3-O-(trans-4-feruloyl)ergosterol

• 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: 3-O-(trans-4-feruloyl)ergosterol
• 英文别名: ergosteryl ferulate；[(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] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• 化学式: C₃₈H₅₂O₄
• 分子量: 572.828
• InChiKey: UMFKQSTUSFRXRV-QMHZKOHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-O-(trans-4-O-acetylferuloyl)ergosterol 在 potassium carbonate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 6.0h， 以94%的产率得到3-O-(trans-4-feruloyl)ergosterol
  参考文献：
  名称：

  Microwave (MW) promoted high yield expedient synthesis of steryl ferulates – A class of novel biologically active compounds: A comparative study of their antioxidant activity with that of naturally occurring γ-oryzanol

  摘要：

  Synthetic steryl ferulates [3-O-(trans-4-feruloyl)-sterols] are currently gaining considerable importance in recent years to be used as nutraceuticals and food additives as well as in pharmaceutical applications substituting gamma-oryzanol a class of naturally occurring steryl ferulates having potent antioxidant and other organoleptic properties. Considering the importance of this class of compounds coupled with green technology associated with microwave energy (MW) in organic synthesis, we report here an expedited and high yield synthesis of steryl ferulates from abundant steroids, viz., cholesterol, cholestanol, stigmasterol, stigmastanol, beta-sitosterol, beta-campesterol, beta-campestanol and ergosterol applying MW energy in the crucial step of esterification process of sterols with trans-4-O-acetylferulic acid to furnish their esterified products, viz., 3-O-(trans-4-O-acetylferuloyl)-sterols for their eventual deprotection to their respective steryl ferulates. We further report an efficient and scalable process of producing acetylferulic acid. Testing of synthesized steryl ferulates against antioxidant assays has also been highlighted. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2015.12.017

文献信息

• Microwave (MW) promoted high yield expedient synthesis of steryl ferulates – A class of novel biologically active compounds: A comparative study of their antioxidant activity with that of naturally occurring γ-oryzanol
  作者：Ashma Begum、Preetismita Borah、Pritish Chowdhury

  DOI：10.1016/j.steroids.2015.12.017

  日期：2016.3

  Synthetic steryl ferulates [3-O-(trans-4-feruloyl)-sterols] are currently gaining considerable importance in recent years to be used as nutraceuticals and food additives as well as in pharmaceutical applications substituting gamma-oryzanol a class of naturally occurring steryl ferulates having potent antioxidant and other organoleptic properties. Considering the importance of this class of compounds coupled with green technology associated with microwave energy (MW) in organic synthesis, we report here an expedited and high yield synthesis of steryl ferulates from abundant steroids, viz., cholesterol, cholestanol, stigmasterol, stigmastanol, beta-sitosterol, beta-campesterol, beta-campestanol and ergosterol applying MW energy in the crucial step of esterification process of sterols with trans-4-O-acetylferulic acid to furnish their esterified products, viz., 3-O-(trans-4-O-acetylferuloyl)-sterols for their eventual deprotection to their respective steryl ferulates. We further report an efficient and scalable process of producing acetylferulic acid. Testing of synthesized steryl ferulates against antioxidant assays has also been highlighted. (C) 2015 Elsevier Inc. All rights reserved.