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 one or more unsaturated dienals, the method comprising: (a) subjecting an oil comprising punicic acid, punicic acid ester, elaeostearinic acid, elaeostearinic acid ester, linoleic acid, linoleic acid ester, or a combination thereof to air oxidation at a temperature of 70 to 200° C. and forming a mixture comprising: (i) dienals selected from 2,4-nonadienal, 2,4-decadienal, and a combination thereof; and (ii) residual oil; and (b) separating dienals from the mixture of (a) to obtain purified or concentrated dienals selected from 2,4-nonadienal, 2,4-decadienal, and a combination thereof, and a residue separate from the purified or concentrated dienals.

2. The method of claim 1, wherein the residue of (b) is reused in (a).

3. The method of claim 1, wherein the oil of (a) is mixed with one or more solvents to form an oil and solvent mixture that is subjected to the air oxidation .

4. The method of claim 1, wherein the air oxidation of (a) is carried out by subjecting the oil to 10 to 1,000 I/h of air per kg of the oil.

5. The method of claim 1, wherein the air oxidation of (a) is carried out at a temperature of 100 to 130° C.

6. The method of claim 1, wherein the air oxidation of (a) is carried out for 1 to 30 hours.

7. The method of claim 1, further comprising heating the mixture of (a) formed by the air oxidation .

8. The method of claim 1, wherein the dienals are separated in (b) by distillation.

9. The method of claim 1, wherein one or more solvents are added to the mixture of (a) before separating the dienals from the mixture in (b).

10. The method of claim 1, further comprising washing the mixture of (a) with an aqueous alkaline solution before separating the dienals from the mixture in (b).

11. The method of claim 3, wherein the one or more solvents are selected from triacetin, triethyl citrate, and a combination thereof.

12. The method of claim 3, wherein the oil and solvent mixture comprises 2 to 20 wt. % of the one or more solvents, based on the total weight of the oil.

13. The method of claim 6, wherein the air oxidation of (a) is carried out for 4 to 12 hours.

14. The method of claim 7, wherein the mixture of (a) is heated to a temperature of 100 to 200° C. for 0.5 to 5 hours.

Description

Example 1

Reaction of Pomegranate Seed Oil

(1) 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).

(2) 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.

(3) Evaluation (smell): lamb meat, fatty, rancid.

Example 2

Reaction of Pomegranate Seed Oil

(4) 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).

(5) 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.

(6) Evaluation (smell): fatty, sour, sweet, lamb meat.

Example 3

Reaction of Pomegranate Seed Oil

(7) 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).

(8) 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.

(9) Evaluation (smell): lamb meat, fatty, rancid.

Example 4

Reaction of Pomegranate Seed Oil

(10) 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).

(11) 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.

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

(13) 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.

(14) Evaluation of smell (fraction 2): fatty, lamb, slightly rancid.

(15) 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.

(16) Evaluation of smell (fraction 3): lamb meat, fatty, slightly nutty.

(17) 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

(18) 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.).

(19) 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.

(20) Application of the previously obtained aromatic blends in semi-finished products or, respectively, compositions

Application Example 1

Chicken Flavour

(21) 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

(22) This aromatic blend is used in the subsequently described application examples.

Application Example 2

Spray Dried Aroma Composition

(23) A spray dried aroma composition is—starting from the previously described application example 1—prepared, which is subsequently further used:

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

(25) 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

(26) A=composition for comparison

(27) B=composition according to the invention

(28) 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

(29) 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

(30) A=composition for comparison

(31) B=composition according to the invention

(32) 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

(33) 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

(34) A=composition for comparison

(35) B=composition according to the invention

(36) 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

(37) 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

(38) A=composition for comparison

(39) B=composition according to the invention

(40) 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

(41) 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

(42) A=composition for comparison

(43) B=composition according to the invention

(44) 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

(45) 6 g of the spice mixture are applied on 94 g of potato chips.

Application Example 8

Chicken Meat Spice Mixture for (Instant) Noodles

(46) 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

(47) All ingredients are mixed until a homogeneous mixture is obtained.

Application Example 9

Pear Flavour

(48) 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

(49) Typically, 10 g of the flavour described herein are used per 100 L instant drink.

Application Example 10

Passionfruit Flavour

(50) 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

(51) Typically, 10 g of the flavour described herein are used per 100 L instant drink.

Application Example 11

Mushroom Flavour

(52) 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

(53) Typically, 10 g of the flavour described herein are needed per 100 kg soup.