1-亚油酸甘油 | 2258-92-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 1-亚油酸甘油
• 英文名称: (R)-2,3-dihydroxypropyl (9Z,12Z)-9,12-octadecadienoate
• 英文别名: linoleic acid α-monoglyceride；1-linoleoyl-sn-glycerol；glycerol monolinoleate；(R)-1-monolinolein；L-(-)-α-Linoloyl-glycerin；3-Linoleoyl-sn-glycerol；[(2R)-2,3-dihydroxypropyl] (9Z,12Z)-octadeca-9,12-dienoate
• CAS: 2258-92-6
• 化学式: C₂₁H₃₈O₄
• 分子量: 354.53
• InChiKey: WECGLUPZRHILCT-KKFOGOCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  1-亚油酸甘油 在 吡啶 、 水 作用下， 生成 L-(+)-α-Linoloyl-β-stearoyl-glycerin
  参考文献：
  名称：

  Dorofeeva,L.T. et al., Journal of general chemistry of the USSR, 1964, vol. 34, p. 2970 - 2973

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 Dowex 50 W 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-亚油酸甘油
  参考文献：
  名称：

  Lp-PLA2 inhibitory activities of fatty acid glycerols isolated from Saururus chinensis roots

  摘要：

  (R)-Glycerol-monolinoleate 4 and (R)-glycerol-monostearate 5 were isolated from the ethyl acetate extracts of Saururus chinensis roots and (R)- or (S)-fatty acid glycerols 4 and 5 were synthesized for confirming their structures and evaluating their inhibitory activities against Lp-PLA(2). The (R)-4 and (S)-4 exhibited Lp-PLA2 inhibitory activities with IC50 values of 45.0 and 52.0 mu M, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.056

文献信息

• Pheromone synthesis. Part 253: Synthesis of the racemates and enantiomers of triglycerides of male Drosophila fruit flies with special emphasis on the preparation of enantiomerically pure 1-monoglycerides
  作者：Kenji Mori

  DOI：10.1016/j.tet.2012.07.086

  日期：2012.10

  3-ditigloyloxypropyl esters of palmitic, palmitoleic, stearic, oleic, and linoleic acids) of male Drosophila fruit flies were synthesized in three steps from the racemate and enantiomers of 2,3-acetoneglycerol (2) via 1-monoglycerides 4a–e derived from the above fatty acids. Appropriate conditions were established for the preparation of enantiomerically pure 1-monoglycerides 4a–e, and their enantiomeric purities

  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。
• Nostochopcerol, a new antibacterial monoacylglycerol from the edible cyanobacterium <i>Nostochopsis lobatus</i>
  作者：Naoya Oku、Saki Hayashi、Yuji Yamaguchi、Hiroyuki Takenaka、Yasuhiro Igarashi

  DOI：10.3762/bjoc.19.13

  日期：——

  A new antibacterial 3-monoacyl-sn-glycerol, nostochopcerol (1), was isolated from a cultured algal mass of the edible cyanobacterium Nostochopsis lobatus MAC0804NAN. The structure of compound 1 was established by the analysis of NMR and MS data while its chirality was established by comparison of optical rotation values with synthetically prepared authentics. Compound 1 inhibited the growth of Bacillus subtilis and Staphylococcus aureus at MIC of 50 μg/mL and 100 μg/mL, respectively.

  从可食用蓝藻 Nostochopsis lobatus MAC0804NAN 的培养藻块中分离出了一种新的抗菌 3-monoacyl-sn-glycerol, nostochopcerol (1)。化合物 1 的结构是通过核磁共振和质谱数据分析确定的，其手性则是通过与合成的真品进行旋光度比较确定的。化合物 1 抑制枯草杆菌和金黄色葡萄球菌生长的 MIC 值分别为 50 μg/mL 和 100 μg/mL。
• Lp-PLA2 inhibitory activities of fatty acid glycerols isolated from Saururus chinensis roots
  作者：Woo Song Lee、Mi Jeong Kim、Young-Il Beck、Yong-Dae Park、Tae-Sook Jeong

  DOI：10.1016/j.bmcl.2005.05.056

  日期：2005.8

  (R)-Glycerol-monolinoleate 4 and (R)-glycerol-monostearate 5 were isolated from the ethyl acetate extracts of Saururus chinensis roots and (R)- or (S)-fatty acid glycerols 4 and 5 were synthesized for confirming their structures and evaluating their inhibitory activities against Lp-PLA(2). The (R)-4 and (S)-4 exhibited Lp-PLA2 inhibitory activities with IC50 values of 45.0 and 52.0 mu M, respectively. (c) 2005 Elsevier Ltd. All rights reserved.
• Dorofeeva,L.T. et al., Journal of general chemistry of the USSR, 1964, vol. 34, p. 2970 - 2973
  作者：Dorofeeva,L.T. et al.

  DOI：——

  日期：——