CH537709A - Tobacco, food and beverages - aromatised by treatment with amides, esters, ketones and phenol derivs - Google Patents

Abstract

The organoleptic props. of tobacco and other prods. are improved or modified by adding (i) a cpd. of formula (I): R-C(O)NHR1 (where R and R1 are 1-6 alkyl or H); (ii) cycloaliphatic esters and ketones; (iii) phenol derivs.; (iv) heterocyclic ketones of formula (II): with a double bond in the posn. of 1 of the dotted lines, where X is H or OH if the double bond is in the ring, or O if the double bond is outside the ring; R2 and R3 are lower alkyl and Z is O or S; (v) caryophyllene derivs. or (vi) epoxy-beta-ionone, 6-methyl-hepta-3,5-diene-2-one, 3-isopropylcyclopent-2-ene-1-one, octa-3,5-diene-2-one, nonane-2,5,8-trione, 2-methyl-5-(alpha-methyl-alpha-hydroxyethyl)cyclohex-2-ene-1-one, or 4-methylthiobutan-2-one. Food, fodder, drinks and pharmaceuticals may be treated, as well as tobacco. The taste of tea, coffee and lime-flower tea can be modified; the additives may be used in meat, esp. smoked meat, and cocoa.

Description

  

  
 



   It is well known that tobacco intended for the preparation of cigarettes, for example, consists essentially of a mixture of different types of tobacco, said mixture being necessary to produce a characteristic taste and aroma when the tobacco is smoked.



   The tobacco for cigarettes currently on the market are in fact made up for the most part by mixtures of tobacco from Virginia, Maryland or Kentucky, and Turkish or oriental tobacco. The respective proportions of these different types of tobacco in said mixtures are variable and depend on the taste and the aroma that it is desired to obtain. A practice currently employed today consists in adding to said mixtures additive substances such as for example flavoring and humectant substances.



   An object of the present invention is that of providing a smoking tobacco which exhibits improved organoleptic characteristics compared to the basic tobacco by incorporating said basic tobacco with a flavoring composition.



   The term tobacco as used in the present description should be understood in its broadest sense, and is used to denote tobacco for cigarettes, cigars or pipe, both of natural and artificial origin.



   The present invention consists of the use of at least one synthetic chemical compound of formula
EMI1.1
 wherein each of the symbols R1 and R2 represents either a monovalent residue derived from a saturated or unsaturated, cyclic or acyclic aliphatic hydrocarbon. linear or branched, either one of them represents an acyl residue and the other a monovalent residue of the same type as that indicated above or hydrogen, together with at least one compound belonging to the group of phenolic derivatives or ethers formula
EMI1.2
 in which each of the substituents R3 and R4 represents either hydrogen or a monovalent residue derived from a saturated or unsaturated, linear or branched aliphatic hydrocarbon,

   either either one of them represents an acyl or alkoxy residue and the other a monovalent residue of the same type as that indicated above, and R5 represents hydrogen or an alkyl residue, as flavoring agents for the aromatization of the tobacco of natural or artificial origin.



   The compounds mentioned above have been divided into groups which take into account their similarity in chemical structure rather than their organoleptic properties, these can in fact be very varied and depend on the nature of the other components of the flavoring mixture considered.



   The flavoring compositions the use of which constitutes the object of the present invention can be made available to flavorers in a wide variety of forms. It is preferable to use said compositions in the form of a solution. However, the chemical nature of the compound considered, its solubility, its stability will determine the form of the composition in which it can be used.



   A commonly used method of flavoring tobacco is to sprinkle an alcoholic solution of the flavoring compounds on already cut tobacco. Mixtures of alcohol-water or propylene glycol can advantageously be used for this purpose.



   The proportions according to which these compounds can be used to produce flavoring effects can vary between limits which are very distant from one another and depend very particularly on the desired effect and on the very nature of the product which is used. Thus, for example, proportions of the order of 100 ppm relative to the total weight of the product to be flavored can already produce interesting organoleptic effects. These proportions can range up to 5 or 10% of the total weight of the product to be flavored.



   It is understood that the proportions given above do not represent absolute limits and concentrations lower or higher than those indicated can be used.



   In the following specific description of the compounds belonging to the groups indicated above, the structural formula is given first, followed by a list of members of the group having excellent properties for this said use. Immediately after the chemical designation of each member, the commercial source or the literature references giving the method for their preparation are indicated. Commercially available products are identified by the abbreviation p.c., and can be purchased from Fluka AG, Buchs S.G., Switzerland; Eastman-Kodak, Rochester N.Y., USA, and K. & K. Laboratories Inc.,
Plainview N.Y., USA.



   1 - Pyrazines
Compounds of this class have the formula
EMI1.3
 in which each of the symbols R1 and R2 represents either a monovalent residue derived from a saturated or unsaturated, cyclic or acyclic, linear or branched aliphatic hydrocarbon, or one of them represents an acyl residue and the other a monovalent residue of same type as shown above.



   Typical compounds are:
 I. a. 2-methyl-6-vinyl-pyrazine, J. Org. Chem., 27, 1363 (1962); b. 2-methyl-5-ethyl-pyrazine, British Patent No. 1,156,484; c.



     2-methyl-3-acetyl-pyrazine, anticipated publication of Dutch application 68899.



   2 - Phenols and their ether derivatives
The compounds of this group have the general formula
EMI1.4
 in which each of the substituents R3 and R4 represents either a monovalent residue derived from a saturated or unsaturated, linear or branched aliphatic hydrocarbon, or one of them represents an acyl or alkoxy residue and the other a monovalent residue of the same type as that indicated above, and R5 represents hydrogen or an alkyl residue.



   Typical compounds are:
   II. at. pvinyl guaiacol, Helv.Chim.Acta, 15, 145 (1932); b. 3 methyl-Ghydroxy-acetophone, bw; vs. 2-methyl-5-isopropenylanisole Helv.Chim.Acta, 48, 1057 (1965).



   The invention is illustrated in more detail by the following example.



   Example
 A flavoring composition was prepared by mixing the following ingredients (parts by weight): n-hexanol 0.05 6-methyl-hept-5-en-2-one 0.10 2-methyl-6-vinyl-pyrazine 0, 15 10% 3-methyl-6-hydroxy-acetophenone * 0.40 octane-2,3-dione 0.20 2,6,6-trimethyl-1-trans-crotonoyl-cyclohex-1-ene 10% * 0.05
 -ionone 10% 0.05 vanilla extract 0.15 geranylacetone 0.15 dimethylmaleic anhydride 0.05 rum 3.65 ethyl alcohol 95% 5.00
 10.00 * in 95% ethyl alcohol.

 

   A mixture of tobacco of the American blend type (100 g) was sprinkled with 10 g of a 1% solution of the above flavoring composition in 95% alcohol. The flavored tobacco was used in the preparation of cigarettes which were subjected to organoleptic evaluation by a group of experts. The latter defined the taste and aroma of the smoke of cigarettes prepared as described as being characterized by a green, flowery, woody, slightly fruity note.

 

Claims (1)

CLAIM Use of at least one synthetic chemical compound of formula EMI2.1 in which each of the symbols R1 and R2 represents either a monovalent residue derived from a saturated or unsaturated, cyclic or acyclic, linear or branched aliphatic hydrocarbon, or one of them represents an acyl residue and the other a monovalent residue of same type as that indicated above or hydrogen, together with at least one compound belonging to the group of phenolic derivatives or ethers of formula EMI2.2 in which each of the substituents R3 and R4 represents either hydrogen or a monovalent residue derived from a saturated or unsaturated, linear or branched aliphatic hydrocarbon, either one of them represents an acyl or alkoxy residue and the other a monovalent residue of the same type as that indicated above and R5 represents hydrogen or an alkyl residue, as flavoring agents for flavoring tobacco of natural or artificial origin. SUB-CLAIMS 1. Use according to claim, characterized in that at least one compound of the group below is employed as compound of formula I: a. 2-methyl-6-vinyl-pyrazine; b. 2-methyl-5-ethyl-pyrazine; vs. 2-methyl-3-acetyl-pyrazine. 2. Use according to claim, characterized in that at least one compound of the group below is employed as compound of formula II: a. p-vinyl guaiacol; b. 3-methyl-6-hydroxy-acetophenone; vs. 2-methyl-5-isopropenyl-anisole.