1,22-cis-docos-9-enedioic acid | 1123248-65-6

• 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: 1,22-cis-docos-9-enedioic acid
• 英文别名: 1,22-cis-9-docosenedioic acid；ω-carboxyl EA
• CAS: 1123248-65-6
• 化学式: C₂₂H₄₀O₄
• 分子量: 368.557
• InChiKey: UHODXFUBERXNHW-HYXAFXHYSA-N

物化性质

• 沸点：
  502.4±23.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.73
• 重原子数：
  26.0
• 可旋转键数：
  20.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 1,22-cis-docos-9-enedioic acid 在 三氟化硼 作用下， 反应 0.33h， 生成 1,22-cis-docos-9-enedioic acid dimethyl ester
  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：

  芥酸 在 C_. tropicalis ATCC₂₀₉₆₂ 作用下， 反应 72.0h， 生成 1,22-cis-docos-9-enedioic 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