CAS: 2485-71-4; 13-Methyltetradecanoic Acid

该化合物是一种含有分子式C15H30O2的分链脂肪酸,其特点是四十二酸脊的第13碳的甲基组,具有独特的物理化学特性.该化合物用于有机合成,脂质研究,并用作专门表面活性剂或生物活性分子的前体.其分支结构会提高非极溶剂的溶性,影响熔化行为,与线性类似物相比.该酸对于细菌膜脂脂和代谢途径的研究也感兴趣.在高纯度情况下,它适合于需要定义明确的脂肪酸衍生物的分析和研究应用.

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diazomethane isomyristic acid methyl 13-methyltetradecanoate (R)-15-Methyl-3-(13-methyl-tetradecanoyloxy)-hexadecanoic acid benzhydryl ester (S)-15-Methyl-3-(13-methyl-tetradecanoyloxy)-hexadecanoic acid benzhydryl ester (S)-2-Amino-hexanedioic acid 6-benzyl ester 1-((S)-1-carbamoylmethyl-13-methyl-tetradecyl) ester

合成工艺路线路线简述

    13-甲基十四烷酸甲酯置于sodium Hydroxide体系中,用 乙醇 用作溶剂,化学反应 4.0H,以89%的收率获得13-甲基十四烷酸
    参考文献:扩展支链脂肪酸的构效关系:不饱和度和支链基团大小对抗癌活性的影响.
    标题:扩展支链脂肪酸的构效关系:不饱和度和支链基团大小对抗癌活性的影响.
    摘要:支链脂肪酸(bcfa)是一类具有非常好抗癌活性的脂肪酸.Bcfa 13-甲基十四烷酸(13-Mtd)在体内抑制肿瘤生长而无毒性,但功效受限于中等效力,这是所有已知bcfa共有的特性.Bcfas的作用机理尚未完全阐明,在缺乏明确定义的靶标的情况下,Bcfa效能的优化必须依赖于结构-活性关系.我们目前对促进bcfa抗癌活性的结构特征的理解受到所报道的bcfa的低结构多样性的限制.本研究的目的是研究两种新的结构修饰-不饱和和支链基团大小-对bcfa活性的影响.因此,饱和和顺式的同源序列合成了带有甲基,乙基,丙基和丁基支化基团的-δ11不饱和bcfa,并在体外针对三种人类癌细胞系进行了筛选.将新bcfa的效力与13-Mtd和带有顺式-δ11双键的直链单未饱和脂肪酸(mufa)进行了比较.出现的主要发现是,Bcfa的抗癌活性受到较大分支基团的不利影响,但通过在bcfa烷基链中引入顺式-δ11双键而显着
    Doi:10.1016/j.Chemphyslip.2020.104952

    海关参考信息

    专利信息


    专利号:US-2008300418-A1
    优先权日:2004-11-08
    标 题:Synthesis of Cardiolipin Analogues and Uses Thereof
    发明人:AHMAD MOGHIS U; UKKALAM MURALI K; ALI SHOUKATH M; AHMAD IMRAN
    权利人:AHMAD MOGHIS U; UKKALAM MURALI K; ALI SHOUKATH M; AHMAD IMRAN
    摘要:The invention provides novel synthetic methodologies for preparing cardiolipin, migrated caridiolipin (1,2-positional isomer of cardiolipin) and their analogues having varying fatty acids and/or alkyl chains with varying length and degrees of saturation/unsaturation. The method comprises (a) reacting an optically pure 1,2-O-dialkyl-sn-glycerol or 1,2-O-dialkyl-sn-glycerol with one or more phosphoramidite reagent(s), wherein a phosphite triester is produced; (b) coupling the product of (a) with glycerol, wherein a protected cardiolipin is produced; and (c) deprotecting the protected cardiolipin, such that cardiolipin is prepared. The cardiolipins and analogues thereof, prepared by the present methods, can be incorporated into liposomes, which can also include active agents such as hydrophobic or hydrophilic drugs, antisense nucleotides or diagnostic agents. Such liposomes can be used to treat diseases or can be used in diagnostic and/or analytical assays.

    专利号:US-2017246690-A1
    优先权日:2014-06-20
    标 题:Stabilizing agent-free metal nanoparticle synthesis and uses of metal nanoparticles synthesized therefrom
    发明人:MURPHY RYAN J; DREYFUS REMI; HOUGH LAWRENCE ALAN; MALASSIS LUDIVINE; MURRAY CHRISTOPHER; DONNIO BERTRAND
    权利人:RHODIA OPERATIONS; CENTRE NAT RECH SCIENT; UNIV PENNSYLVANIA
    摘要:Described herein are methods of synthesizing metal nanoparticles and the metal nanoparticles synthesized therefrom. Further described in the present disclosure are methods of modifying the surfaces of metal nanoparticles and the metal nanoparticles modified thereby. Also described herein are uses of such metal nanoparticles.

    专利号:US-2008286351-A1
    优先权日:2004-06-29
    标 题:Pegylated Cardiolipin Analogs, Methods of Synthesis, and Uses Thereof
    发明人:AHMAD MOGHIS U; UKKALAM MURALI K; ALI SHOUKATH M; AHMAD IMRAN
    权利人:AHMAD MOGHIS U; UKKALAM MURALI K; ALI SHOUKATH M; AHMAD IMRAN
    摘要:The invention provides synthetic methods for PEGylated cardiolipins with varying linkers. The methods can be employed to prepare PEGylated cardiolipin with different fatty acid and/or alkyl chain length with or without unsaturation. The PEGylated cardiolipin, prepared by the present methods, can be incorporated into liposomes that can also include active agents such as hydrophilic or hydrophobic drugs for the treatment of human and animal diseases. In addition, the PEGylated cardiolipin can be incorporated into liposomes that include compounds for therapeutic and diagnostic imaging. The use of such liposomes with PEGylated cardiolipin prolongs the period of liposomal circulation without disrupting the lipid bilayer.

    专利号:US-2005266068-A1
    优先权日:2002-05-24
    标题 :Cardiolipin molecules and methods of synthesis
    发明人:AHMAD MOGHIS U; UKKALAM MURALI K; AHMAD IMRAN
    权利人:NEOPHARM INC
    摘要:The invention provides new synthetic routes for cardiolipin with different fatty acids and/or alkyl chains with varying chain length and also with or without unsaturation, particularly a short-chain cardiolipin. The methods comprise reacting a 1,2-O-sn-diacyl/1,2-O-sn-dialkyl glycerol or a 2-O-protected glycerol, with a phosphoramidite reagent or a phosphate triester to produce a protected cardiolipin, which is deprotected to prepare the short chain cardiolipin. The reaction schemes can be used to generate new variants of cardiolipin. The cardiolipin prepared by the present methods can be incorporated into liposomes, which can also include active agents such as hydrophobic or hydrophilic drugs. Such liposomes can be used to treat diseases or in diagnostic and/or analytical assays. Liposomes can also include ligands for targeting a particular cell type or specific tissue.

    专利号:US-6214875-B1
    优先权日:1998-04-14
    标题:Anticancer effects of specific branched-chain fatty acids and related production process
    发明人:YANG ZHENHUA
    摘要:A group of specific branched-chain fatty acids, with significant anticancer effects on human and animals; methods of making using either chemical synthesis or biosynthesis methods; and methods of treating cancer.

    专利号:CN-106852132-A
    优先权日:2014-06-20
    标题:Stabilizer-free synthesis of metal nanoparticles and use of metal nanoparticles synthesized therefrom
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    主要参考文献


    1: Han Y, Wang Y, Tombosa S, Wright S, Huffman J, Yuen G, Qian G, Liu F, Shen Y, Du L. Identification of a small molecule signaling factor that regulates the biosynthesis of the antifungal polycyclic tetramate macrolactam HSAF in Lysobacter enzymogenes. Appl Microbiol Biotechnol. 2015 Jan;99(2):801-11. doi: 10.1007/s00253-014-6120-x. Epub 2014 Oct 10.

    合成参考文献


    参考文献:10.1099/ijs.0.02733-0
    摘要:Donachie SP, Bowman JP, Alam M. Psychroflexus tropicus sp. nov., an obligately halophilic Cytophaga-Flavobacterium-Bacteroides group bacterium from an Hawaiian hypersaline lake. Int J Syst Evol Microbiol. 2004 May;54(Pt 3):935–40. doi: 10.1099/ijs.0.02733-0.
    参考文献:10.1042/bj0570297
    摘要:HANSEN RP, SHORLAND FB, COOKE NJ. The branched-chain fatty acids of butterfat. IV. The isolation of (+)-12-methyltetradecanoic acid and of 13-methyltetradecanoic acid. Biochem J. 1954 Jun;57(2):297–301.
    参考文献:10.1016/j.bbalip.2003.10.010
    摘要:Naka T, Fujiwara N, Yano I, Maeda S, Doe M, Minamino M, Ikeda N, Kato Y, Watabe K, Kumazawa Y, Tomiyasu I, Kobayashi K. Structural analysis of sphingophospholipids derived from Sphingobacterium spiritivorum, the type species of genus Sphingobacterium. Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 2003 Dec;1635(2-3):83–92. doi: 10.1016/j.bbalip.2003.10.010.
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