Council of Scientific and Industrial Research

Madhusudhana Kuncha

Badari Narayana Prasad Rachapudi

Ramakrishna Sistla

Lakshmi Anu Prabhavathi Devi Bethala

Nadpi Gangadhar Katkam

Vijayalakshmi Kunkuma

Vamanrao Diwan Prakash

Vijayalakshi Kunkuma

Hexadecyl cis-9-tetradecenoate commonly known as Cetyl myristoleate (CMO) is being used for the treatment of osteoarthritis and other joint inflammatory diseases, cis-9-Tetradecenoic acid (cis-9-myristoleic acid) is the main precursor for the preparation of CMO. As there are limited natural plant sources for cis-9-tetradecenoic acid, the present invention aimed at the synthesis of cis-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. cis-10-Tetradecenoic acid methyl ester, an isomer of cis-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 cis-9-tetradecenoate and hexadecyl c/s-10-tetradecenoate were prepared by enzymatic transesterification of cis-9-tetradecenoic acid methyl ester and cis-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.

Process for preparation of hexadecyl cis-9-tetradecenoate and hexadecyl cis-10-tetradecenoate

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Hyderabad Telangana, India

Madhusudhana Kuncha