glycerol 1-(11Z-eicosenoate) | 173848-62-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: glycerol 1-(11Z-eicosenoate)
• 英文别名: 1-(11Z-eicosenoyl)-glycerol；oleyl-acetyl-glycerol；2,3-Dihydroxypropyl (11Z)-icos-11-enoate；2,3-dihydroxypropyl (Z)-icos-11-enoate
• CAS: 173848-62-9
• 化学式: C₂₃H₄₄O₄
• 分子量: 384.6
• InChiKey: HPTOSMWVVSKAGZ-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  27
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  glycerol 1-(11Z-eicosenoate) 、 水 生成 Gondoate 、 甘油 、 氢(+1)阳离子
  参考文献：
  名称：

  Biochemical characterization of the PHARC-associated serine hydrolase ABHD12 reveals its preference for very-long-chain lipids

  摘要：

  Polyneuropathy, hearing loss, ataxia, retinitis pigmentosa, and cataract (PHARC) is a rare genetic human neurological disorder caused by null mutations to the Abhd12 gene, which encodes the integral membrane serine hydrolase enzyme ABHD12. Although the role that ABHD12 plays in PHARC is understood, the thorough biochemical characterization of ABHD12 is lacking. Here, we report the facile synthesis of mono-1-(fatty)acyl-glycerol lipids of varying chain lengths and unsaturation and use this lipid substrate library to biochemically characterize recombinant mammalian ABHD12. The substrate profiling study for ABHD12 suggested that this enzyme requires glycosylation for optimal activity and that it has a strong preference for very-long-chain lipid substrates. We further validated this substrate profile against brain membrane lysates generated from WT and ABHD12 knockout mice. Finally, using cellular organelle fractionation and immunofluorescence assays, we show that mammalian ABHD12 is enriched on the endoplasmic reticulum membrane, where most of the very-long-chain fatty acids are biosynthesized in cells. Taken together, our findings provide a biochemical explanation for why very-long-chain lipids (such as lysophosphatidylserine lipids) accumulate in the brains of ABHD12 knockout mice, which is a murine model of PHARC.

  DOI：

  10.1074/jbc.ra118.005640
• 作为产物：
  描述：

  10-溴-1-癸醇 在 Jones reagent 、 正丁基锂 、 硫酸 、 氢气 、 对甲苯磺酸 、 2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基全氢-1,3,2-二氮杂磷 、 乙二胺 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 0.5h， 生成 glycerol 1-(11Z-eicosenoate)
  参考文献：
  名称：

  Efficient Synthesis of Unsaturated 1-Monoacyl Glycerols for in meso Crystallization of Membrane Proteins

  摘要：

  建立了高度有效的未饱和1-单酰甘油合成方法，以满足膜蛋白结晶中使用的脂质介晶材料迫切需要。

  DOI：

  10.1055/s-0030-1259912

文献信息

• Utilisation non-thérapeutique d'un hydrolysat de protéines de riz en tant que principe actif pigmentant
  申请人：Laboratoires Expanscience

  公开号：EP2049074B1

  公开（公告）日：2010-07-28
• COMPOSITION COMPRENANT UN EXTRAIT DE GRAINES DE QUINOA, UTILISATION DERMATOLOGIQUE
  申请人：Laboratoires Expanscience

  公开号：EP2124982A1

  公开（公告）日：2009-12-02
• COMPOSITION CONTAINING A QUINOA EXTRACT FOR DERMATOLOGICAL USE
  申请人：Msika Philippe

  公开号：US20100136144A1

  公开（公告）日：2010-06-03

  The present invention relates to a composition containing a quinoa grain extract, said extract being a peptidic and osidic extract or a lipidic extract of quinoa grain, said lipid quinoa extract being itself chosen from a group comprising an oil concentrated into its non saponificable fraction, a non saponificable, or a refined oil. The invention also relates to methods for preparing these different extracts and to dermatological or neutraceutic applications of these extracts.
• SCHISANDRA SPHENANTHERA FRUIT EXTRACT AND COSMETIC, DERMATOLOGICAL AND NUTRACEUTICAL COMPOSITIONS COMPRISING SAME
  申请人：Garnier Sebastien

  公开号：US20120121743A1

  公开（公告）日：2012-05-17

  The present invention relates to a cosmetic, dermatological or nutraceutical composition comprising a Schisandra sphenanthera fruit extract. Said Schisandra sphenanthera fruit extract is selected from a peptide and sugar extract, a crude oil, a refined oil, a refined oil concentrate or the unsaponifiable fraction of said concentrate. The invention also relates to a method for preparing a peptide and sugar extract, a refined oil, and a concentrate and an unsaponifiable fraction of oil of Schisandra sphenanthera fruit. Finally, the invention relates to the dermatological, cosmetic and nutraceutical uses of said extracts.
• VIGNA UNGUICULATA SEED EXTRACT AND COMPOSITIONS CONTAINING SAME
  申请人：Msika Philippe

  公开号：US20120237624A1

  公开（公告）日：2012-09-20

  The invention relates to a composition comprising a Vigna unguiculata seed extract. The composition is advantageously cosmetic, pharmaceutical, dermatological or nutraceutical. The invention further relates to a method for extracting a Vigna unguiculata seed extract, as well as to the resulting extract. The invention further relates to one such composition or one such extract for use in the prevention or treatment of disorders or pathologies of the skin, mucosae or appendages, for use in the prevention or treatment of vascular disorders, or for use in the prevention or treatment of adipose tissue alterations. Finally, the invention relates to a method for cosmetic care of the skin, appendages or mucosae, in order to improve the condition or appearance thereof, comprising the administration of one such composition or one such extract.