Organic compounds

Abstract

A compound according to the formula (I) or edible salts thereof, ##STR00001##
Wherein R together with the carbonyl group to which it is attached is a residue of a carboxylic acid. Said compounds may be used in edible compositions such as foods and beverages to impart or modify flavour and mouth feel to said compositions.

Claims

1. A flavour composition for use in an edible composition comprising a compound according to the formula (I) or an edible salt thereof, ##STR00006## wherein: R together with the carbonyl group to which it is attached is a residue of a carboxylic acid, wherein the said compound or edible salt thereof confers a modified taste characteristic of the edible composition in which it is present, when said compound or edible salt thereof is present in the edible composition in a concentration of 1 ppb-10 ppm.

2. A flavour composition according to claim 1 wherein the compound according to formula (I) is selected from the group consisting of: 2-methyl-2-oleamidopropanoic acid, 2-methyl-2-((9Z, 12Z)-octadeca-9,12-dienamido)propanoic acid, 2-methyl-2-stearamidopropanoic acid, 2-methyl-2-palmitamidopropanoic acid, (Z)-2-(dodec-5-enamido)-2-methylpropanoic acid, 2-dodecanamido-2-methylpropanoic acid, and, 2-hexanamido-2-methylpropanoic acid.

3. A flavour composition according to claim 1 which further comprises at least one flavour co-ingredient selected from the group consisting of: sugars, fats, salt, MSG, calcium ions, phosphate ions, organic acids, proteins, purines and mixtures thereof, and which flavor composition optionally further comprises a carrier material and/or an adjuvant.

4. An edible composition comprising 1 ppb-10 ppm of a compound according to formula (I) or an edible salt thereof, ##STR00007## wherein: R together with the carbonyl group to which it is attached is a residue of a carboxylic acid wherein the said compound or edible salt thereof confers a modified taste characteristic of the edible composition.

5. A flavour composition according to claim 3, wherein the compound of formula (I) is selected from the group consisting of: 2-methyl-2-oleamidopropanoic acid, 2-methyl-2-((9Z, 12Z)-octadeca-9,12-dienamido)propanoic acid, 2-methyl-2-stearamidopropanoic acid, 2-methyl-2-palmitamidopropanoic acid, (Z)-2-(dodec-5-enamido)-2-methylpropanoic acid, 2-dodecanamido-2-methylpropanoic acid, and, 2-hexanamido-2-methylpropanoic acid.

6. An edible composition according to claim 4, wherein the compound of Formula (I) is selected from the group consisting of: 2-methyl-2-oleamidopropanoic acid, 2-methyl-2-((9Z, 12Z)-octadeca-9,12-dienamido)propanoic acid, 2-methyl-2-stearamidopropanoic acid, 2-methyl-2-palmitamidopropanoic acid, (Z)-2-(dodec-5-enamido)-2-methylpropanoic acid, 2-dodecanamido-2-methylpropanoic acid, and, 2-hexanamido-2-methylpropanoic acid.

Description

EXAMPLE 1

Synthesis of Compounds of Formula (I)

(1) ##STR00005##
General Procedure for Making the Compounds:

(2) To a solution of 2-amino-2-methylpropanoic acid (0.69 g, 6.78 mmol) in 1:1 THF:2N NaOH (50 ml:50 ml) at rt was added oleoyl chloride (2.4 g, 6.78 mmol) dropwise. The reaction was stirred at rt for 7 h. THF was removed under vaccumn. To this aqueous layer, conc. HCl was used to adjust the pH to 2. The aqueous layer was then extrated with EtOAc 3× and the organic layers were combined. The organic layer was washed with water, brine, dried (Na.sub.2SO.sub.4) and concentrated. The residue chromatographed on silica gel (5% MeOH/DCM, 0.1% formic acid) to give 0.7 g (28%) of the product as a white solid.

2-methyl-2-oleamidopropanoic Acid

(3) 28% yield; .sup.1H NMR (300 MHz, CD.sub.3OD) δ ppm 0.92 (t, J=7.5 Hz, 3H), 1.31-1.68 (m, 28H), 2.02-2.08 (m, 2H), 2.18 (t, J=7.5 Hz, 2H), 5.31-5.41 (m, 2H). .sup.13C NMR (300 MHz, CD.sub.3OD) δ ppm 12.96, 22.24, 23.92, 25.37, 26.65, 26.67, 28.70, 28.77, 28.86, 28.89, 29.95, 29.12, 29.35, 31.57, 35.31, 55.24, 129.33, 129.36, 174.07, 176.54.

2-methyl-2-((9Z, 12Z)-octadeca-9,12-dienamido)propanoic Acid

(4) 20%; .sup.1H NMR (300 MHz, CD.sub.3OD) δ ppm 0.91 (t, J=7.8 Hz, 3H), 1.31-1.45 (m, 21H), 1.57-1.62 (m, 2H), 2.03-2.10 (m, 4H), 2.17 (t, J=7.5 Hz, 2H), 2.78 (t, J=6.3 Hz, 2H), 5.27-5.41 (m, 4H). .sup.13C NMR (300 MHz, CD.sub.3OD) δ ppm 12.93, 22.12, 23.91, 25.04, 25.36, 26.66, 26.68, 28.68, 28.77, 28.88, 28.97, 29.24, 31.16, 35.29, 55.22, 127.56, 127.58, 129.41, 129.44, 174.07, 176.54.

2-methyl-2-stearamidopropanoic Acid

(5) 26%; .sup.1H NMR (300 MHz, CD.sub.3OD) δ 0.92 (t, J=8.7 Hz, 3H), 1.31-1.65 (m, 36H), 2.18 (t, J=7.2 Hz, 2H). .sup.13C NMR (300 MHz, CD.sub.3OD) δ ppm 14.45, 23.74, 25.41, 26.88, 30.20, 30.49, 30.65, 30.74, 30.80, 33.09, 36.81, 56.75, 175.60, 178.09.

2-methyl-2-palmitamidopropanoic Acid

(6) 9.6%; .sup.1H NMR (300 MHz, CD.sub.3OD) δ 0.91 (t, J=8.2 Hz, 3H), 1.25-1.45 (m, 31H), 2.52-1.67 (m, 2H), 2.16 (t, J=6.9 Hz, 2H), 8.08 (s, 1H). .sup.13C NMR (300 MHz, CD.sub.3OD) δ ppm 12.93, 22.23, 23.90, 25.36, 28.69, 28.97, 29.14, 29.28, 31.57, 35.28, 55.26, 173.87, 176.46.

(Z)-2-(dodec-5-enamido)-2-methylpropanoic Acid

(7) 12%; .sup.1H NMR (300 MHz, CD.sub.3OD) δ 0.92 (t, J=8.4 Hz, 3H), 1.29-1.38 (m, 8H), 1.47 (s, 6H), 1.59-1.70 (q, J=7.8 Hz, 2H), 2.02-2.13 (m, 4H), 2.19 (t, J=7.8 Hz, 2H), 5.31-5.45 (m, 2H). .sup.13C NMR (300 MHz, CD.sub.3OD) δ ppm 14.43, 23.72, 25.41, 26.95, 27.62, 28.21, 30.09, 30.85, 32.95, 36.3256.75, 129.91, 131.72, 175.36, 178.02.

2-dodecanamido-2-methylpropanoic Acid

(8) 21% .sup.1H NMR (300 MHz, CD.sub.3OD) δ 0.90 (t, J=8.1 Hz, 3H), 1.29-1.45 (m, 23H), 1.54-1.65 (m, 2H), 2.16 (t, J=8.1 Hz, 2H). .sup.13C NMR (300 MHz, CD.sub.3OD) δ ppm 12.93, 22.22, 23.90, 25.36, 28.68, 28.97, 29.13, 29.23, 31.57, 35.28, 55.21, 174.09, 176.53.

2-hexanamido-2-methylpropanoic Acid

(9) 6% .sup.1H NMR (300 MHz, CD.sub.3OD) δ 0.93 (t, J=8.1 Hz, 3H), 1.32-1.36 (m, 4H), 1.47 (s, 6H), 1.56-1.68 (m, 2H), 2.18 (t, J=8.1 Hz, 2H).). .sup.13C NMR (300 MHz, CD.sub.3OD) δ ppm 14.42, 23.59, 25.58, 26.68, 32.55, 36.88, 56.86, 175.74, 178.20.

EXAMPLE 2

Blanco Verdunde Kikkoman low Salt 1 g Salt/100 ml

(10) The samples were evaluated by a panel of experienced tasters.

(11) When 0.25 ppm of 2-methyl-2-oleamidopropanoic acid was dosed to Kikkoman soy sauce, the panel agreed that this sample tasted cleaner, more upfront body, salty, less fermented, more upfront, more salty bitter and sweet, fermented.

(12) When 0.25 ppm of 2-methyl-2-stearamidopropanoic acid was dosed to the Kikkoman soy sauce, the panel agreed that this sample tasted salty upfront, no aftertaste expanding, bitter aftertaste not negative, more upfront salty, not as bitter and sweet, fermented.

(13) When 0.25 ppm of 2-methyl-2-palmitamidopropanoic acid was dosed to the Kikkoman soy sauce, the panel agree that this sample tasted strong salty, more upfront, fermented, slightly bitter and sweet.