9-epoxyoctadecanedioic acid | 50632-64-9

• 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: 9-epoxyoctadecanedioic acid
• 英文别名: cis-9,10-epoxy-1,18-octadecanedioic acid；8,8'-(Oxirane-2,3-diyl)dioctanoic acid；8-[3-(7-carboxyheptyl)oxiran-2-yl]octanoic acid
• CAS: 50632-64-9
• 化学式: C₁₈H₃₂O₅
• 分子量: 328.449
• InChiKey: HBJUPPWOEYNGBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 9-epoxyoctadecanedioic acid 在 三氟化硼 作用下， 反应 0.33h， 生成 dimethyl 8,8'-(oxirane-2,3-diyl)dioctanoate
  参考文献：
  名称：

  Two-Step Biocatalytic Route to Biobased Functional Polyesters from ω-Carboxy Fatty Acids and Diols

  摘要：

  Biobased omega-carboxy fatty acid monomers 1,18-cis-9-octadecenedioic, 1,22-cis-9-docosenedioic, and 1,18-cis-9, 10-epoxy-octadecanedioic acids were synthesized in high conversion yields from oleic, erucic and epoxy stearic acids by whole-cell biotransformations catalyzed by C. tropicalis ATCC20962. Maximum volumetric yields in shake-flasks were 17.3, 14.2, and 19.1 g/L after 48 h conversion for oleic acid and 72 h conversions for erucic and epoxy stearic acids, respectively. Studies in fermentor with better control of pH and glucose feeding revealed that conversion of oleic acid to 1,18-cis-9-octadecenedioic acid by C tropicalis ATCC20962 occurred with productivities up to 0.5 g/L/h. The conversion of omega-carboxy fatty acid monomers to polyesters was then studied using immobilized Candida antarctica Lipase B (N435) as catalyst. Polycondensations with diols were performed in bulk as well its in diphenyl ether. The retension of functionality from fatty acid, to omega-carboxy fatty acid monomer and to corresponding polyesters resulted in polymers with with unsaturated and epoxidized repeat units and M(w) values ranging from 25000 to 57000 g/mol. These functional groups along chains disrupted crystallization giving materials that are low melting (23-40 degrees C). In contrast, saturated polyesters prepared from 1, 18-octadecanedioic acid and 1,8-octanediol have correspondingly higher melting transitions (88 degrees C). TGA results indicated that all synthesized polyesters showed high thermal stabilities. Thus, the preparation of functional monomers from C. tropicalis omega-oxidation of fatty acids provides a wide range of new monomer building blocks to construct functional polymers.

  DOI：

  10.1021/bm901112m
• 作为产物：
  描述：

  cis-3-octyloxiraneoctanoic acid 在 C_. tropicalis ATCC₂₀₉₆₂ glucose 作用下， 反应 72.0h， 生成 9-epoxyoctadecanedioic acid
  参考文献：
  名称：

  [EN] METHOD FOR PREPARING LONG-CHAIN HYDROXYACIDS, DIACIDS AND OLIGOMERS AND POLYLMERS THEREOF
  [FR] PROCÉDÉ DE PRÉPARATION D'HYDROXYACIDES, DE DIACIDES ET D'OLIGOMÈRES À LONGUE CHAÎNE, ET DE POLYMÈRES DE CEUX-CI

  摘要：

  一种制备蓖麻油酸类似物、寡聚体和含有这种蓖麻油酸类似物的聚合物的方法和过程。

  公开号：

  WO2010022200A1

文献信息

• [EN] METHOD FOR PREPARING LONG-CHAIN HYDROXYACIDS, DIACIDS AND OLIGOMERS AND POLYLMERS THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION D'HYDROXYACIDES, DE DIACIDES ET D'OLIGOMÈRES À LONGUE CHAÎNE, ET DE POLYMÈRES DE CEUX-CI
  申请人：POLYTECHNIC INST OF NEW YORK U

  公开号：WO2010022200A1

  公开（公告）日：2010-02-25

  A method and process for the preparation of ricinoleic acid analogs and oligomers and polymers containing such ricinoleic acid analogs.

  一种制备蓖麻油酸类似物、寡聚体和含有这种蓖麻油酸类似物的聚合物的方法和过程。
• METHOD FOR PREPARING LONG-CHAIN HYDROXYACIDS, DIACIDS AND OLIGOMERS AND POLYMERS THEREOF
  申请人：Gross Richard A.

  公开号：US20090054610A1

  公开（公告）日：2009-02-26

  A method and process for the preparation of ricinoleic acid analogs and oligomers and polymers containing such ricinoleic acid analogs.

  一种用于制备蓖麻油酸类似物、含有该类似物的寡聚体和聚合物的方法和过程。
• Glycerol-derived ester oligomers from cork suberin
  作者：José Graça、Sara Santos

  DOI：10.1016/j.chemphyslip.2006.08.001

  日期：2006.10

  The cork suberin polyester was partially depolymerized by a methanolysis reaction catalyzed by calcium hydroxide. The methano-lisate was analysed by ESI-MS/MS in the form of [M + Li](+) adduct-ions. This reaction solubilized a mixture of monomers and oligomers, including a set of glycerol-derived dimeric and trimeric esters. Four types of glycerol esters were identified: monoacyl-glycerols of alpha,omega-diacids, of omega-hydroxyacids and of monoacids; diglycerol diesters of alpha,omega-diacids; diacylglycerols of alpha,omega-diacids; monoacylglycerols of linear dimeric esters of alpha,omega-diacids and omega-hydroxyacids. The alpha,omega-diacids and omega-hydroxyacids found as monomer residues in the glycerol esters are the main ones found as cork suberin monomers. It is concluded that suberin is a glycerol-derived lipid of polymeric dimensions. Due to the protective and insulating role that it plays in plants, suberin should be considered together with the other known glycerolipids that build up biological membranes. (c) 2006 Elsevier Ireland Ltd. All rights reserved.
• METHOD FOR PREPARING LONG-CHAIN HYDROXYACIDS, DIACIDS AND OLIGOMERS AND POLYLMERS THEREOF
  申请人：Polytechnic Institute of New York University

  公开号：EP2324001A1

  公开（公告）日：2011-05-25
• BIOSYNTHETIC ROUTES TO LONG-CHAIN ALPHA,OMEGA-HYDROXYACIDS, DIACIDS AND THEIR CONVERSION TO OLIGOMERS AND POLYMERS
  申请人：Gross Richard A.

  公开号：US20100285545A1

  公开（公告）日：2010-11-11

  A substantially pure Candida host cell for the production of a α-carboxyl-ω-hydroxy fatty acid having a carbon chain length in the range from C6 to C22, a α,ω-dicarboxylic fatty acid having a carbon chain length in the range from C6 to C22, or mixtures thereof, is provided. The Candida host cell is characterized by a first genetic modification class and a second genetic modification class. The first genetic modification class comprises one or more genetic modifications that disrupt the peroxisomal β-oxidation pathway. The second genetic modification class comprises one or more genetic modifications that collectively or individually disrupt at least one gene selected from the group consisting of a CYP52A type cytochrome P450, a fatty alcohol oxidase, and an alcohol dehydrogenase.