Organic compounds

Abstract

A flavour composition comprising a compound according to the formula (I) or edible salts thereof, ##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 flavour composition comprising 1 ppb-10 ppm N-oleoyl-aspartic acid, or an edible salt thereof selected from chlorides, sulphates, phosphates, gluconates, sodium, citrates, carbonates, acetates, and lactates; and at least one flavour co-ingredient selected from the group consisting of sugars, fats, flavour oils, flavour aromatics, oleoresins, essences, distillates, extracts, spices, seasonings, salt, salt tastants, umami tastants, MSG, calcium ions, phosphate ions, organic acids, proteins, purines, savoury flavour compounds, natural flavours, artificial flavours, aldehydes, esters, and mixtures thereof.

2. The 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.

3. The flavour composition according to claim 1 further comprising a carrier material and an adjuvant.

4. The flavour composition according to claim 3 wherein the adjuvant is an antioxidant.

5. The flavour composition according to claim 1 in the form of an emulsion.

6. The flavour composition according to claim 1 in the form of a powder.

7. The flavour composition according to claim 6 wherein the powder is formed by spray drying.

8. An edible composition comprising the flavour composition according to claim 1.

9. A caloric or non-caloric beverage comprising the flavour composition according to claim 1.

10. The caloric or non-caloric beverage according to claim 9 containing carbohydrate sweeteners, selected from sucrose, high fructose corn syrup, fructose and glucose, or high intensity, non-nutritive sweeteners selected from aspartame, acesulfame K, sucralose, cyclamate, sodium saccharin, neotame, rebaudioside A, and/or other stevia-based sweeteners.

11. An edible constituent composition adapted to be added to or to form part of an edible composition selected from a foodstuff and a beverage composition, the edible constituent composition comprising N-oleoyl-aspartic acid, wherein the N-oleoyl-aspartic acid accentuates an existing flavor or existing mouth feel characteristics of the edible composition selected from a foodstuff composition and a beverage composition comprising at least one flavor co-ingredient selected from the group consisting of sugars, fats, flavour oils, flavour aromatics, oleoresins, essences, distillates, extracts, spices, seasonings, salt, salt tastants, umami tastants, MSG, calcium ions, phosphate ions, organic acids, proteins, purines, savoury flavour compounds, natural flavours, artificial flavours, aldehydes, esters, and mixtures thereof, when the N-oleoyl-aspartic acid is incorporated in the edible composition in an amount of 1 ppb-10 ppm.

12. An edible composition selected from a foodstuff and a beverage composition, the edible composition comprising: N-oleoyl-aspartic acid in an amount of 1 ppb-10 ppm based on the total weight of the edible composition; and at least one flavour co-ingredient selected from the group consisting of sugars, fats, flavour oils, flavour aromatics, oleoresins, essences, distillates, extracts, spices, seasonings, salt, salt tastants, umami tastants, MSG, calcium ions, phosphate ions, organic acids, proteins, purines, savoury flavour compounds, natural flavours, artificial flavours, aldehydes, esters, and mixtures thereof, wherein the N-oleoyl-aspartic acid accentuates an existing flavour or existing mouth feel characteristics of the edible composition.

13. The edible constituent composition according to claim 11 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.

14. The edible composition according to claim 12 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.

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.

(3) 1 g of 85-90% pure product could be obtained.

(4) 1.2 Route B (DCC Method with Protection Group)

(5) Step 1:

(6) 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%.

(7) Step 2:

(8) 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.

(9) 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%.

(10) 1.3 Route C (Acid Chloride)

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

(12) 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 add (2.99 ml, 36.4 mmol) and extracted with ethylacetate.

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

(14) 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%).

(15) 1.4 Table of Synthesized Compounds

(16) TABLE-US-00001 TABLE 1 List of synthesized compounds Amino Carboxylic Structure 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.1 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 Glutamine C10:0 C 36 Glutamine C12:0 C 37 Glutamine C10:2 A 38 Glutamine C16:0 C 39 Glutamine C18:0 C 40 Glutamine C18:1 C 41 Glutamine C18:2 0 A 42 Methionine C10:0 A 43 Methionine C12:0 A 44 Methionine C12:1 A 45 Methionine C16:0 A 46 Methionine C18:1 A 47 Methionine 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 Iso- leucine C18:1 C 65 Valine C16:0 C 66 Valine C18:0 C 67 Valine C18:1 C 68 Valine C18:2 A

(17) ##STR00078##

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

(19) .sup.13C NMR (150 MHz, CHLOROFORM-d) δ 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))

(20) 2.2 Structure 7 GABA-C10:0

(21) ##STR00079##

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

(23) .sup.13C NMR (150 MHz, DMSO-d.sub.6) δ 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))

(24) 2.3 Structure 8 GABA-C12:0

(25) ##STR00080##

(26) .sup.1H NMR (600 MHz, DMSO-d.sub.6) δ ppm 0.85 (t, J=6.87 Hz, 3H, H—C(12)) 1.15-1.33 (m, 16H, H—C(4, 5, 6, 7, 8, 9, 10, 11) 1.41-1.51 (m, 2H, H—C(3)) 1.59 (quin, J=7.22 Hz, 2H, H—C(16)) 2.02 (t, J=7.56 Hz, 2H, H—C(2)) 2.19 (t, J=7.56 Hz, 2H, H—C(15)) 3.02 (q, J=6.53 Hz, 2H, (H—C(17)) 7.77 (t, 0.1=5.33 Hz, 1H, H—N(13))

(27) .sup.13C NMR (150 MHz, DMSO-d.sub.6) δ 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))

(28) 2.4 Structure 17 GABA-C18:2

(29) ##STR00081##

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

(31) .sup.13C NMR (150 MHz, CHLOROFORM-d) δ ppm 14.08 (C(18) 22.58C(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)) 31.49C(7)) 31.52C(16)) 36.73C(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))

(32) 2.5 Structure 22 Beta-Alanine-C18:2

(33) ##STR00082##

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

(35) .sup.13C NMR (150 MHz, DMSO-d.sub.6) δ 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))

(36) 2.6 Structure 28 Asp-C18:2

(37) ##STR00083##

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

(39) .sup.13C NMR (150 MHz, DMSO-d.sub.6) δ 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))

(40) 2.7 Structure 33 Glu-C18:1

(41) ##STR00084##

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

(43) .sup.13C NMR (150 MHz, CHLOROFORM-d) δ 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))

(44) 2.8 Structure 37 Gln-C10:2

(45) ##STR00085##

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

(47) .sup.13C NMR (150 MHz, CHLOROFORM-d) δ 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))

(48) 2.9 Structure 44 Met-C12:1

(49) ##STR00086##

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

(51) .sup.13C NMR (300 MHz, CD.sub.3OD) δ 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))

(52) 2.10 Structure 46 Met-C18:1

(53) ##STR00087##

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

(55) .sup.13C NMR (300 MHz, CD.sub.3OD) δ 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)).

(56) 2.11 Structure 51 Proline-C18:2

(57) ##STR00088##

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

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

(60) 2.12 Structure 55 Serine-18:2

(61) ##STR00089##

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

(63) .sup.13C NMR (150 MHz, DMSO-d.sub.6) δ 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))

(64) 2.12 Structure 59 Leucine 16:1

(65) ##STR00090##

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

(67) .sup.13C NMR (150 MHz, CHLOROFORM-d) δ 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))

(68) 2.13 Structure 61 Leu-C18:1

(69) ##STR00091##

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

(71) .sup.13C NMR (150 MHz, CHLOROFORM-d) δ 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))

(72) Structure 65 Val-C16:0

(73) ##STR00092##

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

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

APPLICATION EXAMPLES

(76) Condiments and Fats

(77) The following formulations were prepared and tasted by trained panelists.

(78) 1. Soy Based Product

(79) Salt level pure product between 5-40%

(80) Salt level in application 0.3-1.0%

(81) C18:2 gaba—(0.5 ppm) was added to a 1% diluted salt reduced kikoman soy sauce (9% salt). The resultant composition was considered to be stronger, more umami, long lasting, richer

(82) C18:2 gaba—(0.5 ppm) was added to pure salt reduced kikoman soy sauce (9% salt). The resultant composition was considered to be strong in body and mouthfeel, and more salty.

(83) C18:1-ACCA—(0.5 ppm) was added to pure salt reduced kikoman soy sauce (9% salt). The resultant composition was considered to have strong upfront saltiness lingering, very strong saltiness.

(84) 2. Fish Based

(85) Salt level pure product between 5-40%

(86) Salt level in application 0.3-1.0%

(87) C18:2 gaba—(0.5 ppm) was added to a 1% diluted fish sauce (0.27% salt). The resultant composition was deemed to be stronger in umami, longer lasting and richer.

(88) C18:2 gaba—(0.5 ppm) was added to pure fish sauce (27% salt). The resultant composition was considered to be strong in body and mouthfeel, more salty, richer with more rounded fish notes.

(89) C18:1-ACCA—(0.5 ppm) was added to pure fish sauce. The composition was considered to exhibit strong saltiness lingering and with a strong body and mouthfeel.

(90) 3. Emulsions-Colloids

(91) 3.1—Water in Oil

(92) Butter

(93) Fat levels 20-90%

(94) Salt levels 0.1-1.7%

(95) Blueband 82% fat 1.5% salt

(96) C18:2 gaba added at 1 ppm. The composition was considered to exhibit a more authentic butter taste, with more mouthfeel

(97) Pilaf

(98) Standard cooked rice with 10% of the above mentioned 18:2 gaba flavoured butter was deemed to have more mouthfeel, with a lingering creamy authentic butter taste.

(99) 3.2—Oil in Water

(100) Mayonnaise

(101) Fat levels between 10-80%

(102) Low fat Mayonnaise (27% Fat, 9% carbohydrates (of which 5% sugar), 1.4% salt)

(103) C18:1-ACCA (0.5 ppm) added to the mayonnaise was deemed to produce a nicely balanced compositions with a full mouthfeel and a more eggy taste.

(104) C18:2 gaba (0.5 ppm) added to the mayonnaise was deemed to produce a creamy, thick mouthfeel with a full fat impression.

(105) 3.3—Dressings

(106) Oil levels 0.5-50%

(107) Acidity PH 3-6

(108) low fat salad dressing (13.6% Fat, 8%, carbohydrates (of which 5.3% sugar))

(109) C18:1-ACCA (0.5 PPM) was added to the dressing and produced a composition with more mouthfeel with body and less acidic.

(110) C18:2 gaba (0.5 PPM) was added to the dressing and produced a better mouthfeel that was impressively creamy.

(111) 4—Soups and Bouillons

(112) Fat levels 0.1-10%

(113) Salt levels 0.3-1.4%

(114) Standard Chicken bouillon base, 0.7% salt, 0.5% fat

(115) C10:0 ACCA @ 0.5 PPM—Nice strong salty. Umami lingering body, better chicken profile

(116) C10:0 ACCA @ 0.2 PPM—More umami lingering body

(117) C18:1-ACCA @ 0.5 PPM—More body and fatty notes, Salivating and good aftertaste

(118) C18:1-ACCA @ 0.2 PPM—Saltier, Stronger and more umami

(119) C18:2 ACCA @ 0.2 PPM—Creamy, full body, more fatty chicken

(120) Geranoyl ACCA @ 0.2 PPM—Saltier Umami lingering Mouthfeel

(121) Beef Bouillon base 1.0% salt, 0.5% fat

(122) C18:1 met @ 1.0 PPM—Full bodied, long lasting, more mouthfeel

(123) C18:1 met @ 0.5 PPM—Very salty and rich

(124) C18:2 gaba @ 0.5 PPM—Strong, Salty, Umami, mouthfeel

(125) C16:1 leu @ 0.5 PPM—Strong salty and rich

(126) C18:2 val @ 0.5 PPM—more body and mouthfeel, more umami

(127) 5—Jus and Fonds

(128) Beef jus

(129) C18:1-ACCA @ 40 PPB—more salty, fatty, total profile is enhanced

(130) 6—Cheese

(131) Fat level 1-40%

(132) Salt 0.3-2%

(133) Spreadable cheese ERU

(134) C18:2 gaba @ 0.5 PPM—Full, Salty, cheese bite, more mature

(135) C18:1-ACCA @ 0.5 PPM—Strong umami, lingering cheese bite

(136) Cheese sauce: 5% fat 1.6% salt

(137) C18:2 gaba @ 0.5 PPM—Full, Salty, cheese bite expanding

(138) C18:1-ACCA @ 0.5 PPM—Strong umami, cheese bite, expanding

(139) 7—Beef and Poultry

(140) Differentiator high temperature 100-250 degrees Celcius in a frying in oil process

(141) C18:2 gaba @ 2.0 PPM in 135 gram frying oil (blue band 82% Fat) 450 gram chicken filet 2 minutes high fire and 5 minutes medium fire.

(142) Taste of the chicken is more juicy, succulent, lingering more white meat

(143) Also the oil has more savoury golden brown notes.

(144) 8—Baked Goods and Pizza

(145) Differentiator high temperature 100-250 degrees Celcius in hot air baking process

(146) C18:2 gaba @ 0.5 PPM in the crust and @ 0.5 PPM in the tomato sauce

(147) The pizza was topped off with cheese and baked in a hot air oven @ 200 degrees Celcius

(148) The crust was less dry, more succulent and the tomato was richer, sweeter and the total lingering aftertaste was very rich and pleasant

(149) 9—Snack Product

(150) 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:

(151) C18:2 gaba 1 ppm: Fatty full, cheesy, cheese crust, long lasting,

(152) C18:2 gaba 0.5 ppm: increased dairy, cheesy.

(153) C18:1-ACCA 1 ppm: Increased Umami, salty.

(154) C18:1-ACCA 0.5 ppm: Increased salty

(155) C18:1 met 0.5 ppm: Increased cheese, creamy, salty and succulent

(156) C18:1 met 0.25 ppm: Salty, aged cheese, succulent

(157) 10—Air Expanded Base

(158) 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:

(159) C18:2 gaba 1 ppm: Fatty full, cheesy, cheese crust, long lasting, cover base

(160) C18:2 gaba 0.5 ppm: Increased dairy, cheese.

(161) C18:1-ACCA 1 ppm: Increased Umami, salty.

(162) C18:1-ACCA 0.5 ppm: Increased salty

(163) 11—Testing in Dairy Products

(164) The following tests were carried out on dairy products processed by fermentation, pasteurization or UHT. The products contain fat, protein and calcium.

(165) UHT Milk Cream Flavoured, Non Sweetened and Different Fat Levels

(166) In a UHT milk containing 0%9, 1.5% and 3% fat, flavoured with a proprietary cream flavour dosed at 0.03% C18:2 gaba was added at 2 ppm.

(167) Samples were evaluated by expert tasters.

(168) Tasters were asked to describe the samples focusing on authentic taste, mouthfeel, fullness, salivation, sweetness, juiciness, richness, long lastingness and fattiness. The results are presented below:—

(169) UHT milk 0% fat, Cream flavour (0.03%): Milky, watery, card board aftertaste

(170) UHT milk 0% fat, Cream flavour (0.03%) but with C18:2 gaba added at 2 ppm: Very creamy, milky, long lasting.

(171) UHT milk 1.5% fat. Cream flavour (0.03%): Milky, slightly creamy

(172) UHT milk 1.5% fat. Cream flavour (0.03%) with added C18:2 gaba at 2 ppm: very creamy, milky, long lasting, salivating.

(173) UHT milk 3.0% fat, Cream flavour (0.03%): Milky, slightly creamy

(174) UHT milk 3.0% fat, Cream flavour (0.03%) with added C18:2 gaba at 2 ppm: very creamy, milky, long lasting, taste like whipped cream.

(175) UHT Sweetened Banana Flavoured Milk, with Different Fat Levels

(176) In a UHT milk with 0% and 3% fat sweetened with 4% sucrose by weight, flavoured with proprietary banana flavour dosed at 0.04%, C18:2 gaba was added at 0.25 ppm, 0.5 ppm and 1 ppm.

(177) 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.

(178) UHT milk 0% fat, Banana flavour (0.04%): Strong banana, estery, eugenol-like, unbalanced.

(179) UHT milk 0% fat, Banana flavour (0.04%) C18:2-gaba (0.25 ppm): fuller banana, more authentic, more sweet

(180) UHT milk 0% fat, Banana flavour (0.04%), C18:2-gaba (0.5 ppm): fuller banana, authentic, creamy and sweet, more mouthfeel

(181) UHT milk 0% fat. Banana flavour (0.04%), C18:2-gaba (1 ppm): creamy, creamy banana, sweet aftertaste, more mouthfeel and very longlasting

(182) UHT milk 3% fat, Banana flavour (0.04%): strong estery banana, eugenol like, spicy

(183) UHT milk 3% fat, Banana flavour (0.04%), C18:2-gaba (0.25 ppm): more authentic, less estery and more round

(184) UHT milk 3% fat. Banana flavour (0.04%), C18:2-gaba (0.5 ppm): creamy banana

(185) UHT milk 3% fat, Banana flavour (0.04%), C18:2-gaba (1 ppm): creamy long lasting and more authentic and more impact

(186) Yoghurt Cream Flavoured, Non-Sweetened and Different Fat Levels

(187) In a Yoghurt containing 0% 1.5% and 3% fat, flavoured with proprietary cream flavour dosed at 0.03%, C18:2-gaba was added at 2 ppm. Samples were evaluated by expert tasters. Tasters were asked to describe the samples focusing on authentic taste, acidity, mouthfeel, fullness, salivation, sweetness, juiciness, richness, long lastingness and fattiness.

(188) Yoghurt 0% fat, Cream flavour (0.03%): very acidic, metallic

(189) Yoghurt 0% fat, Cream flavour (0.03%), C18:2-gaba 2 ppm: less acidic, slight creamy aftertaste

(190) Yoghurt 1.5% fat, Cream flavour (0.03%): mild creamy yoghurt

(191) Yoghurt 1.5% fat, Cream flavour (0.03%), C18:2-gaba 2 ppm: very creamy, thick, nice long lasting, whipped cream note.

(192) Yoghurt 3% fat, Cream flavour (0.03%): acidic, creamy aftertaste

(193) Yoghurt 3% fat, Cream flavour (0.03%), C18:2-gaba 2 ppm: less acidic, much more creamy, very long lasting creamy aftertaste.

(194) Strawberry Flavoured Sugar Sweetened Yoghurt

(195) In a 1.5% fat yoghurt base, sweetened with 8% sucrose by weight, flavoured with a proprietary strawberry flavour @ 0.015% several different N-acyl aminoacids were added.

(196) Base: fruity, strawberry

(197) Base plus C18:2-gaba at 2 ppm: very creamy and fresh strawberry

(198) Base plus C18:0-leu at 5 ppm: Very juicy full, 3D, stronger nicer strawberry, salivating long lasting.

(199) Base plus C18:0 leu at 2 ppm: Very juicy full, 3D, stronger nicer strawberry, long lasting nice creamy aftertaste.

(200) Base plus C18:0-gaba at 2 ppm: juicy full, jammy

(201) Base plus C18:0-gln at 2 ppm: Sweet full juicy, nice, slight enhanced sulphury

(202) Base plus C18:1-gln at 2 ppm: Juicy, nice, fatty aftertaste.

(203) Base plus C18:2-asn at 2 ppm: green fresh, nice, fatty nice fuller

(204) Activa Strawberry Yoghurt

(205) In a Full fat, Activa strawberry flavoured yoghurt containing 13.5% sugar, 3.2% fat C18:2-gaba and C18:0-leu at 2 ppm

(206) Activa: jammy strawberry, green and creamy

(207) Activa plus C18:2-gaba at 2 ppm: very creamy, full and fresh strawberry

(208) Activa plus C18:0-leu at 2 ppm: very juicy strawberry full, 3D, stronger strawberry, long lasting and creamy.

(209) Vanilla Flavoured Milk 3.0% Fat

(210) In a 3% fat milk drink, sweetened with 4% sucrose by weight, flavoured with Vaniline @10 ppm and a Vanilla extract @ 0.03% C18:2-gaba, C18:1-ACCA and C18:1-glu were added at 0.5 or 2 ppm.

(211) 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.

(212) Base: Milk 3% fat, 4% sugar, vanillin 10 ppm, vanilla extract 0.03%

(213) Base: sweet vanillic, very slightly beany

(214) Base: C18:2-gaba 2 ppm: beany, fatty, authentic, sweet

(215) Base: C18-ACCA (cyclo propyl) 0.5 ppm: sweet, sugar-like, vanillic

(216) Base: C18:1-glu 2 ppm: full, fatty, vanilla bean enhanced, whipped cream like

(217) Chocolate Milk with Different Fat Content

(218) In a chocolate milk 1.8% and 2.7% fat C18:2-gaba was added at 0.5 and 1 ppm.

(219) 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.

(220) Chocolate milk 1.8% fat: cocoa powder taste, sweet, slightly creamy

(221) Chocolate milk 1.8% fat C18:2-gaba at 0.5 ppm: stronger cocoa note, more chocolate vs cocoa

(222) Chocolate milk 1.8% fat C18:2-gaba at 1 ppm: very creamy, chocolate, long-lasting creamy and chocolate taste.

(223) Chocolate milk 3% fat: cocoa powder taste, sweet, creamy

(224) Chocolate milk 3% fat C18:2-gaba at 0.5 ppm: very creamy, enhanced cocoa note.

(225) Chocolate milk 3% fat C18:2-gaba at 1 ppm: very creamy, lasting, sweet, almost taste like chocolate ice cream.

(226) Soy Milk

(227) In a soy milk (1.8% fat) sweetened with 5% sucrose by weight, flavoured with a proprietary milk flavour at a dosage of 0.1%, C18:2-gaba was added at 2 ppm

(228) 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.

(229) Soy milk, 5% sucrose, milk flavor @ 0.1%: sweet, dry, green, soy bean taste

(230) Soy milk, 5% sucrose, milk flavor @ 0.1%, C18:2-gaba at 2 ppm: clean, creamy, good masking of the soy bean taste, creamy and milky.

(231) 12—Caloric & Non Caloric Beverages

(232) Testing in beverage products containing carbohydrate sweeteners such as Sucrose, High Fructose Corn Syrup, Fructose and Glucose; or high intensity, non-nutritive sweeteners such as Aspartame Acesulfame K, Sucralose, Cyclamate, Na+ Saccharin, Neotame, Rebaudioside A and/or other stevia based sweeteners.

(233) Sweetener in beverage applications ranges from 0-20%.

EXAMPLES

(234) Carbonated Soft drink: <1% to 15% sweetener

(235) Still beverages (non-alcoholic): <1% to 15% sweetener

(236) Juice beverages; <1% to 15% sweetener

(237) Powdered Soft drinks: <1% to 20% sweetener

(238) Liquid concentrates: <1% to 20% sweetener

(239) Alcoholic beverages: <1% to 40% sweetener

(240) Functional beverages: <1% to 20% sweetener

(241) Coffee based beverages: <1% to 15% sweetener

(242) Tea based beverages: <1% to 15% sweetener

(243) Test in 3 in 1 Coffee

(244) 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.

(245) 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.

(246) Base is 3-in-1 Coffee beverage (market product) sweetened with sucrose and containing creamer with fat

(247) Base: coffee, sweet, mild dairy

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

(249) Test on Tang

(250) 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.

(251) 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

(252) Base is Orange flavoured Tang

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

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

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

(256) 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.

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

(258) 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.

(259) 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.

(260) 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.

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

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

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

(264) 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

(265) 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

(266) 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.

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

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

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

(270) 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

(271) 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

(272) 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.

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

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

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

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

(277) 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.

(278) 13—Testing in Alcoholic Beverage Products

(279) Test on Baileys Cream Liqueur:

(280) In Baileys cream liqueur (Market Product) containing 17% alcohol, carbohydrates 25% and 13% fat C18:2-gaba was added at 1 ppm.

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

(282) Base is Baileys cream liqueur

(283) Base: alcoholic, cream, cocoa

(284) Base plus C18:2-gaba at 1 ppm: strongly enhanced alcohol effect, more cocoa, very creamy and long lasting aftertaste.

(285) Test on Heineken Beer:

(286) In Heineken beer (Market Product) containing 4% alcohol C18:2-gaba was added at 0.5 ppm.

(287) Samples were evaluated by expert tasters. Tasters were asked to describe the samples focusing on authentic taste, alcohol impact, malt taste, hop taste, mouthfeel, fullness, salivation, sweetness, bitterness, richness, long lastingness and fattiness.

(288) Base is Heineken beer

(289) Base: Bitter, hop like, fruity, malty, alcoholic

(290) Base plus C18:2-gaba at 0.5 ppm: more hoppy, more bitter, more malt and stronger alcohol impact.

(291) Test on Breezer Orange:

(292) In Breezer Orange (Market Product) containing 4% alcohol C18:2-gaba was added at 1 ppm.

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

(294) Base is Breezer Orange

(295) Base: Bitter, orange, soapy, burning, alcoholic

(296) Base plus C18:2-gaba at 0.5 ppm: more alcoholic, sweeter, more juicy orange, less soapy

(297) 14—Testing with Beverages Containing Organic Acids from 0.01% to 7%

(298) Test 18:2 Gaba on Organic Acids in a Beverage.

(299) In a solution containing water, 7% sucrose by weight, and different organic acids, 18:2 gaba was added at 1 ppm. We observed taste effects on the acid perception upon addition of 18:2 gaba.

(300) 7% Sucrose Plus Tartaric Acid at 0.121% by Weight

(301) Base is water, 7% Sucrose by weight, Tartaric acid at 0.121% by weight

(302) Base: sharp acidic, astringent aftertaste

(303) Base plus C18:2-gaba at 1 ppm decreased sharp acidic perception, full body mouthfeel, higher mouthwatering, more immediate (upfront hit), and an impression of the flesh of fruit (grape, apple, banana, pear-like)

(304) 7% Sucrose Plus Malic Acid at 0.1081% by Weight

(305) Base is water, 7% Sucrose by weight, Malic acid at 0.1081% by weight

(306) Base: acidic, green, slightly astringent

(307) Base plus C18:2-gaba at 1 ppm decreased sharp acidic perception, give fuller body, mouthfeel, higher mouthwatering, and an impression of the flesh and skin notes of fruit (apple)

(308) 7% Sucrose Plus Citric Acid at 0.1% by Weight

(309) Base is water, 7% Sucrose by weight, Citric acid at 0.1% by weight

(310) Base: fresh sharp, acidic

(311) Base plus C18:2-gaba at 1 ppm decreased sharp acidic perception, full body mouthfeel, higher mouthwatering, and an impression of the juicy notes of citrus fruit (orange, lemon)

(312) 7% Sucrose Plus Fumaric Acid at 0.0936% by Weight

(313) Base is water, 7% Sucrose by weight, Fumaric acid at 0.0936% by weight

(314) Base: musty, acidic, astringent

(315) Base plus C18:2-gaba at 1 ppm: decreased sharp acidic perception, full body mouthfeel effects, higher sweet effects, and an impression of the full notes characteristic of sweet red & vanillic flavor types (vanilla, chocolate, raspberry, cherry, especially benzaldhyde)

(316) 15-Testing of Gaba and Beta Ala Derivatives

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

(318) Test on Kikkoman Soy Sauce Low Salt

(319) Base is Kikkoman soy sauce

(320) Base: salty, dark roast taste, umami

(321) Base plus C18:2-gaba at 0.5 ppm: much more salty, sweet and long lasting.

(322) Test on “Eru Prestige” Spreadable Cheese

(323) Base is Eru prestige (market product)

(324) Base: Yeasty, cheese bite, slightly bitter

(325) Base plus C18:2-gaba at 0.5 ppm full salty, much more cheese bite, umami, lingering, long lasting.

(326) Test on Menthol Fondant (1%)

(327) Base is Fondant 65%, sugar syrup 34% and a proprietary menthol flavour at 1%

(328) Base: Cooling menthol, sweet

(329) Base plus C18:2-gaba at 2 ppm: increased menthol impact, stronger cooling more sweet, long lasting, fresh.

(330) Calve Salad Dressing Low Fat (13.6% Fat:

(331) Base is Calve salad dressing (market product)

(332) Base: acidic, rancid, watery

(333) Base plus C18:2-gaba at 0.5 ppm much fuller, creamy, rich, less acidic.

(334) Calve 60% Reduced Fat Mayonnaise

(335) Base is Calve Mayonnaise 60% reduced fat (market Product)

(336) Base: rancid, acidic, empty

(337) Base plus C18:2-gaba at 0.5 ppm full, rich, creamy, more egg yolk taste.

(338) Comparison in a Mango Juice Drink

(339) Base is 8% sucrose, 0.1% citric acid, 1% clear mango juice, and a proprietary mango flavour at 0.05%.

(340) Base: fruity mango

(341) Base plus C16:1 gaba at 2 ppm: Juicy, rich, full authentic

(342) Base plus C18:1 gaba at 2 ppm: juicy, long lasting, rich

(343) Base plus C18:2 gaba at 2 ppm: fatty skin like, juicy, authentic

(344) Base: fruity mango

(345) Base plus C16:0-beta ala at 2 ppm more juicy

(346) Base plus C18:1-beta ala at 2 ppm more juicy, longlasting

(347) Base plus C18:2-beta ala at 2 ppm full long lasting nice juicy, almost a bit salty

(348) Comparison in Beef Bouillon

(349) Base is Maggi beef bouillon 1 tablet in 500 ml of hot water

(350) Base: salty, umami, powdery

(351) Base plus C16:0-beta ala at 2 ppm more salty salivating umami

(352) Base plus C18:1-beta ala at 2 ppm more salty salivating umami

(353) Base plus C18:2-beta ala at 2 ppm salty, savoury, full

(354) Comparison in a Strawberry Drink

(355) Base is 7% sucrose, 0.1% citric acid, and a proprietary strawberry flavour @ 0.015%

(356) Base: sweet, fruity, estery strawberry

(357) Base plus C16:1-gaba at 2 ppm juicy, fruity, fatty, long lasting, good mouthfeel

(358) Base plus C18:1-gaba at 2 ppm fatty and long lasting strawberry

(359) Base plus C18:2-gaba at 2 ppm fatty mouthfeel, creamy strawberry, fruity and Juicy

(360) Base plus C18:0-gaba at: 0.5 ppm mild creamy, fruity, juicy and long lasting

(361) Test in a Strawberry Yoghurt

(362) Base: Yoghurt 1.5% fat yoghurt, 8% sucrose, proprietary strawberry flavour @ 0.015%

(363) Base: fruity, strawberry

(364) Base plus C18:2-gaba at 3 ppm, creamy, fruity authentic strawberry, stronger strawberry, ripe, long lasting, juicy

(365) Test in Vanilla Milk:

(366) Base: Milk 0.15% fat, sweetened with 4% sucrose by weight, flavoured with proprietary Vaniline flavour @ 10 ppm+Vanilla ext. @ 0.03%

(367) Base: sweet vanillic, slightly beany taste

(368) Base plus C18:2-gaba at 2 ppm: fatty, long lasting authentic vanilla, vanilla bean taste is enhanced

(369) Test in Chocolate Flavoured Drink:

(370) Base: Water, 4% sucrose, proprietary chocolate flavor at 0.03%

(371) Base: sweet vanillic, cocoa

(372) Base plus C18:2-gaba at 2 ppm: full, sweeter, more vanillic, milk chocolate is enhanced, very long lasting

(373) Test in Pear Flavored Drink:

(374) Base: water, 7% sugar, 0.1% citric acid, proprietary pear flavour at 0.025%

(375) Base: nice pear, fruity estery, green

(376) Base plus C18:2-gaba at 1 ppm: long lasting juicy and fatty skin like very authentic, like eating the fruit instead of drinking a drink

(377) Test in Peach Flavoured Drink:

(378) Base is water, 8% sugar, 0.1% citric acid, and proprietary peach flavour at 0.05%

(379) Base: fruity peach

(380) Base plus C18:2-gaba at 1 ppm fruity peach, long lasting, juicy and fatty skin like very authentic

(381) Test in Pineapple Flavoured Drink:

(382) Base is water, 8% sugar, 0.1% citric acid and proprietary pineapple flavour at 0.03%

(383) Base: candy pineapple, jammy

(384) Base plus C18:2-gaba at 1 ppm very ripe, jammy, long lasting and sweet

(385) 16—Testing of C18 Amino Cyclopropanic Acid (ACCA) Derivative

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

(387) Test on Kikkoman Soy Sauce Low Salt

(388) Salt level pure product between 5-40%

(389) Salt level in application 0.3-1.0%

(390) C18:1-ACCA: 0.5 ppm Strong upfront saltiness lingering, very strong saltiness

(391) Testing Fish Sauce

(392) Salt level pure product between 5-40%

(393) Salt level in application 0.3-1.0%

(394) C18:1-ACCA 0.5 ppm, Strong saltiness lingering, strong body mouthfeel

(395) Test in Mayonnaise

(396) Fat levels between 1.0-80%

(397) Low fat Mayonnaise (27% Fat)

(398) C18:1-ACCA 0.5 ppm—Nice balanced, full mouthfeel, increased eggyness

(399) Test in Dressings

(400) Oil levels 0.5-50%

(401) Acidity PH 3-6

(402) Low fat salad dressing (13.6% Fat)

(403) C18:1-ACCA 0.5 ppm—Increased mouthfeel body less acidic

(404) Test in Soups and Bouillons

(405) Fat levels 0.1-10%

(406) Salt levels 0.3-1.4%

(407) Standard Chicken Bouillon Base

(408) 0.7% salt 0.5% fat

(409) C18:1-ACCA 0.5 ppm—More body and fatty notes, salivating and good aftertaste

(410) C18:1-ACCA 0.2 ppm—Saltier, Stronger and more umami

(411) Test in Jus and Fonds

(412) C18:1-ACCA 40 ppb—more salty, fatty, total profile is enhanced

(413) Test in Cheese

(414) Fat level: 1-40%

(415) Salt: 0.3-2%

(416) Spreadable Cheese ERU

(417) C18:1-ACCA 0.5 ppm—Strong umami, lingering cheese bite

(418) Cheese Sauce: 5% Fat 1.6% Salt

(419) C18:1-ACCA 0.5 ppm—Strong umami, cheese bite, expanding

(420) 17—Testing Glutamic Acid and Aspartic Acid Derivatives

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

(422) Comparison in a Mango Juice Drink

(423) Base is water, 8% sucrose, 0.1% citric acid, 1% clear mango juice, proprietary mango flavour @ 0.05%

(424) Base: fruity mango

(425) Base plus C18:1-glu at 1 ppm heavy, Jammy, enhanced mango, more sulfury, sl umami

(426) Base plus C16:1-glu at 1 ppm full, heavy, jammy, long lasting

(427) Base plus C18:0-glu at 1 ppm fatty, full, sweet juicy

(428) Base plus C16:0-glu at 1 ppm slightly more juicy impact

(429) Comparison in a Mango Juice Drink

(430) Base is water, 8% sucrose, 0.1% citric acid, 1% clear mango juice, proprietary mango flavour @ 0.05%

(431) Base: fruity mango

(432) Base plus C16:0-asp at 1 ppm fatty, soft, apple skin

(433) Base plus C18:1-asp at 1 ppm juicy fruit like

(434) Base plus C18:0-asp at 1 ppm fatty, fruity, long lasting

(435) Base plus C18:2-asp at 1 ppm fatty, authentic fruit like, slight raspberry and pear note

(436) Comparison in a Strawberry Drink

(437) Base is water, 7% sucrose, 0.1% citric acid, proprietary strawberry flavour @ 0.015%

(438) Base: sweet, fruity, estery strawberry

(439) Base plus C18:1-glu at 0.5 ppm: nice mouthfeel, more natural strawberry, full juicy

(440) Base plus C16:1-glu at 0.5 ppm: full, fatty, creamy

(441) Base plus C18:0-glu at 0.5 ppm: fruity, juicy, long lasting

(442) Comparison in a Vanilla Milk Drink

(443) Base: Milk 0.15% fat, sweetened with 4% sucrose by weight, flavoured with proprietary Vaniline @ 10 ppm+Vanilla extract @ 0.03%

(444) Base: sweet vanillic, slightly beany taste

(445) Base plus C18:0-glu at 1 ppm full, fatty, whipped cream like

(446) Base plus C16:1-glu at 1 ppm full, fatty, creamy, sweet vanilla

(447) Base plus C16:0-glu at 1 ppm ice cream like, sweet, very full

(448) Base plus C18:1-glu at 1 ppm full, beany, more sweet

(449) Base: sweet vanillic, slightly beany taste

(450) Base plus C18:2-asp at 2 ppm: sweet full very natural vanilla

(451) Test in Chocolate Flavoured Drink Flavoured

(452) Base: Water, 4% sucrose, proprietary chocolate flavour @ 0.03%

(453) Base: sweet vanillic, cocoa

(454) Base plus C18:2-asp at 2 ppm: cardboard, sweet dry

(455) Base: sweet vanillic, cocoa

(456) Base plus C18:1-glu at 0.5 ppm full cocoa, nice sweet

(457) Base plus C16:0-glu at 0.5 ppm sweet, fatty cocoa, sulphur is enhanced, enhanced nib note

(458) Comparison in a Bouillon

(459) Base is Maggi beef bouillon 1 tablet in 500 ml of hot water

(460) Base: salty, umami, powdery

(461) Base plus C16:0-asp at 1 ppm salty, peppery

(462) Base plus C18:1-asp at 1 ppm not special

(463) Base plus C1; 8:0-asp at 1 ppm lot off fullness and body, less salty

(464) Comparison in a Pear Drink

(465) Base: water, 7% sugar, 0.1% citric acid, proprietary pear flavour at 0.025%

(466) Base: nice pear, fruity estery, green

(467) Base plus C18:1-glu at 0.5 ppm nice fatty, juicy, long lasting

(468) Base plus C16:0-glu at 0.5 ppm fatty long lasting

(469) Base: nice pear, fruity estery, green

(470) Base plus C18:2-asp at 1 ppm very juicy, authentic, texture like pear 3D

(471) Comparison in a Peach Drink

(472) Base is water, 8% sugar, 0.1% citric acid, proprietary peach flavour at 0.05%

(473) Base: fruity peach

(474) Base plus C18:1-glu at 1 ppm ripe, much more juicy, long lasting, more fatty and sweet

(475) Base plus C16:0-glu at 1 ppm fruity, nice juicy, sweet, soft peach skin

(476) Base: fruity peach

(477) Base plus C18:2-asp at 1 ppm fatty skin like, slight apple note

(478) Test on Baileys Cream Liqueur:

(479) Base: Baileys cream liqueur (containing 17% alcohol, carbohydrates 25% and 13% fat)

(480) Base: alcoholic, cream, cocoa

(481) Base plus C18:2 gaba 1 ppm: strongly enhanced alcohol effect, more cocoa, very creamy and long lasting aftertaste.

(482) Test on Heineken Beer:

(483) Base: Heineken beer (containing 4% alcohol)

(484) Base: Bitter, hop like, fruity, malty, alcoholic

(485) Base plus C18:2 gaba 0.5 ppm: more hoppy, more bitter, more malt and stronger alcohol impact.

(486) Test on Mouthwash

(487) Base: Paradontax alcohol free mouthwash.

(488) Base: spicy, eugenol, minty, cooling, burning, bitter

(489) Base plus C18:2 gaba 1 ppm: much less bitter, very sweet, smooth, less burning, round spicy, more minty and more cooling.

(490) 18—Testing Leucine, Isoleucine and Valine Derivatives

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

(492) Comparison in a Mango Juice Drink

(493) Base is water, 8% sucrose, 0.1% citric acid, 1% clear mango juice, proprietary mango flavour @0.05%

(494) Base: fruity mango

(495) Base plus C16:0-leu at 2 ppm very fruity, ripe mango taste, strawberry note

(496) Base plus C18:1-leu at 2 ppm very long lasting, ripe, fruity, juicy

(497) Base plus C18:0-leu at 2 ppm fruity strawberry like, ripe, long lasting

(498) Base: fruity mango

(499) Base plus C18:2-val at 1 ppm ripe, very juicy nice, full body, long lasting

(500) Test in a Strawberry Drink

(501) Base is 7% sucrose, 0.1% citric acid, proprietary strawberry flavour @ 0.015%

(502) Base: sweet, fruity, estery strawberry

(503) Base plus C18:0-leu at 0.5 ppm fruity authentic strawberry, stronger strawberry, ripe, long lasting, juicy

(504) Test in a Strawberry Yoghurt

(505) Base: Yoghurt 1.5% fat yoghurt, 8% sucrose, proprietary strawberry flavour @ 0.015%

(506) Base: fruity, strawberry

(507) Base plus C18:0-leu at 2 ppm fruity authentic strawberry, stronger strawberry, ripe, long lasting, juicy, creamy yoghurt.

(508) Test in Peach Flavoured Drink:

(509) Base is water, 8% sugar, 0.1% citric acid, proprietary peach flavour at 0.05%

(510) Base: fruity peach

(511) Base plus C18:1-val at 1 ppm tropical, fatty, skin, juicy

(512) Base plus C16:0-val at 1 ppm very juicy

(513) Test in Beef Bouillon:

(514) Base is Maggi beef bouillon 1 tablet in 500 ml of hot water

(515) Base: salty, umami, powdery

(516) Base plus C18:2-val at 1 ppm more umami, salivating, salty

(517) 19—Testing Proline Derivatives

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

(519) Comparison in a Mango Juice Drink

(520) Base is water, 8% sucrose, 0.1% citric acid, 1% clear mango juice, proprietary mango flavour @ 0.05%

(521) Base: Fruity mango

(522) Base plus C16:0-pro at 1 ppm overripe, orange like, long lasting after taste

(523) Base plus C18:1-pro at 1 ppm sweet, orange albedo

(524) Test in Orange Beverage

(525) Base is water, 7% sugar, 0.1% citric acid, proprietary orange flavour @ 0.06%.

(526) Base: orange, fruity, slightly candy

(527) Base plus C18:2-pro at 1 ppm: very juicy, authentic orange

(528) Test in Lemon Beverage

(529) Base is water, 7% sucrose, 0.15% citric acid, proprietary lemon flavor

(530) Base: floral, citral, lemon

(531) Base plus C18:2-pro at 1 ppm: very juicy, more citral like, very authentic.

(532) Test in Bouillon

(533) Base is Maggi beef bouillon 1 tablet in 500 ml of hot water

(534) Base: salty, umami, powdery

(535) Base plus C16:0-pro at 1 ppm: more salty, full, darker, more meat-like

(536) Base plus C18:1-pro at 1 ppm: full, more umami, long lasting

(537) 20—Testing with Methionine Derivatives

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

(539) Comparison in a Mango Juice Drink

(540) Base is 8% sucrose, 0.1% citric acid, 1% clear mango juice, proprietary mango flavour @0.05%

(541) Base: fruity mango

(542) Base plus C18:2-met at 1 ppm: fresh nice juicy

(543) Base plus C18:1-met at 1 ppm: sweeter, juicy, salivating.

(544) Base plus C16:0-met at 1 ppm: fatty, full body, juicy, metallic

(545) Base plus C12:1-met at 1 ppm: ripe full, more juicy, slightly metallic

(546) Base plus 8:0-met at 1 ppm: green fresh, no additional body

(547) Comparison in Beef Bouillon

(548) Base is Maggi beef bouillon 1 tablet in 500 ml of hot water

(549) Base: salty, umami, powdery

(550) Base plus C18:2-met at 1 ppm: salivating salty, umami

(551) Base plus C18:1-met at 1 ppm: very strong salty impact and aftertaste

(552) Base plus C16:0-met at 1 ppm: salty, full, nice salivating, lingering

(553) Base plus C12:1-met at 1 ppm: more salty

(554) Base plus C8:0-met at 1 ppm: more salty, no additional fullness

(555) Base: salty, umami, powdery

(556) Base plus C18:1-met at 1 ppm: very strong salty impact and aftertaste, more fatty, mouthfeel, lingering full bodied

(557) Base plus C18:1-met at 50 ppb: more salty, more bouillon taste

(558) Base plus C18:1-met at 25 ppb: more peppery, more salty

(559) Test in Orange Beverage

(560) Base is water, 7% sugar, 0.1% citric acid, proprietary orange flavour @ 0.06%

(561) Base: orange, fruity, slightly candy

(562) Base plus C16:0-met at 1 ppm: slightly metallic, fresh

(563) Base plus C18:1-met at 1, ppm: very juicy fresh, authentic, juicy

(564) Base plus C12:1-met at 1 ppm: nice orange, fresh

(565) Test in Lemon Beverage

(566) Base is water, 7% sucrose, 0.15% citric acid, proprietary lemon flavor

(567) Base: floral, citral, lemon

(568) Base plus C18:1-met at 1 ppm: fresh, less floral, very juicy, very authentic

(569) Base plus C12:1-met at 1 ppm: fresh, slightly more citral

(570) 21—Testing Serine Derivatives

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

(572) Comparison in a Mango Juice Drink

(573) Base is water, 8% sucrose, 0.1% citric acid, 1% clear mango juice, proprietary mango flavour @ 0.05%.

(574) Base: fruity mango

(575) Base plus C18:0-ser at 1 ppm: nice sweet, pineapple, long lasting

(576) Base plus C18:2-ser at 1 ppm: apple note, less acidic, juicy

(577) Comparison in Beef Bouillon

(578) Base is Maggi beef bouillon 1 tablet in 500 ml of hot water

(579) Base: salty, umami, powdery

(580) Base plus C18:0-ser at 1 ppm: more salty, richer, more umami

(581) Base plus C18:2-ser at 1 ppm: more umami, slightly more salty, sweet

(582) Test in Orange Beverage

(583) Base is water, 7% sugar, 0.1% citric acid, proprietary orange flavour @ 0.06%.

(584) Base: orange, fruity, slightly candy

(585) Base plus C18:2-ser at 1 ppm: very fresh, authentic, slightly less sweet, more juicy

(586) 22—Testing Glycine Derivatives

(587) 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

(588) Comparison in an Orange Drink

(589) Base: water, 8% sucrose, 0.1% citric acid, proprietary orange flavour @ 0.06%.

(590) Base: orange, fruity, slightly candy

(591) Base plus C16:0-gly at 1 ppm sweet after taste juicy

(592) Base plus C18:3-gly at 1 ppm sweet upfront, juicy, authentic, long lasting and sweet 20 aftertaste

(593) Base plus C18:2-gly at 1 ppm very juicy, salivating, authentic, long lasting and sweet aftertaste.

(594) 23—Testing Asparagine and Glutamate Derivatives

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

(596) Test in Pineapple Flavoured Drink:

(597) Base is water, 8% sugar, 0.1% citric acid and proprietary pineapple flavour at 0.03%

(598) Base: candy pineapple, jammy

(599) Base plus C18:2-asn at 1 ppm very ripe, jammy, long lasting, authentic

(600) Test in Pear Flavoured Drink:

(601) Base is water, 8% sugar, 0.1% citric acid, proprietary pear flavour at 0.025%

(602) Base: nice pear, fruity estery, green

(603) Base plus C18:2-asn at 1, ppm very ripe, authentic pear, very juicy, long lasting

(604) Base plus C18:1-glu at 1 ppm ripe, authentic pear, juicy, fatty skin like

(605) Test in a Strawberry Drink

(606) Base is 7% sucrose, 0.1% citric acid, proprietary strawberry flavour @ 0.015%

(607) Base: sweet, fruity, estery strawberry

(608) Base plus C18:2-asn at 0.5 ppm fuller, sweeter, jammy aftertaste, long lasting

(609) Base plus C18:1-gln at 0.5 ppm more juicy, creamy, fruity long lasting

(610) Comparison in a Vanilla Milk Drink

(611) Base: Milk 0.15% fat, sweetened with 4% sucrose by weight, flavoured with proprietary Vaniline @ 10 ppm+Vanilla extract @ 0.03%

(612) Base: sweet vanillic, slightly beany taste

(613) Base plus C18:2-asn at 1 ppm sweeter more fatty round

(614) Base plus C18:1-glu at 1 ppm sweet vanillic

(615) Base plus C18:2-glu at 1 ppm sweet vanillic, creamy, beany

(616) 24—Testing Alanine Derivatives

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

(618) Test in a Mango Juice Drink

(619) Base is 8% sucrose, 0.1% citric acid, 1% clear mango juice, proprietary mango flavour @0.05%

(620) Base: fruity mango

(621) Base plus C18:2-ala at 1 ppm: fatty, juicy, apple skin taste

(622) Test in a Strawberry Drink

(623) Base is 7% sucrose, 0.1% citric acid, proprietary strawberry flavour @ 0.015%

(624) Base: sweet, fruity, estery strawberry

(625) Base plus C18:2-ala at 0.5 ppm creamy, fruity, juicy, green, long lasting, strawberry

(626) Test in Peach Flavoured Drink:

(627) Base is water, 8% sugar, 0.1% citric acid, proprietary peach flavour at 0.05%

(628) Base: fruity peach

(629) Base plus C18:2-ala at 1 enhanced sulfur note, powdery, soft peach skin like, authentic peach, slight raspberry note