threo-9,10,18-trihydroxyoctadecanoic acid methyl ester | 14918-20-8

• 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: threo-9,10,18-trihydroxyoctadecanoic acid methyl ester
• 英文别名: Phloionolic acid methyl ester；methyl (9R,10R)-9,10,18-trihydroxyoctadecanoate
• CAS: 14918-20-8
• 化学式: C₁₉H₃₈O₅
• 分子量: 346.508
• InChiKey: FAQXXHHGYOIFAQ-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯甲醛二甲缩醛 、 threo-9,10,18-trihydroxyoctadecanoic acid methyl ester 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成
  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
• 作为产物：
  描述：

  9-epoxy-18-hydroxyoctadecanoic acid methyl ester 在 硫酸 、 水 作用下， 以16 mg的产率得到threo-9,10,18-trihydroxyoctadecanoic acid methyl 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

文献信息

• Cork Suberin Molecular Structure: Stereochemistry of the C₁₈Epoxy and<i>vic</i>-Diol ω-Hydroxyacids and α,ω-Diacids Analyzed by NMR
  作者：Sara Santos、Vanessa Cabral、José Graça

  DOI：10.1021/jf400577k

  日期：2013.7.24

  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.