(R)-2,3-dihydroxypropyl (Z)-9-octadecenoate | 25496-72-4

• 物质功能分类: 催化剂及助剂 - 塑料橡胶助剂 - 增塑剂
• 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: (R)-2,3-dihydroxypropyl (Z)-9-octadecenoate
• 英文别名: oleic acid α-monoglyceride；1-oleoyl-sn-glycerol；3-oleoyl-sn-glycerol；(R)-1-monoolein；sn-Glyceryl-3-oleat；(2r)-2,3-Dihydroxypropyl (9z)-Octadec-9-Enoate；[(2R)-2,3-dihydroxypropyl] (Z)-octadec-9-enoate
• CAS: 25496-72-4
• 化学式: C₂₁H₄₀O₄
• 分子量: 356.546
• InChiKey: RZRNAYUHWVFMIP-GDCKJWNLSA-N

物化性质

• 熔点：
  35-37 °C
• 沸点：
  449.35°C (rough estimate)
• 密度：
  0.96 g/cm3 (25 ºC)
• 溶解度：
  氯仿：50 mg/mL，澄清，无色
• 物理描述：
  DryPowder; Liquid; OtherSolid
• 颜色/状态：
  PLATES FROM ETHANOL
• 气味：
  SWEET
• 味道：
  FATTY TASTE
• 折光率：
  INDEX OF REFRACTION: 1.4626 @ 40 °C/D

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  25
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

ADMET

毒理性

• 人类毒性摘录

用人红细胞幽灵膜与融合脂质甘油单油酸酯处理增加了膜脂的流动性，而非融合脂质甘油单硬脂酸酯没有效果。

TREATMENT OF HUMAN ERYTHROCYTE GHOST MEMBRANES WITH THE FUSOGENIC LIPID GLYCEROL MONOOLEATE INCREASED THE FLUIDITY OF THE MEMBRANE LIPIDS, BUT THE NONFUSOGENIC LIPID GLYCEROL MONOSTEARATE HAD NO EFFECT.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

如果这些酯类中有任何一种具有显著毒性，那么应该归咎于酸部分，而不是甘油。/甘油酯/

IF ANY OF THESE ESTERS IS SIGNIFICANTLY TOXIC, THE ACID PORTION MUST BE HELD RESPONSIBLE, NOT THE GLYCEROL. /GLYCEROL ESTERS/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品运输编号：
  NONH for all modes of transport
• WGK Germany：
  1

制备方法与用途

用途

• 用作增稠剂
• 用作表面活性剂、润滑剂及医药原料等
• 非离子表面活性剂，具有乳化、增稠和消泡性能。在日化工业中，可用作生产膏霜类化妆品、液体洗涤香波的乳化剂、增溶剂、遮光剂以及消泡剂；在纺织工业中用作织物整理剂，并可作为颜料研磨添加剂。此外，也可用作消泡剂，具有降粘和抑泡作用。

反应信息

• 作为反应物：
  描述：

  (R)-2,3-dihydroxypropyl (Z)-9-octadecenoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 油酸
  参考文献：
  名称：

  Patra, Amarendra; Chaudhuri, Swapan Kumar, Journal of the Indian Chemical Society, 1988, vol. 65, p. 367 - 368

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl (Z)-9-octadecenoate 在 水 、 溶剂黄146 作用下， 反应 2.0h， 以974 mg的产率得到(R)-2,3-dihydroxypropyl (Z)-9-octadecenoate
  参考文献：
  名称：

  信息素合成。第253部分：果蝇雄性果蝇甘油三酸酯的外消旋物和对映体的合成，特别着重于对映体纯的1-甘油单酸酯的制备

  摘要：

  蝇果蝇的果蝇的外消旋体和对映异构体（2，3-丙酮甘油的外消旋体和对映异构体）通过三个步骤合成了甘油三酸酯1a – e（果蝇的果蝇的棕榈酸，棕榈油酸，硬脂酸，油酸和亚油酸的2,3-二聚二羟甲氧基丙基酯）。（2）通过1-甘油单酸酯4a - e衍生自上述脂肪酸。建立了制备对映体纯的1-甘油单酸酯4a - e的适当条件，并通过相应的bis-（R）-MTPA酯的NMR分析确定了它们的对映体纯度。

  DOI：

  10.1016/j.tet.2012.07.086

文献信息

• Regioselective and stereospecific acylation across oxirane- and silyloxy systems as a novel strategy to the synthesis of enantiomerically pure mono-, di- and triglycerides
  作者：Stephan D. Stamatov、Jacek Stawinski

  DOI：10.1039/b713246h

  日期：——

  acyl residue at the central carbon of the silylated synthons with a subsequent Et(3)N.3HF-promoted, direct trichloroacetylation across the siloxy system by trichloroacetic anhydride (TCAA), followed by cleavage of the trichloroacetyl group, affords the respective 1,2(2,3)-diacyl- or 1(3)-O-alkyl-2-acyl-sn-glycerols. Alternatively, a reaction sequence involving: (i) attachment of a trichloroacetyl fragment

  三氟乙酸催化带有三氟乙酸酐（TFAA）的带有烯丙基酰基或烷基官能团的缩水甘油基衍生物的环氧乙烷环的开环，可有效进入构型均质的1（3）-酰基-或1（3）-O-烷基-sn -甘油。在这些关键中间体的末端位置选择性引入叔丁基二甲基甲硅烷基-（TBDMS）或三异丙基甲硅烷基-（TIPS）瞬态保护可确保1（3）-酰基-或1（3）-O-烷基-3（1）- O-TBDMS（或TIPS）-sn-甘油作为1,2（2,3）-二酰基-，1（3）-O-烷基-2-酰基-和1,3-二酰基-sn-的一般双功能前体甘油和三酯等排体。通过三氯乙酸酐（TCAA）在甲硅烷基化的合成子的中央碳原子上引入必要的酰基残基，并随后进行Et（3）N.3HF促进的，直接的三氯乙酰化作用穿过硅烷氧基体系 然后裂解三氯乙酰基，得到各自的1,2（2,3）-二酰基-或1（3）-O-烷基-2-酰基-sn-甘油。可选择地，反应序列包括：（i）三氯乙酰基片段连接在单甲硅烷基化甘油酯的立体C
• Hydrolysis of neutral lipid substrates by rat hepatic lipase
  作者：Rebecca W. Wilcox、Tom Thuren、Patricia Sisson、Gregory L. Kucera、Moseley Waite

  DOI：10.1007/bf02537138

  日期：1991.4

  mumol/min/mg for PA, 50 mumol/min/mg for PE and 4 mumol/min/mg for PC. In addition, the mole fraction of lipid substrate at half maximal velocity (K) in the surface dilution plot was lower for the neutral lipid substrates as compared to those obtained for the phospholipid substrates. When the hydrolysis of 1,3-dioleoyl-sn-glycerol mixed micelles was studied as a function of time, cleavage at the sn-1 and sn-3

  大鼠肝脂肪酶是一种参与脂蛋白分解代谢的酶，其定义尚不明确，具有中性脂质和磷脂水解活性。我们确定了在Triton X-100混合胶束态下，肝脂肪酶对1-油酰基-sn-甘油，1,2-油酰基-sn-甘油和1,3-油基-sn-甘油的底物特异性，并进行了比较结果与以前在我们实验室中获得的磷脂底物磷脂酸（PA），磷脂酰乙醇胺（PE）和磷脂酰胆碱（PC）的结果相同。通过用Triton X-100稀释胶束表面中的底物浓度来确定Vmax值。对于1-油酰基-sn-甘油，获得的Vmax值为144摩尔/分钟/毫克，对于1,2-油酰基-sn-甘油为163摩尔/分钟/毫克，对于1,3-油酰基的为145摩尔/分钟/毫克。 -sn-甘油。这些值高于先前获得的磷脂值，PA为67摩尔/分钟/毫克，PE为50摩尔/分钟/毫克，PC为4摩尔/分钟/毫克。另外，与从磷脂底物获得的那些相比，对于中性脂质底物，在表面稀释图中半数最大速
• Stereospecific and regioselective opening of an oxirane system. A new efficient entry to 1- or 3-monoacyl- and 1- or 3-monoalkyl-sn-glycerols
  作者：Stephan D. Stamatov、Jacek Stawinski

  DOI：10.1016/j.tetlet.2005.01.093

  日期：2005.3

  Acyl or alkyl glycidols in the presence of trifluoroacetic anhydride (TFAA) and trifluoroacetate anions, undergo a regioselective and stereospecific opening of the oxirane system to produce the bis(trifluoroacetylated) derivatives, from which the corresponding 1(3)-monoacyl-sn-glycerols or 1(3)-monoalkyl-sii-glycerols can be obtained directly in high purity (>99%) and in quantitative yields. (C) 2005 Elsevier Ltd. All rights reserved.
• Purification and Characterization of a Catalytic Domain of Rat Intestinal Phospholipase B/Lipase Associated with Brush Border Membranes
  作者：Hiromasa Tojo、Tetsuichi Ichida、Mitsuhiro Okamoto

  DOI：10.1074/jbc.273.4.2214

  日期：1998.1

  A brush border membrane-associated phospholipase B/lipase was solubilized from the distal two-thirds of rat small intestine by autolysis during storage at -35 degrees C over 1 month, and then the enzyme was purified to homogeneity and characterized enzymatically and structurally, The purified enzyme exhibited broad substrate specificity including esterase, phospholipase A(2), lysophospholipase, and lipase activities. SDS-gel electrophoretic and reverse-phase high performance liquid chromatographic analyses demonstrated that a single enzyme catalyzes these activities. It preferred hydrolysis at the sn-2 position of diacylphospholipid and diacylglycerol without strict stereoselectivity, whereas it apparently exhibited no positional specificity toward triacylglycerol. Diisopropyl fluorophosphate, an irreversible inhibitor of serine esterases and lipases, inhibited purified enzyme, When the position of enzyme on SDS-gel electrophoresis under the non-reducing conditions was determined by assaying the activity eluted from sliced gels, brush border membrane-associated enzyme corresponded to a similar to 150-kDa protein; autolysis gave a 35-kDa product, in agreement with the results of immunoblot analysis, The purified 35-kDa enzyme consisted of a 14-kDa peptide and a glycosylated 21-kDa peptide. Their NH2-terminal amino acid sequences were determined and found in the second repeat of 161-kDa phospholipase B/lipase with 4-fold tandem repeats of similar to 38 kDa each, which we cloned and sequenced in the accompanying paper (Takemori, H., Zolotaryov, F,, Ting, L., Urbain, T,, Komatsubara, T., Hatano, O., Okamoto, M,, and Tojo, H. (1998) J. Biol. Chem. 273, 2222-2231). These results indicate that the purified enzyme is the catalytic domain derived from the second repeat of brush border membrane-associated phospholipase B/lipase.
• Fredrikson G.; Belfrage P., J Biol Chem, 1983, 0021-9258, 14253-6
  作者：Fredrikson G.、Belfrage P.

  DOI：——

  日期：——