threo-9,10-dihydroxyoctadecanedioic acid dimethyl ester | 23200-14-8

• 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-dihydroxyoctadecanedioic acid dimethyl ester
• 英文别名: phloionic acid dimethyl ester；Phloionsaeure-dimethylester；Dimethyl phloionate, (+/-)-；dimethyl (9R,10R)-9,10-dihydroxyoctadecanedioate
• CAS: 23200-14-8；23200-17-1；37179-66-1；37428-14-1；67852-29-3；67878-17-5
• 化学式: C₂₀H₃₈O₆
• 分子量: 374.518
• InChiKey: OMYZAYMSFKGQEX-QZTJIDSGSA-N

物化性质

• 沸点：
  481.5±35.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  threo-9,10-dihydroxyoctadecanedioic acid dimethyl ester 在 一水合肼 作用下， 生成 Phloionsaeure-bishydrazid
  参考文献：
  名称：

  合成这些 einiger Phloionsäureamide 和 des Phloionsäurebishydrazids

  摘要：

  Es wird über die Synthese einiger Phloionsäurediamide und des Phloionsäurebishydrazids berichtet。Untersuchungen黚模具Wasserlöslichkeitsowie巢穴EinflußDER dargestellten Verbindungen奥夫DASWasseraufnahmevermögen冯Kohlenwasserstoff-Gelen（凡士林）zeigten，DASS在einigen下降第三人以Zusatz冯PhloionsäurediamidenEINEgrößereWasseraufnahme erreicht werden卡恩ALS第三人以Zusatz冯entsprechendenPhloionsäureestern。

  DOI：

  10.1002/ardp.19723050505
• 作为产物：
  描述：

  Octadecanedioic acid, 9,10-bis(acetyloxy)-, dimethyl ester, (R*,R*)- 在 氢氧化钾 作用下， 生成 threo-9,10-dihydroxyoctadecanedioic acid dimethyl ester
  参考文献：
  名称：

  Ruzicka; Plattner; Widmer, Helvetica Chimica Acta, 1942, vol. 25, p. 1090

  摘要：

  DOI：

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.
• Zetzsche; Baehler, Helvetica Chimica Acta, 1931, vol. 14, p. 847,848
  作者：Zetzsche、Baehler

  DOI：——

  日期：——