Patent EP-2524959-A1 (EP)
Inventor: HOELSCHER BERND
IPC: A23L27/20
Filed: 2011-05-17
Abstract: Perfume and/or flavoring composition comprises >= 1-3 substituted 4-vinyl-[1,3]dioxolane derivatives (I) and their stereoisomers, and at least >= 3-8 further perfumes and/or flavoring substances, which does not comprise (I), where the composition does not comprise 2-hexyl-4-vinyl-1,3-dioxolane. Perfume and/or flavoring composition comprises >= 1-3 substituted 4-vinyl-[1,3]dioxolane derivatives of formula (I) and their stereoisomers, and at least >= 3-8 further perfumes and/or flavoring substances, which does not comprise (I), where the composition does not comprise 2-hexyl-4-vinyl-1,3-dioxolane. R 3, R 4=H or 1-15C organic group optionally containing 1-3 O atoms, preferably H or saturated or unsaturated, aromatic or aliphatic, branched or unbranched, cyclic or linear, bridged or unbridged 1-15C group (optionally substituted by 1-3 alkyl, alkenyl and/or 1 or 2 OH, or R 3+ R 4=ring containing 5-8C atoms and optionally 1 or 2 double bonds and/or optionally 1-3 O atoms (optionally substituted by at least 1 branched or unbranched, bridged or unbridged alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, arylalkyl, alkoxyalkyl or alkoxyaryl) groups, and R 3and R 4comprise 3-30C atoms, or R 1, R 2=H or Me, preferably H, provided that: when a carbon-carbon single bond is present in position 3 to position 4 of R 4, then R 4is 4-15C alkyl (optionally branched and optionally contains >= 1-2 double bonds); or when R 3is not hydrogen, then R 4is 2-15C alkyl (optionally branched and optionally contains >= 1-2 double bonds). Independent claims are also included for: (1) (I) and their stereoisomers excluding 61 compounds e.g. 2-ethyl-4-vinyl-[1,3]dioxolane, 2-propyl-4-vinyl-[1,3]dioxolane, 2-isopropyl-4-vinyl-[1,3]dioxolane, 2-butyl-4-vinyl-[1,3]dioxolane, 2-isobutyl-4-vinyl-[1,3]dioxolane, 2-pentyl-4-vinyl-[1,3]dioxolane, 2-hexyl-4-vinyl-[1,3]dioxolane, 2-heptyl-4-vinyl-[1,3]dioxolane, 2-cyclohexyl-4-vinyl-[1,3]dioxolane, 2-phenyl-4-vinyl-[1,3]dioxolane, 2-o-tolyl-4-vinyl-[1,3]dioxolane, 2-m-tolyl-4-vinyl-[1,3]dioxolane, 2-p-tolyl-4-vinyl-[1,3]dioxolane, 2-(2-methoxy-phenyl)-4-vinyl-[1,3]dioxolane, 2-(3-methoxy-phenyl)-4-vinyl-[1,3]dioxolane, 2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxolane, 5-(4-vinyl-[1,3]dioxolan-2-yl)-benzo[1,3]dioxole, 2-furan-3-yl-4-vinyl-[1,3]dioxolane, 2-ethyl-2-methyl-4-vinyl-[1,3]dioxolane, 2-methyl-2-propyl-4-vinyl-[1,3]dioxolane, 2-butyl-2-methyl-4-vinyl-[1,3]dioxolane, 2-isopropyl-2-methyl-4-vinyl-[1,3]dioxolane, 2-methyl-2-(3-methylbutyl)-4-vinyl-[1,3]dioxolane, 2-methyl-2-(4-methylpentyl)-4-vinyl-[1,3]dioxolane, 2,2-diethyl-4-vinyl-[1,3]dioxolane, 2,2-dipropyl-4-vinyl-[1,3]dioxolane, 2,2-diisopropyl-4-vinyl-[1,3]dioxolane, 2-methyl-2-pentyl-4-vinyl-[1,3]dioxolane, 2-hexyl-2-methyl-4-vinyl-[1,3]dioxolane, 2-methyl-2-octyl-4-vinyl-[1,3]dioxolane, 2-methyl-2-nonyl-4-vinyl-[1,3]dioxolane, 2-methyl-2-phenyl-4-vinyl-[1,3]dioxolane, 2-cyclohexyl-2-methyl-4-vinyl-[1,3]dioxolane, 2-cyclopentyl-4-vinyl-[1,3]dioxolane, 2-cycloheptyl-4-vinyl-[1,3]dioxolane, 2,2-pentamethylene-4-vinyl-[1,3]dioxolane, 2-methyl-2-isopropyl-4-vinyl-[1,3]dioxolane, 2,2-hexamethylene-4-vinyl-[1,3]dioxolane, 2-but-3-enyl-2-methyl-4-vinyl-[1,3]dioxolane, (S)-2,2-diethyl-4-vinyl-[1,3]dioxolane or (R)-2-vinyl-1,4-dioxa-spiro[4.5]decane, (S)-2-vinyl-1,4-dioxa-spiro[4.5]decane, 2-((E)-propenyl)-4-vinyl-[1,3]dioxolane, 2-(4-vinyl-[1,3]dioxolan-2-yl)phenol, 2,4-divinyl-[1,3]dioxolane, 2-tert-butyl-2-methyl-4-vinyl-[1,3]dioxolane, 2-butyl-2-ethyl-4-vinyl-[1,3]dioxolane, 2-(2-methyl-cyclohexyl)-4-vinyl-[1,3]dioxolane, 2-(4-methyl-cyclohexyl)-4-vinyl-[1,3]dioxolane and (S)-2-methyl-2-vinyl-1,4-dioxaspiro[4.5]decane; (2) preparing (I), comprising reacting substituted but-2-ene-1,4-diol compounds of formula R 1-C(CH 2-OH)=C(CH 2-OH)-R 2(III) with aldehyde compounds of formula R 3-CO-R 4(IV) in presence of copper(I) chloride; and (3) providing, modifying and/or intensifying odor and/or flavor without providing the odor and/or flavor of pineapple note, comprising contacting or mixing the perfume and/or flavoring composition or (I) with an article for providing, modifying and/or intensifying odor- and/or flavor notes, preferably flowery-, greasy-, leathery-, bloomy-, phenolic-, metallic- or watery notes or notes of green olives, fruit, green, rose, myrrh, pear, mango, grapefruit, melon, lemon, linalool, mirabelle, spearmint, mushroom, chamomile, apple, carbinol, aromatic, fresh or herb notes. [Image].