methyl 9,10-methanohexadecanoate

• 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 9,10-methanohexadecanoate
• 英文别名: (±)-methyl cis-9,10-methylenehexadecanoate；methyl cis-9,10-methylenehexadecanoate；cis-DL-9.10-Methylen-palmitinsaeure-methylester；DL-cis-9.10-Methylen-hexadecansaeure-methylester；methyl 8-[(1R,2S)-2-hexylcyclopropyl]octanoate
• 化学式: C₁₈H₃₄O₂
• 分子量: 282.467
• InChiKey: LQYIDOFTTFCXEO-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 9,10-methanohexadecanoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.0h， 以65%的产率得到(±)-cis-9,10-methylenehexadecanoic acid
  参考文献：
  名称：

  Ascaroside Signaling in the Bacterivorous Nematode Caenorhabditis remanei Encodes the Growth Phase of Its Bacterial Food Source

  摘要：

  A novel class of species-specific modular ascarosides that integrate additional fatty acid building blocks was characterized in the nematode Caenorhabditis remanei using a combination of HPLC-ESI- (-)-MS/MS precursor ion scanning, microreactions, HR-MS/MS, MSn, and NMR techniques. The structure of the dominating component carrying a cyclopropyl fatty acid moiety was established by total synthesis. Biogenesis of this female-produced male attractant depends on cyclopropyl fatty acid synthase (cfa), which is expressed in bacteria upon entering their stationary phase.

  DOI：

  10.1021/acs.orglett.9b01914
• 作为产物：
  描述：

  棕榈油酸 在 diethylzinc 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.83h， 生成 methyl 9,10-methanohexadecanoate
  参考文献：
  名称：

  Ascaroside Signaling in the Bacterivorous Nematode Caenorhabditis remanei Encodes the Growth Phase of Its Bacterial Food Source

  摘要：

  A novel class of species-specific modular ascarosides that integrate additional fatty acid building blocks was characterized in the nematode Caenorhabditis remanei using a combination of HPLC-ESI- (-)-MS/MS precursor ion scanning, microreactions, HR-MS/MS, MSn, and NMR techniques. The structure of the dominating component carrying a cyclopropyl fatty acid moiety was established by total synthesis. Biogenesis of this female-produced male attractant depends on cyclopropyl fatty acid synthase (cfa), which is expressed in bacteria upon entering their stationary phase.

  DOI：

  10.1021/acs.orglett.9b01914

文献信息

• Configurational Analysis of Cyclopropyl Fatty Acids Isolated from <i>Escherichia coli</i>
  作者：Laura J. Stuart、James P. Buck、Amy E. Tremblay、Peter H. Buist

  DOI：10.1021/ol052550d

  日期：2006.1.1

  The absolute configuration of methyl lactobacillate and its 9,10 homologue, both isolated from Escherichia coli B-ATCC 11303, was found to be 11R,12S and 9R,10S, respectively.
• TERMONIA, M.;WYBAUW, M.;BRONCKART, J.;JACOBS, H., J. HIGH RESOLUT. CHROMATOGR., 12,(1989) N0, C. 685-688
  作者：TERMONIA, M.、WYBAUW, M.、BRONCKART, J.、JACOBS, H.

  DOI：——

  日期：——
• DOUMENO, P.;GUILIANO, M.;BERTRAND, J. C.;MILLE, G., APPL. SPECTROSC., 44,(1990) N, C. 1355-1359
  作者：DOUMENO, P.、GUILIANO, M.、BERTRAND, J. C.、MILLE, G.

  DOI：——

  日期：——
• PRODUCTION OF BRANCHED CHAIN FATTY ACIDS AND DERIVATIVES THEREOF IN RECOMBINANT MICROBIAL CELLS
  申请人：REG Life Sciences, LLC

  公开号：EP2663636B1

  公开（公告）日：2018-08-08
• US8530221B2
  申请人：——

  公开号：US8530221B2

  公开（公告）日：2013-09-10