methyl trans-11,12-methylene-octadecanoate | 5965-63-9

• 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 trans-11,12-methylene-octadecanoate
• 英文别名: (+/-)-10-(trans-2-hexyl-cyclopropyl)-decanoic acid methyl ester；(+/-)-10-(trans-2-Hexyl-cyclopropyl)-decansaeure-methylester；methyl 10-[(1R,2R)-2-hexylcyclopropyl]decanoate
• CAS: 5965-63-9；21003-29-2；42199-25-7；112418-57-2
• 化学式: C₂₀H₃₈O₂
• 分子量: 310.521
• InChiKey: HASAQWANQLNRRS-RTBURBONSA-N

物化性质

• 沸点：
  362.7±10.0 °C(Predicted)
• 密度：
  0.896±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二碘甲烷 、 反式-11-十八烯酸甲酯 在 diethylzinc 作用下， 以 苯 为溶剂， 反应 6.0h， 以40 mg的产率得到methyl trans-11,12-methylene-octadecanoate
  参考文献：
  名称：

  Bioactive lipids from the sponge Spirastrella abata

  摘要：

  Three sphingosine 4-sulfates (1-3) and a lysophosphatidylglycerol (4) were isolated from the Korean sponge Spirastrella abata. The structures of these compounds were determined based on the combined results of spectroscopic analyses. Based on the results of combined synthesis and comparison of specific rotation and circular dichroism, the absolute configurations of 1-3 were found to be enantiomeric to the previously isolated metabolites. The configurations of 4 were also partially determined by similar chemical and spectroscopic methods. The compounds exhibited significant cytotoxicity and weak antimicrobial activity (1), as well as weak-to-moderate inhibitory activity against isocitrate lyase and Na+/K+-ATPase. A structure-activity relationship was found for the sphingosine 4-sulfates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.105

文献信息

• VEYS, ALBERT;CALLEWAERT, WALTER;WAELKENS, ETIENNE;VAN, DEN ABBEELE KAREL, J. CLIN. MICROBIOL., 27,(1989) N, C. 1538-1542
  作者：VEYS, ALBERT、CALLEWAERT, WALTER、WAELKENS, ETIENNE、VAN, DEN ABBEELE KAREL

  DOI：——

  日期：——
• Bioactive lipids from the sponge Spirastrella abata
  作者：Kyoung Hwa Jang、Yoonyeong Lee、Chung J. Sim、Ki-Bong Oh、Jongheon Shin

  DOI：10.1016/j.bmcl.2011.11.105

  日期：2012.1

  Three sphingosine 4-sulfates (1-3) and a lysophosphatidylglycerol (4) were isolated from the Korean sponge Spirastrella abata. The structures of these compounds were determined based on the combined results of spectroscopic analyses. Based on the results of combined synthesis and comparison of specific rotation and circular dichroism, the absolute configurations of 1-3 were found to be enantiomeric to the previously isolated metabolites. The configurations of 4 were also partially determined by similar chemical and spectroscopic methods. The compounds exhibited significant cytotoxicity and weak antimicrobial activity (1), as well as weak-to-moderate inhibitory activity against isocitrate lyase and Na+/K+-ATPase. A structure-activity relationship was found for the sphingosine 4-sulfates. (C) 2011 Elsevier Ltd. All rights reserved.