Patents

Hexadecyl c/s-9-tetradecenoate commonly known as Cetyl Myristoleate (CMO) is being used for the treatment of osteoarthritis and other joint inflammatory diseases. c/s-9-Tetradecenoic acid (c/s-9-myristoleic  acid) is the main precursor for the preparation of CMO. As there are limited natural plant sources for c/s-9-tetradecenoic acid, the invention aimed at the synthesis of c/s-9-tetradecenoic acid methyl ester from oleic acid methyl ester. As oleic acid is not available in pure form, this has to be isolated from oleic acid-rich oils like olive oil. c/s-10-Tetradecenoic acid methyl ester, an isomer of c/'s-9-tetradecenoic acid was also prepared from undecenoic acid methyl ester, a derivative of castor oil. Undecenoic acid is easily available commercially in pure form. Hexadecyl c/'s-9 tetradecenoate and hexadecyl c/s-10-tetradecenoate were prepared by enzymatic transesterification of c/s-9-tetradecenoic acid methyl esterand c/s-10-tetradecenoic acid methyl ester with 1-hexadecanol (cetyl  alcohol) respectively. Both the isomers of cetyl myristoleate were evaluated for anti arthritis, blocking inflammation and reduction of adjuvant-induced arthritis in rats.