cis-9-epoxyoctadecanedioic acid dimethyl ester | 65492-88-8

• 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: cis-9-epoxyoctadecanedioic acid dimethyl ester
• CAS: 65492-88-8
• 化学式: C₂₀H₃₆O₅
• 分子量: 356.503
• InChiKey: JXUYSPXEQDPSDU-HDICACEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  25.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  65.13
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  cis-9-epoxyoctadecanedioic acid dimethyl ester 在 硫酸 、 水 作用下， 以44.7 mg的产率得到threo-9,10-dihydroxyoctadecanedioic acid dimethyl ester
  参考文献：
  名称：

  Cork Suberin Molecular Structure: Stereochemistry of the C₁₈Epoxy andvic-Diol ω-Hydroxyacids and α,ω-Diacids Analyzed by NMR

  摘要：

  Suberin is the biopolyester that protects the secondary tissues of plants against environmental variability and aggressions. Cork suberin is composed mostly of C-18 omega-hydroxyacids and alpha,omega-diacids, 9,10-substituted with an unsaturation, an epoxide ring, or a vic-diol group. Although determinant for suberin macromolecular structure, the stereochemistry of these monomers is poorly studied, sometimes with contradictory results. An NMR technique was used here to assign the configuration of the 9,10-epoxy and 9,10-diol groups in C-18 suberin acids, comparing the chemical shifts of diagnostic H-1 and C-13 signals with the ones of model compounds, before and after conversion of the vic-diol group into benzylidene acetal derivatives. The relative configuration was proved to be cis in the C-18 9,10-epoxy and threo in the C-18 9,10-diol suberin acids. These monomers were present in suberin probably as racemic mixtures, as shown by polarimetry. The revealed stereochemistry allows the suberin macromolecule to be built as an ordered array of midchain kinked C-18 acids, reinforced by intramolecular hydrogen bonding.

  DOI：

  10.1021/jf400577k