N-acylated methionine derivatives as food flavoring compounds

Abstract

A flavour composition comprising a compound of formula (I) ##STR00001## and 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.

Claims

1. A caloric or non-caloric beverage comprising a compound selected from the group consisting of: N-geranoyl-Met, N-palmitenoyl-Met, N-oleoyl-Met, N-stearoyl-Met, N-linoleoyl-Met and N-linolenoyl-Met and wherein, when the compound is present in the beverage at a level of 1 ppb-10 ppm in the beverage composition, which, further contains at least one carbohydrate sweetener selected from: sucrose, high fructose corn syrup, fructose and glucose, or at least one high intensity, non-nutritive sweetener selected from: aspartame, acesulfame K, sucralose, cyclamate, sodium saccharin, neotame, rebaudioside A, and/or stevia-based sweetners.

2. A soy-based edible composition comprising a compound selected from the group consisting of: N-geranoyl-Met, N-palmitenoyl-Met, N-oleoyl-Met, N-stearoyl-Met, N-linoleoyl-Met and N-linolenoyl-Met and wherein, when the compound is present in the edible composition at a level of from 1 ppb-10 ppm in the edible composition.

3. An edible product comprising a at least one flavour co-ingredient, and a stock solution comprising 0.01 to 1% by weight of a compound selected from the group consisting of: N-geranoyl-Met, N-palmitenoyl-Met, N-oleoyl-Met, N-stearoyl-Met, N-linoleoyl-Met and N-linolenoyl-Met and wherein, when the compound is present in the edible product at a level of 1 ppb-10 ppm in the edible product, wherein the compound induces salivation.

4. An edible product comprising a at least one flavour co-ingredient, and a stock solution comprising 0.01 to 1% by weight of a compound selected from the group consisting of: N-geranoyl-Met, N-palmitenoyl-Met, N-oleoyl-Met, N-stearoyl-Met, N-linoleoyl-Met and N-linolenoyl-Met and wherein, when the compound is present in the edible product at a level of 1 ppb-10 ppm in the edible product, wherein the compound imparts an umami boosting effect.

5. An edible product comprising a at least one flavour co-ingredient, and a stock solution comprising 0.01 to 1% by weight of a compound selected from the group consisting of: N-geranoyl-Met, N-palmitenoyl-Met, N-oleoyl-Met, N-stearoyl-Met, N-linoleoyl-Met and N-linolenoyl-Met and wherein, when the compound is present in the edible product at a level of 1 ppb-10 ppm in the edible product, wherein the compound imparts improved mouthfeel.

6. An edible product comprising a at least one flavour co-ingredient, and a stock solution comprising 0.01 to 1% by weight of a compound selected from the group consisting of: N-geranoyl-Met, N-palmitenoyl-Met, N-oleoyl-Met, N-stearoyl-Met, N-linoleoyl-Met and N-linolenoyl-Met and wherein, when the compound is present in the edible product at a level of 1 ppb-10 ppm in the edible product, wherein the compound imparts increased fat perception.

7. An edible product comprising a at least one flavour co-ingredient, and a stock solution comprising 0.01 to 1% by weight of a compound selected from the group consisting of: N-geranoyl-Met, N-palmitenoyl-Met, N-oleoyl-Met, N-stearoyl-Met, N-linoleoyl-Met and N-linolenoyl-Met and wherein, when the compound is present in the edible product at a level of 1 ppb-10 ppm in the edible product wherein the compound imparts upfront sweetness perception and mouthfeel reminiscent of sugar.

8. A powder soft drink composition comprising: a stock solution comprising 0.01 to 1% by weight of a compound selected from the group consisting of: N-geranoyl-Met, N-palmitenoyl-Met, N-oleoyl-Met, N-stearoyl-Met, N-linoleoyl-Met and N-linolenoyl-Met and wherein, when the compound is present in the powder soft drink composition at a level of 1 ppb-10 ppm in the powder soft drink composition, and, a flavor oil.

9. The powder soft drink composition according to claim 8, wherein the flavor oil is a citrus oil.

10. An alcoholic beverage comprising: a stock solution comprising 0.01 to 1% by weight of a compound selected from the group consisting of: N-geranoyl-Met, N-palmitenoyl-Met, N-oleoyl-Met, N-stearoyl-Met, N-linoleoyl-Met and N-linolenoyl-Met and wherein, when the compound is present in the beverage at a level of 1 ppb-10 ppm in the alcoholic beverage.

11. An edible product comprising 1 ppb-10 ppm of a compound selected from the group consisting of: N-geranoyl-Met, N-palmitenoyl-Met, N-oleoyl-Met, N-stearoyl-Met, N-linoleoyl-Met and N-linolenoyl-Met and wherein, the compound accentuates the taste or mouth feel characteristics the edible product in which it is incorporated.

12. A flavour composition comprising a flavor co-ingredient and a compound selected from the group consisting of: N-geranoyl-Met, N-palmitenoyl-Met, N-oleoyl-Met, N-stearoyl-Met, N-linoleoyl-Met and N-linolenoyl-Met and wherein, the compound accentuates the taste or mouth feel characteristics of edible products in which it is present at a level of from 1 ppb-10 ppm in the edible product.

13. The flavour composition of claim 12, wherein the flavour co-ingredient is at least one of sugars, fats, salt, MSG, calcium ions, phosphate ions, organic acids, proteins, purines and mixtures thereof.

14. An edible product comprising 1 ppb-10 ppm of a compound selected from the group consisting of: N-geranoyl-Met, N-palmitenoyl-Met, N-oleoyl-Met, N-stearoyl-Met, N-linoleoyl-Met and N-linolenoyl-Met.

Description

NMR DATA (EXAMPLES)

3.1 Structure 3 Met-C12:1

(1) ##STR00010##

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

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

3.2 Structure 5 Met-C18:1

(4) ##STR00011##

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

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

Application Examples

Testing with Methionine Derivatives

(7) 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

(8) Comparison in a Mango Juice Drink

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

(10) Base: fruity mango

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

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

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

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

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

(16) Comparison in Beef Bouillon

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

(18) Base: salty, umami, powdery

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

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

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

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

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

(24) Base: salty, umami, powdery

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

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

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

(28) Test in Orange Beverage

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

(30) Base: orange, fruity, slightly candy

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

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

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

(34) Test in Lemon Beverage

(35) Basis water, 7% sucrose, 0.15% citric acid, proprietary lemon flavor

(36) Base: floral, citral, lemon

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

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