methyl 14-hydroxypentadecanoate | 88785-28-8

• 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: methyl 14-hydroxypentadecanoate
• CAS: 88785-28-8
• 化学式: C₁₆H₃₂O₃
• 分子量: 272.428
• InChiKey: BBUCKLDUWZJDFD-UHFFFAOYSA-N

物化性质

• 熔点：
  44-45 °C
• 沸点：
  140 °C(Press: 0.002 Torr)
• 密度：
  0.926±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 14-hydroxypentadecanoate 生成 methyl (14R)-14-hydroxypentadecanoate
  参考文献：
  名称：

  Schneider, Silke; Wubbolts, Marcel G.; Sanglard, Dominique, Tetrahedron Asymmetry, 1998, vol. 9, # 16, p. 2833 - 2844

  摘要：

  DOI：
• 作为产物：
  描述：

  14-oxo-pentadecanoic acid methyl ester 在 sodium tetrahydroborate 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 3.0h， 生成 methyl 14-hydroxypentadecanoate
  参考文献：
  名称：

  Schneider, Silke; Wubbolts, Marcel G.; Sanglard, Dominique, Tetrahedron Asymmetry, 1998, vol. 9, # 16, p. 2833 - 2844

  摘要：

  DOI：

文献信息

• Microbiological oxidation of long-chain aliphatic compounds. Part III. 1-Halogenoalkanes, 1-cyanohexadecane, and 1-alkoxyalkanes
  作者：D. F. Jones、R. Howe

  DOI：10.1039/j39680002816

  日期：——

  glucose, the yeast Torulopsis gropengiesseri effects the following transformations: (a) long-chain 1-halogenoalkanes to αω-alkanedioic acids; (b) 1-cyanohexadecane to the cyanohydrin derivative of 16-oxohexadecanoic acid; (c) long-chain 1-methoxyalkanes and 1-ethoxyalkanes to ω-hydroxyalkanoic acids; (d) long-chain 1-propoxyalkanes to ω- and ω-1-hydroxyalkoxyalkanoic acids. The transformation products

  在含有葡萄糖的培养基中，灰鹤菌酵母进行以下转化：（a）将长链1-卤代烷烃转变为αω-链烷二酸；（a）将长链1-卤代烷烃转化为αω-链烷二酸；（b）1-氰基十六烷为16-氧代十六烷酸的氰醇衍生物；（c）长链的1-甲氧基烷烃和1-乙氧基烷烃成ω-羟基链烷酸；（d）长链的1-丙氧基烷烃为ω-和ω-1-羟基烷氧基链烷酸。转化产物作为糖脂与培养基分离。提出了解释这些转化的代谢途径。
• Facile determination of the absolute stereochemistry of hydroxy fatty acids by GC: application to the analysis of fatty acid oxidation by a P450BM3 mutant
  作者：Max J. Cryle、James J. De Voss

  DOI：10.1016/j.tetasy.2007.01.034

  日期：2007.3

  The determination of the absolute stereochemistry of hydroxy fatty acid methyl esters as their (S)-ibuprofen esters is possible via standard gas chromatographic techniques. Analyses of various racemic and nonracemic standards and mixtures from enzymic oxidation show excellent resolution of the resultant diastereomers, with the (S,S)-diastereomers eluting first in all cases studied. The stereochemistry of the oxidation of dodecanoic acid by P450(BM3), which has not been previously reported, was determined by this method and indicated a preference for (R)-hydroxylation. The sensitivity of this technique allows the analysis of very small quantities of product, which has revealed that the oxidation of dodecanoic and hexadecanoic acids by the T268A mutant of P450(BM3) display the same stereochemical efficiency and produce (R)-hydroxy fatty acids in the same manner as wildtype P450(BM3), despite the poor coupling efficiency of these substrates. This stereochemistry implies that hydroxylation catalysed by the T268A mutant of P450(BM3) occurs through residual levels of the normal hydroxylating species. (c) 2007 Elsevier Ltd. All rights reserved.
• Schneider, Silke; Wubbolts, Marcel G.; Sanglard, Dominique, Tetrahedron Asymmetry, 1998, vol. 9, # 16, p. 2833 - 2844
  作者：Schneider, Silke、Wubbolts, Marcel G.、Sanglard, Dominique、Witholt, Bernard

  DOI：——

  日期：——