(9S,12S,13R)-(E)-9,12,13-trihydroxy-10-octadecenoic acid | 135214-49-2

• 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: (9S,12S,13R)-(E)-9,12,13-trihydroxy-10-octadecenoic acid
• 英文别名: (9S,12S,13R)-pinellic acid；(9S,12S,13R)-trihydroxy-10E-octadecanoic acid；(9S,12S,13R)-(E)-9,12,13-trihydroxy-10-octadecaenoic acid；(-)-pinellic acid；Dihydromalyngic acid；(E,9S,12S,13R)-9,12,13-trihydroxyoctadec-10-enoic acid
• CAS: 135214-49-2
• 化学式: C₁₈H₃₄O₅
• 分子量: 330.465
• InChiKey: MDIUMSLCYIJBQC-XFMWCYPDSA-N

物化性质

• 熔点：
  91-94 °C(Solv: methanol (67-56-1))
• 沸点：
  531.5±50.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 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：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  8-溴辛酸 在 吡啶 、 硫酸 、 potassium carbonate 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 48.0h， 生成 (9S,12S,13R)-(E)-9,12,13-trihydroxy-10-octadecenoic acid
  参考文献：
  名称：

  不饱和三羟基C 18脂肪酸的合成

  摘要：

  从三-O-乙酰基-d-葡糖醛开始合成了两个三羟基不饱和C 18脂肪酸[（9R，12S，13R）-三羟基-10E-十八烯酸3及其9-受体4 ]。

  DOI：

  10.1016/s0040-4039(00)93494-4

文献信息

• Total synthesis and adjuvant activity of all stereoisomers of pinellic acid
  作者：Tatsuya Shirahata、Toshiaki Sunazuka、Kiminari Yoshida、Daisuke Yamamoto、Yoshihiko Harigaya、Takayuki Nagai、Hiroaki Kiyohara、Haruki Yamada、Isao Kuwajima、Satoshi Ōmura

  DOI：10.1016/s0960-894x(02)01069-7

  日期：2003.3

  Pinellic acid is a novel and potentially useful oral adjuvant when used in conjunction with intranasal inoculation of influenza HA vaccines. All stereoisomers of pinellic acid have been synthesized via regioselective asymmetric dihydroxylation, regioselective inversion, and stereoselective reduction, and their adjuvant activities were characterized. Among this series of isomers, 9S, 12S, 13S compound

  松果酸与鼻内接种HA流感疫苗一起使用时，是一种新颖且可能有用的口服佐剂。已通过区域选择性不对称二羟基化，区域选择性反转和立体选择性还原合成了所有松果酸立体异构体，并对其佐剂活性进行了表征。在这一系列异构体中，9S，12S，13S化合物具有最强的佐剂活性。讨论了构效关系。
• Total synthesis, elucidation of absolute stereochemistry, and adjuvant activity of trihydroxy fatty acids
  作者：Tatsuya Shirahata、Toshiaki Sunazuka、Kiminari Yoshida、Daisuke Yamamoto、Yoshihiro Harigaya、Isao Kuwajima、Takayuki Nagai、Hiroaki Kiyohara、Haruki Yamada、Satoshi Ōmura

  DOI：10.1016/j.tet.2006.06.088

  日期：2006.10

  Pinellic acid from the tuber of Pinellia ternate, an active herbal component of the traditional Japanese herbal (Kampo) medicine Sho-seiryu-to, is a C18 trihydroxy fatty acid whose absolute stereochernistry has now been determined. All stereoisomers of pinellic acid were synthesized via regioselective asymmetric dihydroxylation, regioselective inversion, and stereoselective reduction in order to determine their absolute stereochemistries and adjuvant activities. Among this series of isomers, the (9S,12S,13S)-compound, which is a natural product, exhibited the most potent adjuvant activity. Spectral data for all of the stereoisomers of the 1,2-allylic diols were compared and related to their stereochemistries. (c) 2006 Published by Elsevier Ltd.
• Synthesis of unsaturated trihydroxy C18 fatty acids
  作者：Patrick Quinton、Thierry Le Gall

  DOI：10.1016/s0040-4039(00)93494-4

  日期：1991.9

  Two trihydroxy unsaturated C18 fatty acids [(9R, 12S, 13R)-trihydroxy-10E-octadecenoic acid 3 and its 9-epimer 4] were synthesized, starting from tri-O-acetyl-d-glucal.

  从三-O-乙酰基-d-葡糖醛开始合成了两个三羟基不饱和C 18脂肪酸[（9R，12S，13R）-三羟基-10E-十八烯酸3及其9-受体4 ]。