METHOD FOR PRODUCING AN AROMA MIXTURE CONTAINING UNSATURATED DIENALS

Abstract

The present invention primarily relates to a method for producing an aromatic blend comprising unsaturated dienals. The invention further relates to aromatic blends obtained or obtainable by a method according to the invention and compositions or semi-finished products for producing said compositions, comprising aromatic blends according to the invention. A further aspect of the present invention relates to the use of an aromatic blend according to the invention for aromatizing a composition, preferably a composition serving for food or pleasure, or a semi-finished product for producing such a composition.

Claims

1. A method for producing an aromatic blend comprising one or more unsaturated dienal(s), comprising: a) air oxidizing one or more educt(s) comprising one or more substance(s) selected from the group consisting of punicic acid, punicic acid ester, elaeostearinic acid, elaeostearinic acid ester, linoleic acid and linoleic acid ester, b) optionally disintegrating a part or all or substantially all peroxides in the mixture obtained in a), c) purifying or, respectively, concentrating the dienal(s) produced in a) of the mixture obtained in a) and/or b), if present.

2. The method according to claim 1, wherein after purifying or, respectively, concentrating in c) a residue is obtained comprising a residual amount of educt(s) and wherein the method additionally comprises: d) repeating a), optionally b), and c), wherein the residue obtained from purifying or, respectively, concentrating in c) is used in a).

3. The method according to claim 1, wherein a) is performed in the presence of one or more solvent(s).

4. The method according to claim 1, wherein an amount of air of 10 to 1000 l/h per kg educt(s) is used for the air oxidizing in a).

5. The method according to claim 1, wherein the air oxidizing in a) is performed at a temperature of from 30 to 200 C.

6. The method according to claim 1, wherein the air oxidizing in a) is performed over a time of from 1 to 30 h.

7. The method according to claim 1, wherein the disintegrating of a part or all or substantially all peroxides of the mixture obtained in a) is performed in b) by heating to a temperature of from 100 to 200 C.

8. The method according to claim 1, wherein the purifying or, respectively, concentrating in c) is performed by distillation.

9. The method according to claim 1, wherein one or more solvents is/are added before purifying or, respectively, concentrating in c).

10. The method according to claim 1, wherein washing with an alkaline, aqueous solution is performed before purifying or, respectively, concentrating in c).

11. An aromatic blend obtained or obtainable by the method according to claim 1.

12. The aromatic blend according to claim 11, comprising a weight ratio of 2E/4E-decadienal to 2E/4Z decadienal of 1:1 to 20:1 and/or a weight ratio of 2E/4E-nonadienal to 2E/4Z nonadienal of 1:5 to 20:1 and/or comprising a proportion of 2,4-decadienal, relative to the total weight of the aromatic blend, of 0.1 to 10 wt.-%, and/or a proportion of 2,4-nonadienal, relative to the total weight of the aromatic blend, of 0.001 to 7.5 wt.-%.

13. A composition comprising an aromatic blend according to claim 11 in an amount sufficient for imparting, modifying and/or enhancing one or several olfactory and/or gustatory scents selected from the group consisting of meat, fatty, rancid, nutty, sour, sweet, vegetable or fruit, and dairy.

14. The composition according to claim 13 comprising a proportion of the aromatic blend, relative to the total weight of the composition, of 0.0001 wt.-% to 30 wt.-%.

15. (canceled)

16. The method according to claim 3, wherein the one or more solvent(s) comprises triacetin and/or tiethyl citrate.

17. The method according to claim 3, wherein the one or more solvent(s) is in an amount of 2 to 20 wt. %, relative to the total weight of the educt(s).

18. The method according to claim 5, wherein the air oxidizing in a) is performed at a temperature of from 100 to 130 C.

19. The method according to claim 6, wherein the air oxidizing in a) is performed for 4 to 12 h.

20. The method according to claim 7, wherein the disintegrating of a part or all or substantially all peroxides of the mixture obtained in a) is performed in b) by heating to a temperature of from 100 to 200 C. for 0.5 to 5 h.

Description

Example 1

Reaction of Pomegranate Seed Oil

[0099] 10 g pomegranate seed oil are treated with air (20 L/h) at 120 C. for 6 h. Subsequently, the reaction mixture is heated to 170 C. for 1 h. Subsequently, 8.5 g of this raw material are mixed with 0.8 g triacetin and the desired product is subsequently distilled together with the triacetin (conditions: 0.5 mbar, 180 C., 1 h).

[0100] After distillative purification, the obtained solution (0.83 g) contains 96.04% triacetin, 0.22% 2E,4Z-nonadienal as well as 0.25% 2E,4E-nonadienal.

[0101] Evaluation (smell): lamb meat, fatty, rancid.

Example 2

Reaction of Pomegranate Seed Oil

[0102] 11 g of pomegranate seed oil are treated with air (20 L/h) at 50 C. for 6 h. Subsequently, the reaction mixture is heated to 170 C. for 1 h. Subsequently, 10 g of this raw material are mixed with 1.0 g triacetin and the desired product is subsequently distilled together with the triacetin (conditions: 0.5 mbar, 180 C., 1 h).

[0103] After distillative purification, the obtained solution (1.01 g) contains 96.50% triacetin, 0.22% 2E,4Z-nonadienal as well as 0.07% 2E,4E-nonadienal.

[0104] Evaluation (smell): fatty, sour, sweet, lamb meat.

Example 3

Reaction of Pomegranate Seed Oil

[0105] 11 g of pomegranate seed oil are treated with air (20 L/h) at 170 C. for 6 h. Subsequently, 10 g of this raw material are mixed with 1.0 g triacetin and the desired product is subsequently distilled together with the triacetin (conditions: 0.5 mbar, 180 C., 1 h).

[0106] After distillative purification, the obtained solution (1.03 g) contains 96.50% triacetin, 0.12% 2E,4Z-nonadienal as well as 0.27% 2E,4E-nonadienal.

[0107] Evaluation (smell): lamb meat, fatty, rancid.

Example 4

Reaction of Pomegranate Seed Oil

[0108] 10 g of pomegranate seed oil are treated with air (20 L/h) at 170 C. for 6 h. Subsequently, the reaction mixture is heated to 170 C. for 1 h. Subsequently, 9.5 g of this raw material are mixed with 0.9 g triacetin and the desired product is subsequently fractionated distilled together with the triacetin at the (Kugelrohr) ball tube distillery (conditions: 0.5 mbar, 180 C., 1 h).

[0109] Fraction 1 (0.5 mbar, 90 C., 0.5 h) contains 98.22% triacetin, 0.04% 2E,4Z-nonadienal as well as 0.03% 2E,4E-nonadienal.

[0110] Evaluation of smell (fraction 1): sour, olive scent, fruity, slightly green.

[0111] Fraction 2 (0.5 mbar, 130 C., 0.5 h) contains 96.55% triacetin, 0.42% 2E,4Z-nonadienal as well as 0.50% 2E,4E-nonadienal.

[0112] Evaluation of smell (fraction 2): fatty, lamb, slightly rancid.

[0113] Fraction 3 (0.5 mbar, 160 C., 0.5 h) contains 92.93% triacetin, 0.30% 2E,4Z-nonadienal as well as 0.51% 2E,4E-nonadienal.

[0114] Evaluation of smell (fraction 3): lamb meat, fatty, slightly nutty.

[0115] This example shows that by separating the more slightly volatile components via a fractionated distillation, the sensorial value of these compounds is clearly increased.

Example 5

Reaction of Sunflower Oil

[0116] 1.0 kg of sunflower oil are treated with air (32 L/h) at 120 C. for 6 h. Subsequently, the reaction mixture is heated to 150 C. for 2 h as well as subsequently for 0.5 h to 170 C. Subsequently, this approach is mixed with 56.0 g triacetin and the desired product is subsequently distilled together with the triacetin (conditions: 0.2 mbar, inner temperature: 175 C.).

[0117] After distillative purification, the obtained solution (34.8 g) contains 87.7% triacetin, 4.26% 2E,4Z-decadienal as well as 0.88% 2E,4E-decadienal.

[0118] Application of the previously obtained aromatic blends in semi-finished products or, respectively, compositions

Application Example 1

Chicken Flavour

[0119]

TABLE-US-00001 Component (g) Acetylmethyl carbinol 0.20 Butyric acid 2.00 Capronic acid 1.00 Caprylic acid 1.00 2,4-Decadienal (Example 5) 16.00 Decenal-tr.2 0.20 Dimethyloxyfuron/Sotolon (1% solution) 0.40 Furaneol (10% solution) 20.00 Indol (1% solution) 0.40 2,3-Methylfuranthiol 0.80 Methyltetrahydrofuranthiol 0.30 Methylthiopropanal-3 0.15 2,4-Nonadienal (analogous example 4, fraction 2) 30.00 Thiobutanone-3,2 1.00 Vegetable oil triglycerides 926.55 Sum 1000.00

[0120] This aromatic blend is used in the subsequently described application examples.

Application Example 2

Spray Dried Aroma Composition

[0121] A spray dried aroma composition isstarting from the previously described application example 1prepared, which is subsequently further used:

TABLE-US-00002 Ingredient A Capsule 200 g Maltodextrin 600 g Aroma composition application example 1 200 g Water 1000 g

[0122] The ingredients are dissolved in demineralized water and subsequently spray dried. These are used in the subsequent application examples.

Application Example 3

Instant Soup, Type Chicken Soup with Noodles

[0123] A=composition for comparison

[0124] B=composition according to the invention

TABLE-US-00003 Ingredient A B Starch 16 g 16 g Sodium chloride 7 g 7 g Saccharose, refined 3.2 g 3.2 g Sodium glutamate 3.2 g 3.2 g Sodium inosinate/sodium guanylate in a ratio 0.8 g 0.8 g of 1:1 Acid hydrolyzed plant protein 8.0 g 8.0 g Fat powder 2.0 g 2.0 g Vegetable fat, spray dried 1.0 g 1.0 g Freeze-dried chicken meat, in pieces 2.15 g 2.15 g Soup noodles 32.0 g 32.0 g Maltodextrin 12.0 g 7.6 g Chinese vegetables, freeze-dried 4.6 g 4.6 g Chicken flavour 8.0 g 6.9 g Food dye riboflavin 0.05 g 0.05 g Spray dried aroma composition of application / 5.5 g example 2

[0125] 4.6 g of the powder mixture are boiled in 100 ml water for 10 minutes to obtain a ready-to-eat soup. The composition according to the invention B is evaluated with regard to desired fatty flavours reminding of chicken skin as stronger and longer-lasting as composition A, which results in a clearly more authentic profile.

Application Example 4

Bouillon

[0126] A=composition for comparison

[0127] B=composition according to the invention

TABLE-US-00004 Ingredient A B Fat powder 8.77 g 8.77 g Sodium glutamate 8.77 g 8.77 g Yeast extract powder 12.28 g 12.28 g Sodium chloride 29.83 g 29.83 g Maltodextrin 37.28 g 20.78 g Natural vegetable extract 3.07 g 3.07 g Spray dried aroma composition of / 16.5 g application example 2

[0128] 15 g of the powder mixture are infused with 1000 ml of hot water. When tasted by a panel of skilled test persons, the composition according to the invention B is assessed as clearly more rich, balanced, strong and long-lasting with regard to its aroma and taste than the composition for comparison A.

Application Example 5

White Sauce

[0129] A=composition for comparison

[0130] B=composition according to the invention

TABLE-US-00005 Component A B Maltodextrin 26.00 g 23.25 g Sodium chloride 7.50 g 7.50 g Sodium glutamate 2.00 g 2.00 g Vegetable fat 5.00 g 5.00 g Pepper, white 0.02 g 0.02 g Onion powder 1.48 g 1.48 g Pre-gelatinized corn starch 30.00 g 30.00 g Fat powder 28.00 g 28.00 g Spray dried aroma composition of / 2.75 g application example 2

[0131] 90 g of the sauce mixture are infused with 1000 ml hot water and strongly stirred with a whisk. When tasted by a panel of skilled test persons, the composition according to the invention B is assessed as clearly more rich, balanced, strong and long-lasting with regard to its aroma and taste than the composition for comparison A.

Application Example 6

Brown Sauce

[0132] A=composition for comparison

[0133] B=composition according to the invention

TABLE-US-00006 Component A B Starch 40.00 g 40.00 g Maltodextrin 33.10 g 30.35 g Sodium chloride 6.00 g 6.00 g Caramel, spray dried 5.00 g 5.00 g Yeast extract powder 3.00 g 3.00 g Sodium glutamate 2.00 g 2.00 g Sugar 0.50 g 0.50 g Fat powder 5.00 g 5.00 g Tomato powder 3.00 g 3.00 g Natural vegetable extract 1.00 g 1.00 g Onion extract 0.30 g 0.30 g Pepper extract 0.10 g 0.10 g Dry flavour 1.00 g 1.00 g Spray dried aroma composition of / 2.75 g application example 2

[0134] 90 g of the sauce mixture are infused with 1000 ml hot water and strongly stirred with a whisk. When tasted by a panel of skilled test persons, the composition according to the invention B is assessed as clearly more rich, balanced, strong and long-lasting with regard to its aroma and taste than the composition for comparison A.

Application Example 7

Spice Mixture for Potato Chips

[0135] A=composition for comparison

[0136] B=composition according to the invention

TABLE-US-00007 Component A B Sodium glutamate 3.50 g 3.50 g Cheese powder 10.00 g 10.00 g Garlic powder 2.00 g 2.00 g Whey powder 38.86 g 36.86 g Spice extract oil 0.20 g 0.20 g Bell pepper powder 9.80 g 9.80 g Sodium chloride 21.00 g 19.00 g Tomato powder 9.00 g 9.00 g Dry flavour 2.50 g 2.50 g Silicon dioxide 0.02 g 0.02 g Vegetable oil 0.02 g 0.02 g Onion powder 3.00 g 3.00 g Cream flavour concentrate 0.03 g 0.03 g Cheese flavour 0.03 g 0.03 g Tomato flavour concentrate 0.04 g 0.04 g Spray dried aroma composition of / 4.00 g application example 2

[0137] 6 g of the spice mixture are applied on 94 g of potato chips.

Application Example 8

Chicken Meat Spice Mixture for (Instant) Noodles

[0138]

TABLE-US-00008 Ingredient wt.-% Chicken flavour 5.00 Caramel 3.00 Citric acid (water free) 0.40 Chive (drained) 2.00 Maltodextrin (ex Tapoica) 5.30 Mono sodium glutamate 15.00 Onion powder 5.00 Ribotide 0.80 Sodium chloride 39.20 Sugar 2.80 Sweet whey powder 6.50 Spray dried aroma composition of 15.00 application example 2

[0139] All ingredients are mixed until a homogeneous mixture is obtained.

Application Example 9

Pear Flavour

[0140]

TABLE-US-00009 Ingredient (g) Aldehyde C6 (Hexanal) 0.20 Alcohol C6 (Hexanol) 1.00 2,4-nonadienal (Example 2) 0.30 2,4-decadienal (Example 5) 0.02 Butyl acetate 30.00 Ethyl butyrate 2.00 Ethyl decadienoat tr., cis 2,4 4.00 Hexenyl acetate, cis 3 1.00 Hexenyl acetate, trans 2 2.00 Hexyl acetate 35.00 Propylene glycol 924.48 Sum 1000.00

[0141] Typically, 10 g of the flavour described herein are used per 100 L instant drink.

Application Example 10

Passionfruit Flavour

[0142]

TABLE-US-00010 Ingredient (g) Nonalactone, gamma 3.00 Decalactone, gamma 13.00 Decadienal-2,4 tr.tr. (0.1% solution) 0.08 Ethyl butyrate 13.00 Ethyl capronate 13.00 Furfural 12.00 Geraniol 0.30 Ionon, beta 3.00 Isovaleraldehyde 0.20 2,4-Nonadienal (Example 1) 1.20 Thiomentanone-8,3 0.13 Phenylethylalcohol 6.50 Terpineol alpha 10.00 Propylene glycol 924.59 Sum 1000.00

[0143] Typically, 10 g of the flavour described herein are used per 100 L instant drink.

Application Example 11

Mushroom Flavour

[0144]

TABLE-US-00011 Ingredient (g) Octanol-1 4.00 Caprylic acid 15.00 2,4-Decadienal (Example 5) 60.00 Decalactone, delta 7.00 2,4-Nonadienal (example 4, fraction 2) 200.00 Octenol-1,3 50.00 Octenone-1,3 3.00 Triacetin 661.00 Sum 1000.00

[0145] Typically, 10 g of the flavour described herein are needed per 100 kg soup.