Powder flavour composition

Abstract

A powder flavour composition comprising a compound according to the formula (I) or edible salts thereof, and at least one flavour co-ingredient ##STR00001##
wherein R.sub.1 is an alkyl residue containing 6 to 20 carbon atoms, or an alkene residue containing from 9 to 25 carbon atoms with 1 to 6 double bonds, R.sub.1 together with the carbonyl group to which it is attached is a residue of a carboxylic acid, and NR.sub.2R.sub.3, in which R.sub.3 is H or together with R.sub.2 and the N-atom to which they are attached, a 5-membered ring, is a residue of an amino acid, in particular a proteinogenic amino acid, ornithine, gamma-aminobutyric acid or beta alanine, or a 1-amino cycloalkyl carboxylic acid.

Claims

1. A powder flavour composition comprising at least one flavor co-ingredient, the powder flavor composition comprising a compound according to a formula selected from the group consisting of: a compound of formula a) ##STR00093## and edible salts thereof, wherein n is 1, 2, 3 or 4, and, R.sub.1 is an alkyl residue containing 6 to 20 carbon atoms, or is an alkene residue containing from 9 to 25 carbon atoms with 1 to 6 double bonds, R.sub.1 together with the carbonyl group to which it is attached is a residue of a carboxylic acid, and NR.sub.2R.sub.3 , in which R.sub.3 is H or together with R.sub.2 and the N-atom to which they are attached, a 5-membered ring, is a residue of an amino acid; a compound of formula b) ##STR00094## and edible salts thereof, wherein m is 0 or 1, and, R.sub.1 together with the carbonyl group to which it is attached is a residue of a carboxylic acid selected from gamma amino butyric acid (GABA) and beta alanine; a compound of formula c) ##STR00095## and edible salts thereof, selected from: N-geranoyl-Pro, N-palmiteneoyl-Pro, N-stearoyl-Pro, N-linoleoyl-Pro, N-oleoyl-Pro and N-linolenoyl-Pro; and, a compound of formula d) ##STR00096## and edible salts thereof: selected from N-geranoyl-Met, N-palmitoyl-Met, N-palmitenoyl-Met, N-stearoyl-Met, N-linoleoyl-Met, N-oleoyl-Met and N-linolenoyl-Met; wherein the at least one compound according to formula a), and/or the at least one compound according to formula b) and/or the at least one compound according to formula c) and/or the at least one compound according to formula d) is present in an edible composition at a concentration of 1 ppb - 10 ppm.

2. A powder flavour composition according to claim 1, wherein the flavour co-ingredient contains: vanilla, chocolate, coffee, cocoa, citrus oil, selected from lemon, orange, grape, lime and grapefruit; fruit essences selected from apple, pear, peach, strawberry, raspberry, cherry, plum, pineapple and apricot. ingredients containing one or more of the components: acetaldehyde, dimethyl sulfide, ethyl acetate, ethyl propionate, methyl butyrate, and ethyl butyrate; ingredients containing one or more volatile aldehydes or esters selected from: cinnamyl acetate, cinnamaldehyde, citral, diethylacetal, dihydrocarvyl acetate, eugenyl formate, and p-methylanisole, acetaldehyde, benzaldehyde, cinnamic aldehyde, alpha citral, beta citral, decanal, ethyl vanillin, piperonal, vanillin, alpha-amyl cinnamaldehyde, butyraldehyde, valeraldehyde, citronellal, decanal, aldehyde C-8, aldehyde C-9, aldehyde C-12, 2-ethyl butyraldehyde, trans-2 hexenal, tolyl aldehyde, veratraldehyde, 2,6-dimethyl-5-heptenal, 2-6-dimethyloctanal, 2-dodecenal, cherry, grape, and mixtures thereof.

3. A powder flavour composition according to claim 1 wherein the at least one flavour co-ingredient is selected from the group consisting of: sugars, fats, salt, MSG, calcium ions, phosphate ions, organic acids, proteins, purines and mixtures thereof.

4. A powder flavour composition according to claim 3 which further comprises an anti-oxidant.

5. A powder flavour composition according to claim 1 in the form of a spray dried powder.

6. An edible composition comprising a powder flavour composition according to claim 1.

7. An edible composition according to claim 6 in the form of a powdered soft drink or a dry mix composition.

8. An edible composition according to claim 6 in the form of a snack food.

9. An edible composition according to claim 6 in the form of an alcoholic beverage.

10. An edible composition according to claim 6 in the form of an orally administrable tablet, capsule, powder or multiparticulate.

11. An edible composition according to claim 6 in the form of a caloric or non-caloric beverage containing at least one carbohydrate sweetener selected from: sucrose, high fructose corn syrup, fructose and glucose, a high intensity, non-nutritive sweetener selected from: aspartame, acesulfame K, sucralose, cyclamate, sodium saccharin, neotame, rebaudioside A, and/or stevia-based sweeteners.

12. An edible composition according to claim 6 in the form of a soy-based composition.

13. A powder flavour composition according to claim 1, wherein the residue of the amino acid is a proteinogenic amino acid, ornithine, gamma-aminobutyric acid or beta alanine, or a 1-amino cycloalkyl carboxylic acid.

14. A powder flavour composition according to claim 1, wherein the compound is in the form of an edible salt.

15. A powder flavour composition according to claim 1, wherein the edible salt is selected from chlorides, sulphates, phosphates, gluconates, sodium, citrates, carbonates, acetates and lactates.

16. A powder flavour composition according to claim 3, which further comprises an adjuvant.

17. A powder flavour composition according to claim 4, which further comprises an adjuvant.

Description

SYNTHESIS EXAMPLES

(1) 1.1 Route A: (DCC Method)

(2) In a 250 mL round-bottomed flask was mixed fatty acid (3.93 mmol) with 1-hydroxypyrrolidine-2,5-dione (0.498 g, 4.32 mmol) in dioxane (50 ml) to give a colorless solution. The solution was cooled to 10 C. and DCC (0.892 g, 4.32 mmol) was added while stirring. Stirring was continued for three hours at room temperature. The formed solids were filtered (dicyclohexylurea) and the filtrate was added to a solution of amino acid (6.48 mmol) in a 2% solution of sodiumbicarbonate (0.363 g, 4.32 mmol) in water. The reaction mixture was stirred for 4 hours at 50 C. Dioxane was evaporated and the aqueous residue was further diluted with water, acidified with a diluted hydrochloric acid solution and extracted with ethylacetate. Organic layers were combined, washed with brine, dried and evaporated to yield 1.3 g of a white solid. Product was purified by flash column chromatography, eluent DCM/methanol. 1 g of 85-90% pure product could be obtained.

(3) 1.2 Route B (DCC Method with Protection Group)

(4) Step 1:

(5) To a solution of an O-methylated amino acid (16.51 mmol) in DCM (100 ml) was added triethylamine (1.519 g, 15.01 mmol) at minus 15 C. A fatty acid (0.01 mmol) was added while stirring. A solution of DCC (15.01 mmol) in 10 mL of DCM was added dropwise at 0 C. The reaction mixture was stirred at 0 C. for 1 hour and stirring was continued at room temperature for 3 hours. The dicyclohexylurea was removed by filtration from the reaction mixture. Filtrate was washed with a saturated sodiumbicarbonate solution, diluted hydrochloric acid solution and water. Organic layer was separated, dried and evaporated to yield 3 g of an oil. This oil was purified by flash column chromatography, eluent DCM/methanol The intermediate ester compound could be isolated in a purity of 95%.

(6) Step 2:

(7) The O-methylated N-acyl-amino-acid (4.91 mmol) was dissolved in a mixture of Ethanol (8.00 ml) and water (8 ml). To this mixture was added a 32% solution of sodiumhydroxide (2.453 g, 19.63 mmol) and mixture was stirred at room temperature for three hours. Mixture stand over for 14 hours.

(8) After 14 hours the mixture was acidified with a concentrated hydrochloric acid solution (1.612 ml, 19.63 mmol), diluted with water and extracted with mtbe. Organic layer was separated, dried and evaporated. 1.3 g of a half solid yellow residue was obtained. NMR confirmed the structure of the title compound, purity 95%

(9) 1.3 Route C (Acid Chloride)

(10) An amino acid (20 mmol) was dissolved in a solution of sodiumhydroxide (54.5 mmol) in water (40 ml).

(11) Tetrahydrofuran (60 ml) was added. Fatty acid chloride (18.18 mmol) was added dropwise at room temperature. Stirring was continued for 2 hours. Mixture was diluted with water, acidified with a 37% solution of hydrochloric acid (2.99 ml, 36.4 mmol) and extracted with ethylacetate.

(12) Organic layers were combined, dried and evaporated.

(13) The residue contains about 20% free fatty acid according NMR. The solids were stirred with heptane for 30 minutes, filtered and dried. This resulted in 2.4 g of the title compound as a creamy colored solid. (purity 95%).

(14) 1.4 All Synthesized Compounds

(15) TABLE-US-00001 TABLE 1 List of synthesized compounds Car- box- Struc- Amino ylic ture acid acid Structure Route 1 ACC C10:0 0 C 2 ACC C10:2 A 3 ACC C16:0 C 4 ACC C18:0 C 5 ACC C18:1 C 6 ACC C18:2 A 7 GABA C10:0 C 8 GABA C12:0 C 9 GABA C12:1 C 10 GABA C10:2 C 11 GABA C14:0 0 C 12 GABA C16:0 C 13 GABA C16:1 A 14 GABA C18:0 C 15 GABA C18:1.sub.c C 16 GABA C18:1.sub.t C 17 GABA C18:2 A 18 GABA C18:3 A 19 GABA C22:1 C 20 Beta- alanine C16:1 A 21 Beta- alanine C18:1 0 C 22 Beta- alanine C18:2 A 23 Aspartic acid C10:0 C 24 Aspartic acid C10:2 B 25 Aspartic acid C16:0 C 26 Aspartic acid C18:0 C 27 Aspartic acid C18:1 C 28 Aspartic acid C18:2 A 29 Glutamic acid C10:0 C 830 Glutamic acid C16:0 C 31 Glutamic acid C16:1 0 A 32 Glutamic acid C18:0 C 33 Glutamic acid C18:1 C 34 Glutamic acid C18:2 A 35 Gluta- mine C10:0 C 36 Gluta- mine C12:0 C 37 Gluta- mine C10:2 A 38 Gluta- mine C16:0 C 39 Gluta- mine C18:0 C 40 Gluta- mine C18:1 C 41 Gluta- mine C18:2 0 A 42 Methi- onine C10:0 A 43 Methi- onine C12:0 A 44 Methi- onine C12:1 A 45 Methi- onine C16:0 A 46 Methi- onine C18:1 A 47 Methi- onine C18:2 A 48 Proline C10:2 A 49 Proline C16:0 C 50 Proline C16:0 C 51 Proline C18:2 0 A 52 Serine C10:2 B 53 Serine C16:0 C 54 Serine C18:1 C 55 Serine C18:2 A 56 Leucine C-8:0 C 57 Leucine C10:2 B 58 Leucine C16:0 C 59 Leucine C16:1 A 60 Leucine C18:0 C 61 Leucine C18:1 0 C 62 Leucine C18:2 B 63 Leucine C22:1 A 64 Isoleucine C18:1 C 65 Valine C16:0 C 66 Valine C18:0 C 67 Valine C18:1 C 68 Valine C18:2 A
2 NMR Data (Examples)
2.1 Structure 5 ACC-C18:1

(16) ##STR00078##

(17) .sup.1H NMR (600 MHz, CHLOROFORM-d) ppm 0.88 (t, J=7.05 Hz, 3 H, HC(18)) 1.09-1.21 (m, 2 H HC(22,23)) 1.21-1.1.39 (m, 20 H, HC(4, 5, 6, 7, 12, 13, 14, 15, 16, 17)) 1.54-1.68 (m, 4 H, HC(3, 22, 23)) 1.91-2.07 (m, 4 H, HC(8, 11)) 2.18 (t, J=7.73 Hz, 2 H, HC(2)) 5.26-5.44 (m, 2 H, HC(9, 10)) 6.28 (s, 1 H, HN(19))

(18) .sup.13C NMR (150 MHz, CHLOROFORM-d) ppm 14.13 (C(18) 18.01 (C(22, 23)) 22.69 (C(17)), 25.45 (C(3)), 27.19 (C(11) 27.23 (C11)) 29.16 (C4)) 29.18 (C6)) 29.26 (C(5)) 29.33 (C(13, 15)) 29.45 (C(14)) 29.72 (C(7)) 29.78 (C(12)) 31.91 (C(16, 21)) 33.47 (C(2)) 129.76 (C(10)) 129.99 (C(9)) 175.15 (C(1)) 177.39 (C(20))

(19) 2.2 Structure 7 GABA-C10:0

(20) ##STR00079##

(21) .sup.1H NMR (600 MHz, DMSO-d.sub.6) ppm 0.83-0.87 (m, 3 H, HC(10)) 1.18-1.29 (m, 12 H, HC(4, 5, 6, 7, 8, 9) 1.46 (quin, J=7.22 Hz, 2 H, HC(14)) 1.59 (quin, J=7.22 Hz, 2 H, HC(3)) 2.02 (t, J=7.39 Hz, 2 H, HC(2)) 2.19 (t, J=7.39 Hz, 2 H, HC(13)) 3.00-3.05 (m, 2 H, HC(15)) 7.77 (t, J=5.50 Hz, 1 H, HN(15)

(22) .sup.13C NMR (150 MHz, DMSO-d.sub.6) ppm 13.95 (C(10)) 22.09 (C(9)) 24.64 (C(14)) 25.29 (C(3)) 28.64 (C(5)) 28.66 (C(7)) 28.78 (C(6)) 28.90 (C(4)) 31.07 (C(13)) 31.27 (C(8)) 35.38 (C(2)) 35.77 (C(15)) 172.03 (C(1)) 174.21 (C(12))

(23) 2.3 Structure 8 GABA-C12:0

(24) ##STR00080##

(25) .sup.1H NMR (600 MHz, DMSO-d.sub.6) ppm 0.85 (t, J=6.87 Hz, 3 H, HC(12)) 1.15-1.33 (m, 16 H, HC(4, 5, 6, 7, 8, 9, 10, 11) 1.41-1.51 (m, 2 H, HC(3)) 1.59 (quin, J=7.22 Hz, 2 H, HC(16)) 2.02 (t, J=7.56 Hz, 2 H, HC(2)) 2.19 (t, J=7.56 Hz, 2 H, HC(15)) 3.02 (q, J=6.53 Hz, 2 H, (HC(17)) 7.77 (t, J=5.33 Hz, 1 H, HN(13))

(26) .sup.13C NMR (150 MHz, DMSO-d.sub.6) ppm 13.95 (C(12)) 22.09 (C(11)) 24.64 (C(16((25.29 (C(3)) 28.64 (C(9)) 28.71 (C(15)) 28.77 (C(6)) 28.95 (C(8)) 29.00 (C(5)) 29.02 (C(4)) 31.06 (C(7)) 31.29 (C(10)) 35.77 (C(17)) 172.02 (C(1)) 174.20 (C14))

(27) 2.4 Structure 17 GABA-C18:2

(28) ##STR00081##

(29) .sup.1H NMR (600 MHz, CHLOROFORM-d) ppm 0.89 (t, J=6.87 Hz, 3 H, HC(18)) 1.26-1.39 (m, 14 H, HC(4, 5, 6, 7, 15, 16, 17) 1.57-1.65 (m, 2 H, HC(3)) 1.84 (quin, J=6.96 Hz, 2 H, HC(22)) 2.05 (q, J=7.22 Hz, 4 H, HC(8), HC(14)) 2.19 (t, J=7.73 Hz, 2 H, HC(2)) 2.40 (t, J=7.05 Hz, 2H, HC(21)) 2.77 (t, J=6.87 Hz, 2 H, HC(11)) 3.33 (q, J=6.53 Hz, 2 H, HC(23)) 5.30-5.41 (m, 4 H, HC(9, 10, 12,13) 5.96 (br. s., 1 H, HN(19))

(30) .sup.13C NMR (150 MHz, CHLOROFORM-d) ppm 14.08 (C(18) 22.58 C(17)) 24.74 (C3)) 25.63 (C(22)) 25.75 (C(11)) 27.20 (C 8, 14)) 29.15 (C(6)) 29.26 (C(5, 21)) 29.35 (C(15)) 29.62 (C(4)) 31.49 C(7)) 31.52 C(16)) 36.73 C(2)) 38.84 (C23)) 127.90 (C12)) 128.06 (C(10)) 130.03 (C(9) 130.25 (C(13)), 174.17 (C(1) 177.43 (C(20))

(31) 2.5 Structure 22 Beta-Alanine-C18:2

(32) ##STR00082##

(33) .sup.1H NMR (600 MHz, DMSO-d.sub.6) ppm 0.85 (t, J=7.05 Hz, 3 H, HC(18)) 1.11-1.37 (m, 14 H, HC(4, 5, 6, 7, 15. 16, 17) 1.37-1.53 (m, 2 H, HC(3)) 1.94-2.08 (m, 6 H, HC(2, 8, 14) 2.34 (t, J=6.87 Hz, 2 H, HC(21)) 2.73 (t, J=6.70 Hz, 2 H, HC(11)) 3.13-3.27 (m, 2 H, HC(22)) 5.24-5.40 (m, 4 H, HC(12, 13)) 7.84 (t, J=5.67 Hz, 1 H, HN(19))

(34) .sup.13C NMR (150 MHz, DMSO-d.sub.6) ppm 13.91 (C(18)) 21.97 (C(17)) 25.21 (C(3)) 25.24 (C(11)) 26.60 (C(8)) 26.63 (C(14)) 28.58 (C(6)) 28.63 (C(5)) 28.68 (C(15)) 28.73 (C(4)) 29.04 (C(7)) 30.89 (C(16)) 33.98 (C(21)) 34.70 (C(22)) 35.27 (C(2)) 127.73 (C(10, 12)) 129.71 (C(9, 13)) (C(1)) 172.91 (C(20))

(35) ##STR00083##
2.6 Structure 28 Asp-C18:2

(36) .sup.1H NMR (600 MHz, DMSO-d.sub.6) ppm 0.86 (t, J=6.87 Hz, 3 H, HC(18)) 1.17-1.38 (m, 14 H, HC(4, 5, 6, 7, 15, 16, 17) 1.42-1.50 (m, 2 H, HC(3) 2.01 (q, J=7.10 Hz, 4 H, HC(8, 14) 2.06-2.10 (m, 2 H, HC(2)) 2.48-2.55 (m, 1 H, HC(22)) 2.62-2.68 (m, 1 H, HC(22)) 2.73 (t, J=6.87 Hz, 2 H, HC(11)) 4.49 (d, J=6.53 Hz, 1 H, HC(21)) 5.18-5.42 (m, 4 H, HC(9, 10, 12, 13) 8.09 (d, J=7.90 Hz, 1 H, HN(19))

(37) .sup.13C NMR (150 MHz, DMSO-d.sub.6) ppm 13.93 (C(18) 21.97 (C(17)) 25.21 (C(3), 26.60 (C(11)) 26.65 (C(8)) 28.55 (C(14)) 28.59 (C(6)) 28.70 (C(4)) 28.73 (C(5)) 29.05 (C(15)) 30.69 (C(7)) 30.89 (C(16)) 35.06 (C(2)) 36.25 (C(22) 48.49 (C(21)) 127.75 (C(10, 12)) 129.74 (C(9, 13) 171.73 (C(20)) 172.02 (C(1)) 172.61 (C23))

(38) 2.7 Structure 33 Glu-C18:1

(39) ##STR00084##

(40) .sup.1H NMR (600 MHz, CHLOROFORM-d) ppm 0.88 (t, J=7.05 Hz, 3 H, HC(18) 1.19-1.39 (m, 20 H, HC(4, 5, 6, 7, 12, 13, 14, 15, 16, 17) 1.56-1.68 (m, 2 H, HC(3)) 1.94-2.04 (m, 4 HC(8, 12)) 2.08 (dt, J=13.83, 6.66 Hz, 1 H, HC(22)) 2.20-2.25 (m, 3 H, HC(22)) 2.43-2.55 (m, 2 H, HC(23)) 4.64 (q, J=6.87 Hz, 1 H, HC(21)) 5.30-5.38 (m, 2 H, HC(9,10)) 6.70 (d, J=7.22 Hz, 1 H, HN(19))

(41) .sup.13C NMR (150 MHz, CHLOROFORM-d) ppm 14.13 (C(18) 22.69 (C(17)) 25.57 (C(3) 26.81 (C(22) 27.20 (C(11) 27.24 (C(8) 29.18 (C(6)) 29.22 (C(4)) 29.26 (C(5) 29.33 (C(13, 15) 29.55 (C(14)) 29.75 (C(7)) 29.78 (C(12)) 29.88 (C(23) 31.91 (C(16)) 36.36 (C(2)) 51.60 (C(21)) 129.71 (C(10)) 130.02 (C(9)) 174.62 (C(1)) 175.66 (C(20) 177.95 (C(24))

(42) 2.8 Structure 37 Gln-C10:2

(43) ##STR00085##

(44) .sup.1H NMR (600 MHz, CHLOROFORM-d) ppm 1.56-1.61 (s, 3 H, HC(10) 1.67 (s, 3 H, HC(8)) 2.05-2.14 (m, 6 H, HC(4, 14, 15) 2.15-2.20 (m, 3 H, HC(9)) 2.39 (dd, J=15.46, 7.22 Hz, 2 H, HC(5)) 4.51 (d, J=6.19 Hz, 1 H, HC(13)) 5.01-5.13 (m, 1 H, HC(6) 5.60-5.72 (s, 1 H, HC(2)) 6.63 (br. s., 1H, HN(11)) 7.14 (br. s., 2 H, H.sub.2-N))

(45) .sup.13C NMR (150 MHz, CHLOROFORM-d) ppm 17.69 (C(10) 18.52 (C(9) 25.67 (C(8)) 26.17 (C(5)) 30.95 (C(14)) 31.68 (C(15) 40.97 (C(4)) 51.92 (C(13)) 117.22 (C(2)) 123.14 (C(6)) 132.39 (C(7)) 156.33 (C(3)) 167.95 (C(1) 174.69 (C(16)) 177.12 (C(12))

(46) 2.9 Structure 44 Met-C12:1

(47) ##STR00086##

(48) .sup.1H NMR (300 MHz, CD.sub.3OD) ppm 0.92 (t, J=6.9 Hz, 3H, HC(12)), 1.32-1.38 (m, 8H, HC(8, 9, 10, 11), 1.63-1.73 (q, J=7.5 Hz, 2H, HC(3)), 1.98-2.16 (m, 9H, HC(4, 7, 16, 18), 2.28 (t, J=7.2 Hz, 2H, HC(2)), 2.48-2.65 (m, 2H, HC(17)), 4.56 (d, d, J=5.1, 9.9 Hz, 1H, HC(15)), 5.33-5.46 (m, 2H, HC(5, 6)).

(49) .sup.13C NMR (300 MHz, CD30D) ppm 14.43 (C(12) 15.21 (C(18)) 23.71 (C(11)) 27.01 (C(4)) 27.70 (C(3)) 28.22 (C(7)) 30.08 (C(9)) 30.83 (C(17)) 31.31 (C(8)) 32.19 (C(16)) 32.95 (C(10)) 36.37 (C(2)) 52.59 (C(15)) 129.81 (C(5)) 131.80 (C(6)) 175.17 (C(14)) 176.28 (C(1))

(50) 2.10 Structure 46 Met-C18:1

(51) ##STR00087##

(52) .sup.1H NMR (300 MHz, CD.sub.3OD) ppm 0.90 (t, J=6.6 Hz, 3H, HC(18)), 1.27-1.34 (m, 20H, HC(4, 5, 6, 7, 12, 13, 14, 15, 16, 17), 1.60-1.65 (m, 2H, HC(3)), 1.90-2.19 (m, 9H, HC(8, 11, 22, 24), 2.25 (t, J=6.3 Hz, 2H, HC(C-H(2)), 2.49-2.62 (m, 2H, HC(23)), 4.55 (d, d, J=4.8, 9.9 Hz, 1H, HC(21)), 5.30-5.40 (m, 2H, HC(9, 10).

(53) .sup.13C NMR (300 MHz, CD.sub.3OD) ppm 14.44 (C(18)), 15.24 (C(24)), 23.76, (C(17)) 26.96 (C(3)), 28.16 (C(11)), 30.26 (C(8)), 30.28(C(6)), 30.37 (C(4)), 30.47 (C(5)), 30.62 (C(15), 30.85 ((C13, 14)), 30.87 (C(23)), 31.33 (C(7,12)), 32.18 (C(22)), 33.12 (C(16)), 36.84 (C(2)), 52.60 (C(21)), 131.22 (C(9, 10)), 175.20 (C(1)), 176.61 (C(20)).

(54) 2.11 Structure 51 Proline-C18:2

(55) ##STR00088##

(56) .sup.1H NMR (600 MHz, CHLOROFORM-d) ppm 0.78-0.85 (m, 3 H, HC(18)) 1.18-1.33 (m, 14 H, HC(4, 5, 6, 7, 15, 16, 17) 1.54-1.65 (m, 2 H, HC(3)) 1.84-1.92 (m, 1 H, H_C(22)) 1.92-2.03 (m, 6 H, H_C(8, 14, 23)) 2.26-2.32 (m, 2 H, HC(2)) 2.44 (ddd, J=12.29, 6.10, 2.92 Hz, 1 H, HC(22)) 2.70 (t, J=6.70 Hz, 2 H, HC(11)) 3.39 (td, J=9.62, 6.87 Hz, 1 H, HC(24)) 3.47-3.53 (m, 1 H, HC(24)) 4.53 (dd, J=8.08, 1.89 Hz, 1 H, HC(21)) 5.16-5.36 (m, 4 H, HC(9, 10, 12, 13)

(57) .sup.13C NMR (150 MHz, CHLOROFORM-d) ppm 14.07 (C(18)) 22.57 (C(17)) 24.48 (C(3)) 24.79 C(23)) 25.62 (C11)) 27.05 (C(22)) 27.17 (C(8)) 27.19 (C(14)) 29.10 C(6)) 29.27 (C(4, 15)) 29.34 (C(5)) 29.60 C(7)) 31.51 C((16)) 34.45 C(2)) 47.98 C(24)) 60.25 (C(21)) 128.07 (C(12)) 128.07 (C(10)) 130.00 (C(9)) 130.24 C(13)) 171.87 (C(1)) 175.87 (C20))

(58) 2.12 Structure 55 Serine-C18:2

(59) ##STR00089##

(60) .sup.1H NMR (600 MHz, DMSO-d.sub.6) ppm 0.85 (t, J=6.87 Hz, 3 H, HC(18) 1.18-1.35 (m, 16 H, HC(3, 4, 5, 6, 7, 15, 16, 17) 1.43-1.51 (m, 2 H, HC(2)) 2.01 (q, J=6.87 Hz, 4 H, HC(8, 14)) 2.12 (t, J=7.39 Hz, 2 H, HC(2) 2.73 (t, J=6.70 Hz, 2 H, HC(11)) 3.58 (dd, J=10.83, 4.30 Hz, 1 H, HC(22)) 3.65 (dd, J=10.83, 4.30 Hz, 1 H, HC(22) 4.21-4.27 (m, 1 H, HC(21)) 5.26-5.38 (m, 4 H, HC(9, 10, 12, 13)) 7.90 (d, J=7.90 Hz, 1 H, HN(19)_

(61) .sup.13C NMR (150 MHz, DMSO-d.sub.6) ppm 13.91 (C(18)) 22.01 (C(17)) 25.22 (C(3)) 25.24 (C(11)) 26.63 (C(8)) 26.68 (C(14)) 28.65 (C(6)) 28.69 (C(4)) 28.77 (C(5. 15)) 20.09 (C(7)) 30.93 (C16)) 35.07 (C(2)) 54.55 (C(21)) 61.49 (C(22)) 127.74 (C(10, 12)) 129.72 (C(9, 13)) 172.19 (C(1)) 172.27 (C(20))

(62) 2.12 Structure 59 Leucine16:1

(63) ##STR00090##

(64) .sup.1H NMR (600 MHz, CHLOROFORM-d) ppm 0.85-0.90 (m, 3 H, HC(16)) 0.91-0.98 (m, 6 H, HC(22, 23)) 1.19-1.40 (m, 14 H, HC(4, 5, 6, 7, 12, 13, 14)) 1.49-1.75 (m, 7 H, HC(3, 15, 20, 21)) 2.01 (q, J=6.07 Hz, 4 H, HC(8, 11)) 2.24 (t, J=7.73 Hz, 2 H, HC(2)) 4.54-4.59 (m, 1 H,HC(19)) 5.24-5.43 (m, 2 H, HC(9, 10)) 6.14 (d, J=8.25 Hz, 1 H, HN(19))

(65) .sup.13C NMR (150 MHz, CHLOROFORM-d) ppm 14.11 (C16)) 21.9 (C(15) 22.66 (C(22) 22.86 (C(23) 24.91 (C21)) 25.63 (C(3)) 27.18 (C(11)) 27.23 (C(8)) 28.99 (C(6)) 29.16 (C(4)) 29.20 (C(5)) 29.25 (C(13)) 29.71 (C(7)) 29.73 (C(12)) 31.79 (C(14)) 36.51 (C(2)) 41.32 (C(20)) 50.87 (C(19)) 129.73 (C(9)) 130.00 (C(10)) 173.95 (C(1)) 176.38 (C(18))

(66) 2.13 Structure 61 Leu-C18:1

(67) ##STR00091##

(68) .sup.1H NMR (600 MHz, CHLOROFORM-d) ppm 0.77-0.84 (m, 3 H, HC(18)) 0.85-0.93 (m, 6 H, HC(24, 25)) 1.14-1.29 (m, 20 H, HC(4, 5, 6, 7, 12, 13, 14, 15, 16, 17) 1.48-1.59 (m, 3 H, HC(3, 22) 1.60-1.69 (m, 2 H, C-H(22, 23) 1.90-1.99 (m, 4 H, HC(8, 11)) 2.17 (t, J=7.39 Hz, 2 H, HC(2)) 4.55 (td, J=8.51, 4.64 Hz, 1 H, HC(21)) 5.15-5.35 (m, 2 H, HC(9,10) 5.95 (d, J=7.56 Hz, 1 H, HN(19))

(69) .sup.13C NMR (150 MHz, CHLOROFORM-d) ppm 13.68 (C(18)) 21.43 (C(17)) 22.24 (C(25) 22.40 (C(24) 24.45 (C(23)) 25.14 (C(3)) 26.74 (C(11) 26.78 (C(8)) 28.71 (C(6)) 28.73 (C(4)) 28.78 (C(5)) 28.88 (C(13, 15)) 29.09 (C(14)) 29.26 (C(7)) 31.46 (C16)) 36.04 (C(2)) 40.70 (C(22)) 50.41 (C(21)) 129.28 (C(9, 10) 173.64 (C(1) 176.11 (C(20))

(70) ##STR00092##
Structure 65 Val-C16:0

(71) .sup.1H NMR (600 MHz, CHLOROFORM-d) ppm 0.88 (t, J=7.05 Hz, 3 H, HC(16)) 0.95 (d, J=6.87 Hz, 3 H, HC(21)) 0.98 (d, J=6.87 Hz, 3 H, HC(20)) 1.19-1.37 (m, 24 H, HC(3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14) 1.59-1.71 (m, 2 H, HC(3)) 2.20-2.32 (m, 3 H, HC(3)) 4.59 (dd, J=8.59, 4.81 Hz, 1 H, HC(18)) 6.19 (d, J=8.59 Hz, 1 H, HN(17))

(72) .sup.13C NMR (150 MHz, CHLOROFORM-d) ppm 14.13 C(16)) 17.70 C(20)) 19.02 C(21)) 22.71 C(15)) 25.78 C(3)) 29.25 C(6)) 29.35 C(9)) 29.38 (C(13) 29.52 C(5)) 29.64 C(4)) 29.68 (C(7, 10)) 29.72 C(8, 11, 12)) 31.00 (C(19)) 31.94 (C(14)) 36.69 (C(2)) 57.08 C(18)) 174.23 (C(1)) 175.49 C(22)

APPLICATION EXAMPLES

(73) Snack Product

(74) A snack product consisting of a fried potato base, containing 35% fat and flavored with cheese seasoning containing salt, MSG, dairy, organic acids, sugars, and a flavour formulation. The following compounds were added to the snack product at the indicated levels and the tasting results are reported: C18:2 gaba 1 ppm: Fatty full, cheesy, cheese crust, long lasting, C18:2 gaba 0.5 ppm: increased dairy, cheesy. C18:1-ACCA 1 ppm: Increased Umami, salty. C18:1-ACCA 0.5 ppm: Increased salty C18:1 met 0.5 ppm: Increased cheese, creamy, salty and succulent C18:1 met 0.25 ppm: Salty, aged cheese, succulent
Air Expanded Base

(75) An air expanded base (Rice, wheat, Tapioca, potato, salt, sugar, modified starch), containing 3% fat and flavored with cheese seasoning containing salt, MSG, dairy, organic acids, sugars and flavor. The following compounds were added to the base at the indicated levels and the tasting results are reported: C18:2 gaba 1 ppm: Fatty full, cheesy, cheese crust, long lasting, cover base C18:2 gaba 0.5 ppm: Increased dairy, cheese. C18:1-ACCA 1 ppm: Increased Umami, salty. C18:1-ACCA 0.5 ppm: Increased salty
Test in 3 in 1 Coffee

(76) In a 3 in 1 Coffee beverage from Nestle (market product) sweetened with sucrose 13.2% and containing creamer (2.1% fat) C18:2-gaba was added.

(77) Samples were evaluated by expert tasters. Tasters were asked to describe the samples focusing on authentic taste, mouthfeel, fullness, salivation, sweetness, juiciness, richness, long lastingness and fattiness.

(78) Base is 3-in-1 Coffee Beverage (Market Product) Sweetened with Sucrose and Containing Creamer with Fat

(79) Base: coffee, sweet, mild dairy

(80) Base plus C18:2-gaba at 1 ppm: very nice mouthfeel effect, creamy as if coffee creamer is added, more sweet.

(81) Test on Tang

(82) In an orange flavoured Tang powdered soft drink (market product) sweetened with sucrose plus high intensity sweetener and containing citric acid, C18:2-gaba and C18:2-pro were tested.

(83) All samples were evaluated by expert tasters. Tasters were asked to describe the samples focusing on authentic taste, mouthfeel & body, enhancement, richness, juiciness, long lastingness, salivation, sweetness, masking off notes of high intensity sweetener

(84) Base is Orange Flavoured Tang

(85) Base: sweet, orange, licorice, and lingering high intensity sweetener offnotes, bitter, thin

(86) Base plus C18:2-gaba at 0.5 ppm: enhances sweet juicy orange notes, enhanced mouthfeel.

(87) Additionally, the off-notes of the high intensity sweetener were suppressed.

(88) Base plus C18:2-Pro at 1 ppm: very fresh, enhances sweet juicy orange notes, characteristic of authentic fresh orange fruit. Additionally, the off-notes of the high intensity sweetener were suppressed.

(89) Mango Flavoured Still Beverage Containing Different Levels of Juice.

(90) In a Mango flavoured still beverage, sweetened with 8% sucrose and containing 0.1% citric acid and 1%, 4% and 6% clear mango juice flavoured with a proprietary Mango flavour @ 0.05% , C18:2-gaba and C18:2-Pro were added, as such (separate) and in combination.

(91) All samples were evaluated by expert tasters. Tasters were asked to describe the samples focusing on authentic taste, juicy mouthfeel, enhancement, richness, juiciness, long lastingness, salivation, sweetness.

(92) In a Mango flavoured still beverage, sweetened with 8% sucrose & containing 0.1% citric acid and 1% clear mango juice flavoured with proprietary Mango flavour @ 0.05%, C18:2-gaba and C18:2-Pro were added, as such (separate) and in combination.

(93) Base is water, 8% sucrose, 0.1% citric acid, 1% clear mango juice (very low juice %), flavoured with Mango flavor, dosed at 0.05%

(94) Base: sweet, fruity, mango, thin

(95) Base plus C18:2-Pro at 0.5 ppm: more sweet, sugar-like, very juicy and long lasting sweet, salivating

(96) Base plus C18:2-gaba at 1 ppm: fatty skin-like, very juicy, authentic mango, much more mouthfeel, long lasting mango taste, mouthfeel is close to the full juice product

(97) Base plus C18:2-Pro at 0.5 ppm and C18:2-gaba at 1 ppm: very juicy and sweet, authentic mango, long lasting sweet and long lasting mango taste, very close in mouthfeel to a full juice product

(98) In a Mango flavoured still beverage, sweetened with 8% sucrose & containing 0.1% citric acid and 4% clear mango juice flavoured with Mango flavour @ 0.05% , C18:2-gaba and C18:2-Pro were added, as such (separate) and in combination.

(99) Base is water, 8% sucrose, 0.1% citric acid, 4% clear mango juice (30% reduced juice), flavoured with Mango flavor, dosed at 0.05%

(100) Base: sweet, fruity, mango, some low mouthfeel

(101) Base plus C18:2-Pro at a range 0.5 ppm: more sweet, sugar-like, very juicy and long lasting sweet, salivating

(102) Base plus C18:2-gaba at 1 ppm: fatty skin-like, very juicy, authentic mango, long lasting mango taste, more mouthfeel than the full juice product

(103) Base plus C18:2-Pro at 0.5 ppm and C18:2-gaba at 1 ppm: very juicy and sweet, thick authentic mango, long lasting sweet and long lasting mango taste, more mouthfeel than a full juice product

(104) In a Mango-flavoured still beverage, sweetened with 8% sucrose & containing 0.1% citric acid and 6% clear mango juice flavoured with Mango flavour @ 0.05%, C18:2-gaba and C18:2-Pro were added, as such (separate) and in combination.

(105) Base is water, 8% sucrose, 0.1% citric acid, 6% clear mango juice (full juice), flavoured with Mango flavor, dosed at 0.05%.

(106) Base: Sweet, fruity mango, full mouthfeel

(107) Base plus C18:2-Pro at 0.5 ppm more sweet, sugar-like, very juicy and long lasting sweet, salivating, syrupy.

(108) Base plus C18:2-gaba at 1 ppm: fatty skin-like, very thick juicy, authentic mango, long lasting mango taste, rich.

(109) Base plus C18:2-Pro at 0.5 ppm and C18:2-gaba at 1 ppm: juicy and sweet, thick authentic mango, long lasting sweet and long lasting mango taste, very rich.