17-羟基油酸 | 27304-77-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 17-羟基油酸
• 英文名称: 17-hydroxyoleic acid
• 英文别名: 17-Hydroxy-cis-9-octadecensaeure；(Z,17S)-17-hydroxyoctadec-9-enoic acid
• CAS: 27304-77-4
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: UMIZOHMCQYCZRX-KYVUIXNKSA-N

物化性质

• 沸点：
  409.8±20.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17-羟基油酸 在 chromium(VI) oxide 作用下， 以 溶剂黄146 为溶剂， 生成 17-氧代十八酸
  参考文献：
  名称：

  HYDROXY FATTY ACID GLYCOSIDES OF SOPHOROSE FROM TORULOPSIS MAGNOLIAE

  摘要：

  在Torulopsis magnoliae菌株发酵过程中形成的油主要由部分乙酰化的2-O-β-D-葡萄糖吡喃基-D-葡萄糖吡喃糖单元组成，以β-糖苷键连接到17-L-羟基十八烷酸和17-L-羟基-9-十八烯酸上。

  DOI：

  10.1139/v61-104
• 作为产物：
  描述：

  (S,Z)-methyl 17-hydroxyoctadece-9-enoate 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 17-羟基油酸
  参考文献：
  名称：

  槐糖脂衍生的多羟基脂肪酸

  摘要：

  AbstractStarting from 17‐hydroxyoleic acid, which is readily available from acid alcoholysis of sophorolipids, several new polyhydroxy fatty acids have been synthesized. These compounds contain from 2 to 4 hydroxy groups, in some instances combined with other functional groups. The added hydroxy groups can be incorporated in the C18 chain in a variety of geometries, for example spaced widely throughout the chain at C1, C8, and C17. This regiochemical control will be of use in structure/function studies involving materials constructed from these hydroxy fatty acids. A further benefit is that the hydroxy groups can be present in protected or free states. The principal reactions used to introduce extra hydroxy groups are selenium oxide‐mediated allylic hydroxylation, osmium‐catalyzed dihydroxylation, and borohydride reduction of a carboxylic ester. These new compounds are expected to be of use in a number of areas, but particularly as building blocks for polymers or components of lubricant formulations.

  DOI：

  10.1007/s11746-007-1054-4

文献信息

• HYDROXY FATTY ACID GLYCOSIDES OF SOPHOROSE FROM TORULOPSIS MAGNOLIAE
  作者：P. A. J. Gorin、J. F. T. Spencer、A. P. Tulloch

  DOI：10.1139/v61-104

  日期：1961.4.1

  The oil formed during fermentation by a strain of Torulopsismagnoliae consisted mainly of partly acetylated 2-O-β-D-glucopyranosyl-D-glucopyranose units attached β-glycosidically to 17-L-hydroxyoctadecanoic and 17-L-hydroxy-9-octadecenoic acids.

  在Torulopsis magnoliae菌株发酵过程中形成的油主要由部分乙酰化的2-O-β-D-葡萄糖吡喃基-D-葡萄糖吡喃糖单元组成，以β-糖苷键连接到17-L-羟基十八烷酸和17-L-羟基-9-十八烯酸上。
• Polyhydroxy Fatty Acids Derived from Sophorolipids
  作者：Jonathan A. Zerkowski、Daniel K. Y. Solaiman

  DOI：10.1007/s11746-007-1054-4

  日期：2007.5.10

  AbstractStarting from 17‐hydroxyoleic acid, which is readily available from acid alcoholysis of sophorolipids, several new polyhydroxy fatty acids have been synthesized. These compounds contain from 2 to 4 hydroxy groups, in some instances combined with other functional groups. The added hydroxy groups can be incorporated in the C18 chain in a variety of geometries, for example spaced widely throughout the chain at C1, C8, and C17. This regiochemical control will be of use in structure/function studies involving materials constructed from these hydroxy fatty acids. A further benefit is that the hydroxy groups can be present in protected or free states. The principal reactions used to introduce extra hydroxy groups are selenium oxide‐mediated allylic hydroxylation, osmium‐catalyzed dihydroxylation, and borohydride reduction of a carboxylic ester. These new compounds are expected to be of use in a number of areas, but particularly as building blocks for polymers or components of lubricant formulations.