N-Acyl Derivatives of Gamma Amino - Butyric Acid and Beta Alanine as Food Flavouring Compounds

Abstract

A flavour composition comprising a compound according to the formula (I) edible salts thereof, 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 m is 0 or 1.

##STR00001##

Claims

1. A compound according to formula (I): ##STR00024## or edible salts thereof, wherein 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, and m is 0 or 1, an wherein, the compound of formula (I) accentuates the existing flavor or existing mouth feel characteristics of an edible foodstuff product further comprising at least one flavor co-ingredient, or of a beverage further comprising at least one flavor co-ingredient, when the compound of formula (I) is incorporated in an amount of 1 ppb to 10 ppm within the edible foodstuff product, or within the beverage product.

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29. The composition of claim 1, wherein m=1, the amino acid residue connected to the carbonyl carbon atom is a residue of gamma amino butyric acid (GABA).

30. The composition of claim 1, wherein m=0, the amino acid residue connected to the carbonyl carbon atom is a residue of beta-alanine (Beta Ala).

31. The composition of claim 1, wherein the compound of formula (I) includes a carboxylic acid residue having 10, 12, 14, 16 or 18 carbon atoms which may be saturated or unsaturated and may contain one or two double bonds, and the amino acid residue is a residue of gamma amino butyric acid (GABA) or is a residue of beta-alanine (Beta Ala).

32. The composition of claim 31, wherein the compound of formula (I) includes a carboxylic acid residue having 18 carbon atoms which may be saturated or unsaturated and may contain one or two double bonds, and the amino acid residue is a residue of gamma amino butyric acid (GABA).

33. The composition of claim 31, wherein the compound of formula (I) includes a carboxylic acid residue having 18 carbon atoms which may be saturated or unsaturated and may contain one or two double bonds, and the amino acid residue is a residue of beta-alanine (Beta Ala).

34. A caloric or non-caloric beverage comprising 1 ppb to 10 ppm of a compound according to formula (I) ##STR00025## or edible salt thereof, wherein 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, and m is or 1, an wherein, the compound of formula (I) accentuates the existing flavor or existing mouth feel characteristics of the beverage which further comprises at least one flavor co-ingredient.

35. The beverage of claim 34, which further comprises a carbohydrate sweetener selected from: sucrose, high fructose corn syrup, fructose and glucose, or a high intensity, non-nutritive sweetener selected from: aspartame, acesulfame K, sucralose, cyclamate, sodium saccharin, neotame, rebaudioside A, and/or other stevia-based sweeteners.

36. The beverage of claim 34, wherein the compound of formula (I) includes a carboxylic acid residue having 10, 12, 14, 16 or 18 carbon atoms which may be saturated or unsaturated and may contain one or two double bonds, and the amino acid residue is a residue of gamma amino butyric acid (GABA) or is a residue of beta-alanine (Beta Ala).

37. The beverage of claim 36, wherein the compound of formula (I) includes a carboxylic acid residue having 18 carbon atoms which may be saturated or unsaturated and may contain one or two double bonds, and the amino acid residue is a residue of gamma amino butyric acid (GABA).

38. The beverage of claim 36, wherein the compound of formula (I) includes a carboxylic acid residue having 18 carbon atoms which may be saturated or unsaturated and may contain one or two double bonds, and the amino acid residue is a residue of beta-alanine (Beta Ala).

38. A soy-based edible composition comprising 1 ppb to 10 ppm of a compound according to formula (I) ##STR00026## or edible salt thereof, wherein 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, and m is or 1, an wherein, the compound of formula (I) accentuates the existing flavor or existing mouth feel characteristics of the soy-based edible composition which further comprises at least one flavor co-ingredient.

39. The soy-based edible composition of claim 38, wherein the compound of formula (I) includes a carboxylic acid residue having 10, 12, 14, 16 or 18 carbon atoms which may be saturated or unsaturated and may contain one or two double bonds, and the amino acid residue is a residue of gamma amino butyric acid (GABA) or is a residue of beta-alanine (Beta Ala).

40. The soy-based edible composition of claim 39, wherein the compound of formula (I) includes a carboxylic acid residue having 18 carbon atoms which may be saturated or unsaturated and may contain one or two double bonds, and the amino acid residue is a residue of gamma amino butyric acid (GABA).

41. The soy-based edible composition of claim 39, wherein the compound of formula (I) includes a carboxylic acid residue having 18 carbon atoms which may be saturated or unsaturated and may contain one or two double bonds, and the amino acid residue is a residue of beta-alanine (Beta Ala).

42. A snack food edible composition comprising 1 ppb to 10 ppm of a compound according to formula (I) ##STR00027## or edible salt thereof, wherein 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, and m is or 1, an wherein, the compound of formula (I) accentuates the existing flavor or existing mouth feel characteristics of the snack food edible composition edible composition which further comprises at least one flavor co-ingredient.

43. The snack food edible composition of claim 42, wherein the compound of formula (I) includes a carboxylic acid residue having 10, 12, 14, 16 or 18 carbon atoms which may be saturated or unsaturated and may contain one or two double bonds, and the amino acid residue is a residue of gamma amino butyric acid (GABA) or is a residue of beta-alanine (Beta Ala).

44. The snack food edible composition of claim 43, wherein the compound of formula (I) includes a carboxylic acid residue having 18 carbon atoms which may be saturated or unsaturated and may contain one or two double bonds, and the amino acid residue is a residue of gamma amino butyric acid (GABA).

45. The snack food edible composition of claim 43, wherein the compound of formula (I) includes a carboxylic acid residue having 18 carbon atoms which may be saturated or unsaturated and may contain one or two double bonds, and the amino acid residue is a residue of beta-alanine (Beta Ala).

46. The snack food edible composition of claim 42, wherein the snack food edible composition is selected from: extruded snacks, puffed products, potato chips, crisps, nuts, tortilla-tostada, pretzels, cheese snacks, corn snacks, potato-snacks, corn chips, puffed products, ready-to-eat popcorn, microwaveable popcorn, pork rinds, nuts, crackers, and cracker snacks.

47. The snack food edible composition of claim 42, wherein the snack food edible composition contains about 40% or less by weight of fat.

48. The snack food edible composition of claim 47, wherein the snack food edible composition contains about 30% or less by weight of fat.

49. The snack food edible composition of claim 48, wherein the snack food edible composition contains about 25% or less by weight of fat.

50. The snack food edible composition of claim 48, wherein the snack food edible composition contains about 10% or less by weight of fat.

51. The snack food edible composition of claim 48, wherein the snack food edible composition contains about 5% or less by weight of fat.

Description

SYNTHESIS EXAMPLES

1. General Structure

[0154] ##STR00003##

[0155] where

[0156] R.sup.1=is a straight chain hydrocarbon group having 9 to 21 carbon atoms and containing zero to three double bonds

[0157] or

[0158] R.sup.1 is a [(1E)-2,6-dimethylhepta-1,5-dien-1-yl]-group.

[0159] and

[0160] n=1 or 2

2. Synthesis

2.1 Route A: (DCC Method)

[0161] 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.

[0162] 1 g of 85-90% pure product could be obtained.

2.2 Route B (DCC Method With Protection Group)

Step 1:

[0163] 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%.

Step 2:

[0164] 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.

[0165] 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%

2.3 Route C (Acid Chloride)

[0166] An amino acid (20 mmol) was dissolved in a solution of sodiumhydroxide (54.5 mmol) in water (40 ml).

[0167] 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.

[0168] Organic layers were combined, dried and evaporated.

[0169] 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%).

2.4 All Synthesized Compounds

[0170]

TABLE-US-00001 TABLE 1 List of synthesized compounds Amino Carboxylic Structure acid acid Structure Route 1 GABA C10:0 [00004] C 2 GABA C12:0 [00005] C 3 GABA C12:1 [00006] C 4 GABA C10:2 [00007] C 5 GABA C14:0 [00008] C 6 GABA C16:0 [00009] C 7 GABA C16:1 [00010] A 8 GABA C18:0 [00011] C 9 GABA C18:1.sub.c [00012] C 10 GABA C18:1.sub.t [00013] C 11 GABA C18:2 [00014] A 12 GABA C18:3 [00015] A 13 GABA C22:1 [00016] C 14 Beta- alanine C16:1 [00017] A 15 Beta- alanine C18:1 [00018] C 16 Beta- alanine C18:2 [00019] A

3. NMR Data (Examples)

3.1 Structure 1 GABA-C10:0

[0171] ##STR00020##

[0172] .sup.1H NMR (600 MHz, DMSO-d.sub.6)

ppm 0.83-0.87 (m, 3 H, H-C(10)) 1.18-1.29 (m, 12 H, H-C(4, 5, 6, 7, 8, 9) 1.46 (quin, J=7.22 Hz, 2 H, H-C(14)) 1.59 (quin, J=7.22 Hz, 2 H, H-C(3)) 2.02 (t, J=7.39 Hz, 2 H, H-C(2)) 2.19 (t, J=7.39 Hz, 2 H, H-C(13)) 3.00-3.05 (m, 2 H, H-C(15)) 7.77 (t, J=5.50 Hz, 1 H, H-N[15]

[0173] .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(.SUP.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))

3.2 Structure 2 GABA-C12:0

[0174] ##STR00021##

[0175] .sup.1H NMR (600 MHz, DMSO-d.sub.6)

ppm 0.85 (t, J=6.87 Hz, 3 H, H-C(12)) 1.15-1.33 (m, 16 H, H-C(4, 5, 6, 7, 8, 9, 10, 11) 1.41-1.51 (m, 2 H, H-C(3)) 1.59 (quin, J=7.22 Hz, 2 H, H-C(16)) 2.02 (t, J=7.56 Hz, 2 H, H-C(2)) 2.19 (t, J=7.56 Hz, 2 H, H-C(15)) 3.02 (q, J=6.53 Hz, 2 H, (H-C(17)) 7.77 (t, J=5.33 Hz, 1 H, H-N(13))

[0176] .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))

3.3 Structure 11 GABA-C18:2

[0177] ##STR00022##

[0178] .sup.1H NMR (600 MHz, CHLOROFORM-d)

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

[0179] .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))

3.4 Structure 16 beta-Alanine-C18:2

[0180] ##STR00023##

[0181] .sup.1H NMR (600 MHz, DMSO-d.sub.6)

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

APPLICATION EXAMPLES

Condiments and Fats

[0182] The following formulations were prepared and tasted by trained panelists.

Soy Based Product

[0183] Salt level pure product between 5-40%

[0184] Salt level in application 0.3-1.0%

[0185] 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

[0186] 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.

Fish Based

[0187] Salt level pure product between 5-40%

[0188] Salt level in application 0.3-1.0%

[0189] C18:2-gaba-(0.5 ppm) was added to a 1% diluted fish sauce sauce (0.27% salt). The resultant composition was deemed to be stronger in umami, longer lasting and richer.

[0190] 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.

Emulsions-Colloids

Water in Oil

Butter

[0191] Fat levels 20-90%

[0192] Salt levels 0.1-1%

[0193] Blueband halvarine 39% fat 0.35% salt

[0194] C18:2-gaba added at 1 ppm. The composition was considered to exhibit a more authentic butter taste, with more mouthfeel

Pilaf

[0195] Standard cooked rice with 10% of the above mentioned C18:2-gaba flavoured butter was deemed to have more mouthfeel, with a lingering creamy authentic butter taste.

Oil in Water

Mayonnaise

[0196] Fat levels between 10-80%

[0197] Low fat Mayonnaise (27% Fat)

[0198] C18:2-gaba (0.5 ppm) added to the mayonnaise was deemed to produce a creamy, thick mouthfeel with a full fat impression.

Dressings

[0199] Oil levels 0.5-50%

[0200] Acidity PH 3-6

[0201] low fat salad dressing (13.6% Fat)

[0202] C18:2-gaba (0.5PPM) was added to the dressing and produced a better mouthfeel that was impressively creamy.

Soups and Bouillons

[0203] Fat levels 0.1-10%

[0204] Salt levels 0,3-1,4%

[0205] Standard Chicken bouillon base, 0.7% salt, 0.5% fat

[0206] C18:2-gaba@ 0.5 PPMStrong, Salty, Umami, mouthfeel

6-Cheese

[0207] Fat level 1-40%

[0208] Salt 0.3-2%

[0209] Spreadable cheese ERU

[0210] C18:2-gaba @ 0.5 PPM Full, Salty, cheese bite, more mature

[0211] Cheese sauce: 5% fat 1.6% salt

[0212] C18:2-gaba @ 0.5 PPM Full, Salty, cheese bite expanding

Beef and Poultry

[0213] Differentiator high temperature 100-250 degrees Celcius in a frying in oil process

[0214] 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.

[0215] Taste of the chicken is more juicy, succulent, lingering more white meat

[0216] Also the oil has more savoury golden brown notes.

Baked Goods and Pizza

[0217] Differentiator high temperature 100-250 degrees Celcius in hot air baking process

[0218] C18:2-gaba @ 0,5PPM in the crust and @ 0.5 PPM in the tomato sauce

[0219] The pizza was topped off with cheese and baked in a hot air oven @ 200 degrees Celcius

[0220] The crust was less dry, more succulent and the tomato was richer, sweeter and the total lingering aftertaste was very rich and pleasant

Snack Product

[0221] 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 arc reported:

[0222] C18:2-gaba 1ppm: Fatty full, cheesy, cheese crust, long lasting,

[0223] C18:2-gaba 0.5ppm: increased dairy, cheesy.

Air Expanded Base

[0224] 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:

[0225] C18:2-gaba 1 ppm: Fatty full, cheesy, cheese crust, long lasting, cover base C18:2-gaba 0.5 ppm: Increased dairy, cheese.

Testing in Dairy Products

[0226] The following tests were carried out on dairy products processed by fermentation, pasteurization or UHT. The products contain fat, protein and calcium.

UHT Milk Cream Flavoured, Non Sweetened and different Fat Levels

[0227] In a UHT milk containing 0% 1.5% and 3% fat, flavoured with a proprietary cream flavour dosed at 0.03%

[0228] C18:2-gaba was added at 2 ppm.

[0229] Samples were evaluated by expert tasters.

[0230] 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:

[0231] UHT milk 0% fat, Cream flavour (0.03%): Milky, slightly creamy, card board aftertaste

[0232] UHT milk 0% fat, Cream flavour (0.03%) but with C18:2 gaba added at 2 ppm: Very creamy, milky, long lasting.

[0233] UHT milk 1.5% fat, Cream flavour (0.03%): Milky, slightly creamy

[0234] UHT milk 1.5% fat, Cream flavour (0.03%) with added C18:2 gaba at 2 ppm: very creamy, milky, long lasting, salivating.

[0235] UHT milk 3.0% fat, Cream flavour (0.03%): Milky, slightly creamy

[0236] 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.

UHT Sweetened Banana Flavoured Milk, With Different Fat Levels

[0237] 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.

[0238] 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.

[0239] UHT milk 0% fat, Banana flavour (0.04%): Strong banana, estery, eugenol-like, unbalanced.

[0240] UHT milk 0% fat, Banana flavour (0.04%) C18:2-gaba (0.25 ppm): fuller banana, more authentic, more sweet.

[0241] UHT milk 0% fat, Banana flavour (0.04%), C18:2-gaba (0.5 ppm): fuller banana, authentic, creamy and sweet

[0242] UHT milk 0% fat, Banana flavour (0.04%), C18:2-gaba (1 ppm): creamy, creamy banana, sweet aftertaste.

[0243] UHT milk 3% fat, Banana flavour (0.04%): strong estery banana, eugenol like, spicy

[0244] UHT milk 3% fat, Banana flavour (0.04%), C18:2-gaba (0.25 ppm): more authentic, less estery and more round

[0245] UHT milk 3% fat, Banana flavour (0.04%), C18:2-gaba (0.5 ppm): creamy banana

[0246] UHT milk 3% fat, Banana flavour (0.04%), C18:2-gaba (1 ppm): creamy long lasting and more authentic and more impact.

Yoghurt Cream Flavoured Non-sweetened And Different Fat Levels

[0247] 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, mouthfeel, fullness, salivation, sweetness, juiciness, richness, long lastingness and fattiness.

[0248] Yoghurt 0% fat, Cream flavour (0.03%): very acidic, metallic

[0249] Yoghurt 0% fat, Cream flavour (0.03%), C18:2-gaba 2 ppm: less acdic, slight creamy aftertaste

[0250] Yoghurt 1.5% fat, Cream flavour (0.03%): mild creamy yoghurt

[0251] Yoghurt 1.5% fat, Cream flavour (0.03%), C18:2-gaba 2 ppm: very creamy, thick, nice long lasting, whipped cream note.

[0252] Yoghurt 3% fat, Cream flavour (0.03%): acidic, creamy aftertaste

[0253] Yoghurt 3% fat, Cream flavour (0.03%), C18:2-gaba 2 ppm: less acidic, much more creamy, very long lasting creamy aftertaste.

Strawberry Flavoured Sugar Sweetened Yoghurt

[0254] The base consisted of a 1.5% fat yoghurt base, sweetened with 8% sucrose by weight, flavoured with a proprietary strawberry flavour @ 0.015%.

[0255] Base: fruity, strawberry

[0256] Base plus C18:2-gaba at 2 ppm: very creamy and fresh strawberry

[0257] Base plus C18:0-gaba at 2 ppm: juicy full, jammy

Activa Strawberry Yoghurt

[0258] In a Full fat, Activa strawberry flavoured yoghurt C18:2-gaba

[0259] Activa: jammy strawberry, green and creamy

[0260] Activia plus C18:2-gaba at 2 ppm: very creamy, full and fresh strawberry

Vanilla Flavoured Milk 3.0% Fat

[0261] 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, was added at 0.5 or 2 ppm.

[0262] 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.

[0263] Base: Milk 3% fat, 4% sugar, vanillin 10 ppm, vanilla extract 0.03%

[0264] Base: sweet vanillic, very slightly beany

[0265] Base: C18:2-gaba 2 ppm: beany, fatty, authentic, sweet

Chocolate Milk With Different Fat Content

[0266] In a chocolate milk 1.8% and 3% fat C18:2-gaba was added at 0.5 and 1 ppm.

[0267] 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.

[0268] Chocolate milk 1.8% fat: cocoa powder taste, sweet, slightly creamy

[0269] Chocolate milk 1.8% fat C18:2-gaba at 0.5 ppm: stronger cocoa note, more chocolate vs cocoa

[0270] Chocolate milk 1.8% fat C18:2-gaba at 1 ppm: very creamy, chocolate, long-lasting creamy and chocolate taste.

[0271] Chocolate milk 3% fat: cocoa powder taste, sweet, creamy

[0272] Chocolate milk 3% fat C18:2-gaba at 0.5 ppm: very creamy, enhanced cocoa note.

[0273] Chocolate milk 3% fat C18:2-gaba at 1 ppm: very creamy, lasting, sweet, almost taste like chocolate ice cream.

Soy Milk

[0274] In a soy milk 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

[0275] 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.

[0276] Soy milk, 5% sucrose, milk flavor @ 0.1%: sweet, dry, green, soy bean taste

[0277] 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.

Caloric & Non Caloric Beverages

[0278] 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.

[0279] Sweetener in beverage applications ranges from 0-20%.

Examples

[0280] Carbonated Soft drink: <1% to 15% sweetener

[0281] Still beverages (non-alcoholic): <1% to 15% sweetener

[0282] Juice beverages; <1% to 15% sweetener

[0283] Powdered Soft drinks: <1% to 20% sweetener

[0284] Liquid concentrates: <1% to 20% sweetener

[0285] Alcoholic beverages: <1% to 40% sweetener

[0286] Functional beverages: <1% to 20% sweetener

[0287] Coffee based beverages: <1% to 15% sweetener

[0288] Tea based beverages: <1% to 15% sweetener

Test in 3 In 1 Coffee

[0289] In a 3 in 1 Coffee beverage from Nestle (market product) sweetened with sucrose and containing creamer with fat C18:2-gaba was added.

[0290] 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.

[0291] Base is 3-in-1 Coffee beverage (market product) sweetened with sucrose and containing creamer with fat

[0292] Base: coffee, sweet, mild dairy

[0293] Base plus C18:2-gaba at 1 ppm: very nice mouthfeel effect, creamy as if coffee creamer is added, more sweet.

Test On Tang

[0294] In an orange flavoured Tang powdered soft drink (market product) sweetened with sucrose plus high intensity sweetener and containing citric acid and C18:2-gaba.

[0295] 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

[0296] Base is Orange flavoured Tang

[0297] Base: sweet, orange, licorice, and lingering high intensity sweetener offnotes, bitter, thin

[0298] Base plus C18:2-gaba at 0.5 ppm: enhances sweet juicy orange notes, enhanced mouthfeel. Additionally, the off-notes of the high intensity sweetener were suppressed.

Mango Flavoured Still Beverage Containing Different Levels Of Juice.

[0299] 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 was added, as such.

[0300] 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.

[0301] 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 was added, as such.

[0302] Base is water, 8% sucrose, 0.1% citric acid, 1% clear mango juice (very low juice %) , flavoured with Mango flavor, dosed at 0.05%

[0303] Base: sweet, fruity, mango, thin

[0304] 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

[0305] 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.

[0306] Base is water, 8% sucrose, 0.1% citric acid, 4% clear mango juice (30% reduced juice), flavoured with Mango flavor, dosed at 0.05%

[0307] Base: sweet, fruity, mango, some low mouthfeel

[0308] 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

[0309] 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

[0310] Base is water, 8% sucrose, 0.1% citric acid, 6% clear mango juice (full juice), flavoured with Mango flavor, dosed at 0.05%.

[0311] Base: Sweet, fruity mango, full mouthfeel

[0312] Base plus C18:2-gaba at 1ppm: fatty skin-like, very thick juicy, authentic mango, long lasting mango taste, rich.

Testing in Alcoholic Beverage Products

Test on Baileys Cream Liqueur:

[0313] In Baileys cream liqueur (Market Product) C18:2-gaba was added at 1 ppm.

[0314] 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.

[0315] Base is Baileys cream liqueur

[0316] Base: alcoholic, cream, cocoa

[0317] Base plus C18:2-gaba at 1 ppm: strongly enhanced alcohol effect, more cocoa, very creamy and long lasting aftertaste.

Test on Heineken Beer:

[0318] In Heineken beer (Market Product) C18:2-gaba was added at 0.5 ppm.

[0319] 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.

[0320] Base is Heineken beer

[0321] Base: Bitter, hop like, fruity, malty, alcoholic

[0322] Base plus C18:2-gaba at 0.5 ppm: more hoppy, more bitter, more malt and stronger alcohol impact.

Test on Breezer Orange:

[0323] In Breezer Orange (Market Product) C18:2-gaba was added at 1 ppm.

[0324] 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.

[0325] Base is Breezer Orange

[0326] Base: Bitter, orange, soapy, burning, alcoholic

[0327] Base plus C18:2-gaba at 0.5 ppm: more alcoholic, sweeter, more juicy orange, less soapy

Testing With Beverages Containing Organic Acids From 0.01% to 7%

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

[0328] In a solution containing water, 7% sucrose by weight, and different organic acids, C18:2-gaba was added at 1 ppm. We observed taste effects on the acid perception upon addition of C18:2-gaba.

7% Sucrose Plus Tartaric Acid at 0.121% By Weight

[0329] Base is water, 7% Sucrose by weight, Tartaric acid at 0.121% by weight

[0330] Base: sharp acidic, astringent aftertaste

[0331] 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)

7% Sucrose Plus Malic Acid at 0.1081% By Weight

[0332] Base is water, 7% Sucrose by weight, Malic acid at 0.1081% by weight

[0333] Base: acidic, green, slightly astringent

[0334] 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)

7% Sucrose Plus Citric Acid at 0.1% By Weight

[0335] Base is water, 7% Sucrose by weight, Citric acid at 0.1% by weight

[0336] Base: fresh sharp, acidic

[0337] Base plus C18:2-gaba at 1 ppm decreased sharp acidic perception, full body mouthfeel, higher higher mouth watering, and an impression of the juicy notes of citrus fruit (orange, lemon)

7% Sucrose Plus Fumaric Acid at 0.0936% By Weight

[0338] Base is water, 7% Sucrose by weight, Fumaric acid at 0.0936% by weight

[0339] Base: musty, acidic, astringent

[0340] 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)

Test on Kikkoman Soy Sauce Low Salt

[0341] Base is Kikkoman soy sauce

[0342] Base: salty, dark roast taste, umami

[0343] Base plus C18:2-gaba at 0.5 ppm: much more salty, sweet and long lasting.

Test on Eru Prestige

[0344] Base is Eru prestige

[0345] Base: Yeasty, cheese bite, slightly bitter

[0346] Base plus C18:2-gaba at 0.5 ppm full salty, much more cheese bite, umami, lingering, long lasting.

Test on Menthol Fondant (1%)

[0347] Base is Fondant 65%, sugar syrup 34% and a proprietary menthol flavour at 1%

[0348] Base: Cooling, menthol, sweet

[0349] Base plus C18:2-gaba at 2 ppm: increased menthol impact, stronger cooling more sweet, long lasting, fresh.

Calve Salad Dressing Low Fat:

[0350] Base is Calve salad dressing (market product)

[0351] Base: acidic, rancid, watery

[0352] Base plus C18:2-gaba at 0.5 ppm much fuller, creamy, rich, less acidic.

Calve 60% Reduced Fat Mayonnaise

[0353] Base is Calve Mayonnaise 60% reduced fat (market Product)

[0354] Base: rancid, acidic, empty

[0355] Base plus C18:2-gaba at 0.5 ppm full, rich , creamy, more egg yolk taste.

Comparison in a Mango Juice Drink

[0356] Base is 8% sucrose, 0.1% citric acid, 0.18 g clear mango juice, and a proprietary mango flavour at 0.05%.

[0357] Base: fruity mango

[0358] Base plus C18:2 gaba at 2 ppm: fatty skin like, juicy, authentic

[0359] Base: fruity mango Base plus C18:2-gaba at 2 ppm full long lasting nice juicy, almost a bit salty

Comparison in Beef Bouillon

[0360] Base is Maggi beef bouillon 1 tablet in 500 ml of hot water

[0361] Base: salty, umami, powdery

[0362] Base plus C18:2-gaba at 2 ppm salty, savoury, full

Comparison in a Strawberry Drink

[0363] Base is 7% sucrose, 0.1% citric acid, and a proprietary strawberry flavour @0.015%

[0364] Base: sweet, fruity, estery strawberry

[0365] Base plus C18:2-gaba at 2 ppm fatty mouthfeel, creamy strawberry, fruity and juicy

[0366] Base plus C18:0-gaba at 0.5 ppm mild creamy, fruity, juicy and long lasting

Test in a Strawberry Yoghurt

[0367] Base: Yoghurt 1.5% fat yoghurt, 8% sucrose, proprietary strawberry flavour @ 0,015%

[0368] Base: fruity, strawberry

[0369] Base plus C18:2-gaba at 2ppm, creamy, fruity authentic strawberry , stronger strawberry, ripe, long lasting, juicy

Test in Vanilla Milk:

[0370] Base: Milk 0.15% fat, sweetened with 4% sucrose by weight, flavoured with proprietary

[0371] Vaniline flavour @ 10 ppm +Vanilla ext. @ 0.03%

[0372] Base: sweet vanillic, slightly beany taste

[0373] Base plus C18:2-gaba at 2 ppm: fatty, long lasting authentic vanilla, vanilla bean taste is enhanced

Test in Chocolate Flavoured Drink:

[0374] Base: Water, 4% sucrose, proprietary chocolate flavour at 0.03%

[0375] Base: sweet vanillic, cocoa

[0376] Base plus C18:2-gaba at 2 ppm: full, sweeter, more vanillic, milk chocolate is enhanced, very long lasting

Test in Pear Flavoured Drink:

[0377] Base: water, 7% sugar, 0.1% citric acid, proprietary pear flavour at 0.025%

[0378] Base: nice pear, fruity estery, green

[0379] 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

Test in Peach Flavoured Drink:

[0380] Base is water, 8% sugar, 0.1% citric acid, and proprietary peach flavour at 0.05%

[0381] Base: fruity peach

[0382] Base plus C18:2-gaba at 1 ppm: fruity peach, long lasting, juicy and fatty skin like very authentic

Test in Pineapple Flavoured Drink:

[0383] Base is water, 8% sugar, 0.1% citric acid and proprietary pineapple flavour at 0.03%

[0384] Base: candy pineapple, jammy

[0385] Base plus C18:2-gaba at 1 ppm very ripe, jammy, long lasting and sweet