1,2-bis-hexanoyloxy-3-stearoyloxy-propane | 56149-04-3

• 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: 1,2-bis-hexanoyloxy-3-stearoyloxy-propane
• 英文别名: 1,2-Bis-hexanoyloxy-3-stearoyloxy-propan；2,3-Bis(hexanoyloxy)propyl octadecanoate；2,3-di(hexanoyloxy)propyl octadecanoate
• CAS: 56149-04-3
• 化学式: C₃₃H₆₂O₆
• 分子量: 554.852
• InChiKey: PFUKHRZVJUFMPJ-UHFFFAOYSA-N

物化性质

• 沸点：
  578.6±17.0 °C(Predicted)
• 密度：
  0.949±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.2
• 重原子数：
  39
• 可旋转键数：
  32
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 水 、 N,N'-二环己基碳二亚胺 作用下， 生成 1,2-bis-hexanoyloxy-3-stearoyloxy-propane
  参考文献：
  名称：

  1H-Nuclear magnetic resonance spectroscopic studies of saturated, acetylenic and ethylenic triacylglycerols

  摘要：

  DOI：

  10.1016/0009-3084(95)02463-s

文献信息

• Fatty Acid Phytyl Ester Synthesis in Chloroplasts of <i>Arabidopsis</i>
  作者：Felix Lippold、Katharina vom Dorp、Marion Abraham、Georg Hölzl、Vera Wewer、Jenny Lindberg Yilmaz、Ida Lager、Cyrille Montandon、Céline Besagni、Felix Kessler、Sten Stymne、Peter Dörmann

  DOI：10.1105/tpc.112.095588

  日期：2012.5

  During stress or senescence, thylakoid membranes in chloroplasts are disintegrated, and chlorophyll and galactolipid are broken down, resulting in the accumulation of toxic intermediates, i.e., tetrapyrroles, free phytol, and free fatty acids. Chlorophyll degradation has been studied in detail, but the catabolic pathways for phytol and fatty acids remain unclear. A large proportion of phytol and fatty acids is converted into fatty acid phytyl esters and triacylglycerol during stress or senescence in chloroplasts. We isolated two genes (PHYTYL ESTER SYNTHASE1 [PES1] and PES2) of the esterase/lipase/thioesterase family of acyltransferases from Arabidopsis thaliana that are involved in fatty acid phytyl ester synthesis in chloroplasts. The two proteins are highly expressed during senescence and nitrogen deprivation. Heterologous expression in yeast revealed that PES1 and PES2 have phytyl ester synthesis and diacylglycerol acyltransferase activities. The enzymes show broad substrate specificities and can employ acyl-CoAs, acyl carrier proteins, and galactolipids as acyl donors. Double mutant plants (pes1 pes2) grow normally but show reduced phytyl ester and triacylglycerol accumulation. These results demonstrate that PES1 and PES2 are involved in the deposition of free phytol and free fatty acids in the form of phytyl esters in chloroplasts, a process involved in maintaining the integrity of the photosynthetic membrane during abiotic stress and senescence.

  在压力或衰老期间，叶绿体中的类囊体膜会分解，叶绿素和半乳糖脂也会分解，导致有毒中间产物（即四吡咯、游离植物醇和游离脂肪酸）的积累。对叶绿素的降解进行了详细研究，但植物醇和脂肪酸的分解代谢途径仍不清楚。在压力或衰老期间，叶绿体中的大部分植物醇和脂肪酸会转化为脂肪酸植物酯和三酰甘油。我们从拟南芥中分离出酯酶/脂肪酶/硫酯酶家族中的两个基因（植物酯合成酶1 [PES1]和PES2），它们参与叶绿体中脂肪酸植物酯的合成。在衰老和氮缺乏期间，这两种蛋白质的表达量很高。在酵母中的异源表达表明，PES1和PES2具有植物酯合成和二酰甘油酰基转移酶活性。这些酶具有广泛的底物特异性，可以使用酰基-CoA、酰基载体蛋白和半乳糖脂作为酰基供体。双突变体植物（pes1 peS2）生长正常，但植物酯和三酰甘油的积累减少。这些结果表明，PES1和PES2参与游离植物醇和游离脂肪酸以植物酯的形式在叶绿体中的沉积，这一过程在非生物胁迫和衰老期间参与维持光合膜的完整性。
• The Polymorphism of 1-Stearyl- and 1-Palmityldiacetin, -dibutyrin, -dicaproin and 1-Stearyldipropionin
  作者：F. L. Jackson、E. S. Lutton

  DOI：10.1021/ja01139a029

  日期：1952.10