CH568024A5 - Flavour-improving compsns contng substd pyrazines and - substd cyclohexenones and/or 2-substd thiazolidines - Google Patents

Abstract

Compns. contg. (a) >=1 cmpd. of formula (I) together with (b) >=1 cpd of formula (II) and/or (c) >=1 cpd. of formula (III) where R1-R4 each = H or (un)satd., cyclic or acyclic hydrocarbon or R3 + R4= -CH-CHCH=CH-, or acyl residue, R5 - R9 = H or a (un)satd., cyclic or acyclic hydrocarbon, and R10 = H or (un)satd., cyclic or acyclic, aliphatic, aromatic, or araliphatic hydrocarbon, are of use as flavour improvers or modifiers for food stuff, drinks, pharmaceuticals and tobacco.

Description

  

  
 



   The present invention relates to a flavoring composition, characterized in that it contains, as active ingredient, at least one synthetic chemical compound of formula
EMI1.1
 in which each of the symbols Rs to R9 represents either hydrogen or a monovalent radical derived from a saturated or unsaturated, cyclic or acyclic, linear or branched aliphatic hydrocarbon.



   A subject of the invention is also the use of the above composition in order to modify or improve the organoleptic characteristics of foods for humans and animals, of drinks and of tobacco.



   The compounds of formula I, derived from cyclohexenone, represent a class of compounds which are relatively well known and the synthesis of which has already been studied in the past. It is in particular described in J. Chem. Soc. 1944, 430, J. Am. Chem. Soc. 71, 2028 (1949) and J. Org. Chem. 21, 612 (1956). However, it should be noted that none of the above references mentions the use of the derivatives of formula I as flavoring ingredients.



   We have in fact found, surprisingly, that the addition of compositions containing said compounds of formula I to various foods, drinks, pharmaceutical preparations or tobacco, modifies, improves or appreciably reinforces the organoleptic properties of said products.



   The organoleptic characteristics obtained vary in particular according to the nature of the foods considered, according to the nature of the flavoring composition used and, in particular, according to the respective concentrations of said ingredients within the composition.



   Thus, flavoring compositions as defined above can, inter alia, give the products in which they have been incorporated a taste note of a roasted or grilled character, sometimes earthy. Depending on the case, it has also been possible to obtain, using such compositions, a taste of meat, cereal, nuts, hazelnut or cocoa. The term food, as used within the present description, should be understood in its broadest sense: it is used in particular to designate products such as tea, coffee or chocolate.



   Artificial flavors such as flavors of nuts, hazelnuts, peanuts, pistachios, chocolate, coffee, caramel, toasted cereals, meat or various spices for example, can be favorably modified by the addition of the compounds of formula I, due in particular to the roasted and burnt shade which said compounds provide to the flavoring composition in question.



   The proportions used to obtain flavoring effects as described above can vary widely. Interesting effects can be obtained by using a flavoring composition in an amount of 0.1 ppm of the total weight of the flavored material. Depending on the nature of the food or drink considered, it may sometimes be more advantageous to use said compositions in higher proportions, for example of the order of 1 to 10 ppm. The aforementioned amounts do not however represent absolute limits, amounts greater or less than these can also be used.



   The compounds of formula I, the use of which as flavoring ingredients constitutes the object of the present invention, can be used in the form of dilute solutions, in an amount of 0.1 to 5% for example. Among the non-toxic solvents suitable for such use, there may be mentioned propylene glycol, triacetin,
Benzyl alcohol, for example, or else tasteless edible oils, such as pure peanut oil for example.



   Below is the list of compounds of formula I, the use of which constitutes the object of the present invention. Next to the name of each of said compounds is the reference indicating the method of preparation or the commercial source.



  In the latter case, the abbreviation p.c. is used.



   New compounds are designated by the abbreviation c.n. . Their preparation and analytical data will be described in detail.



     VS,
 1.cyclohex-2-en-one bw.



  C1
 2. 2-methyl-cyclohex-2.en-one Ann. 379, 17 (1911)
 3. 3-methyl-cyclohex-2.ene-one bw.



   4. 4-methyl-cyclohex-2-en-one J. Chem. Soc. 1960, 3563
 5. 5-methyl-cyclohex-2-en-one J. Chem. Soc. 1946, 595
 6. 6-methyl-cyclohex-2-en-one J. Am. Chem. Soc. 78, 4604 (1956)
C2
 7. 2,6-dimethyl-cyclohex-2-en-one J. Chem. Soc. 1944, 430
 8. 3,4-dimethyl-cyclohex-2-en-one Compt.Rend. 205, 680 (1937)
 9. 3,5-dimethyl-cyclohex-2-en-one J. Chem. Soc. 1960, 3563
 10. 3,6-dimethyl-cyclohex-2-en-one J. Chem. Soc. 1944, 430
 11. 4,6-Dimethyl-cyclohex-2ene-one J. Chem. Soc. 1944, 430
 12. 2,3-dimethyl-cyclohex-2-en-one J. Org. Chem. 4, 266 (1939)
 13. 2,4-dimethyl-cyclohex-2-en-one C.A. 61, 585 c
 14. 2,5-dimethyl-cyclohex-2-en-one J. Chem. Soc. 1944, 430
 15. 4,5-dimethyl-cyclohex-2-en-one C.A. 64, 19436 f
 16. 5,6-dimethyl-cyclohex-2-ene-one J. Org.

  Chem. 21, 612 (1956)
 17. 2-ethyl-cyclohex-2-en-one Ann. 360, 49 (1908)
 18. 3-ethyl-cyclohex-2-en-one J.Am.Chem. Soc. 71, 2028 (1949)
 19. 4-ethyl-cyclohex-2-en-one C.A. 64, 11099 b
 20. 5-ethyl-cyclohex-2-en-one c.n., *
 21. 6-ethyl-cyclohex-2-en-one c.n., *
 * Prepared according to the method indicated in J.Chem. Soc. 1944, 430.



     5-Ethyl-cyclohex-2-en-one:
MS: m / e = 124 (17), 69 (3), 68 (100), 67 (6), 55 (4), 41 (7), 40 (8),
 39 (12), 27 (5).



     6-Ethyl-cyclohex-2-en-one:
MS: m / e = 124 (7), 96 (46), 95 (7), 68 (100), 55 (5), 41 (7), 40 (10),
 39 (14), 27 (8).



   The invention is illustrated in more detail with the aid of the examples below.



  Example I
 A basic flavoring composition was prepared by mixing the following ingredients (parts by weight):
   2-methyl-pyrazine 5.0
 2,5-dimethyl-pyrazine 8.0
 2-methyl-6-ethyl-pyrazine 1.0
 2-methyl-3-ethyl-pyrazine 2.5
 3,5-dimethyl-2-ethyl-pyrazine 1.0
 2,5-dimethyl-3-ethyl-pyrazine 2,0
 propylene glycol 980.5
 1000.0
 The above basic composition was added in an amount of 0.01% to a 0.5% (w / v) solution of sodium chloride in water and to a 1% (v / v) aqueous solution. / vo.



  lume) of a commercial protein hydrolyzate. The solutions thus obtained were then divided into four equal parts, these being finally flavored by the respective addition of the following ingredients (parts by weight relative to the total weight of the solution):
 1.5-methyl-cyclohex-2-en-one 5 ppm
 2.6-methyl-cyclohex-2-en-one 5 ppm
 3.36-dimethyl-cyclohex-2-ene-one 5 ppm
 4.6-dimethyl-cyclohex-2-en-one 5 ppm
 The flavored solutions were subjected to organoleptic evaluation by a group of experts. They defined the taste of solutions as follows:
 1. Green hazelnuts
 2. Meat character
 3. Burnt, roasted meat character,
 slightly earthy
 4. Similar to that indicated under number 3.



  Example 2
 A basic flavoring composition was prepared by mixing the following ingredients (parts by weight):
 dimethyl sulfide 0.03
 2-methyl-3-ethyl-pyrazine 0.15
 2-acetyl-pyrazine 0.20
 2-ethyl-6-methyl-pyrazine 0.20
 indole 0.20
   2,5-dimethyl-3 ethyl-pyrazine 0.30
 2,3,5-trimethyl-pyrazine 0.50
 2,5-dimethyl-pyrazine 0.50
 capric acid 1.00
 caprylic acid 2.00
 n-butyric acid 2.00
 caproic acid 3.50
 vegetable oil 89.42
 100.00
 The above base composition was added at 0.01% to a solution of 25 g of commercial instant roast juice in 600 ml of water.

  The solution thus obtained was divided into two equal parts and these fractions were then flavored by the addition of the ingredients indicated below (parts by weight calculated on the total weight of the flavored solution):
 1.6-methyl-2-cyclohex-2-en-one 5 ppm
 2. 4,5-dimethyl-2-cyclohex-2-en-one 5 ppm
 The flavored solutions thus obtained were subjected to an organoleptic evaluation by a group of experts who defined the taste of said solutions as follows:
 1. Has a roasted cereal note. Said character was
 missing from control solution.



   2. Cereal note, meaty character, more rounded taste than 1.

 

Claims (1)

I Flavoring composition, characterized in that it contains, as active ingredient, at least one synthetic chemical compound of formula EMI2.1 in which each of the symbols Rs to R9 represents either hydrogen or a monovalent radical derived from a saturated or unsaturated, cyclic or acyclic, linear or branched aliphatic hydrocarbon. II Use of the composition according to claim I in order to modify or improve the organoleptic characteristics of foods for humans and animals, of beverages and of tobacco.