glyceryl γ-linolenate | 157500-74-8

• 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: glyceryl γ-linolenate
• 英文别名: 2,3-dihydroxypropyl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate
• CAS: 157500-74-8
• 化学式: C₂₁H₃₆O₄
• 分子量: 352.514
• InChiKey: XQBHBEXBUZDCRY-QNEBEIHSSA-N

物化性质

• 沸点：
  484.8±45.0 °C(predicted)
• 密度：
  0.993±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 硼酸 作用下， 以 甲乙醚 为溶剂， 生成 glyceryl γ-linolenate
  参考文献：
  名称：

  Monoglycerides from the brown alga Sargassum sagamianum: Isolation, synthesis, and biological activity

  摘要：

  Polyunsaturated fatty acid-derived monoglycerides were characterized from the marine brown alga Sargassum sagamianum, collected from Jeju Island, Korea. A new compound of this structural class was isolated and determined to be 1-octadecatetraenoyl glycerol, by combined spectroscopic methods. Based on the structures and bioactivity of these compounds, a series of monoglycerides were synthesized using glycerol and various fatty acids. Several compounds exhibited moderate to significant inhibition of phospholipase A(2) and cyclooxygenase-2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.008

文献信息

• WO2006/92623
  申请人：——

  公开号：——

  公开（公告）日：——
• Glycerol acyl-transfer kinetics of a circular permutated Candida antarctica lipase B
  作者：Joseph A. Laszlo、Ying Yu、Stefan Lutz、David L. Compton

  DOI：10.1016/j.molcatb.2011.06.002

  日期：2011.11

  Triacylglycerols containing a high abundance of unusual fatty acids, such as gamma-linolenic acid, or novel arylaliphatic acids, such as ferulic acid, are useful in pharmaceutical and cosmeceutical applications. Candida antarctica lipase B (CALB) is quite often used for non-aqueous synthesis, although the wildtype enzyme can be rather slow with bulky and sterically hindered acyl donor substrates. The catalytic performance of a circularly permutated variant of CALB, cp283, with various acyl donors and glycerol was examined. In comparison to wild-type CALB, butyl oleate and ethyl gamma-linolenate glycerolysis rates were 2.2- and 4.0-fold greater, respectively. Cp283 showed substrate inhibition by glycerol, which was not the case with the wild-type version. With either ethyl ferulate or vinyl ferulate acyl donors, cp283 matched the performance of wild-type CALB. Changes in active site accessibility resulting from circular permutation led to increased catalytic rates for bulky fatty acid esters but did not overcome the steric hindrance or energetic limitations experienced by arylaliphatic esters. Published by Elsevier B.V.
• Monoglycerides from the brown alga Sargassum sagamianum: Isolation, synthesis, and biological activity
  作者：Hyeun Wook Chang、Kyoung Hwa Jang、Doohyun Lee、Hee Ryong Kang、Tae-Yoon Kim、Bong Ho Lee、Byoung Wook Choi、Sanghee Kim、Jongheon Shin

  DOI：10.1016/j.bmcl.2008.05.008

  日期：2008.6

  Polyunsaturated fatty acid-derived monoglycerides were characterized from the marine brown alga Sargassum sagamianum, collected from Jeju Island, Korea. A new compound of this structural class was isolated and determined to be 1-octadecatetraenoyl glycerol, by combined spectroscopic methods. Based on the structures and bioactivity of these compounds, a series of monoglycerides were synthesized using glycerol and various fatty acids. Several compounds exhibited moderate to significant inhibition of phospholipase A(2) and cyclooxygenase-2. (C) 2008 Elsevier Ltd. All rights reserved.