METHOD FOR PRODUCING UNSATURATED DECANALS

Abstract

The present invention relates to a flavour mixture containing 2E,4Z,7Z- and 2E,4E,7Z-tridecatrienal. This flavour mixture can be produced advantageously from arachidonic acid or oils containing esters thereof.

Claims

1. A method for producing unsaturated decanals comprising: a) air oxidizing an educt comprising arachidonic acid or arachidonic acid ester, b) decomposing a resulting peroxide, and c) concentrating unsaturated decanals.

2. The method according to claim 1 further comprising: d) repeating a) to c) in that order.

3. The method according to claim 1, wherein a) comprises gassing with air at an air volume10-1000 l/h per kg.

4. The method according to claim 1, wherein a) is carried out at a temperature of100 C. and200 C.

5. The method according to claim 1, wherein a) is carried out for a period of >1 h to <20 h.

6. The method according to claim 1, wherein b) is carried out by heating at a temperature from100 C. and200 C.

7. The method according to claim 1, wherein b) is carried out for0.5 h-5 h.

8. The method according to claim 1, wherein c) comprises a fractional distillation.

9. A flavour mixture, producible by a method according to claim 1.

10. Food or food supplement comprising a flavour mixture according to claim 9.

11. The method according to claim 2, wherein a) comprises gassing with air at an air volume10-1000 l/h per kg.

12. The method according to claim 11, wherein a) is carried out at a temperature of100 C. and200 C.

13. The method according to claim 12, wherein a) is carried out for a period of1 h to20 h.

14. The method according to claim 13, wherein b) is carried out by heating at a temperature from100 C. and200 C.

15. The method according to claim 14, wherein b) is carried out for0.5 h-5 h.

16. The method according to claim 15, wherein c) comprises a fractional distillation.

17. A flavour mixture, producible by a method according to claim 16.

18. Food or food supplement comprising a flavour mixture according to claim 17.

Description

Example 1

[0079] 100 g of oil containing Arachidonic acid (40% Arachidonic acid) is diluted with 10 g Triacetin and gassed at 120 C. with air (40 L/h) for 6 h. Subsequently, the reaction mixture is heated for 2 h at 130 C. The raw product is distilled in vacuum. Firstly, the readily volatile compounds are separated (Conditions: 0.1 mbar, 100 C., 30 min). The desired product is then distilled off with Triacetin. (Conditions: 0.1 mbar, 170 C., 1 h (F2)).

[0080] After destillative purification, the obtained solution (5.7 g) contains 50 mg of 2E,4Z,7Z- and 2E,4E,7Z-tridecatrienal in the ratio of 1:1.

Example 2

[0081] The process according to Example 1 is repeated four times in total. 23.3 g of solution containing 120 mg of 2E,4Z,7Z- and 2E,4E,7Z-tridecatrienal in the ratio of 1:1 are obtained.

[0082] This solution is subsequently diluted with Triacetin, so that a mixture is generated, which contains in total 0.2 wt.-% of the corresponding 2E,4Z,7Z- and 2E,4E,7Z-tridecatrienals.

Example 3

[0083] 100 g of oil containing Arachidonic acid (40% Arachidonic acid) is gassed at 170 C. with air (40 L/h) for 2 h. Subsequently, the reaction mixture is heated for 1 h at 170 C. The raw product is diluted with 10 g Triacetin and distilled in vacuum. Firstly, the readily volatile compounds are separated (Conditions: 0.1 mbar, 100 C., 30 min). The desired product is then distilled off with Triacetin. (Conditions: 0.1 mbar, 170 C., 1 h (F2)).

[0084] After destillative purification, the obtained solution (7.7 g) contains 80 mg of 2E,4Z,7Z- and 2E,4E,7Z-tridecatrienal in the ratio of 1:4.

Example 4

[0085] The process from Example 3 is repeated four times in total. 29.7 g of solution containing 230 mg of 2E,4Z,7Z- and 2E,4E,7Z-tridecatrienal in the ratio of 1:4 are obtained.

[0086] This solution is subsequently diluted with Triacetin, so that a mixture is generated, which contains in total 0.2 wt.-% of the corresponding 2E,4Z,7Z- and 2E,4E,7Z-tridecatrienals.

Application of the Flavour Mixture

[0087] In the following, uses of a flavour mixture according to the inventive procedure are described. These areto avoid confusionreferred to as compositions.

Example 1: Production of a Chicken Flavour Mixture Comprising the Inventive Flavour Mixture

[0088] Mixed are:

TABLE-US-00001 Component [G] Acetylmethylcarbinol 0.2 Butanoic acid 2 Caproic acid 1 Caprylic acid 1 Decadienal trans, trans-2,4 0.8 2E-Decenal 0.2 Dimethyloxyfuranone/Sotolon 1% Solution in alcohol 0.4 Furaneol 10% Solution in Triacetin 20 Indole 1% Solution in alcohol 0.4 2,3-Methylfuranthiol 0.8 Methyltetrahydrofuranthiol 0.3 Methylthiopropanal-3 0.15 3,2-Thiobutanon 1 Reaction product from Example 4 15 Plant oil triglycerides 956.75 Sum 1000

[0089] This flavour composition is used in the Application Examples described in the following.

Example 2: Production of a Cattle Marrowbone Flavour Mixture

[0090] Mixed are:

TABLE-US-00002 Component [G] Acetylmethylcarbinol 2 Alcohol C6 0.5 p-Cresol 1% Solution in PG 5 Decadienal trans, trans-2,4 5% in Triacetin 50 delta-Decalactone 1.4 delta-Dodecalactone 3.5 Furaneol 10% Solution in Triethyl citrate 30 Furfurylmercaptan 1% in Triethyl citrate 3 Indole 1% in alcohol 5 2,3-Methylfuranthiol 5% A 1% in Triacetin 60 Methylthiopropanal-3 1% in Triethylcitrat 15 Myristinsure 4 2,3-Pentandion 3 3,2-Thiobutanon 10% in plant oil triglycerides 12 2,3,5-Trimethylpyrazin 1 Reaction product from Example 2 4 plant oil triglycerides 800.6 Sum 1000

[0091] This flavour composition is used in the Application Examples described in the following.

Application Example 3: Egg Pudding Flavour Composition

[0092] Mixed are:

TABLE-US-00003 Component [G] Acetylpyrazine-2 3 Butanoic acid 1 Capric acid 200 Decadienal trans, trans-2,4 0.01% in Propylene glycol 0.05 delta-Decalactone 50 Diacetyl 0.1 delta-Dodecalactone 100 Furaneol 15% Solution in Propylene glycol 0.1 Indole FF 1% Propylene glycol 0.75 2,3-Methylfuranthiol 0.005% in Triacetin 40 1,2-Propylenglycol 535 Reaction product from Example 4 50 Vanillin 20 Sum

[0093] This flavour composition is used in the Application Examples described in the following.

Application Example 4: Spray Dried Flavour Composition

[0094] Based on the Application Examples 1 to 3 described above, four flavour compositions 4A to 4C are produced, which will be used further in the following:

TABLE-US-00004 Ingredient A B C Capsul 200 g 200 g 200 g Maltodextrin 600 g 600 g 600 g Flavour composition 200 g Composition Application Example 1 Flavour composition 200 g Composition Application Example 2 Flavour composition 200 g Composition Application Example 3 Water 1000 g 1000 g 1000 g

[0095] The components are dissolved in demineralized water and subsequently spray dried. These are used in the following Application Examples.

Application Example 5: Instant Soup, Type Chicken Soup with Noodles

[0096] A=comparative preparation

[0097] B=preparations according to the invention

TABLE-US-00005 Ingredient A B Starch 16 g 16 g Cooking salt 7 g 7 g Sucrose, refined 3.2 g 3.2 g Sodium glutamate 3.2 g 3.2 g Sodium inosinate/Sodium guanylate in the ratio 0.8 g 0.8 g 1:1 Plant protein hydrolysed by acid 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 vegetable, freeze dried 4.6 g 4.6 g Chicken flavour 8.0 g 6.9 g Food colouring Riboflavin 0.05 g 0.05 g Spray dried flavour compositions from 5.5 g Application Example 4A

[0098] 4.6 g of the respective powder mixture are boiled for 10 minutes in 100 ml water each to obtain a ready-to-eat soup. The inventive preparation B is rated stronger and longer lasting in terms of desired greasy aromas, reminiscent of chicken skin, resulting in a distinctly more authentic profile.

Application Example 6: Instant Soup, Type Beef Soup with Noodles

[0099] A=comparative preparation

[0100] B=preparations according to the invention

TABLE-US-00006 Ingredient A B Starch 16 g 16 g Cooking salt 7 g 7 g Sucrose, refined 3.2 g 3.2 g Sodium glutamate 3.2 g 3.2 g Sodium inosinate/Sodium guanylate in the ratio 0.8 g 0.8 g 1:1 Plant protein hydrolysed by acid 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 beef, in pieces 2.15 g 2.15 g Soup noodles 32.0 g 32.0 g Maltodextrin 12.0 g 11.1 g Vegetable, freeze dried 4.6 g 4.6 g Meat flavour 8.0 g 7.8 g Food colouring Riboflavin 0.05 g 0.05 g Spray dried flavour compositions from 1.1 g Application Example 4B

[0101] 4.6 g of the respective powder mixture is boiled for 10 minutes in 100 ml of water each to obtain a ready-to-eat soup. By the use of the inventive flavour composition with Tridecatrienal, a greasy, full-bodied taste with an authentic profile is achieved, which was preferred to preparation A in the tasting by a panel of trained test persons.

Application Example 7: Bouillon

[0102] A=comparative preparation

[0103] B, C=preparations according to the invention

TABLE-US-00007 Ingredient A B C Fat powder 8.77 g 8.77 g 8.77 g Sodium glutamate 8.77 g 8.77 g 8.77 g Yeast extract powder 12.28 g 12.28 g 12.28 g Cooking salt 29.83 g 29.83 g 29.83 g Maltodextrin 37.28 g 20.78 g 33.78 g Natural vegetable extract 3.07 g 3.07 g 3.07 g Spray dried flavour composition 16.5 g Application Example 4A Spray dried flavour composition 3.5 g Application Example 4B

[0104] 15 g of the respective powder mixture is infused with 1000 ml of hot water. During the tasting by a panel of trained test persons, the inventive preparations B and C are evaluated as significantly richer, more balanced, stronger and more long-lasting than the comparative preparation A with respect to their flavour and taste.

Application Example 8: Vanilla Cooked Pudding

[0105] A=comparative preparation

[0106] B=preparations according to the invention

TABLE-US-00008 Ingredient A B Sucrose 7.8 g 7.8 g Starch 3.0 g 3.0 g Skimmed milk powder 1.5 g 1.5 g Aubygel MR50 0.5 g 0.5 g Extract of vanilla beans, spray dried, 0.1 g 0.1 g Symrise Spray dried flavour compositions 0.25 g Application Example 4C Milk 1.5% fat content ad 100 g

[0107] The solids are provided and stirred with the milk. The mixture is warmed to 95 C. for 2 minutes while stirring well, bottled and cooled to 5-8 C. The milk is then added to the mixture. By the use of the inventive flavour composition with Tridecatrienal, a clearly greasy, authentic taste with a pronounced egg note is achieved.

Application Example 9: White Sauce

[0108] A=comparative preparation

[0109] B, C=preparation according to the invention

TABLE-US-00009 Component A B C Maltodextrin 26.00 g 23.25 g 25.40 g Cooking salt 7.50 g 7.50 g 7.50 g Sodium glutamate 2.00 g 2.00 g 2.00 g Plant fat 5.00 g 5.00 g 5.00 g Pepper, white 0.02 g 0.02 g 0.02 g Onion powder 1.48 g 1.48 g 1.48 g pregelatinised maize starch 30.00 g 30.00 g 30.00 g Fat powder 28.00 g 28.00 g 28.00 g Spray dried composition 2.75 g Application Example 4A Spray dried composition 0.6 g Application Example 4B

[0110] 90 g of the sauce mixture is infused with 1000 ml of hot water and stirred vigorously with the wire whisk. During the tasting by a panel of trained test persons, the inventive preparations B and C are evaluated as significantly richer, more balanced, stronger and longer-lasting than the comparative preparation A with regard to their flavour and taste.

Application Example 10: Brown Sauce

[0111] A=comparative preparation

[0112] B=preparation according to the invention

TABLE-US-00010 Component A B C Starch 40.00 g 40.00 g 40.00 g Maltodextrin 33.10 g 30.35 g 32.50 g Cooking salt 6.00 g 6.00 g 6.00 g Caramels, spray dried 5.00 g 5.00 g 5.00 g Yeast extract powder 3.00 g 3.00 g 3.00 g Sodium glutamate 2.00 g 2.00 g 2.00 g Sugar 0.50 g 0.50 g 0.50 g Fat powder 5.00 g 5.00 g 5.00 g Tomato powder 3.00 g 3.00 g 3.00 g Natural vegetable extract 1.00 g 1.00 g 1.00 g Onion extract 0.30 g 0.30 g 0.30 g Pepper extract 0.10 g 0.10 g 0.10 g Dry flavour 1.00 g 1.00 g 1.00 g Spray dried composition 2.75 g Application Example 4A Spray dried composition 0.6 g Application Example 4B

[0113] 90 g of the sauce mixture is infused with 1000 ml of hot water and stirred vigorously with the wire whisk. During the tasting by a panel of trained test persons, the inventive preparations B and C are evaluated as significantly richer, more balanced, stronger and longer-lasting than the comparative preparation A with regard to their flavour and taste.

Application Example 11: Seasoning Mixture for Potato Chips

[0114] A=comparative preparation

[0115] B=preparations according to the invention

TABLE-US-00011 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 Paprika powder 9.80 g 9.80 g Cooking salt 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 Plant 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 composition 4.00 g Application Example 4A

[0116] 6 g of the seasoning mixture are spread on 94 g of potato chips.

Application Example 12: Beef Seasoning Mixture for (Instant) Noodles

[0117]

TABLE-US-00012 Ingredient Gew.-% Cattle fat flavour 5.00 Caramel 3.00 Citric acid (water free) 0.40 Wild chive (drained) 2.00 Maltodextrin (ex Tapoica) 10.30 Monosodium glutamate 15.00 Onion powder 5.00 Ribotide 0.80 Sodium chloride 44.20 Sugar 2.80 Sweet whey powder 6.50 Spray dried composition Application Example 4B 5.00

[0118] All ingredients are mixed, until a homogeneous mixture is obtained.

Application Example 13: Chicken Meat Seasoning Mixture for (Instant) Noodles

[0119]

TABLE-US-00013 Ingredient Gew.-% Chicken flavour 5.00 Caramel 3.00 Citric acid (water free) 0.40 Wild chive (drained) 2.00 Maltodextrin (ex Tapoica) 5.30 Monosodium glutamate 15.00 Onion powder 5.00 Ribotide 0.80 Sodium chloride 39.20 Sugar 2.80 Sweet whey powder 6.50 Spray dried composition Application Example 4A 15.00

[0120] All ingredients are mixed, until a homogeneous mixture is obtained.

[0121] The individual combinations of the components and features of the above-mentioned statements are exemplary; the exchange and substitution of these teachings with other teachings contained in this publication with the cited publications are also expressly considered. The person skilled in the art recognizes that variations, modifications and other embodiments described here may also occur without deviating from the inventive idea and the scope of the invention. Accordingly, the above description is to be regarded as exemplary and not restrictive. The word comprise used in the claims does not exclude other elements or steps. The indefinite article a does not exclude the meaning of a plural. The mere fact that certain measures are recited in mutually different claims does not make it clear that a combination of these measures cannot be used to advantage. The scope of the invention is defined in the following claims and the corresponding equivalents.