EP0506952A1 - Amides derived from sugar alcohols suitable as sugar substitutes - Google Patents
Amides derived from sugar alcohols suitable as sugar substitutesInfo
- Publication number
- EP0506952A1 EP0506952A1 EP19920902519 EP92902519A EP0506952A1 EP 0506952 A1 EP0506952 A1 EP 0506952A1 EP 19920902519 EP19920902519 EP 19920902519 EP 92902519 A EP92902519 A EP 92902519A EP 0506952 A1 EP0506952 A1 EP 0506952A1
- Authority
- EP
- European Patent Office
- 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.)
- Withdrawn
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, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- 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 COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- 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 COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- 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
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- 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 present invention relates generally to novel compositions suitable for incorporation into foods. Specifically, the invention relates to novel sugar substitutes suitable for replacing sucrose and other sugars incorporated into formulated foods.
- the sugar substitutes are particularly characterized by being amides or polyamides derived from non-reducing amino-deoxy sugar alcohols, amino alcohols or amines and sugar carboxylic acids.
- Sucrose ⁇ -D-glucopyranosyl- ⁇ -D-fructofuranoside
- cane or beet sugar is a widely used sweetening agent for foods and beverages.
- Sucrose is cariogenic and caloric. For these reasons, strong efforts have been expended to reduce the intake of sucrose and other sweeteners so disadvantaged. As a consequence of these efforts, high-potency sweeteners such as aspartame, saccharin and the like, which are in effect
- sucrose as a consequence of its bulk properties, provides actual physical structure, texture, freezing point depression, moisture retention, density and appearance characteristics to formulated foods. These properties are in a large part due to the number of sucrose molecules, as well as the volume occupied by sucrose and are therefore considered bulk properties.
- sucrose be replaced by high potency sweeteners in formulated foods, it is therefore desirable to incorporate agents which simulate the structure, texture, freezing point depression, moisture retention, density, water solubility, solution viscosity properties, stability, non-reactivity with other ingredients and appearance characteristics of sucrose without adding the calories that sucrose would provide.
- the agents that are typically used are carbohydrates.
- carbohydrates For example,
- Mitsuhashi, et al., in U.S. Patent 3,741,776 discloses the use of maltitol (4-0- ⁇ -D-glucopyranosyl-D-sorbitol) as a sweet sugar substitute for incorporation into low-calorie foods and
- 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.
- the sugar substitute prepared according to the disclosed method is said to comprise a viscous syrup which contains as a major component about 70% of the isomeric ⁇ -anomers of glucosylsorbitol, i.e. 1,2,3,4,5 and 6-glucopyranosyl-D-sorbitol.
- the sugar substitute further includes various minor components, including about 1% sorbitol and 15% other carbohydrates.
- U. S. Patent No. 4,902,525 discloses the use of mesoerythritol ((HOCH 2 CHOH) 2 ) a crystalline sugar alcohol, as a sugar
- the patent suggests combining mesoerythritol with a high potency sweetener to approximate the taste and physical properties of sucrose.
- Pfizer Inc. has developed Polydextrose for use as a sugar substitute. This compound is described in greater detail in U. S. Patent No. 3,876,794 and in S. Cooley et al., Br. J. Nutrition, 57, 235-243, 1987.
- Procter and Gamble has been working on a class of compounds used as sugar substitutes. These compounds are described in greater detail in published European Application Nos. 341 062 and 341 063 and are reported to be 5-C-hydroxymethyl hexose-based compounds or derivatives of 5-C-hydroxymethyl-D-aldohexose and their bicyclic anhydro tautomeric forms. Other materials have been suggested for use as sugar substitutes. These include lactitol, fructooligosaccharide sweeteners, cellulose, leucrose and dextrans. A major problem associated with nearly all of these sugar substitutes is that they typically undergo fermentation when in the large intestine.
- the present invention provides novel amide based, non-caloric sugar substitutes derived from sugar carboxylic acids and amino alcohols, as well as non-reducing amino-deoxy sugar alcohols, which possess similar physical, rheological and colligative properties to sucrose. These sugar substitutes are suited for incorporation into formulated foods and are not fermented by the bacteria of the human gastrointestinal system.
- the sugar substitutes may be used in association with another sweetener (high potency or other) and may be used in confectionery products, beverages, bakery products and the like. Accordingly, one embodiment of the present invention comprises novel compositions of formula (I):
- R 3 H, C 1 -C 10 alkyl, C 2 -C 10 hydroxyalkyl or C 2 -C 10 polyhydroxyalkyl or an integral part of R 2 as a carbocyclic residue; provided that one or both of R 2 and R 3 contains one or more hydroxy groups.
- novel compositions of formula (II) are provided: 0 R 2 R 3 0
- R 1 - C - N - A - N - C - R 4 (II) where R 1 a mono- or polyhydric aliphatic alcohol residue;
- R 2 H, C 1 -C 10 alkyl, C 2 -C 10 hydroxyalkyl or
- R 3 H, C 1 -C 10 alkyl, C 2 -C 10 hydroxyalkyl, C 2 -C 10 polyhydroxyalkyl or an integral part of R 2 as a carbocyclic residue;
- R 4 a mono- or polyhydric aliphatic alcohol residue
- A C 1 -C 10 alkyl, C 2 -C 10 hydroxyalkyl or
- A represents either
- compositions of formulas (I) and (II) are particularly useful as sugar substitutes.
- a sweetened sugar substitute comprises a high potency sweetener and the
- the high potency sweetener comprises aspartame.
- a novel confectionery product, beverage or bakery product is provided. These products include the above-defined sugar substitutes. Accordingly, it is an object of the present invention to provide a sugar substitute which possesses similar physical, rheological and colligative properties to sucrose without possessing the calories and cariogenic drawbacks of sucrose. It is a further object of the present invention to provide a sugar substitute which does not ferment in the large intestine.
- 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.
- An additional object of the present invention is to provide a novel confectionery product, beverage or bakery product including a novel sweetened sugar substitute.
- 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.
- composition used as a sugar substitute is a highly water soluble polyhydroxylated compound having one or more amide linkages.
- the compounds according to the present invention are of formula (I) and (II):
- R 1 a mono- or polyhydric aliphatic alcohol residue
- R 2 H, C 1 -C 10 alkyl, C 2 -C 10 hydroxyalkyl or
- R 3 H, C 1 -C 10 alkyl, C 2 -C 10 hydroxyalkyl,
- R 2 as a carbocyclic residue; provided that one or both of R 2 and R 3 contains one or more hydroxy groups. 0 R 2 R 3 0
- R 1 - C - N - A - N - C - R 4 (II) where R 1 a mono- or polyhydric aliphatic alcohol residue;
- R 2 H, C 1 -C 10 alkyl, C 2 -C 10 hydroxyalkyl or C 2 -C 10 polyhydroxyalkyl;
- R 3 H, C 1 -C 10 alkyl, C 2 -C 10 hydroxyalkyl,
- R 2 as a carbocyclic residue
- R 4 a mono- or polyhydric aliphatic alcohol residue
- A C 1 -C 10 alkyl, C 2 -C 10 hydroxyalkyl or
- R 1 is derived from ⁇ -D-gluconolactone, L-gulono- ⁇ -lactone, L-ascorbic acid, lactobiono- ⁇ -lactone or ⁇ -D-glucoheptonic- ⁇ -lactone and R 3 is selected from the following groups:
- the above compounds are produced by reacting an amino- or diamino alcohol with a carboxylic acid or derivative (i.e. R 1 COOH or R 1 COX where X is 0-alkyl).
- a carboxylic acid or derivative i.e. R 1 COOH or R 1 COX where X is 0-alkyl.
- the amino group of the amine, amino alcohol or amino-deoxy sugar undergoes a condensation reaction with the carboxylic acid derivative to form an amide bond between the amino group and the carboxyl group.
- compositions of formulas (I) and (II) are non-toxic (tested in an Ames' mutagenicity assay and by oral acute single dose to mice (4000 mpk)), are non-fermentable by the microbial flora of the human gastrointestinal system, and can range from tasteless to substantially sweet at a 20% concentration in water.
- the reduced calorie sugar substitutes of the invention may be added directly to formulated foods as separate ingredients and an appropriate high potency sweetener may likewise be added as a separate ingredient to accomplish the same final effect as sucrose in formulated foods.
- the sweetener and sugar substitute can be combined to form a novel sweetened sugar substitute.
- the use of the present sugar substitute, when sweetened with a high potency sweetener such as aspartame, will be non-caloric or nearly so. This is because the sugar
- High potency sweeteners useful in the present invention include aspartame, saccharin, cyclamate, acesulfame-K, alitame,
- the sugar substitutes of the present invention may be combined with various high potency sweetening agents in any desired proportion. Typical proportions range between about 0.2 to 2.0 parts sweetener per 100 parts sugar substitute. For example 0.5 to 1.0 parts aspartame can be added per 100 parts of sugar substitute.
- the sugar substitute may be subjected to drying procedures such as spray-drying, milling, vacuum-drum drying or other techniques known in the art.
- the sugar substitute of the present invention preferably including a high potency sweetener, can conveniently be
- formulated foods such as confectionery products, beverages and bakery products.
- Specific examples include candy, cookies, ice cream, pastries, cakes, jellies, preserves, chocolate coatings, puddings, soft drinks, syrups and the like.
- a sweetened sugar substitute product is provided that can replace sucrose altogether and make foods that are otherwise highly caloric much lower in caloric content.
- Mass spectroscopy analysis exhibited a highest m/e peak at 269 consistent with a calculated molecular weight at 269.29 D.
- the compound was not fermented by human colonic microflora in an in vitro assay.
- 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.
- the compound was not fermented by human colonic microflora in an in vitro assay.
- Mass spectroscopy analysis exhibited a highest m/e peak at 238 consistent with a calculated molecular weight at
- Mass spectroscopy analysis exhibited a highest m/e peak at 239 consistent with a calculated molecular weight at
- Mass spectroscopy analysis exhibited a highest m/e peak at 253 consistent with a calculated molecular weight at
- TGA 1st at 223°C (54%); 2nd transition at 552°C (24%).
- 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.
- TGA 1st at 190°C (48%); 2nd transition at 539°C (30%).
- tris[hydroxymethyl]aminomethane were added to sixty parts methanol with vigorous overhead stirring. The reaction was refluxed for three hours at which point a yellow color appeared. The reaction was cooled and excess solvent was removed under reduced pressure. The concentrated reaction mix was then brought up in water and twice slurried with Amberlite IR 120 cation exchange resin (H + ) form, stirred for 30 minutes, and then filtered. With the excess tris removed, the solution was concentrated under reduced pressure and passed through an BioRad AG3-X4A anion exchange resin (Cl-) form. This yielded the product with a purity of 93+% (by HPLC).
- Mass spectroscopy analysis exhibited a highest m/e peak at 299 consistent with a calculated molecular weight at 299.27 D.
- 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.
- Mass spectroscopy analysis exhibited a highest m/e peak at 283 consistent with a calculated molecular weight at 283.28 D.
- Mass spectroscopy analysis exhibited a highest m/e peak at 313 consistent with a calculated molecular weight at 313.30 D.
- TGA First transition: 30.54% midpoint 217°C
- Example 1 (Examples 1, 2, 3, 4, 5, 6, 7, 9, 10, 13, 14, 15 and 16) were measured using the Advanced Micro-Osmometer Model 3M0. The control and test compounds were run in duplicate at several concentrations. A 0.3g sample of the material was dissolved in lml of water, then diluted to the approximate test concentration (5, 10, 15, 20, 25 and 30 percent).
- the data obtained for osmolality and freezing point measurements are shown in the attached Tables.
- a yellow cake was made by mixing together the following
- the sugar substitutes were as follows:
- 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.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Mycology (AREA)
- Seasonings (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Saccharide Compounds (AREA)
- Peptides Or Proteins (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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.The invention relates to compositons represented by formulas (I) and (II). In formula (I), R1 represents a residue of monohydric or polyhydric aliphatic alcohol; R2 represents H, C1-C10 alkyl, C2-C10 hydroxyalkyl or C2-C10 polyhydroxyalkyl; and R3 represents H, C1-C10 alkyl, C2-C10 hydroxyalkyl, C2-C10 polyhydroxyalkyl or an integral part of R2 in the form of a carbocyclic residue; provided that at least one of the elements R2 and R3 contains one or more hydroxy groups. In formula (II), R1 represents a residue of monohydric or polyhydric aliphatic alcohol; R2 represents H, C1-C10 alkyl, C2-C10 hydroxyalkyl or C2-C10 polyhydroxyalkyl; R3 represents H, C1-C10 alkyl, C2-C10 hydroxyalkyl, C2-C10 polyhydroxyalkyl or an integral part of R2 in the form of a carbocyclic residue; R4 represents a residue of monohydric or polyhydric aliphatic alcohol; and A represents C1-C10 alkyl, C2-C10 hydroxyalkyl or C2-C10 polyhydroxyalkyl; provided that at least one of the elements R2 R3 and A contains one or more hydroxy groups. These compounds are particularly useful as sugar substitutes.
Description
Claims
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US596793 | 1984-04-04 | ||
US59679390A | 1990-10-11 | 1990-10-11 | |
US65025691A | 1991-02-04 | 1991-02-04 | |
US650256 | 1991-02-04 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0506952A1 true EP0506952A1 (en) | 1992-10-07 |
EP0506952A4 EP0506952A4 (en) | 1993-02-10 |
Family
ID=27082634
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19920902519 Withdrawn EP0506952A4 (en) | 1990-10-11 | 1991-10-11 | Amides derived from sugar alcohols suitable as sugar substitutes |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0506952A4 (en) |
JP (1) | JPH05503307A (en) |
AU (1) | AU8914391A (en) |
CA (1) | CA2071633A1 (en) |
WO (1) | WO1992006601A1 (en) |
Families Citing this family (17)
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GB9022560D0 (en) * | 1990-10-17 | 1990-11-28 | G B Biotechnology Limited | Processing of waste |
JP2884123B2 (en) * | 1992-01-17 | 1999-04-19 | 高砂香料工業株式会社 | Biodegradable optically active polymer, intermediate oligomer thereof, and production method thereof |
DE4446632A1 (en) * | 1994-12-24 | 1996-06-27 | Solvay Deutschland | Process for the preparation of aldobionic acid amide |
DE19634605B4 (en) * | 1996-08-27 | 2005-02-03 | Schill + Seilacher "Struktol" Ag | Use of sugar amides as EP additives and EP additives containing gluconic and / or glucoheptonic acid amides |
JP2004033109A (en) * | 2002-07-03 | 2004-02-05 | Ueno Seiyaku Oyo Kenkyusho:Kk | Baked confectionery and method for producing the same |
JP2004033108A (en) * | 2002-07-03 | 2004-02-05 | Ueno Seiyaku Oyo Kenkyusho:Kk | Dough for whipping-stabilized baked confectionery, and method for producing the baked confectionery by baking the dough |
KR101414249B1 (en) | 2004-04-20 | 2014-07-01 | 지보당 네덜란드 서비시즈 비.브이. | Taste improving substances |
AU2012200442B2 (en) * | 2004-07-20 | 2014-07-17 | Givaudan Nederland Services B.V. | Taste improving substances |
WO2006009425A1 (en) * | 2004-07-20 | 2006-01-26 | Quest International Services B.V. | Taste improving substances |
WO2006046854A2 (en) * | 2004-10-29 | 2006-05-04 | Quest International B.V. | Flavour modulating substances |
AU2006285498B2 (en) * | 2005-09-02 | 2012-12-06 | Quest International Services B.V. | Improved flavour compositions |
US9101160B2 (en) | 2005-11-23 | 2015-08-11 | The Coca-Cola Company | Condiments with high-potency sweetener |
ATE444280T1 (en) | 2006-05-05 | 2009-10-15 | Givaudan Nederland Services B | COMPOSITION FOR IMPROVEMENT OF TASTE |
DE102006032061B4 (en) * | 2006-07-11 | 2009-01-02 | Mark, Christoph, Dr. | Process for the preparation of optically active amines |
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 |
EP2149539A4 (en) * | 2007-05-23 | 2011-05-11 | Kowa Co | Boron adsorbent utilizing sugar amide derivative, and boron removal method |
WO2012054528A2 (en) * | 2010-10-19 | 2012-04-26 | Elcelyx Therapeutics, Inc. | Chemosensory receptor ligand-based therapies |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1258248A (en) * | 1968-07-17 | 1971-12-22 | ||
US3803223A (en) * | 1970-07-20 | 1974-04-09 | Searle & Co | 3-amino-n-substituted succinamic acids and intermediates thereto |
DE2217628C2 (en) * | 1972-04-12 | 1974-06-06 | Sueddeutsche Zucker Ag | Process for the production of alpha-D-glucopyranosido square bracket on 1-6 square bracket to sorbitol (isomaltite) |
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 |
-
1991
- 1991-10-11 WO PCT/US1991/007534 patent/WO1992006601A1/en not_active Application Discontinuation
- 1991-10-11 JP JP4500699A patent/JPH05503307A/en not_active Expired - Lifetime
- 1991-10-11 AU AU89143/91A patent/AU8914391A/en not_active Abandoned
- 1991-10-11 CA CA002071633A patent/CA2071633A1/en not_active Abandoned
- 1991-10-11 EP EP19920902519 patent/EP0506952A4/en not_active Withdrawn
Non-Patent Citations (2)
Title |
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No further relevant documents disclosed * |
See also references of WO9206601A1 * |
Also Published As
Publication number | Publication date |
---|---|
AU8914391A (en) | 1992-05-20 |
EP0506952A4 (en) | 1993-02-10 |
JPH05503307A (en) | 1993-06-03 |
WO1992006601A1 (en) | 1992-04-30 |
CA2071633A1 (en) | 1992-04-12 |
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