ergosterol laurate | 29398-23-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: ergosterol laurate
• 英文别名: [(3S,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] dodecanoate
• CAS: 29398-23-0
• 化学式: C₄₀H₆₆O₂
• 分子量: 578.963
• InChiKey: NMBSWEUSWULRQZ-FYTMFRGKSA-N

物化性质

• 熔点：
  116 °C
• 沸点：
  626.0±54.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  月桂酸 、 麦角固醇 在 iron(III) chloride hexahydrate 作用下， 以 均三甲苯 为溶剂， 反应 24.0h， 以99%的产率得到ergosterol laurate
  参考文献：
  名称：

  FeCl3·6H2O作为脂肪酸酯化甾体醇的多功能催化剂

  摘要：

  FeCl 3 ˙6H 2 O是一种活性催化剂，用于在均三甲苯为溶剂的共沸回流条件下，一些甾醇与脂肪酸的酯化反应。

  DOI：

  10.1055/s-0028-1083175

文献信息

• Efficient Synthesis and Characterization of Ergosterol Laurate in a Solvent-Free System
  作者：Wen-Sen He、Ji Yin、Han-Shan Xu、Qiu-Ying Qian、Cheng-Sheng Jia、Hai-Le Ma、Biao Feng

  DOI：10.1021/jf504516q

  日期：2014.12.3

  Ergosterol and its derivatives have attracted much attention for a variety of health benefits, such as anti-inflammatory and antioxidant activities. However, ergosterol esters are advantageous because this compound has better solubility than the free ergosterol. In this work, ergosterol laurate was efficiently synthesized for the first time by direct esterification in a solvent-free system. The desired product was purified, characterized by Fourier transform infrared spectroscopy, mass spectrometry, and nuclear magnetic resonance, and finally confirmed to be ergosterol laurate. Meanwhile, the effect of various catalysts, catalyst dose, reaction temperature, substrate molar ratio, and reaction time were studied. Both the conversion of ergosterol and the selectivity of the desired product can reach above 89% under the selected conditions: sodium dodecyl sulfate + hydrochloric acid as the catalyst, 2:1 molar ratio of lauric acid/ergosterol, catalyst dose of 4% (w/w), 120 degrees C, and 2 h. The oil solubility of ergosterol and its laurate was also compared. The results showed that the solubility of ergosterol in oil was significantly improved by direct esterification with lauric acid, thus greatly facilitating the incorporation into a variety of oil-based systems.