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United States Patent 19 L L 3,928,456 Kováts Et Al

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United States Patent 19 L L 3,928,456 Kováts Et Al United States Patent 19 l l 3,928,456 Kováts et al. (45) Dec. 23, 1975 (54) CYCLOALPHATIC UNSATURATED 260/488 H; 260/.514 J; 260/.530 N; 260/544 L; KETONES AS ODOUR AND 260/546; 260/586 C; 260/586 F; 260/586 P; TASTE-MODIFYING AGENTS 260/595; 260/598; 260/601 R; 260/617 R; (75) Inventors: Ervin Kováts, Lausanne; Edouard 260/617 E; 260/617 F; 260/632 Y; 260/638 R; Demole, Geneva; Cinther Ohloff, 260/638 Y; 260/642; 260/666 R; 426/155; Bernex,Geneva, Switzerland; Max 426/170; 426/175; 426/190; 426/192; Stoll, deceased, late of Lully, 426/193; 426/213; 426/214; 426/221; 426/229 Geneva, Switzerland, by Suzanne (51) int. Cl’.......................................... CO7C 49/61 Stoll, executrix 58 Field of Search................................. 260/586 R 73 Assignee: Firmenich S.A., Geneva, 56) References Cited Switzerland OTHER PUBLICATIONS 22) Filed: Sept. 6, 1974 Demole et al., “Helv. Chim. Acta.,' Vol. 53, Fasc. 21 Appl. No.: 503,794 3(1970) pp. 541-551. Related U.S. Application Data Primary Examiner-Norman Morgenstern 60 Division of Ser. No. 35,594, May 7, 1970, Attorney, Agent, or Firm-Pennie & Edmonds abandoned, which is a continuation-in-part of Ser. No. 774,179, Nov. 7, 1968, abandoned. 57 ABSTRACT New cycloaliphatic unsaturated ketones and their use (30) Foreign Application Priority Data as perfuming and odour-modifying agents in the man Nov. 9, 1967 Switzerland....................... 5667/67 ufacture of perfumes and perfumed products, and as Nov. 1, 1968 Switzerland....................... 16309/68 flavouring and taste-modifying agents in the prepara May 7, 1969 Switzerland......................... 6976/69 tion of foodstuffs in general and imitation flavours for Aug. 8, 1969 Switzerland....................... 12065,169 foodstuffs, beverages, animal feeds, pharmaceutical Apr. 14, 1970 Switzerland...... ............... 5559770 preparations and tobacco products. Apr. 17, 1970 Switzerland......................... 5725/70 Methods for the preparation of said cycloaliphatic (52) U.S. Cl................ 260/586 R; 131/17; 252/522; unsaturated ketones. 260/348 R; 260/348 C; 260/469; 260/488 R; 13 Claims, No Drawings 3,928,456 1 2 The compounds of the invention increase the power CYCLOALPHATIC UNSATURATED KETONES AS and the diffusion ability of perfume compositions and ODOUR AND TASTE-MODIFYING AGENTS impart to them a natural richness. This is a division of application Ser. No. 35,594 filed The compounds of the invention possess also very May 7, 1970, which in turn is a continuation-in-part of 5 interesting flavouring properties. Depending on the application Ser. No. 774,179, filed Nov. 7, 1968 both nature of the products to which they are added, they now abandoned. will develop fruity, herb-like, winy, woody, floral or waxy flavour notes or any combinations of these fla SUMMARY OF THE INVENTION vour notes. In some instances they will impart to prod The invention relates to a new class of cycloaliphatic 10 ucts a red berry-like flavour and can be used for im unsaturated ketones having the formula proving the taste and aroma of artificial strawberry, cranberry, cherry or redcurrant flavour compositions and the like. Surprisingly, the new ketones can even be RT used for enhancing the taste and flavour of such prod 15 ucts as honey and red wines. R6 co-cH2 ==== 6-CH.3. R' The proportions in which the new compounds can be 2-n used to produce desirable odoriferous effects vary within wide limits. In the preparation of perfume com 2. 5 2 positions, for instance, interesting effects can be ob 51 S21NS tained with proportions as low as about 100 ppm to R 3. about 5% of the total weight of a perfume composition. I of Y, & Depending on the odoriferous effects wanted, the pro portions of the ketones can be increased to about 10% Or ever Ote. containing one double bond in position 2'- or 3'- of the 25 When the new ketones are used as flavouring agents acyl side-chain and either one double bond in position or additives for modifying the organoleptic properties l- or 2-(as shown in the above formula, the double of foodstuffs, animal feeds, beverages, pharmaceutical bond in the 2 position can be either in the cycle or the preparations and tobacco products, the new com side chain), or two conjugated double bonds in posi pounds can be used in proportions which, again, vary tions 1 - and 3- of the cycle, the double bonds being 30 within wide limits. represented by dotted lines, and wherein n is zero or 1, Interesting flavouring effects, for instance, can be R, R and R represent hydrogen or one of them a achieved by using the compounds of the invention in lower alkyl radical, such as methyl or ethyl, and the proportions from 0.1 to 10 ppm based on the weight of others hydrogen, and R', R, R and R represent hy the products to be flavoured. However, these propor drogen or one of them a lower alkyl radical, such as 35 tions can be increased beyond 10 ppm up to about 100 methyl or ethyl, and the others hydrogen. ppm in order to achieve special flavouring effects. In The invention also relates to methods for the prepa the proparation of flavouring compositions by admix ration of compounds I, of some of the intermediates ing the new compounds to other aromatics, the said used in their preparation and some of their derivatives componds can be used, for example, in proportions of and to the use of said compounds as perfuming and 40 about 0.1% to about 15% of the total weight of the odour-modifying agents in the manufacture of per flavouring composition. In many cases average propor fumes and perfumed products, and as flavouring and tions of about 1 to 10% by weight will give the desired taste-modifying agents in the manufacture of artificial results. flavours for foodstuffs, beverages, animal feeds, phar It is to be understood that the proportions given maceuticals and tobacco. 45 above are in no way absolute values and that higher or lower concentrations of the new compounds may be DESCRIPTION OF THE PREFERRED used depending on the specific odoriferous or flavour EMBODIMENTS ing effects to be developed. The compounds of the invention have particularly According to the invention, the methods of prepara interesting and valuable organoleptic properties and, 50 tion of the compounds of formula 1 are either of general consequently, they are useful as fragrances in the per nature or of more specific type. fume industry, as ingredients for the preparation of According to the invention, a general method for the artificial flavours and as flavour additives in foodstuffs, preparation of compounds of formula animal feeds, beverages, pharmaceutical preparations and tobacco products. 55 The term 'foodstuff" is used in this specification in its broadest sense and is meant to include also products such as coffee, tea and cocoa. In particular, the new ketones and some of their intermediates can be used as odoriferous ingredients in concentrated or diluted per 60 fumes and in perfumed products such as soaps, deter gents, cosmetic products, w...es aid any other prod ucts which may be perfumed to make them commer cially more attractive. Furthermore, the new compounds are very useful as 65 ingredients in the preparation of artificial essential oils containing either one double bond in position l- or 2 Such as jasmin oil, geranium Bourbon oil, rose oil and or two conjugated double bonds in positions 1 - and 3 thr: of the cycle, the double bonds being represented by 3,928,456 3 4 dotted lines, and wherein R, R and R' represent hy Table -continued drogen or one of them a lower alkyl radical, such as methyl or ethyl, and the others hydrogen, and R', R*, R and R represent hydrogen or one of them a lower alkyl radical, for example methyl or ethyl, and the others hydrogen, comprises acylating organo-metallic propene derivatives having the formula OOH l' 2' 3" ME---CH.R 10 cyclisations Ra R2 wherein the symbols R', R* and R8 have the same meaning as above and ME represents a metallic func tion such as Li, Zn, Cd and Mg-halogen, with cycloger anoyl or safranyl derivatives having the formula 15 geranic acid derivatives 20 25 endocyclic double bond in position 2 endocyclic double bond in position 1 1 = exocyclic double bond in position 2 wherein the dotted lines and the symbols R', R, R and 30 R" have the same meaning as above and wherein the symbol X represents a leaving group such as halogen, O-alkyl, O-aryl, O-CO-aryl, O-CO-alkyl. R A preferred mode of operation consists in using, as cyclogeranoyl derivatives, geranoyl halogenides such 35 as, for instance, chlorides, bromides or iodides or halcf.e :- geraniate derivatives such as methyl, ethyl or lithium at ic C : geraniate. The cyclogeranoyl and safranyl derivatives est, cis used in the above mentioned process can be synthe CaO. sized according to different methods, some of which 40 are described hereinafter. For instance, 1. The cyclogeranoyl derivatives of structure a- and 6- can be synthesized from the corresponding cy clogeranic acids by usual methods. The cycloger anic acids may be obtained from the corresponding 45 citral derivatives according to known methods (ef. Gildemeister & 'Hoffman, Die Aetherischen Oele, III d. pp. 137-138, Akademie-Verlag, Berlin (1966)). The process for the preparation of the cyclogeranoyl derivatives of structure o- and 6 50 can be illustrated by the following scheme A wherein the dotted lines and the symbols R have the same meaning as above. 55 Scheme A: RT 2.
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