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    A PROCESS FOR PREPARATION OF HEXADECYL CIS-9-TETRADECENOATE AND HEXADECYL CIS-10-TETRADECENOATE
    2.
    发明公开
    A PROCESS FOR PREPARATION OF HEXADECYL CIS-9-TETRADECENOATE AND HEXADECYL CIS-10-TETRADECENOATE 有权
    制备十六烷基十六-9-十四烯酸酯和十六烷基十六-10-十四烯酸酯的方法

    公开(公告)号：EP2379175A1

    公开(公告)日：2011-10-26

    申请号：EP10706759.7

    申请日：2010-01-12

    申请人： Council of Scientific & Industrial Research

    发明人： BETHALA, Lakshmi, Anu, Prabhavathi, Devi ,  KATKAM, Nadpi, Gangadhar ,  KUNKUMA, Vijayalakshi ,  SISTLA, Ramakrishna ,  KUNCHA, Madhusudhana ,  PRAKASH, Vamanrao, Diwan ,  RACHAPUDI, Badari, Narayana, Prasad

    IPC分类号： A61P19/02 ,  A61P29/00 ,  C07C67/08 ,  C07C67/333 ,  C07C67/343 ,  C07C69/533 ,  C07C69/716 ,  A61K31/231 ,  C12P7/62

    CPC分类号： C07C67/02 ,  C07C67/333 ,  C07C67/343 ,  C11C3/10 ,  C12P7/64 ,  C12P7/649 ,  Y02E50/13 ,  C07C69/716 ,  C07C69/533

    摘要： 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-tetradecenoateand hexadecyl c/s-10-tetradecenoate were prepared by enzymatic transesterification of
    cis -9-tetradecenoic acid methyl esterand
    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.

    摘要翻译： 顺式-9-十四碳烯酸十六烷基酯通常被称为十六烷基肉豆蔻酸酯（CMO），用于治疗骨关节炎和其他关节炎性疾病，顺-9-十四碳烯酸（顺-9-肉豆蔻脑酸）是制备 CMO。 由于顺-9-十四碳烯酸的天然植物来源有限，本发明旨在从油酸甲酯合成顺-9-十四碳烯酸甲酯。 由于油酸不能以纯净形式获得，所以必须从橄榄油等富含油酸的油中分离出来。 顺-10-十四碳烯酸甲酯，顺-9-十四碳烯酸的异构体也由十一碳烯酸甲酯（一种蓖麻油的衍生物）制备。 十一碳烯酸容易以纯的形式商购获得。 顺式-9-十四碳烯酸十六烷基酯和顺式-10-十四碳烯酸十六烷基酯分别通过顺式-9-十四碳烯酸甲酯和顺式-10-十四碳烯酸甲酯与1-十六烷醇（鲸蜡醇）的酶促酯交换制备。 评估十二烷基肉豆蔻酸酯的异构体的抗关节炎，阻断大鼠中的炎症和减少佐剂诱导的关节炎。