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WO1992006601A1 - Amides derives d'alcools de sucre et utilisables comme succedanes du sucre - Google Patents

Amides derives d'alcools de sucre et utilisables comme succedanes du sucre Download PDF

Info

Publication number
WO1992006601A1
WO1992006601A1 PCT/US1991/007534 US9107534W WO9206601A1 WO 1992006601 A1 WO1992006601 A1 WO 1992006601A1 US 9107534 W US9107534 W US 9107534W WO 9206601 A1 WO9206601 A1 WO 9206601A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydroxyalkyl
lactone
polyhydroxyalkyl
alkyl
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1991/007534
Other languages
English (en)
Inventor
Grant E. Dubois
Manssur Yalpani
William Henry Owens
Shawn Yvette Stevens
Glenn Roy
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nutrasweet Co
Original Assignee
Nutrasweet Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nutrasweet Co filed Critical Nutrasweet Co
Priority to NO92920934A priority Critical patent/NO920934L/no
Priority to FI921352A priority patent/FI921352A7/fi
Publication of WO1992006601A1 publication Critical patent/WO1992006601A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/10—Chewing gum characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides
    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT OF FLOUR OR DOUGH FOR BAKING, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS
    • A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
    • A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
    • A21D2/24—Organic nitrogen compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/346—Finished or semi-finished products in the form of powders, paste or liquids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
    • A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
    • A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G2200/00—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G2200/00—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents
    • A23G2200/10—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents containing amino-acids, proteins, e.g. gelatine, peptides, polypeptides

Definitions

  • the agents that are typically used are carbohydrates.
  • carbohydrates For example,
  • Maltitol provides solid volume, body, moisture absorbance, luster and increased viscosity while also providing a sweet taste said "to be greater than that of grape sugar but less than that of sucrose.”
  • the crystalline form of maltitol has also been suggested for use as a sugar substitute.
  • R 4 a mono- or polyhydric aliphatic alcohol residue
  • a still further object of the present invention is to provide a novel sweetened sugar substitute which posesses similar physical, rheological and colligative properties as sucrose without possessing the caloric and cariogenic drawbacks of sucrose.
  • the present invention provides sugar substitutes suitable for incorporation into formulated foods which are lower in calories through the absence of sucrose. These foods, through the of the inventive reduced calorie sugar substitute, retain approximately the same structure, texture, freezing point depression, moisture retention, density, water solubility, solution viscosity properties, stability, non-reactivity with other ingredients, starch gelatinizaton effects and appearance found in formulated foods containing the same amount of sucrose. Further, in contrast to several compositions previously proposed for use as sugar substitutes, the novel sugar substitutes of the present invention are sufficiently altered in structure so as to not ferment upon exposure to the microbial flora of the human gastrointestinal system. As a result, the caloric content of these substances is believed to be zero.
  • Mass spectroscopy analysis exhibited a highest m/e peak at 269 consistent with a calculated molecular weight at 269.29 D.
  • Mass spectroscopy analysis exhibited a highest m/e peak at 446 consistent with a calculated molecular weight at 446.01 D.
  • Mass spectroscopy analysis exhibited a highest m/e peak at 283 consistent with a calculated molecular weight at
  • the compound was not fermented by human colonic microflora in an in vitro assay.
  • Second transtion 23% 372-465°C midpoint 402°C.
  • Lactobionic acid one part, free acid
  • 10 parts dimethylformamide (DMF) and 7.5 parts hexane were added to 10 parts dimethylformamide (DMF) and 7.5 parts hexane, and heated to reflux with vigorous stirring, using a Dean-Stark apparatus to remove the residual water. After the water and hexane had been removed, DMF was removed under reduced pressure, yielding lactobionolactone as a very viscous, brown syrup.
  • 3-Amino-1,2 propanediol one part
  • 100 parts methanol were added to the lactobionolactone syrup with vigorous stirring. The mixture was heated to reflux for three hours, and then cooled to ambient temperatures.
  • aspartame To produce a table top sweetener, about 1 part of aspartame would be milled with 100 parts of Compound 1 using a commercial milling apparatus. To aid in the milling operation a flowing agent such as calcium stearate could optionally be added to the mixture. It is further envisioned that any amount of aspartame ranging between about .3 and about 2 parts of bulking agent (Compound 1) could be used. Other mixing procedures would also be acceptable e.g., spraying of a solution of two materials, etc.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Nutrition Science (AREA)
  • Molecular Biology (AREA)
  • Inorganic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Mycology (AREA)
  • Seasonings (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Peptides Or Proteins (AREA)
  • Fats And Perfumes (AREA)
  • Saccharide Compounds (AREA)
  • Developing Agents For Electrophotography (AREA)

Abstract

L'invention se rapporte à des compositons représentées par les formules (I) et (II). Dans la formule (I), R1 représente un résidu d'alcool aliphatique monohydrique ou polyhydrique; R2 représente H, alkyle C1-C10, hydroxyalkyle C2-C10 ou polyhydroxyalkyle C2-C10; et R3 représente H, alkyle C1-C10, hydroxyalkyle C2-C10, polyhydroxyalkyle C2-C10 ou une partie intégrante de R2 sous la forme d'un résidu carbocyclique; à condition qu'au moins un des éléments R2 et R3 contienne un ou plusieurs groupes hydroxy. Dans la formule (II), R1 représente un résidu d'alcool aliphatique monohydrique ou polyhydrique; R2 représente H, alkyle C1-C10, hydroxyalkyle C2-C10 ou polyhydroxyalkyle C2-C10; R3 représente H, alkyle C1-C10, hydroxyalkyle C2-C10, polyhydroxyalkyle C2-C10 ou une partie intégrante de R2 sous la forme d'un résidu carbocyclique; R4 représente un résidu d'alcool aliphatique monohydrique ou polyhydrique; et A représente alkyle C1-C10, hydroxyalkyle C2-C10 ou polyhydroxyalkyle C2-C10; à condition qu'au moins un des éléments R2 R3 et A contienne un ou plusieurs groupes hydroxy. Ces composés sont particulièrement utiles comme succédanés du sucre.
PCT/US1991/007534 1990-10-11 1991-10-11 Amides derives d'alcools de sucre et utilisables comme succedanes du sucre Ceased WO1992006601A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
NO92920934A NO920934L (no) 1990-10-11 1992-03-10 Amider avledet fra sukkeralkoholer egnet som sukkererstatninger
FI921352A FI921352A7 (fi) 1990-10-11 1992-03-27 Ur sockeralkoholer erhaollna amider som aer laempliga som sockersurrogat.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US59679390A 1990-10-11 1990-10-11
US596,793 1990-10-11
US65025691A 1991-02-04 1991-02-04
US650,256 1991-02-04

Publications (1)

Publication Number Publication Date
WO1992006601A1 true WO1992006601A1 (fr) 1992-04-30

Family

ID=27082634

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1991/007534 Ceased WO1992006601A1 (fr) 1990-10-11 1991-10-11 Amides derives d'alcools de sucre et utilisables comme succedanes du sucre

Country Status (5)

Country Link
EP (1) EP0506952A4 (fr)
JP (1) JPH05503307A (fr)
AU (1) AU8914391A (fr)
CA (1) CA2071633A1 (fr)
WO (1) WO1992006601A1 (fr)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0552896A1 (fr) * 1992-01-17 1993-07-28 Takasago International Corporation Polymères biodégradables et optiquement actifs et leurs intermédiaires oligomériques et procédé de préparation de ceux-ci
EP0718305A1 (fr) * 1994-12-24 1996-06-26 Solvay Deutschland GmbH Procédé de préparation d'amides de l'acide aldobionique
EP0826761A1 (fr) * 1996-08-27 1998-03-04 Schill & Seilacher GmbH & Co. Utilisation d'amides d'acides polyhydroxycarboxyliques en tant qu'additifs extrême-pression
US5968811A (en) * 1990-10-17 1999-10-19 Cpc International Inc. Processing of yeast refuse and resulting product
EP1378168A1 (fr) * 2002-07-03 2004-01-07 Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo Pâte contenant du alpha-D-glucopyranosyl-1,6-sorbitol pour produit de boulangerie et procédé de préparation du dit produit
EP1378167A1 (fr) * 2002-07-03 2004-01-07 Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo Produit de boulangerie comprenant du alpha-D-glucopyranosyl-1,1-mannitol et préparation du dit produit
WO2005102071A1 (fr) * 2004-04-20 2005-11-03 Quest International Services B.V. Substances d'amelioration de gout
WO2006009425A1 (fr) * 2004-07-20 2006-01-26 Quest International Services B.V. Substances d'amelioration de saveur
WO2006046854A3 (fr) * 2004-10-29 2006-10-12 Quest Int Substances de modulation de saveur
WO2007027095A1 (fr) * 2005-09-02 2007-03-08 Quest International Services B.V. Compositions aromatisantes ameliorees
EP1854782A1 (fr) * 2006-05-05 2007-11-14 Quest International Services B.V. Composition pour améliorer les caracteristiques gustatives
WO2008006864A1 (fr) * 2006-07-11 2008-01-17 Christoph Mark Procédé de fabrication d'amines optiquement actives
US8017168B2 (en) 2006-11-02 2011-09-13 The Coca-Cola Company High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith
AU2012200442B2 (en) * 2004-07-20 2014-07-17 Givaudan Nederland Services B.V. Taste improving substances
EP2629609A4 (fr) * 2010-10-19 2014-08-27 Elcelyx Therapeutics Inc Thérapies basées sur un ligand de récepteur chimiosensoriel
US9101160B2 (en) 2005-11-23 2015-08-11 The Coca-Cola Company Condiments with high-potency sweetener

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5503966B2 (ja) * 2007-05-23 2014-05-28 興和株式会社 糖アミド誘導体を利用したホウ素吸着材及びホウ素除去方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3714139A (en) * 1968-07-17 1973-01-30 Searle & Co Optionally substituted aspartyl cyclo-hexylalanine lower alkyl esters, compositions and method
US3803223A (en) * 1970-07-20 1974-04-09 Searle & Co 3-amino-n-substituted succinamic acids and intermediates thereto
US3865957A (en) * 1972-04-12 1975-02-11 Sueddeutsche Zucker Ag Low calorie sweetener and sweetener base
US3971822A (en) * 1974-07-19 1976-07-27 Tanabe Seiyaku Co., Ltd. Aspartyl amide sweetening agents
US4024290A (en) * 1976-03-22 1977-05-17 G. D. Searle & Co. Bulking agent for foods
US4226804A (en) * 1979-03-09 1980-10-07 Dynapol Alpha amino acid dihydrochalcones

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3714139A (en) * 1968-07-17 1973-01-30 Searle & Co Optionally substituted aspartyl cyclo-hexylalanine lower alkyl esters, compositions and method
US3803223A (en) * 1970-07-20 1974-04-09 Searle & Co 3-amino-n-substituted succinamic acids and intermediates thereto
US3865957A (en) * 1972-04-12 1975-02-11 Sueddeutsche Zucker Ag Low calorie sweetener and sweetener base
US3971822A (en) * 1974-07-19 1976-07-27 Tanabe Seiyaku Co., Ltd. Aspartyl amide sweetening agents
US4024290A (en) * 1976-03-22 1977-05-17 G. D. Searle & Co. Bulking agent for foods
US4226804A (en) * 1979-03-09 1980-10-07 Dynapol Alpha amino acid dihydrochalcones

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5968811A (en) * 1990-10-17 1999-10-19 Cpc International Inc. Processing of yeast refuse and resulting product
EP0552896A1 (fr) * 1992-01-17 1993-07-28 Takasago International Corporation Polymères biodégradables et optiquement actifs et leurs intermédiaires oligomériques et procédé de préparation de ceux-ci
EP0718305A1 (fr) * 1994-12-24 1996-06-26 Solvay Deutschland GmbH Procédé de préparation d'amides de l'acide aldobionique
US5644042A (en) * 1994-12-24 1997-07-01 Solvay Pharma Deutschland Gmbh Process for production of aldobionic acid amide
DE19634605B4 (de) * 1996-08-27 2005-02-03 Schill + Seilacher "Struktol" Ag Verwendung von Zuckersäureamiden als EP-Additive und EP-Additive enthaltend Glucon- und/oder Glucoheptonsäureamide
EP0826761A1 (fr) * 1996-08-27 1998-03-04 Schill & Seilacher GmbH & Co. Utilisation d'amides d'acides polyhydroxycarboxyliques en tant qu'additifs extrême-pression
DE19634605A1 (de) * 1996-08-27 1998-03-05 Schill & Seilacher Verwendung von Polyhydroxycarbonsäureamiden als EP-Additive
US5952274A (en) * 1996-08-27 1999-09-14 Schill & Seilacher Gmbh & Co. Use of polyhydroxycarboxylamides as EP additives
EP1378167A1 (fr) * 2002-07-03 2004-01-07 Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo Produit de boulangerie comprenant du alpha-D-glucopyranosyl-1,1-mannitol et préparation du dit produit
EP1378168A1 (fr) * 2002-07-03 2004-01-07 Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo Pâte contenant du alpha-D-glucopyranosyl-1,6-sorbitol pour produit de boulangerie et procédé de préparation du dit produit
WO2005102071A1 (fr) * 2004-04-20 2005-11-03 Quest International Services B.V. Substances d'amelioration de gout
US8778437B2 (en) 2004-04-20 2014-07-15 Givaudan Nederland Services B.V. Taste improving substances
WO2006009425A1 (fr) * 2004-07-20 2006-01-26 Quest International Services B.V. Substances d'amelioration de saveur
AU2012200442B2 (en) * 2004-07-20 2014-07-17 Givaudan Nederland Services B.V. Taste improving substances
CN101022736B (zh) * 2004-07-20 2012-03-21 奎斯特国际服务公司 味道改良物质
US8053013B2 (en) 2004-10-29 2011-11-08 Quest International Services B.V. Flavour modulating substances
WO2006046854A3 (fr) * 2004-10-29 2006-10-12 Quest Int Substances de modulation de saveur
KR101350724B1 (ko) * 2005-09-02 2014-01-14 지보당 네덜란드 서비시즈 비.브이. 향상된 풍미 조성물
AU2006285498B2 (en) * 2005-09-02 2012-12-06 Quest International Services B.V. Improved flavour compositions
WO2007027095A1 (fr) * 2005-09-02 2007-03-08 Quest International Services B.V. Compositions aromatisantes ameliorees
US9155329B2 (en) 2005-09-02 2015-10-13 Givaudan, S.A. Flavour compositions
US9101160B2 (en) 2005-11-23 2015-08-11 The Coca-Cola Company Condiments with high-potency sweetener
US8263161B2 (en) 2006-05-05 2012-09-11 Quest International Services B.V. Taste improving substances
US8691311B2 (en) 2006-05-05 2014-04-08 Givaudan Nederland Services B.V. Taste improving substances
EP1854782A1 (fr) * 2006-05-05 2007-11-14 Quest International Services B.V. Composition pour améliorer les caracteristiques gustatives
WO2008006864A1 (fr) * 2006-07-11 2008-01-17 Christoph Mark Procédé de fabrication d'amines optiquement actives
US8017168B2 (en) 2006-11-02 2011-09-13 The Coca-Cola Company High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith
EP2629609A4 (fr) * 2010-10-19 2014-08-27 Elcelyx Therapeutics Inc Thérapies basées sur un ligand de récepteur chimiosensoriel

Also Published As

Publication number Publication date
AU8914391A (en) 1992-05-20
JPH05503307A (ja) 1993-06-03
EP0506952A4 (en) 1993-02-10
EP0506952A1 (fr) 1992-10-07
CA2071633A1 (fr) 1992-04-12

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