CAS: 56219-06-8; (Z)-Methyl Tetradec-9-Enoate

该化合物是源自本生物酸的单饱和脂肪酸酯,由于脂类分析,气相色谱学和质谱学应用的清晰结构和纯度,通常用作参考标准.该化合物是有机合成和生化研究的宝贵中间体,特别是在脂肪酸代谢和脂类特征分析研究中.在标准实验室条件下的稳定性和与分析技术的兼容性使得它成为定量和定性分析的可靠选择.这种酯化会提高挥发性,使其更适合基于GC的方法.

结构式图片

相似化合物

1120-25-8 2390-09-2 112-62-9

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methanol sodium methylate(Z)-9-tetradecen-1-ol (Z)-9-tetradecen-1-yl acetate cis-9-cetyl myristoleate

合成工艺路线路线简述

    📜油酸甲酯置于正丁基锂,臭氧体系中,用 四氢呋喃,正己烷,二氯甲烷 作为反应溶剂,化学反应 11.5H,反应生成 肉豆蔻脑酸甲酯
    参考文献:Process For Preparation Of Hexadecyl Cis-9-Tetradecenoate And Hexadecyl Cis-10-Tetradecenoate
    标题: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.

    海关参考信息

    专利信息


    专利号:US-12344573-B2
    优先权日:2018-07-16
    标题:Synthesis of straight-chain lepidopteran pheromones through one- or two-carbon homologation of fatty alkenes
    发明人:WAMPLER KEITH M; LEE CHOON WOO; ROZZELL DAVID
    权利人:PROVIVI INC
    摘要:Methods for the preparation of alkenes including insect pheromones are described. The methods include homologation reactions employing reagents such as 1,3-diesters, epoxides, cyanoacetates, and cyanide salts for elongation of starting materials and intermediates by one or two carbon atoms. The alkenes include insect pheromones useful in a number of agricultural applications.

    专利号:US-8816109-B2
    优先权日:2009-01-12
    标题:Process for preparation of hexadecyl cis-9-tetradecenoate and hexadecyl cis-10-tetradecenoate
    发明人:BETHALA LAKSHMI ANU PRABHAVATHI DEVI; KATKAM NADPI GANGADHAR; KUNKUMA VIJAYALAKSHMI; SISTLA RAMAKRISHNA; KUNCHA MADHUSUDHANA; PRAKASH VAMANRAO DIWAN; RACHAPUDI BADARI NARAYANA PRASAD
    权利人:BETHALA LAKSHMI ANU PRABHAVATHI DEVI; KATKAM NADPI GANGADHAR; KUNKUMA VIJAYALAKSHMI; SISTLA RAMAKRISHNA; KUNCHA MADHUSUDHANA; PRAKASH VAMANRAO DIWAN; RACHAPUDI BADARI NARAYANA PRASAD; COUNCIL SCIENT IND RES
    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-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.

    专利号:US-2015065682-A1
    优先权日:2013-08-30
    标 题 :Aliphatic polyesters and copolyesters derived from natural oils and their related physical properties
    发明人:NARINE SURESH; BOUZIDI LAZIZ; LI SHAOJUN; JOSE JESMY; POURFALLAH GHAZALEH
    权利人:ELEVANCE RENEWABLE SCIENCES
    摘要:The synthesis of certain medium and long chain ω-hydroxy esters and certain ω-hydroxy fatty acids is disclosed. Such ω-hydroxy esters and ω-hydroxy fatty acids are derived from natural oils, and their corresponding polymers were obtained by melt polycondensation. Additionally, the present effort investigates the effects of structural and molecular parameters on the thermal and mechanical properties of ω-hydroxy ester based polymers. Additionally, the present effort investigates the co-polymerization of ω-hydroxy ester based polymers.

    专利号:EP-3583088-B1
    优先权日:2017-02-17
    标 题:Synthesis of pheromones and related materials via olefin metathesis

    专利号:BR-112018009885-B1
    优先权日:2015-11-18
    标题:METHODS OF SYNTHESIS OF FATTY OLEFIN DERIVATIVE THROUGH OLEFIN METATHESIS

    专利号:EP-3823946-A1
    优先权日:2018-07-16
    标题 :Synthesis of straight-chain lepidopteran pheromones through one- or two- carbon homologation of fatty alkenes

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    品牌试剂参考报价(招募中)

    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    主要参考文献

    [参考文献]: Oier Aizpurua-Olaizola, Et Al. Optimization Of Supercritical Fluid Consecutive Extractions Of Fatty Acids And Polyphenols From Vitis Vinifera Grape Wastes. J Food Sci. 2015 Jan;80(1):E101-7.
    [参考文献]: Saskia Thurnhofer, Et Al. A Gas Chromatography/electron Ionization-Mass Spectrometry-Selected Ion Monitoring Method For Determining The Fatty Acid Pattern In Food After Formation Of Fatty Acid Methyl Esters. J Agric Food Chem. 2005 Nov 16;53(23):8896-903.
    [参考文献]: Tomás Horák, Et Al. Analysis Of Free Fatty Acids In Beer: Comparison Of Solid-Phase Extraction, Solid-Phase Microextraction, And Stir Bar Sorptive Extraction. J Agric Food Chem. 2009 Dec 9;57(23):11081-5.
    [参考文献]: Zhidong Xu, Et Al. An Improved Method For Determining Medium- And Long-Chain Fames Using Gas Chromatography. Lipids. 2010 Feb;45(2):199-208.

    合成参考文献


    参考文献:10.1007/s10886-014-0452-y
    摘要:Wang H, Brattström O, Brakefield PM, Francke W, Löfstedt C. Identification and Biosynthesis of Novel Male Specific Esters in the Wings of the Tropical Butterfly, Bicyclus martius sanaos. Journal of Chemical Ecology. 2014 Jun 04;40(6):549–59. doi: 10.1007/s10886-014-0452-y.
    摘要:Zhang, M.; Hanson, P. R., Science of Synthesis, (2007) 20, 925.
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