Allyl mercaptan perfume and food flavouring atents - prepd. from allyl xanthates derived from allyl alcohols and carbon disulphide

摘要

Allyl mercaptans are prepd. by heating an allyl xanthate in an aq. medium, pref. at 40-100 degrees C, Pref. allyl xanthates have formula: R1R2C=CR3-CR4R5-O-CSS-Cat+ (where R1 to R5 are H, opt. an O-contg. gp.-carrying loweralkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, where R2 and R3 or R2 and R4 or R3 and R4 can be closed to a ring and Cat+ is a cation of a base) and are converted to a mixt. of allyl mercaptan (Ia) and its allyl re-arrangement prod. (Ib), having formulae R1R2C=CR3-CR4R5-SH (Ia) and HS-CR1R2-CR3=CR4R5 (Ib) which can be separated by distn. Some cpds. (Ia) and (IB) are new, specifically 2-Me-hept-2-ene-3-thiol, 2-Me-hept-2-ene-1-thiol; oct-1-ene-3-thiol, oct-2-ene-1-thiol; 3,7,11-trimethyl-dodeca-1,6,10-triene-1- and -3-thiols (I', I"); 1-(1,1,3-trimethyl-3-cyclohexen-2-yl)-but-2-ene-1-thiol and -but-1-ene-3-thiol, (Ia) and (Ib) have organoleptic properties and are used in perfumes and/or flavouring compsns., esp. with berry, fruit and/or flower notes. As little as 0.1-10 ppm (I) can flavour food, e.g. milk products, sweets and drinks. A 1:1 mixt. (of (I', I") can be used to improve taste of fruit juices by stressing a grape-fruit peel character. 0.001-5 wt.% (Ie can be used in mfr. of perfumes, esp. with wood- and flower-notes, Perfume compsns. can be used for scenting detergents, cleansers, aerosols, cosmetics. Conversion of (II) to (I) takes place without decompsn. to CS2 and allyl alcohol.