hexadecyl cis-10-tetradecenoate | 1234617-82-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: hexadecyl cis-10-tetradecenoate
• 英文别名: hexadecyl (Z)-tetradec-10-enoate
• CAS: 1234617-82-3
• 化学式: C₃₀H₅₈O₂
• 分子量: 450.789
• InChiKey: NGTHLWOGYMUFDQ-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  32
• 可旋转键数：
  27
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  10-烯酸甲酯 在 正丁基锂 、 臭氧 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 19.5h， 生成 hexadecyl cis-10-tetradecenoate
  参考文献：
  名称：

  Process for Preparation of Hexadecyl Cis-9-Tetradecenoate and Hexadecyl Cis-10-Tetradecenoate

  摘要：

  十六烷基顺-9-十四碳烯酸盐通常被称为鲸蜡醇豆蔻酸酯（CMO），目前正被用于治疗骨关节炎和其他关节炎症疾病，顺-9-十四碳烯酸（顺-9-豆蔻酸）是制备CMO的主要前体。由于顺-9-十四碳烯酸的自然植物来源有限，本发明旨在从油酸甲酯合成顺-9-十四碳烯酸甲酯。由于油酸无法以纯净形式获得，因此需要从富含油酸的油类如橄榄油中提取。还从十一烯酸甲酯，即蓖麻油的衍生物，制备了顺-10-十四碳烯酸甲酯，这是顺-9-十四碳烯酸的异构体。十一烯酸在市场上容易以纯净形式获得。通过酶促转酯反应，分别用顺-9-十四碳烯酸甲酯和顺-10-十四碳烯酸甲酯与1-十六醇（鲸蜡醇）反应，制备了十六烷基顺-9-十四碳烯酸盐和十六烷基顺-10-十四碳烯酸盐。这两种鲸蜡醇豆蔻酸酯的异构体都进行了抗关节炎、阻断炎症和在大鼠中减少佐剂诱导关节炎的评价。

  公开号：

  US20110269987A1

文献信息

• Process for preparation of hexadecyl cis-9-tetradecenoate and hexadecyl cis-10-tetradecenoate
  申请人：Bethala Lakshmi Anu Prabhavathi Devi

  公开号：US08816109B2

  公开（公告）日：2014-08-26

  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.

  十六烷基顺式-9-十四烯酸酯常被称为肉豆蔻油酸酯（CMO），用于治疗骨关节炎和其他关节炎症性疾病。顺式-9-十四烯酸（顺式-9-肉豆蔻酸）是制备CMO的主要前体。由于天然植物中顺式-9-十四烯酸的来源有限，因此本发明旨在从油酸甲酯中合成顺式-9-十四烯酸甲酯。由于油酸并不以纯形式存在，因此必须从富含油酸的油中分离出来，例如橄榄油。顺式-10-十四烯酸甲酯是顺式-9-十四烯酸的异构体，也可以从蓖麻油的衍生物十一烯酸甲酯中制备。十一烯酸在市场上很容易以纯形式获得。通过顺式-9-十四烯酸甲酯和顺式-10-十四烯酸甲酯与1-十六醇（硬脂醇）的酶催化酯交换反应，制备了十六烷基顺式-9-十四烯酸酯和十六烷基顺式-10-十四烯酸酯。两种硬脂醇肉豆蔻酸酯异构体均被评估其抗关节炎、抗炎和减少大鼠佐剂诱导关节炎的作用。
• A PROCESS FOR PREPARATION OF HEXADECYL CIS-9-TETRADECENOATE AND HEXADECYL CIS-10-TETRADECENOATE
  申请人：Council of Scientific & Industrial Research

  公开号：EP2379175A1

  公开（公告）日：2011-10-26
• METHOD FOR PREPARING A COMPOSITION COMPRISING CETYLATED FATTY ACIDS
  申请人：ALESCO S.R.L.

  公开号：US20220220414A1

  公开（公告）日：2022-07-14

  A composition is described comprising a mixture of at least one cetylated fatty acid or a mixture of cetylated fatty acids and an antioxidant in reduced percentages by weight, and related methods for treatment of arthritis and of inflammatory joint and musculoskeletal pain. Furthermore a composition is described comprising a mixture of at least one cetylated fatty acid or a mixture of cetylated fatty acids and, optionally, an antioxidant, and related treatment methods for protecting the gastric mucosa and for regulating the blood glucose levels. Additionally, a method is described for preparing the at least one cetylated fatty acid or mixture of cetylated fatty acids and for preparing compositions comprising the cetylated fatty acids and the antioxidant.
• US8816109B2
  申请人：——

  公开号：US8816109B2

  公开（公告）日：2014-08-26
• [EN] A PROCESS FOR PREPARATION OF HEXADECYL CIS-9-TETRADECENOATE AND HEXADECYL CIS-10-TETRADECENOATE<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE CIS-9-TÉTRADÉCÉNOATE D'HEXADÉCYLE ET DE CIS-10-TÉTRADÉCÉNOATE D'HEXADÉCYLE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2010079514A1

  公开（公告）日：2010-07-15

  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.