WO1992006601A1

WO1992006601A1 - Amides derived from sugar alcohols suitable as sugar substitutes

Info

Publication number: WO1992006601A1
Application number: PCT/US1991/007534
Authority: WO
Inventors: Grant E. Dubois; Manssur Yalpani; William Henry Owens; Shawn Yvette Stevens; Glenn Roy
Original assignee: The Nutrasweet Company
Priority date: 1990-10-11
Filing date: 1991-10-11
Publication date: 1992-04-30
Also published as: EP0506952A1; JPH05503307A; CA2071633A1; EP0506952A4; AU8914391A

Abstract

Compositions of formula (I) and (II). In formula (I) R1= a mono- or polyhydric aliphatic alcohol residue; R2= H, C1-C10 alkyl, C2-C10 hydroxyalkyl or C2-C10 polyhydroxyalkyl; and R3= H, C1-C10 alkyl, C2-C10 hydroxyalkyl, C2-C10 polyhydroxyalkyl or an integral part of R2 as a carbocyclic residue; provided that one or both of R2 and R3 contain one or more hydroxy groups. In formula (II) where R1= a mono- or polyhydric aliphatic alcohol residue; R2= H, C1-C10 alkyl, C2-C10 hydroxyalkyl or C2-C10 polyhydroxyalkyl; R3= H, C1-C10 alkyl, C2-C10 hydroxyalkyl, C2-C10 polyhydroxyalkyl or an integral part of R2 as a carbocyclic residue; R4= a mono- or polyhydric aliphatic alcohol residue; and A= C1-C10 alkyl, C2-C10 hydroxyalkyl or C2-C10 polyhydroxyalkyl; provided that at least one of R2, R3 and A contains one or more hydroxy groups are disclosed. The compounds are particularly suitable as sugar substitutes.

Description

AMIDES DERIVED FROM SUGAR ALCOHOLS SUITABLE AS SUGAR

SUBSTITUTES

Background of the Invention

This application is a continuaton in part application of co-pending U.S. Patent Application Serial No. 596,793, filed October 11, 1990. To the extent necessary, this application is hereby incorporated by reference.

1. Field of the Invention

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.

2. Technology Description

Sucrose (α-D-glucopyranosyl-β-D-fructofuranoside), also known as cane or beet sugar, is a widely used sweetening agent for foods and beverages. Sucrose, however, 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

non-caloric, have become increasingly popular. Vhile the use of small amounts of high potency sweeteners such as aspartame is particularly successful in reproducing the taste sensation of sucrose, the use of such high potency sweeteners fails to adequately reproduce other properties of sucrose that are important to its function in formulated foods. In particular, 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.

In order that 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.

Published references disclose the use of various sugar

substitutes for reproduction of such characteristics. The agents that are typically used are carbohydrates. For example,

Mitsuhashi, et al., in U.S. Patent 3,741,776 discloses the use of maltitol (4-0-α-D-glucopyranosyl-D-sorbitol) as a sweet sugar substitute for incorporation into low-calorie foods and

beverages. 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.

Schieweck, et al., in U.S. Patent 3,865,957 discloses the use of isomalt (6-0-α-D-glucopyranosyl-D-sorbitol and

6-0-α-D-glυcopyranosyl-D-mannitol in a 1 to 1 mixture) as a sweet sugar substitute for incorporation into low-calorie foods, either alone or in combination with high potency sweeteners such as aspartame. Isomalt is also referred to as Palatinit^®. Layton, in U. S. Patent 4,024,290 discloses a sugar substitute for incorporation into formulated foods prepared according to a process wherein glucose and sorbitol are subjected to a

condensation reaction at low pressures and elevated temperatures in the presence of an acid-ion exchange resin. 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 β-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.

Commonly assigned U. S. Patent Application Serial No. 336,500, filed on April 12, 1989, discloses the use of cellobiitol

(4-0-β-D-glucopyranosyl-D-sorbitol) as a sugar substitute. This composition is stated to be crystalline platelets having a melting point of 133°C and having a specific rotation in water of [α]_D ²⁵ = -8.7º.

U. S. Patent No. 4,902,525, discloses the use of mesoerythritol ((HOCH₂CHOH)₂) a crystalline sugar alcohol, as a sugar

substitute. More particularly, 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. It is known that the fermentation of the carbohydrate materials produces short chain carboxylic acids (e.g., acetic, propionic and butyric) and their salts. These fermentation products are known to be absorbed from the large intestine, thus providing substantial calories to the host.

Of the above compounds proposed for use as sugar substitutes, the fermentation problem is less noticeable for cellulose and the dextrans. However, these compounds are not ideal sugar

substitutes because they poorly reproduce the physical properties of sucrose.

Accordingly, there exists a need in the art for a sugar

substitute which does not undergo fermentation to carboxylic acids (and salts thereof) when in the large intestine and which exhibits the physical properties of sucrose.

Brief Summary of the Invention

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):

O R₂

(I)

R₁- C - N -R₃ where R₁= a mono- or polyhydric aliphatic alcohol residue; R₂= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl or

C₂-C₁₀ polyhydroxyalkyl; and

R₃= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl or C₂-C₁₀ polyhydroxyalkyl or an integral part of R₂ as a carbocyclic residue; provided that one or both of R₂ and R₃ contains one or more hydroxy groups. In particularly preferred embodiments, R₁ is derived from δ-D-gluconolactone, 1,-gulono-γ-lactone, L-ascorbic acid, lactobiono-δ-lactone or α-D-glucoheptonic-γ-lactone and R₃ is selected from the following groups: -H, CH₃, (CH₂)_nCH₃, n= 1-4, or C(CH₂OH)₃;

-CH(CH₂OH)₂;

-CH₂-(CHOH)_n-CH₂OH, n=0-10;

-(CH₂)_nCHR₄OH, n= 1-4, R₄ =H or CH₃;

-(CH₂)_n-O-(CH₂)_n-OH, n=2-5; or

-C(CH₃)₂CH₂OH.

In accordance with another embodiment of the present invention, novel compositions of formula (II) are provided: 0 R₂ R₃ 0

R₁ - C - N - A - N - C - R₄ (II) where R₁= a mono- or polyhydric aliphatic alcohol residue;

R₂= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl or

C₂-C₁₀ polyhydroxyalkyl; R₃= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl, C₂-C₁₀ polyhydroxyalkyl or an integral part of R₂ as a carbocyclic residue;

R₄= a mono- or polyhydric aliphatic alcohol residue; and

A= C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl or

C₂-C₁₀ polyhydroxyalkyl; provided that at least one of R₂, R₃ and A contains one or more hydroxy groups.

In preferred embodiments, A represents either

-(CH₂)_n-, n=2-6, or -CH₂-CHOH-CH₂-.

The compositions of formulas (I) and (II) are particularly useful as sugar substitutes.

In accordance with another embodiment of the present invention, a sweetened sugar substitute is provided. The sweetened sugar substitute comprises a high potency sweetener and the

above-defined sugar substitutes of formulas (I) and (II).

In a particularly preferred embodiment, the high potency sweetener comprises aspartame. In still another embodiment, 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.

These, and other objects will be readily apparent to one skilled in the art as reference is made to the detailed description of the preferred embodiment.

Detailed Description of the Preferred Embodiment

While referring to the preferred embodiment, certain terminology will be utilized for the sake of clarity. Such terminology is intended to cover the recited embodiment, as well as all technical equivalents which operate in a similar manner for a similar purpose to achieve a similar result.

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.

The 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):

0 R₂

(I)

R₁- C - N -R₃ where R₁= a mono- or polyhydric aliphatic alcohol residue;

R₂= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl or

C₂-C₁₀ polyhydroxyalkyl; and

R₃= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl,

C₂-C₁₀ polyhydroxyalkyl or an integral part of

R₂ as a carbocyclic residue; provided that one or both of R₂ and R₃ contains one or more hydroxy groups. 0 R₂ R₃ 0

R₂= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl or C₂-C₁₀ polyhydroxyalkyl; R₃= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl,

C₂-C₁₀ polyhydroxyalkyl or an integral part of

R₂ as a carbocyclic residue;

R₄= a mono- or polyhydric aliphatic alcohol residue; and

A= C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl or

In preferred embodiments of formula (I), R₁ is derived from δ-D-gluconolactone, L-gulono-γ-lactone, L-ascorbic acid, lactobiono-δ-lactone or α-D-glucoheptonic-γ-lactone and R₃ is selected from the following groups:

-H, CH₃, (CH₂)_nCH₃, n= 1-4, or C(CH₂OH)₃;

-CH(CH₂OH)₂;

-CH₂-(CHOH)_n-CH₂OH, n=0-10;

-(CH₂)_nCHR₄OH, n= 1-4, R₄ =H or CH₃;

-(CH₂)_n-O-(CH₂)_n-OH, n=2-5; or

-C(CH₃)₂CH₂OH. In preferred embodiments of formula (II), A represents either -(CH₂)_n-, n=2-6, or -CH₂-CHOH-CH₂-. Examples of specific compounds falling within the scope of formulas (I) and (II) are shown in Table 1.

Table 1

The above compounds are produced by reacting an amino- or diamino alcohol with a carboxylic acid or derivative (i.e. R₁COOH or R₁COX 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.

The 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.

Quantitatively, this corresponds to a sweetness potency of about 0% to about 100% that of sucrose. The compounds form clear, colorless films upon melting. The compounds further demonstrate some or all of the following qualitative properties:

crystallinity, high solubility in water, osmolality comparable to that of sucrose, Newtonian solution behavior, starch

gelatinization effects comparable to sucrose, low or no

hygroscopicity and compatibility with a large number of food ingredients. Of the above compounds, compounds 1, 2, 3, 8, 9, 12, 13 and 14 exhibit particularly attractive properties, with compound 1 being especially desirable. 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. Alternatively, 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

substitutes are not substantially absorbed from or metabolized in the small intestine or fermented in the large intestine to produce nutritive products which are made available to the host. High potency sweeteners useful in the present invention include aspartame, saccharin, cyclamate, acesulfame-K, alitame,

sucralose, thaumatin, neohesperidin dihydrochalcone, stevioside sweeteners and the like. Particularly preferred is the use of aspartame. 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.

To apply the high potency (or other) sweetener to the 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

incorporated into 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. By combining the sugar substitute with a high potency sweetener such as aspartame, 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.

The invention is further illustrated by the following

non-limiting examples. EXAMPLE 1

Production of N-[1,2-dihydroxyprop-3-yl]-D-gluconamide

(Compound 1) δ-D-Gluconolactone (1 part) and (±)-3-amino-1,2-propanediol (1 part) were heated to 65ºC with vigorous stirring in 130 parts of methanol. After heating for 24h, the solution was cooled to afford a precipitate which was isolated by filtration. The precipitate was dried under vacuum at 60°C to give the product in 50% yield as a white solid. The following data were obtained for the product :

¹H NMR (D₂O): TSP 4.39 (d, 1H); 4.1 (m, 1H); 3.30-3.90 (m, 9H) ppm.

¹³C NMR (D₂O): TSP 44.29, 65.41, 66.02, 66.07, 72.93, 73.08, 73.16, 73.88, 74.95, 76.22, 76.26, 177.55 ppm. IR (KBr): 3370, 3320, 1653, 1027 cm^-1.

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.

Anal. for C₉H_{1 9}NO₈ Calcd: C, 40.14; H, 7.11; N, 5.20; 0, 47.53

Found: C, 40.02; H, 7.26; N, 5.13; 0, 47.49

DSC: 139°C. TGA [transition (weight loss)]: 1st at 217°C (43%); 2nd at 298°C (14%); 3rd transition at 552°C (33%). EXAMPLE 2

Production of N-[1,3-dihydroxyprop-2-yl]-D-gluconamide

(Compound 2) δ-D-Gluconolactone (1 part) and 2-amino-1,3-propanediol (1 part) were heated to 65°C with vigorous stirring in 100 parts of methanol. After heating for 4h, the solution was then cooled to afford a precipitate, which was isolated by filtration. The precipitate was dried under vacuum at 60ºC to give the product in 84% yield as a white solid. The following data were obtained for the compound: ¹H NMR (D₂O): TSP 4.39 (d, 1H), 4.00-4.13 (m, 2H), 3.60-3.85 (m, 8H) ppm.

¹³C NMR (D₂O): TSP 55.53, 63.34, 65.43, 73.12, 73.86, 74.83, 76.27, 177.43 ppm.

IR (KBr): 3500, 3320, 1630 (C=0), 1553 (amide II band),

1050 cm^-1.

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. Anal. for C₉H₁₉NO₈:

Calcd: C, 40.14; H, 7.11; N, 5.20; 0, 47.53

Found: C, 40.12; H, 7.04; N, 5.11; 0, 47.44 DSC: 132° C. TGA: 1st at 216°C (63%); 2nd transition at 574°C (32%).

EXAMPLE 3 Production of N,N'-di-(D)-gluconyl-1,3-diamino-2- hydroxypropane (Compound 3) δ-D-Gluconolactone (2 parts) and 1,3-diamino-2-hydroxypropane (1 part) were heated to 65°C with vigorous stirring in 67 parts of methanol. After heating for 3h, the solution was cooled and the resulting precipitate was isolated by filtration. The precipitate was dissolved in water and passed through a column of activated carbon. The aqueous solution was then cooled to yield a solid material, which was filtered and dried under vacuum at 50°C to obtain the product as a white solid in 60% yield. The following data were obtained for the product :

¹H NMR (D₂O): TSP 4.39 (d, 2H), 4.1 (m, 2H), 3.6-4.0 (m, 9H), 3.3-3.4 (m, 4H) ppm.

¹³C NMR (D₂O): TSP 44.78, 65.40, 71.22, 73.16, 73.88, 74.97, 76.24, 76.30, 177.62 ppm.

IR (KBr): 3396, 3314, 1653 cm^-1.

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.

Anal. for C₁₅H₃₀N₂O₁₃:

Calcd: C, 40.36; H, 6.77; N, 6.27; 0, 46.59

Found: C, 40.32; H, 6.81; N, 6.20; 0, 46.75 DSC: 180°C.

TGA: 1st at 212°C (46%); 2nd transition at 535°C (33%). EXAMPLE 4

Production of N-[2-(Hydroxyethoxy)-ethyl]-D-gluconamide

(Compound 4) δ-D-Gluconolactone (1 part) and 2-(2-aminoethoxy)ethanol (1 part) were heated to 65°C with vigorous stirring in 90 parts of methanol. The reaction mixture became homogeneous after 4h. The solvent was then evaporated to give a solid material which was recrystallized from methanol and dried under vacuum at 60°C to give the product in 76% yield as a white solid. The following data were obtained for the product :

¹H NMR (D₂O): TSP 4.35 (d, 1H), 4.1 (m, 1H), 3.4-3.9 (m, 12H) ppm.

¹³C NMR (D₂O): TSP 41.50, 63.20, 65.41, 71.55, 73.14, 73.84, 74.34, 74.87, 76.18, 177.28 ppm.

IR (KBr): 3370, 3300, 1649, 1137, 1092 cm^-1.

Mass spectroscopy analysis exhibited a highest m/e peak at 238 consistent with a calculated molecular weight at

238.28 D. The compound was not fermented by human colonic microflora in an in vitro assay.

Anal. for C₁₀H₂₁NO₈: Calcd: C, 42.40; H, 7.47; N, 4.95; 0, 45.18

Found: C, 42.24; H, 7.30; N, 4.64; 0, 45.55 DSC: 111°C.

TGA: 1st at 224°C (55%); 2nd transition at 567°C (28%).

EXAMPLE 5 Production of N-[2-(hydroxyethyl)]-D-gluconamide (Compound 5) δ-D-Gluconolactone (1 part) and ethanolamine (1 part) were heated to 65°C with vigorous stirring in 73 parts of methanol. A homogeneous solution was obtained after 5h. The solution was then cooled to afford a precipitate which was isolated by filtration. The precipitate was dried under vacuum at 60°C to give the product in 84.5% yield as a white solid. The following data were obtained for the product :

¹H NMR (D₂O): TSP 4.35 (d, 1H), 4.10 (m, 1H), 3.60-3.9 (m, 6H), 3.40 (m, 2H) ppm.

¹³C NMR (D₂O): TSP 43.97, 62.75, 65.40, 73.12, 73.85, 74.85, 76.16, 177.40 ppm.

IR(KBr): 3650, 3400, 1655, 1037 cm^-1 .

Mass spectroscopy analysis exhibited a highest m/e peak at 239 consistent with a calculated molecular weight at

239.23 D. The compound was not fermented by human colonic microflora in an in vitro assay.

Anal. for C₈H₁₇NO₇ MW 239.23: Calcd: C, 40.17; H, 7.16; N, 5.86; 0, 46.82

Found: C, 40.16; H, 7.07; N, 5.77; 0, 46.75 DSC: 110°C.

TGA: 1st at 217°C (52%); 2nd transition at 540°C (36%).

EXAMPLE 6 Production of N-[2-hydroxypropyl]-D-gluconamide (Compound 6) δ-D-Gluconolactone (1 part) and D,L-1-amino-2-propanol (1 part) were heated to 65°C with vigorous stirring in 70 parts of methanol. A homogeneous solution was obtained after 2h. The methanol was then evaporated to give a solid. After

recrystallization from absolute ethanol and drying under vacuum at 65°C, the product was obtained in 81% yield as a white solid. The following data were obtained for the product:

¹H NMR (D₂O): TSP 4.35 (d, 1H), 4.10 (m, 1H), 3.90-4.05 (m, 1H), 3.60-3.85 (m, 4H), 3.20-3.40 (m, 2H), 1.30 (d, 3H) ppm.

¹³C NMR (D₂O): TSP 22.17, 48.57, 48.61, 65.41, 68.98, 69.10, 73.13, 73.87, 74.96, 76.21, 76.27, 177.83 ppm.

IR (KBr): 3380, 1647, 1085 cm^-1.

Mass spectroscopy analysis exhibited a highest m/e peak at 253 consistent with a calculated molecular weight at

253.25 D. The compound was not fermented by human colonic microflora in an in vitro assay.

Anal. for C₉H₁₉NO₇: Calcd: C, 42.68; H, 7.56; N, 5.53; 0, 44.22

Found: C, 42.57; H, 7.41; N, 5.42; 0, 44.17 DSC: 100ºC.

TGA: 1st at 223°C (54%); 2nd transition at 552°C (24%).

EXAMPLE 7

Production of N-Bis[2-hydroxyethyl]-D-gluconamide (Compound 7) δ-Gluconolactone (1 part), diethanolamine (1 part), and sodium methoxide (0.1 part) were heated to 65°C with vigorous stirring in 44 parts of methanol. A homogeneous solution was obtained after 27h. The reaction mixture was then filtered and the filtrate cooled to give a white solid which was isolated by filtration. After drying, the white solid was determined to have purity of > 98% by HPLC (RI and UV detection on a CHO Interaction 620 column). The following data were obtained for the product:

¹H NMR (D₂O): TSP 4.80 (d, 1H), 3.99-4.01 (d, 1H), 3.65-3.92 (m, 10H), 3.45-3.60 (m, 2H) ppm.

¹³C NMR (D₂O): TSP 48.96, 50.47, 58.92, 59.31, 63.27, 66.65, 69.10, 70.67, 70.94, 175.14 ppm. IR (KBr): 3242, 1621, 1467, 1075 cm^-1.

Mass spectroscopy analysis exhibited a highest m/e peak at 283 consistent with a calculated molecular weight at

283.28 D.

Anal. for C₁₀H₂₁N_O8: Calcd: C, 42.40; H, 7.47; N, 4.94; 0, 45.18

Found:. C, 41.91; H, 7.56; N, 4.74; 0, 44.59

DSC: 136°C.

TGA: 1st at 190°C (48%); 2nd transition at 539°C (30%).

EXAMPLE 8

Production of N-[Tris-(hydroxymethyl)-methyl]-D-glucoheptonamide (Compound 8)

One part α-D-glucoheptonic-γ-lactone and two parts

tris[hydroxymethyl]aminomethane (tris) 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).

¹H NMR (D₂O) TSP 3.37(s); 3.6-4.1 (m, 6H); 3.8 (s, 6H);

4.3 (d, 1H) ppm. ¹³C NMR (D₂O) TSP 63.22, 64.59, 5.49, 71.71, 73.88,

74.70, 75.36, 76.35, 76.91 ppm. EXAMPLE 9

Production of N-[Tris-(hydroxymethyl)-methyl]-D-gluconamide (Compound 9)

One part D-gluconolactone, and one part tris[hydroxymethyl] aminomethane (tris) were mixed in sixty parts of methanol. The reaction was heated to reflux with vigorous stirring

for 48 hours. The product, a white solid, was removed by filtration and dried overnight under reduced pressure. The product was pure (99.5%) by HPLC with a yield of 66.7%.

Additional yield can be obtained from product dissolved in mother liqours. ¹H NMR (D₂O): TSP 3.65-3.85 (m, 3H), 3.8 (s, 6H), 4.1 (t,

1H), 4.3 (d, 1H) ppm.

¹³C NMR (D₂O): TSP 63.11, 64.28, 65.20, 72.85,

73.64, 74.53, 76.03, 177.00 ppm.

IR (KBr): 3380, 1654, 1525, 1061 cm^-1.

Mass spectroscopy analysis exhibited a highest m/e peak at 299 consistent with a calculated molecular weight at 299.27 D.

Analyzed for C₁₀H₂₁NO₉:

Calcd: C, 40.13; H, 7.07; N, 4.68

Found: C, 40.18; H, 7.26; N, 4.57

DSC: midpoint 141°C. TGA: First transition: 46% 180-235°C midpoint 214°C,

Second transtion: 23% 372-465°C midpoint 402°C.

EXAMPLE 10 Production of N-(L)-gulonyl-1-amino-1-deoxy-sorbitol

(Compound 10)

One part L-gulono-γ-lactone and one part D-glucamine were added to forty parts methanol and heated to reflux with vigorous stirring. After ninety minutes, a yellow viscous syrup formed. To complete the reaction, the solvent was decanted off and heating continued for two hours. The yellow syrup crystallized on standing and was brought up in water and.treated with activated charcoal and filtered. Next, the solution was treated with Amberlite IR 120 (H⁺ form) resin, and then with Amberlite IRA 68 (free base form) resin. The pure product was

recrystallized with methanol and dried under reduced pressure. The second batch yielded a pure white solid that was isolated by filtration and dried under reduced pressure. Total yield from both batches was 80%;

¹H NMR (D₂O): TSP 3.32-3.45 (m, 1H), 3.47-3.55 (m, 1H), 3.58-3.98 (m, 12H), 4.30 (d, 1H) ppm.

¹³C NMR (D₂O): TSP 44.38, 65.24, 65.48, 72.80, 72.96, 73.68, 73.76, 74.04, 74.80, 74.97, 75.18, 177.30 ppm.

IR (KBr): 3321, 1615, 1558, 1092, 1081, 1022 cm^-1.

Analyzed for C₁₂H₂₅NO₁₁, MW 359.33.

Calcd: C, 40.11; H, 7.01; N, 3.90.

Found: C, 39.98; H, 7.14; N, 3.77 Mass spectroscopy analysis exhibited a highest m/e peak at 359 consistent with a calculated molecular weight at

359.33D. DSC: 130°C

TGA (transition, percent weight lost): 1st at 217°C(28%); 2nd at 293°C(31%); 3rd at 531°C(33%). THEORETICAL EXAMPLE 11

Production of N-(1-N-1-Deoxy-D-glucit-1-yl)-L-ascorbamide

(Compound 11) This compound is prepared as described in Example 10 using

L-ascorbic acid instead of L-gulono-γ-lactone.

EXAMPLE 12 Production of N-Lactobionoyl-(2,3-dihydroxypropyl) amide

Compound 12

Lactobionic acid (one part, free acid) was 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) and 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. This yielded a clear yellow liquid which was concentrated under reduced pressure, and then vigorously stirred in cold (0°C) ethanol and ether to remove residual DMF. The solid product was removed by filtration. This purification step was repeated at ambient temperature using only ethanol. The product was then dried overnight under reduced pressure and yielded the product as an off-white solid of approximately 90% purity by HPLC (RI).

EXAMPLE 13

Production of N-[1,2-Dihydroxyprop-3-yl]-D-glucoheptonamide (Compound 13) α-D-Glucoheptonic γ-lactone (1 part) and (±)-3-amino-1,2- propanediol (1 part) were heated to 65°C with vigorous stirring in 89 parts of methanol. After heating for 18h the solution was cooled, and the resulting solids were isolated by filtration. After recrystallization from MeOH/H₂O and drying under vacuum at 40°C, the product was obtained in 65% yield as a white solid. The following data were obtained for the product:

¹H NMR (D₂O): TSP 4.3 (d, 1H), 3.95-4.1 (m, 2H), 3.28-3.90 (m, 9H) ppm.

¹³C NMR (D₂O): TSP 41.47, 62.69, 63.25, 68.85, 68.87,

70.18, 71.15, 72.07, 72.33, 72.37, 73.53, 174.43 ppm. IR (KBr): 3358, 3290, 1661, 1551, 1068 cm^-1.

Mass spectroscopy analysis exhibited a highest m/e peak at 299 consistent with a calculated molecular weight at 299.28 D. Anal. for C₁₀H₂₁NO₉

Calcd: C, 40.13; H, 7.07; N, 4.68; 0, 48.11

Found: C, 40.10; H, 7.05; N, 4.62; 0, 48.45 DSC: 136°C TGA [transition (percent weight loss)]: 1st at 223°C (44%); 2nd at 455°C (13%); 3rd transition at 669°C (27%). EXAMPLE 14

Production of N-[2-hydroxypropyl]-D-glucoheptonamide

(Compound 14) α-D-Glucoheptonic γ-lactone (1 part) and D,L-1-amino-2-proρanol (1 part) were heated to 65°C with vigorous stirring in 118 parts of methanol. After heating for 20h the solution was cooled, and the solids were isolated by filtration. After recrystallization from methanol and drying under vacuum at 40°C, the product was obtained in 73% yield as a white solid. The following data were obtained for the product :

¹H NMR (D₂O): TSP 4.3 (d, 1H), 3.6-4.1 (m, 7H), 3.2-3.4

(m, 2H), 1.2 (d, 3H) ppm.

¹³C NMR (D₂O): TSP 22.23, 48.55, 65.46, 68.97, 71.59,

71.62, 73.90, 74.86, 75.11, 75.17, 76.27, 177.02 ppm.

IR (KBr): 3321, 1658, 1546, 1074 cm^-1.

Mass spectroscopy analysis exhibited a highest m/e peak at 283 consistent with a calculated molecular weight at 283.28 D.

Anal. for C₁₀H₂₁NO₈

Calcd: C, 42.40; H, 7.47; N, 4.94; 0, 45.18

Found: C, 42.34; H, 7.58; N, 4.91; 0, 45.22

DSC: 123°C TGA [transition (percent weight loss)]: 1st at 226°C (64%); 2nd at 400°C (14%); 3rd transition at 640°C (22%).

EXAMPLE 15

Production of N-[2-(hydroxyethyl)]-D-glucoheptonamide

(Compound 15) α-D-Glucoheptonic-γ-lactone (1 part) and ethanolamine (1 part) were heated to 65°C with vigorous stirring in 59 parts of methanol. After heating for lh the solution was cooled, and the solids were isolated by filtration. After recrystallization from EtOH/H₂O and drying under vacuum at 40°C, the product was obtained in 85% yield as a white solid. The following data were obtained for the product :

¹H NMR (D₂O): TSP 4.3 (d, 1H), 3.95-4.10 (m, 2H), 3.60-3.90 (m, 6H), 3.38-3.50 (m, 2H) ppm. ¹³C NMR (D₂O): TSP 43.91, 62.73, 65.45, 71.59, 73.90, 74.80, 75.13, 76.24, 177.08 ppm.

IR(KBr): 3320, 1652, 1559, 1076 cm ^-1 . Mass spectroscopy analysis exhibited a highest m/e peak at 269 consistent with a calculated molecular weight at 269.25 D.

Anal. for C₉H₁₉NO₈ Calcd: C, 40.15; H, 7.11; N, 5.20; 0, 47.54

Found: C, 39.81; H, 7.01; N, 5.01; 0, 47.43

DSC: 125°C TGA [transition (percent weight loss)]: 1st at 224°C (52%); 2nd at 448°C (9%); 3rd transition at 621°C (28%). EXAMPLE 16

Production of

N-[2-(Hydroxyethoxy)-ethyl]-D-glucoheptonamide (Compound 16) α-D-Glucoheptonic γ-lactone (1 part) and 2-(2-aminoethoxy)ethanol (1 part) were heated to 65°C with vigorous stirring in 140 parts of methanol. After heating for 20h the solution was cooled, and the solids were isolated by filtration. After recrystallization from methanol and drying under vacuum at 40°C, the product was obtained in 71% yield as a white solid. The following data were obtained for the procuct : ¹H NMR (D₂H): TSP 4.3 (d, 1H), 3.95-4.05 (m, 2H), 3.6-3.85 (m, 10H), 3.44-3.51 (m, 2H) ppm.

¹³C NMR (D₂O): TSP 41.41, 63.15, 65.43, 71.49, 71.56, 73.90, 74.26, 74.89, 75.06, 76.22, 176.95 ppm.

IR(KBr): 3320, 1660, 1552, 1073 cm^-1.

Mass spectroscopy analysis exhibited a highest m/e peak at 313 consistent with a calculated molecular weight at 313.30 D.

Anal, for C₁₁H₂₃NO₉

Calcd: C, 42.17; H, 7.40; N, 4.47; 0, 45.96

Found: C, 42.25; H, 7.32; N, 4.34; 0, 45.83

DSC: 93°C

TGA [transition, percent weight loss)]: 1st at 228°C (51%), 2nd at 401°C (14%), 3rd transition at 632°C (25%) THEORETICAL EXAMPLE 17

Production of N,N-Bis(2-hydroxyethyl)-D-glucoheptonamide

(Compound 17) α-D-Glucoheptonic γ-lactone (1 part), diethanolamine (1 part), and sodium methoxide (0.1) part) are heated in 102 parts of methanol to 65°C with vigorous stirring. After heating for 3 days, the solvent is removed under reduced pressure to yield an oil.

EXAMPLE 18

Production of N-(1-Amino-1-deoxy-sorbitol)-D-ribonamide

(Compound 18)

One part D-ribono-1,4 lactone and one part D-glucamine were heated to reflux in methanol (sixty parts) with vigorous stirring for 2.5 hours. Upon cooling, the product crystallized as a white solid and was isolated by filtration. The solid was then washed three times with methanol and dried under reduced pressure overnight. The reaction yield was 84%, and the product's purity by HPLC (RI) was 99.5%. ¹H NMR (D₂O): TSP 3.3-3.4 (m, 1H), 3.4-3.55 (m, 1H), 3.6-4.0 (m,

10H), 4.4 (d, 1H) ppm.

¹³ C NMR (D₂O): TSP 44.27, 65.49, 65.69, 72.99, 73.56, 73.73,

73.76, 74.07, 75.43, 75.52, 177.01 ppm.

DSC midpoint 148.75°C

TGA: First transition: 30.54% midpoint 217°C,

Second transition: 30.22% midpoint 296°C,

Third transition: 25.16% midpoint 636°C. IR (KBr): 3370, 1665, 1551, 1084, 1058 cm^-1.

Analyzed for C₁₁H₂₃NO₁₀(H₂O)0.18. Calcd: C, 39.73; H, 7.08; N, 4.21

Found: C, 39.86; H, 7.19; N, 4.21

QUALITATIVE AND QUANTITATIVE TESTING OF EXAMPLE COMPOUNDS

VERSUS CONTROL COMPOUNDS

OSMOLALITY MEASUREMENTS

Osmolalities of the control (sucrose) and test compounds

(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).

Freezing point depression could then be calculated from the osmolality data using the formula: mOsm x 0.001858 = freeze point depression. The data obtained for osmolality and freezing point measurements are shown in the attached Tables.

Examples 19A-19E - Yellow Cake Formulation

A yellow cake was made by mixing together the following

ingredients and baking at 350 °F.

Ingredient %(by weight)

Liquid shortening 10.50

Cake Flour 23.55

Non-fat dry milk 28.30

Salt 0.75

Baking Powder 1.40

Water 21.20

Whole Eggs 11.75

Vanilla Extract 0.20

Sugar Substitute 28.30

The sugar substitutes were as follows:

Cake A Sucrose

Cake B Palatinit^®

Cake C Compound 1

Cake D Compound 3

Cake E Compound 9 The cakes exhibited the following physical properties: Volume Index, Surface Color (Hunter L-Value), Internal Color,

Tenderness, Batter pH, Cake pH, moisture, water activity (a_w) and specific gravity:

THEORETICAL EXAMPLE 20- Table Top Sweetener

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.

Having described the invention in detail and by reference to the preferred embodiments thereof, it will be apparent that

modifications and variations are possible without departing from the scope of the appended claims.

Claims

What is claimed is:

1. A composition of formula (I)

0 R₂

(I)

R₁- C - N -R₃ where R₁= a mono- or polyhydric aliphatic alcohol

residue;

R₂= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl or C₂-C₁₀ polyhydroxyalkyl; and R₃= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl,

C₂-C₁₀ polyhydroxyalkyl or an integral part of R₂ as a carbocyclic residue; provided that one or both of R₂ and R₃ contain one or more hydroxy groups.

2. The composition according to claim 1 wherein R₁ is derived from the hydroxyalkyl portion of δ-D-gluconolactone,

α-D-glucoheptonic-γ-lactone, L-gulono-γ-lactone, L-ascorbic acid or lactobiono-δ-lactone.

3. The composition according to claim 1 wherein R₃ is selected from the group consisting of: -H, CH₃, (CH₂)_nCH₃, n= 1-4, or C(CH₂OH)₃;

-CH(CH₂OH)₂;

-CH₂-(CHOH)_n-CH₂OH, n=O-10;

-(CH₂)_nCHR₄OH, n= 1-4, R₄ =H or CH₃;

-(CH₂)_n-O-(CH_2)n-OH, n=2-5; and

-C(CH₃)₂CH₂OH.

4. The composition according to claim 3 wherein said composition is selected from the group consisting of:

N-[1,2-dihydroxyprop-3-yl]-gluconamide,

N-[1,3-dihydroxyprop-2-yl]-gluconamide,

N-[Tris-(hydroxymethyl)-methyl]-D-glucoheptonamide,

N-[Tris-(hydroxymethyl)-methyl]-D-gluconamide,

N-lactobionoyl-1-amino-1-deoxy-glucose,

N-[1,2-Dihydroxyprop-3-yl]-D-glucoheptonamide, and

N-[2-hydroxypropyl]-D-glucoheptonamide.

5. The use of a composition of formula (I) as a sugar substitute for formulated foods

0 R₂

(I)

R₁- C - N -R₃ where R₁ = a mono- or polyhydric aliphatic alcohol

residue;

R₂= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl or

C₂-C₁₀ polyhydroxyalkyl; and R₃= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl,

C₂-C₁₀ polyhydroxyalkyl or an integral part of R₂ as a carbocyclic residue; provided that one or both of R₂ and R₃ contains one or more hydroxy groups.

6. The use according to claim 5 wherein said composition is capable of forming a clear colorless film upon melting.

7. The use according to claim 6 wherein R₁ is derived from the hydroxyalkyl portion of δ-D-gluconolactone, α-D-glucoheptonic-γ- lactone, L-gulono-γ-lactone, L-ascorbic acid or lactobiono-δ- lactone.

8. The use according to claim 6 wherein R₃ is selected from the group consisting of:

-H, CH₃, (CH₂)_nCH₃, n= 1-4, or C(CH₂OH)₃;

-CH(CH₂OH)₂;

-CH₂-(CHOH)_n-CH₂OH, n=0-10;

-(CH₂)_nCHR₄OH, n= 1-4, R₄ =H or CH₃;

-(CH₂)_n-O-(CH₂)_n-OH, n=2-5; and

-C(CH₃)₂CH₂OH.

9. The use according to claim 8 wherein said composition is selected from the group consisting of N-[1,2-dihydroxyprop-3-yl]- gluconamide, N-[1,3-dihydroxyprop-2-yl]-gluconamide, N-[Tris- (hydroxymethyl)-methyl]-D-glucoheptonamide, N-[Tris- (hydroxymethyl)-methyl]-D-gluconamide, N-lactobionoyl-1-amino-1- deoxy-glucose, N-[1,2-Dihydroxyprop-3-yl]-D-glucoheptonamide, and N-[2-hydroxypropyl]-D-glucoheptonamide.

10. The use according to claim 5 wherein said composition is used in combination with a high potency sweetener, in confectionery products, in beverages or in bakery products.

11. A sweetened sugar substitute suitable for incorporation into formulated foods comprising: a high potency sweetener; and a composition of formula (I) 0 R₂

(I)

R₁- C - N -R₃ where R₁= a mono- or polyhydric aliphatic alcohol

residue; R₂= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl or

C₂-C₁₀ polyhydroxyalkyl; and

R₃= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl,

C₂-C₁₀ polyhydroxyalkyl or an integral part of R₂ as a carbocyclic residue. provided that one or both of R₂ and R₃ contain one or more hydroxy groups.

12. The sweetened sugar substitute according to claim 11 wherein said high potency sweetener is selected from the group consisting of cyclamate, saccharin, aspartame, thaumatin, acesulfame-K, alitame, sucralose, stevioside sweeteners, and mixtures thereof.

13. The sweetened sugar substitute according to claim 12 wherein said high potency sweetener comprises aspartame.

14. The sweetened sugar substitute according to claim 13 wherein said agent is capable of forming a clear colorless film upon melting.

15. The sweetened sugar substi tute according to claim 14 wherein R₁ is derived from the hydroxyalkyl portion of

δ-D-gluconolactone, α-D-glucoheptonic-γ-lactone,

L-gulono-γ-lactone, L-ascorbic acid or lactobiono-δ-lactone.

16. The sweetened sugar substitute according to claim 14 wherein R₃ is selected from the group consisting of:

-H, CH₃, (CH₂)_nCH₃, n= 1-4, or C(CH₂OH)₃;

-CH(CH₂OH)₂;

-CH₂-(CHOH)_n-CH₂OH, n=0-10;

-(CH₂)_nCHR₄OH, n= 1-4, R₄ =H or CH₃;

-(CH₂)_n-O-(CH₂)_n-OH, n=2-5; and

-C(CH₃)₂CH₂OH.

17. The sweetened sugar substitute according to claim 16 wherein said composition is selected from the group consisting of N-[1,2- dihydroxyprop-3-yl]-gluconamide, N-[1,3-dihydroxyprop-2-yl]- gluconamide, N-[Tris-(hydroxymethyl)-methyl]-D-glucoheptonamide, N-[Tris-(hydroxymethyl)-methyl]-D-gluconamide, N-lactobionoyl-1- amino-1-deoxy-glucose, N-[1,2-Dihydroxyprop-3-yl]-D- glucoheptonamide, and N-[2-hydroxypropyl]-D-glucoheptonamide.

18. The sweetened sugar substitute according to claim 17 wherein said agent is used in confectionery products, in beverages or in bakery products.

19. A confectionery product, beverage or bakery product including a sugar substitute, said sugar substitute comprising a

composition of formula (I) 0 R₂

(I)

R₁- C - N -R₃ where R₁= a mono- or polyhydric aliphatic alcohol

residue;

17. The product according to claim 16 further comprising a high potency sweetener.

18. The product according to claim 17 wherein said high potency sweetener is selected from the group consisting of cyclamate, saccharin, aspartame, thaumatin, acesulfame-K, alitame and sucralose, stevioside sweeteners and mixtures thereof.

19. The product according to claim 18 wherein said high potency sweetener comprises aspartame.

20. The product according to claim 17 wherein R₁ is derived from the hydroxyalkyl portion of δ-D-gluconolactone, α-D- glucoheptonic-γ-lactone, L-gulono-γ-lactone, L-ascorbic acid or lactobiono-δ-lactone.

21. The product according to claim 17 wherein R₃ is selected from the group consisting of: -H, CH₃, (CH₂)_nCH₃, n= 1-4, or C(CH₂OH)₃;

-CH(CH₂OH)₂;

-CH₂-(CHOH)_n-CH₂OH, n=0-10;

-(CH₂)_nCHR₄OH, n= 1-4, R₄ =H or CH₃;

-(CH₂)_n-O-(CH₂)_n-OH, n=2-5; and

-C(CH₃)₂CH₂OH.

22. The product according to claim 21 wherein said composition is selected from the group consisting of N-[1,2-dihydroxyprop-3-yl]- gluconamide, N-[1,3-dihydroxyprop-2-yl]-gluconamide, N-[Tris- (hydroxymethyl)-methyl]-D-glucoheptonamide, N-[Tris-

(hydroxymethyl)-methyl]-D-gluconamide, N-lactobionoyl-1-amino-1- deoxy-glucose, N-[1,2-Dihydroxyprop-3-yl]-D-glucoheptonamide, and N-[2-hydroxypropyl]-D-glucoheptonamide.

23. A composition of formula (II) 0 R₂ R₃ 0

R₂= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl or C₂-C₁₀ polyhydroxyalkyl;

R₃= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl,

C₂-C₁₀ polyhydroxyalkyl or an integral part of

R₂ as a carbocyclic residue;

R₄= a mono- or polyhydric aliphatic alcohol residue; and

A= C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl or

C₂-C₁₀ polyhydroxyalkyl; provided that at least one of R₂ , R₃ and A contains one or more hydroxy groups.

24. The composition according to claim 23 wherein one or both of R₁ and R₄ are derived from the hydroxyalkyl portion of

δ-D-gluconolactone, α-D-glucoheptonic-γ-lactone,

L-gulono-γ-lactone, L-ascorbic acid or lactobiono-δ-lactone.

25. The composition according to claim 24 wherein A represents either -(CH₂)_n-, n=2-6, or -CH₂-CHOH-CH₂-.

26. The composition according to claim 25 comprising

N,N'-di-(D)-gluconoyl-1,3-diamino-2-hydroxypropane.

27. The use of a composition of formula (II) as a sugar substitute for formulated foods

0 R₂ R₃ 0

|l

R₁ _ C - N - A - N - C - R₄ (II) where R₁= a mono- or polyhydric aliphatic alcohol residue; R₂= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl or

C₂-C₁₀ polyhydroxyalkyl;

R₃= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl, C₂-C₁₀ polyhydroxyalkyl or an integral part of R₂ as a carbocyclic residue;

R₄= a mono- or polyhydric aliphatic alcohol residue; and A= C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl or

28. The use according to claim 27 wherein one or both of R₁ and R₄ are derived from the hydroxyalkyl portion of

δ-D-gluconolactone, α-D-glucoheptonic-γ-lactone,

L-gulono-γ-lactone, L-ascorbic acid or lactobiono-δ-lactone.

29. The use according to claim 28 wherein A represents either -(CH₂)_n-, n=2-6, or -CH₂-CHOH-CH₂-.

30. The use according to claim 29 wherein the composition of formula (II) comprises N,N'-di-(D)-gluconoyl-1,3-diamino-2- hydroxypropane.

31. The use according to claim 27 wherein said composition is used in combination with a high potency sweetener, in

confectionery products, in beverages or in bakery products.

32. A sweetened sugar substitute suitable for incorporation into formulated foods comprising: a high potency sweetener; and a composition of formula (II)

0 R₂ R₃ 0

R₃= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl,

C₂-C₁₀ polyhydroxyalkyl or an integral part of R₂ as a carbocyclic residue;

R₄= a mono- or polyhydric aliphatic alcohol residue; and

A= C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl or

33. The sweetened sugar substitute according to claim 32 wherein said high potency sweetener is selected from the group consisting of cyclamate, saccharin, aspartame, thaumatin, acesulfame-K, alitame, sucralose, stevioside sweeteners, and mixtures thereof.

34. The sweetened sugar substitute according to claim 33 wherein said high potency sweetener comprises aspartame.

35. The sweetened sugar substitute according to claim 34 wherein one or both of R₁ and R₄ are derived from the hydroxyalkyl portion of δ-D-gluconolactone, α-D-glucoheptonic-γ-lactone, L-gulono-γ-lactone, L-ascorbic acid or lactobiono-δ-lactone.

36. The sweetened sugar substitute according to claim 35 wherein A represents either -(CH₂)_n-, n=2-6, or -CH₂-CHOH-CH₂-.

37. The sweetened sugar substitute according to claim 36 wherein the composition of formula (II) comprises

N,N'-di-(D)-gluconoyl-1,3-diamino-2-hydroxypropane.

38. The sweetened sugar substitute according to claim 35 wherein said substitute used in confectionery products, in beverages or in bakery products.

39. A confectionery product, beverage or bakery product including a sugar substitute, said sugar substitute comprising a

composition of formula (II)

0 R₂ R₃ 0

R₃= H, C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl,

C₂-C₁₀ polyhydroxyalkyl or an integral part of

R₂ as a carbocyclic residue;

R₄= a mono- or polyhydric aliphatic alcohol residue; and

A= C₁-C₁₀ alkyl, C₂-C₁₀ hydroxyalkyl or

40. The product according to claim 39 further comprising a high potency sweetener.

41. The product according to claim 40 wherein said high potency sweetener is selected from the group consisting of cyclamate, saccharin, aspartame, thaumatin, acesulfame-K, alitame,

sucralose, stevioside sweeteners, and mixtures thereof.

42. The product according to claim 41 wherein said high potency sweetener comprises aspartame.

43. The product according to claim 42 wherein one or both of R₁ and R₄ are derived from the hydroxyalkyl portion of δ-D- gluconolactone, α-D-glucoheptonic-γ-lactone, L-gulono-γ-lactone, L-ascorbic acid or lactobiono-δ-lactone.

44. The product according to claim 43 wherein A represents either -(CH₂)_n-, n=2-6, or -CH₂-CHOH-CH₂-.

45. The product according to claim 44 wherein the composition of formula (II) comprises N,N'-di-(D)-gluconoyl-1,3-diamino-2- hydroxypropane.