(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraen-1-ol | 181213-43-4

• 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: (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraen-1-ol
• CAS: 181213-43-4
• 化学式: C₁₈H₃₀O
• 分子量: 262.436
• InChiKey: VXPWGJVUJNFEJE-LTKCOYKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraen-1-ol 在 sodium hydroxide 、 sodium 、 triphenylphosphine dibromide 1:1 addition complex 作用下， 以 乙醇 、 二乙二醇二甲醚 、 水 、 乙腈 为溶剂， 反应 7.0h， 生成 (8Z,11Z,14Z,17Z)-8,11,14,17-二十碳四烯酸
  参考文献：
  名称：

  Kuklev; Popkov; Kas'yanov, Russian Journal of Bioorganic Chemistry, 1996, vol. 22, # 3, p. 192 - 195

  摘要：

  DOI：
• 作为产物：
  描述：

  (6Z,9Z,12Z,15Z)-十八碳四烯酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以92%的产率得到(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraen-1-ol
  参考文献：
  名称：

  Chemical C2-elongation of polyunsaturated fatty acids

  摘要：

  Three fatty acids were synthesized from commercially available alpha-linolenic, stearidonic and eicosapentaenoic acids by C2-elongation using a four step preparative technique. The parent fatty acid methyl esters were reduced to alcohols with LiAlH4, converted to bromides by treatment with triphenylphosphine dibromide, coupled with a lithiated C2-elongation block -2,4,4-trimethyl-2-oxazoline - to form the corresponding 2,2-dimethyloxazolines of C2-elongated fatty acids, and finally, converted to the target polyunsaturated fatty acids by acidic alcoholysis. Yields of more than 60% were achieved on a gram scale. The resulting 11Z, 14Z, 17Z-eicosatrienoic, 8Z, 11Z, 14Z, 17Z-eicosatetraenoic and 7Z, 10Z,13Z, 16Z, 19Z-docosapentaenoic acids were obtained as colorless oils with > 98% purity and could be used for biochemical investigations without additional purification. The elongated fatty acids were free of byproducts that could result from Z-E isomerization or migration of double bonds. (c) 2006 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2006.09.002

文献信息

• [EN] FATTY ACID DERIVATIVES FOR TREATING NON-ALCOHOLIC STEATOHEPATITIS<br/>[FR] DÉRIVÉS D'ACIDE GRAS POUR LE TRAITEMENT DE LA STÉATOHÉPATITE NON ALCOOLIQUE
  申请人：BASF AS

  公开号：WO2019111048A1

  公开（公告）日：2019-06-13

  The present disclosure provides a compound for use in therapeutic and/or prophylactic treatment of non-alcoholic steatohepatitis (NASH) and/or alcoholic steatohepatitis (ASH). The compound for use according to the invention, is an unsaturated fatty acid with an oxygen incorporated in the β-position, and further comprising an α-substituent. More particularly, the invention provides a compound for use in treatment of NASH and/or ASH, and a method using this, wherein the compound is of Formula (II), wherein R1, R2, R3, X, and Y are as defined in the specification; and wherein this compound may be administered alone or in combination with an additional active agent.

  本公开提供了一种用于治疗和/或预防非酒精性脂肪肝炎（NASH）和/或酒精性脂肪肝炎（ASH）的化合物。根据本发明使用的化合物是一种在β位含有氧原子的不饱和脂肪酸，并且还包含一个α-取代基。更具体地说，本发明提供了一种用于治疗NASH和/或ASH的化合物以及使用该方法，其中该化合物是公式（II），其中R1、R2、R3、X和Y如说明书中所定义；并且该化合物可以单独使用或与另一种活性剂结合使用。
• Synthesis of Polyunsaturated β-Oxa Fatty Acids via Rhodium Mediated Carbenoid Insertion
  作者：Michael J. Pitt、Christopher J. Easton、Christopher J. Moody、Antonio Ferrante、Alfred Poulos、Deborah A. Rathjen

  DOI：10.1055/s-1997-1355

  日期：1997.11

  Polyunsaturated β-oxa fatty acids 1 are readily obtained from naturally derived polyunsaturated fatty alcohols 2 via rhodium(II) acetate-catalysed reaction with tert-butyl diazoacetate 3, followed by ester cleavage.

  多不饱和β-氧脂肪酸1可以通过与叔丁基二氮乙酸酯3的铑(II)醋酸盐催化反应，从天然来源的多不饱和脂肪醇2中容易获得，随后进行酯裂解。
• [EN] GEMCITABINE PRODRUGS<br/>[FR] PROMÉDICAMENTS À BASE DE GEMCITABINE
  申请人：CURE BIOPHARMA INC

  公开号：WO2020223530A1

  公开（公告）日：2020-11-05

  Provided herein are phosphorylated gemcitabine derivative prodrug compounds, pharmaceutical compositions comprising said compounds, and methods for using said compounds for the treatment of cancer.

  本文提供了磷酸化吉西他滨衍生的前药化合物、含有该化合物的药物组合物，以及使用这些化合物用于治疗癌症的方法。
• Kuklev; Popkov; Kas'yanov, Russian Journal of Bioorganic Chemistry, 1996, vol. 22, # 3, p. 192 - 195
  作者：Kuklev、Popkov、Kas'yanov、Akulin、Bezuglov

  DOI：——

  日期：——
• OMEGA-3 LIPID COMPOUNDS
  申请人：Pronova Biopharma Norge AS

  公开号：EP2129646A2

  公开（公告）日：2009-12-09