris and compositions are described without intending that any tics of Sweetness enhanced Sweetener compositions. 60 Such methods and compositions limit the invention herein. SUMMARY OF THE INVENTION BRIEF DESCRIPTION OF THE DRAWINGS Generally, this invention addresses the above-described FIG.
Load more

Recommended publications
  • Hydrocolloids Structure and Properties the Building Blocks for Structure Timothy J
    Hydrocolloids Structure and Properties The building blocks for structure Timothy J. Foster 18 month Meeting, Unilever Vlaardingen, March 29‐31, 2010 Manufactured Materials Foams Emulsions Natural Materials This shows a layer of onion (Allium) cells. Targeting Hydrocolloids For Specific Applications: Approach Material Ingredient Properties Microstructure Oral Process Response Packaging Distribution Storage Process Controlled oral response Process (mouth/gut) Controlling Structure (taste, flavour, texture) CONSTRUCTION DECONSTRUCTION Designed texture/ Ingredient In body functionality Ingredient appearance/ (enzymes) behaviour Interaction with body mucins Reconstruction (associative and new phase separation) Microstructure changes as a Impact on / of starting function of enzyme action materials / structures Re-assembly of structures as a function of digestion breakdown products and body secretions (micelle formation, delivery vehicles) Single Biopolymer systems Hydrocolloid Structure/ Function Need: - define biopolymer primary structure - understand the nature of the interaction / rates - understand the solvent effects - measure material properties - test influence of primary structure variation and changes in environmental conditions on mechanical properties. Hydrocolloid Materials & Function Gelling Thickening Emulsification Pectin Pectin • Gelatin Alginate Alginate • Milk proteins Starch Starch • Egg proteins Agar LBG Carrageenan • Soya proteins Guar gum Gellan • Pea proteins Gelatin Xanthan • Gum Arabic Milk proteins Egg proteins Hydrocolloid
    [Show full text]
  • 1) Which of the Following Biomolecules Simply Refers to As “Staff of Life”? (A) Lipids (B) Proteins (C) Vitamins (D) Carbohydrates Sol: (D) Carbohydrates
    1) Which of the following Biomolecules simply refers to as “Staff of life”? (a) Lipids (b) Proteins (c) Vitamins (d) Carbohydrates Sol: (d) Carbohydrates. 2) Which of the following is the simplest form of carbohydrates? (a) Carboxyl groups (b) Aldehyde and Ketone groups (c) Alcohol and Carboxyl groups (d) Hydroxyl groups and Hydrogen groups Sol: (b) Aldehyde and Ketone groups. 3) Which of the following monosaccharides is the majority found in the human body? (a) D-type (b) L-type (c) LD-types (d) None of the above Sol: (a) D-type. 4) Which of the following is the most abundant biomolecule on the earth? (a) Lipids (b) Proteins (c) Carbohydrates (d) Nucleic acids. Sol: (c) Carbohydrates. 5) Which of the following are the major functions of Carbohydrates? (a) Storage (b) Structural framework (c) Transport Materials (d) Both Storage and structural framework Sol: (d) Both Storage and structural framework. 6) Which of the following is the general formula of Carbohydrates? (a) (C4H2O)n (b) (C6H2O)n (c) (CH2O)n (d) (C2H2O)n COOH Sol: (c) (CH2O)n. 7) Which of the following is the smallest carbohydrate – triose? (a) Ribose (b) Glucose (c) Glyceraldehyde (d) Dihydroxyacetone Sol: (c) Glyceraldehyde. 8) Which of the following is a reducing sugar? (a) Dihydroxyacetone (b) Erythrulose (c) Glucose (d) All of the above Sol: (c) Glucose. 9) Which of the following is an example of Epimers? (a) Glucose and Ribose (b) Glucose and Galactose (c) Galactose, Mannose and Glucose (d) Glucose, Ribose and Mannose Sol: (b) Glucose and Galactose 10) Which of the following has reducing properties? (a) Mucic acid (b) Glucaric acid (c) Gluconic acid (d) Glucuronic acid Sol: (d) Glucuronic acid.
    [Show full text]
  • WO 2013/070444 Al 16 May 2013 (16.05.2013) W P O P C T
    (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2013/070444 Al 16 May 2013 (16.05.2013) W P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every A23G 4/00 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (21) International Application Number: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, PCT/US20 12/062043 DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, 26 October 2012 (26.10.2012) KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (25) Filing Language: English NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, (26) Publication Language: English RW, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, (30) Priority Data: ZM, ZW. 61/556,546 7 November 20 11 (07. 11.201 1) US (84) Designated States (unless otherwise indicated, for every (71) Applicant (for all designated States except US): WVI. kind of regional protection available): ARIPO (BW, GH, WRIGLEY JR. COMPANY [US/US]; 1132 Blackhawk GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, Street, Chicago, IL 60642 (US).
    [Show full text]
  • 25 05.Html.Ppt [Read-Only]
    25.5 A Mnemonic for Carbohydrate Configurations The Eight D-Aldohexoses CH O H OH CH2OH The Eight D-Aldohexoses All CH O Altruists Gladly Make Gum In H OH Gallon CH2OH Tanks The Eight D-Aldohexoses All Allose CH O Altruists Altrose Gladly Glucose Make Mannose Gum Gulose In Idose H OH Gallon Galactose CH2OH Tanks Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose Gulose Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose Gulose H OH Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose Gulose HO H Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose Gulose H OH Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose H OH Gulose H OH Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose HO H Gulose H OH Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose Gulose HO H Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose H OH Gulose HO H Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose HO H Gulose HO H Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose Mannose H OH Gulose H OH Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose Glucose H OH Mannose H OH Gulose H OH Idose H OH Galactose CH2OH Talose The Eight D-Aldohexoses Allose CH O Altrose
    [Show full text]
  • 20H-Carbohydrates.Pdf
    Carbohydrates Carbohydrates are compounds that have the general formula CnH2nOn Because CnH2nOn can also be written Cn(H2O)n, they appear to be “hydrates of carbon” Carbohydrates are also called “sugars” or “saccharides” Carbohydrates can be either aldoses (ald is for aldehyde and ose means a carbohydrate) or ketoses (ket is for ketone) OH OH O OH CH2OH CH2OH OHC HOH2C OH OH OH OH An Aldose A Ketose (D-Glucose) (D-Fructose) Carbohydrates Due to the multiple chiral centers along a linear carbon chain for carbohydrates, Emil Fischer developed the “Fischer Projection” in order to represent these compounds Remember how to draw a Fischer projection: 1) View the linear carbon chain along the vertical axis (always place the more oxidized carbon [aldehyde in an aldose] towards the top) 2) The horizontal lines are coming out of the page toward the viewer 3) Will need to change the viewpoint for each carbon so the horizontal substituents are always pointing towards the viewer CHO OH OH H OH HO H CH2OH = OHC H OH OH OH H OH CH2OH Emil Fischer (1852-1919) Carbohydrates The aldoses are thus all related by having an aldehyde group at one end, a primary alcohol group at the other end, and the two ends connected by a series of H-C-OH groups CHO CHO CHO CHO CHO H OH H OH H OH H OH HO H CH2OH H OH H OH H OH HO H CH2OH H OH H OH HO H CH2OH H OH HO H CH2OH CH2OH Aldotriose Aldotetrose Aldopentose Aldohexose Aldohexose D-glyceraldehyde D-erythose D-ribose D-allose L-allose The D-aldoses are named according to glyceraldehyde, the D refers to the configurational
    [Show full text]
  • Carbohydrates Hydrates of Carbon: General Formula Cn(H2O)N Plants
    Chapter 25: Carbohydrates hydrates of carbon: general formula Cn(H2O)n Plants: photosynthesis hν 6 CO2 + H2O C6H12O6 + 6 O2 Polymers: large molecules made up of repeating smaller units (monomer) Biopolymers: Monomer units: carbohydrates (chapter 25) monosaccharides peptides and proteins (chapter 26) amino acids nucleic acids (chapter 28) nucleotides 315 25.1 Classification of Carbohydrates: I. Number of carbohydrate units monosaccharides: one carbohydrate unit (simple carbohydrates) disaccharides: two carbohydrate units (complex carbohydrates) trisaccharides: three carbohydrate units polysaccharides: many carbohydrate units CHO H OH HO HO HO H HO HO O HO O glucose H OH HO HO OH HO H OH OH CH2OH HO HO HO O HO O HO HO O HO HO O HO HO HO O O O O O HO HO O HO HO HO O O HO HO HO galactose OH + glucose O glucose = lactose polymer = amylose or cellulose 316 160 II. Position of carbonyl group at C1, carbonyl is an aldehyde: aldose at any other carbon, carbonyl is a ketone: ketose III. Number of carbons three carbons: triose six carbons: hexose four carbons: tetrose seven carbons: heptose five carbons: pentose etc. IV. Cyclic form (chapter 25.5) CHO CHO CHO CHO CH2OH H OH HO H H OH H OH O CH2OH H OH H OH HO H HO H CH2OH H OH H OH H OH CH2OH H OH H OH CH OH 2 CH2OH glyceraldehyde threose ribose glucose fructose (triose) (tetrose) (pentose) (hexose) (hexose) 317 (aldohexose) (ketohexose) 25.2: Depicting carbohydrates stereochemistry: Fischer Projections: representation of a three-dimensional molecule as a flat structure.
    [Show full text]
  • Fundamentals of Glycan Structure 1
    Fundamentals of Glycan Structure 1 Learning Objectives How are glycans named? What are the different constituents of a glycan? How are these represented? Wha t conftiformations do sugar residues adtdopt in soltilution Why do glycan conformations matter? 2 Fundamentals of Glycan Structure CbhdCarbohydrate NlNomenclature Monosaccharides Structure Fisher Representation Cyclic Form Chair Form Mutarotation Monosaccharide Derivatives Reducing Sugars Uronic Acids Other Derivatives Monosaccharide Conformation Inter‐Glycosidic Bond Normal Sucrose Lactose Sequence Specificity and Recognition Branching 3 Carbohydrate Nomenclature The word ‘carbohydrate’ implies “hydrate of carbon” … Cn(H2O)m Glucose (a monosaccharide) C6H12O6 … C6(H2O)6 Sucrose (a disaccharide) C12H22O11 … C12(H2O)11 Cellulose (a polysaccharide) (C6H12O6)n… (C6(H2O)6)n Not all carbohydrates have this formula … some have nitrogen Glucosamine (glucose + amine) …. C6H13O5N… ‐NH2 at the 2‐position of glucose N‐acetyl galactosamine (galactose + amine + acetyl group) …. C8H15O6N … ‐ NHCOCH3 at the 2‐position of galactose Typical prefixes and suffixes used in naming carbohydrates Suffix = ‘‐ose’ & prefix = ‘tri‐’, ‘tetr‐’, ‘pent‐’, ‘hex‐’ Pentose (a five carbon monosaccharide) or hexose (a six carbon monosaccharide) Functional group types Monosaccharides with an aldehyde group are called aldoses … e.g., glyceraldehyde Those with a keto group are called ketoses … e.g., dihydroxyacetone 4 Monosaccharides Struc ture Have a general formula CnH2nOn and contain
    [Show full text]
  • Ose: an Editorial on Carbohydrate Nomenclature Neil P
    Gly l of cob na io r lo u g o y J Price et al., J Glycobiol 2012, 1:2 Journal of Glycobiology DOI: 10.4172/2168-958X.1000e105 ISSN: 2168-958X Editorial Open Access The Name of the – ose: An Editorial on Carbohydrate Nomenclature Neil P. J. Price* National Center for Agricultural Utilization Research, U.S. Department of Agriculture, Agricultural Research Service, 1815 N. University St., Peoria, IL 61604, USA What’s in a name? The term ‘sugar’ is usually applied to the configuration of theD -aldopentose sugars. Perhaps I can suggest “Ribs monosaccharides, disaccharides, and lower oligosaccharides. Are X-rayed Last” for the series ribose, arabinose, xylose, lyxose, so Historically, sugars were often named after their source, for example, that they also conform to the above rules. grape sugar for glucose, cane sugar for saccharose (later called sucrose), Let’s just take the three most commonly occurring hexose sugars, wood sugar for xylose, and fruit sugar for fructose (fruchtzucker, glucose, galactose, and mannose. The IUPAC name for D-glucose is fructose). The term ‘carbohydrate’ (from the French ‘hydrate de (2R,3S,4R,5R)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrol, carbone’) was originally used only for monosaccharides, because although this is used only rarely. By this nomenclature, D-galactose is their composition can be expressed as C (H O) . Glucose was named n 2 n called (2R,3S,4S,5R)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5- in 1838, although much later than this Kekule suggested ‘dextrose’ tetrol and D-mannose is (2S,3S,4R,5R)-6-(hydroxymethyl)tetrahydro- because glucose is dextrorotatory.
    [Show full text]
  • The Carbohydrates
    Title The Carbohydrates [C(H2O)]n Emil Hermann Fischer (1852-1919) F-R Convention The Fischer-Rosanoff Convention CHO CHO CHO H OH H OH C2-OH H OH H OH C3-OH H OH H OH C4-OH H OH H OH C5-OH CH2OH CH2OH C6-CH2OH Fischer Projections Rosanoff Modification D/L Series Fischer-Rosanoff D- and L-Series OH on the right of the highest OH on the left of the highest numbered chiral carbon = D-series. numbered chiral carbon = L-series. D-Aldohexoses The D-Aldohexoses C5 8 right C3 2 right 2 left 2 right 2 left C4 4 right 4 left C2 right left right left right left right left Allose Glucose Gulose Galactose Altrose Mannose Idose Talose All altruists gladly make gum in gallon tanks [L. Fieser] Rxn of Aldoses Reactions of Aldoses CHO =N-NHPh CHO HO OH 3 equiv. PhNHNH2 =N-NHPh 3 equiv. PhNHNH2 OH OH OH OH OH HNO3 OH HNO3 OH OH OH osazone NaBH4 NaBH4 CH2OH CH2OH CH2OH Br2/H2O + PhNH2 + NH3 Br2/H2O CO2H CH2OH CO2H CO2H CH2OH CO2H OH OH OH HO HO HO OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH CH2OH CH2OH CO2H CO2H CH2OH CH2OH aldonic acid alditol aldaric acid aldaric acid alditol aldonic acid achiral achiral Osazones More on Osazones CHO CH2OH CHO O Ca(OH)2 OH Ca(OH)2 HO HO HO HO OH OH OH (Lobry de Bruyn- OH OH Alberda van Eckenstein OH rearrangement, 1895) CH2OH CH2OH CH2OH D-glucose D-fructose D-mannose 1 equiv.
    [Show full text]
  • Principles of Chemical Nomenclature a GUIDE to IUPAC RECOMMENDATIONS Principles of Chemical Nomenclature a GUIDE to IUPAC RECOMMENDATIONS
    Principles of Chemical Nomenclature A GUIDE TO IUPAC RECOMMENDATIONS Principles of Chemical Nomenclature A GUIDE TO IUPAC RECOMMENDATIONS G.J. LEIGH OBE TheSchool of Chemistry, Physics and Environmental Science, University of Sussex, Brighton, UK H.A. FAVRE Université de Montréal Montréal, Canada W.V. METANOMSKI Chemical Abstracts Service Columbus, Ohio, USA Edited by G.J. Leigh b Blackwell Science © 1998 by DISTRIBUTORS BlackweilScience Ltd Marston Book Services Ltd Editorial Offices: P0 Box 269 Osney Mead, Oxford 0X2 0EL Abingdon 25 John Street, London WC1N 2BL Oxon 0X14 4YN 23 Ainslie Place, Edinburgh EH3 6AJ (Orders:Tel:01235 465500 350 Main Street, Maiden Fax: MA 02 148-5018, USA 01235 465555) 54 University Street, Carlton USA Victoria 3053, Australia BlackwellScience, Inc. 10, Rue Casmir Delavigne Commerce Place 75006 Paris, France 350 Main Street Malden, MA 02 148-5018 Other Editorial Offices: (Orders:Tel:800 759 6102 Blackwell Wissenschafts-Verlag GmbH 781 388 8250 KurfUrstendamm 57 Fax:781 388 8255) 10707 Berlin, Germany Canada Blackwell Science KK Copp Clark Professional MG Kodenmacho Building 200Adelaide St West, 3rd Floor 7—10 Kodenmacho Nihombashi Toronto, Ontario M5H 1W7 Chuo-ku, Tokyo 104, Japan (Orders:Tel:416 597-1616 800 815-9417 All rights reserved. No part of Fax:416 597-1617) this publication may be reproduced, stored in a retrieval system, or Australia BlackwellScience Pty Ltd transmitted, in any form or by any 54 University Street means, electronic, mechanical, Carlton, Victoria 3053 photocopying, recording or otherwise, (Orders:Tel:39347 0300 except as permitted by the UK Fax:3 9347 5001) Copyright, Designs and Patents Act 1988, without the prior permission of the copyright owner.
    [Show full text]
  • Chapter 18: Carbohydrates 18.1 Biochemistry--An Overview 18.2
    Chapter 18: Carbohydrates Instructional Objectives 1. Know the difference between complex and simple carbohydrates and the amounts of each recommended in the daily diet. 2. Know the difference between complex and simple carbohydrates and the amounts of each recommended in the daily diet. 3. Understand the concepts of chirality, enantiomers, stereoisomers, and the D and L-families. 4. Recognize whether a sugar is a reducing or a nonreducing sugar. 5. Discuss the use of the Benedict's reagent to measure the level of glucose in urine. Draw and name the common, simple carbohydrates using structural formulas and Fischer projection formulas. 6. Given the linear structure of a monosaccharide, draw the Haworth projection of its a- and 0-cyclic forms and vice versa. Discuss the structural, chemical, and biochemical properties of the monosaccharides, oligosaccharides, and polysaccharides. 7. Know the difference between galactosemia and lactose intolerance. 18.1 Biochemistry--An Overview Biochemistry is the study of the chemical substances found in living organisms and the chemical interactions of these substances with each other. It deals with the structure and function of cellular components, such as proteins, carbohydrates, lipids, nucleic acids, and other biomolecules. There are two types of biochemical substances: bioinorganic substances and Inorganic substances: water and inorganic salts. Bioorganic substances: Carbohydrates, Lipids, Proteins, and Nucleic Acids. Complex bioorganic/inorganic Molecules: Enzymes, Vitamins, DNA, RNA, and Hemoglobin etc. As isolated compounds, bioinorganic/bioorganic/complex substances have no life in and of themselves. Yet when these substances are gathered together in a cell, their chemical interactions are able to sustain life. Plant Materials It is estimated that more than half of all organic carbon atoms are found in the carbohydrate materials of plants.
    [Show full text]
  • WO 2016/179568 Al 10 November 2016 (10.11.2016) P O P C T
    (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2016/179568 Al 10 November 2016 (10.11.2016) P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every A61K 38/28 (2006.01) C07K 14/47 (2006.01) kind of national protection available): AE, AG, AL, AM, A61P 3/10 (2006.01) C07K 14/62 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, (21) Number: International Application DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, PCT/US2016/031361 HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, (22) International Filing Date: KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, 6 May 2016 (06.05.2016) MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, (25) Filing Language: English SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, (26) Publication Language: English TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: (84) Designated States (unless otherwise indicated, for every 62/157,897 6 May 2015 (06.05.2015) US kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, (71) Applicant (for M W only): PROTOMER TECHNOLO¬ TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, GIES, INC.
    [Show full text]