Patent GB-1457671-A (GB)
Title: Flavour
IPC: A23L29/20
Filed: 1974-01-31
Abstract: 1457671 Flavour modifiers WILKINSON SWORD Ltd 29 Jan 1975 [31 Jan 1974 18 April 1974] 04587/74 and 17088/74 Headings A2B and A2C The flavour of ingestible preparations including tobacco is modified by incorporation therein of a compound capable of stimulating the cold receptors of the nervous system of the body when brought into contact therewith but being incorporated into the preparation in an amount below the threshold of practical physiological cooling activity (as hereinbefore defined), said compound being a compound of the formula where, in formula I, R 1  is H or C 1 -C 6  alkyl, R 2  and R 3 , when taken separately, are each alkyl or cycloalkyl of up to 6 carbon atoms, or up to 7 when X is OH or CH 2 OH, R 2  and R 3 , when taken together, represent a C 4 -C 11  straight or branched chain alkylene group, it being provided that: i) when R 1  is H then the alkylene group is branched at a carbon atom in a beta or gamma position relative to the group X; ii) that when X is OH or CH 2 OH, then said alkylene group may contain an OH substituent; and iii) that when R, is H and X is OH, then the cyclic group represented by is other than a p-menth-3-yl group; R 1 , R 2  and R 3  together provide a total of from 6-18 carbon atoms; X is COOR 7 , CONR 8 R 9 , SO x  NR 8 R 9  or SO x R 10 ; R 7  is H, an alkali or alkaline earth metal, ammonium, alkyl- or hydroxyalkyl-substituted ammonium, or a hydroxyalkyl, hydroxyalkoxyalkyl, carboxyalkyl or alkoxycarbonylalkyl group of up to 12 carbon atoms; R 8  and R 9 , when taken separately, are each H or alkyl, hydroxyalkyl, carboxyalkyl or alkoxycarbonylalkyl of up to 12 carbon atoms, with the proviso that when R 8  is H, R 9  may also be cycloalkyl of up to 8 carbon atoms, phenyl or benzyl, or substituted phenyl or benzyl containing hydroxy, C 1 -C 4  alkyl or C 1 -C 4  alkoxy substituents; R 8  and R 9 , when taken together represent an alkylene group of up to 12 carbon atoms, the carbon atom chain of which may optionally be interrupted by oxygen or an -NH- group; R 10  is alkyl, hydroxyalkyl, carboxyalkyl or alkoxycarbonylalkyl of up to 12 carbon atoms; and x is 1 or 2; and where in formula II, R 4  is C 3 -C 20  alkyl; R 5  is C 3 -C 8  alkyl or cycloalkyl; R 6  is C 1 -C 8  alkyl or C 3 -C 8  cycloalkyl or alkylcycloalkyl; it being provided that at least one of R 4 , R 5  and R 6  is branched at a carbon atom in an α, # or γ position relative to the phosphorus atom, and that R 4 , R 5  and R 6  together provide a total of from 10-24 carbon atoms; and where, in formula III, R 11  when taken separately, is H, C 1 -C 6  alkyl or C 3 -C 6  cycloalkyl; R 12 , when taken separately, is C 3 -C 10  alkyl or C 3 -C 10  alkylcycloalkyl, cycloalkyl, or cycloalkylalkyl, with the proviso that R 12  is branched at an α- or #-carbon atom relative to the N atom, this condition to be satisfied, in the case of cyclic groups, when the carbon atom α- or #- to the N atom is part of the cycle; R 11  and R 12 , when taken together, represent a branched chain alkylene group having 3-7 carbon atoms and branching at an α- or #-carbon atom relative to the N atom, and the chain optionally containing an ether (-O-) oxygen atom; R 11  and R 12  when separate groups and when taken together provide a total of at least 5 carbon atoms; Y represents R 13 CO-, R 14 SO 2 - or R 15 R 16 NOC-; R 13  is H, C 1 -C 6  alkyl or alkenyl, C 3 -C 6  cycloalkyl C 1 -C 10  hydroxyalkyl, C 2 -C 10  carboxyalkyl, C 3 -C 10  alkoxycarbonylalkyl, phenyl or phenyl containing C 1 -C 4  alkyl, alkoxy, OH, COOH or NO 2  substituents, with the proviso that when R 13  is C 6  alkyl it is primary in structure; R 14  is C 1 -C 6  alkyl or C 3 -C 6  cycloalkyl, with the proviso that when R 14  is C 5  or C 6  alkyl it is primary in structure; R 15  and R 16 , when taken separately, are each H, C 1 -C 6  alkyl, C 3 -C 6  alkylcycloalkyl, cycloalkyl, or cycloalkylalkyl, C 1 -C 10  hydroxyalkyl, C 2 -C 10  carboxyalkyl or C 3 -C 10  alkoxycarbonylalkyl; or together represent a straight or branched chain C 3 -C 10  alkylene group optionally substituted with oxygen or an oxygen-containing group or containing an ether oxygen atom; and R 11 , R 12  and Y provide a total of from 7-16 carbon atoms. The following classes of compounds fall within the given formulae: cyclic amides, acyclic secondary and tertiary amides, cyclic carboxylic acids, salts and esters, cyclic sulphonamides and sulphinamides, acyclic sulphonamides and sulphinamides, cyclic and acyclic sulphoxides and sulphones, phosphine oxides, acyclic secondary and tertiary alcohols, cyclic alcohols, methylol compounds substituted ureas, amides, sulphonamides, p-methane diols, and acyclic carboxylic acids, salts and esters. Exhaustive lists are included in the specification.