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US 2010/0076077 A1Published application
Esters of 4,5-disubstituted-oxy-2-methyl-3,6-dioxo-cyclohexa-1,4-dienyl alkyl acids and preparation thereof
AssigneeEastman Chemical Company
InventorsMichael Fitzpatrick Wempe, Liu Deng, Stephanie Kay Clendennen, Neil Warren Boaz
Life of this patent
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Abstract
Esters of 4,5-disubstituted-oxy-2-methyl-3,6-dioxo-cyclohexa-1,4-dienyl alkyl acids were prepared chemically and/or enzymatically. Depending upon the ester, improved melanocyte cytotoxicity was achieved. Improved cytotoxicity characteristics are consistent with ester analogs being more physiologically compatible and less irritating to skin than their corresponding acids.
Claims16
A composition, comprising an ester and a dermatologically acceptable carrier, wherein the ester is represented by the general formula 1:
- wherein R and R1 are each independently a C1-C4 alkyl, R2 is a C6-C22 alkyl, C6-C22 alkenyl, C6-C20 dienyl, C6-C22 trienyl, C8-C22-tetraenyl or a mixture thereof, and n is 2-18.
A process for preparing an ester comprising:
- a) reacting an acid, anhydride, or acid derivative of formula 2
- wherein X is —OH, —SH, —F, —Cl, —Br, —I, or —OR3;
- and R and R1 are each independently a C1-C4 alkyl;
- and n is 2-18;
- and
- wherein R3 is C1-C6-alkyl or substituted C1-C6-alkyl.
- with an alcohol of formula 3:
- wherein R4, R5, and R6 are each an aliphatic hydrocarbons containing from about 6 to about 22 carbons
- in the presence of an organic solvent to form at least on ester;
- and
- b) isolating said at least one ester.
8 more elements
Dependencies are inferred from the claim text.