3-O-(trans-4-feruloyl)cholesterol | 164453-91-2

• 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)cholesterol
• 英文别名: Cholesterol ferulate；[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 164453-91-2
• 化学式: C₃₇H₅₄O₄
• 分子量: 562.833
• InChiKey: CPBQNAKTSMCPNH-NXVZWREOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 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)cholesterol 在 potassium carbonate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 6.0h， 以96%的产率得到3-O-(trans-4-feruloyl)cholesterol
  参考文献：
  名称：

  具有多种甾醇结构的阿魏酸阿魏酸酯的合成及其抗氧化活性的比较

  摘要：

  由商业固醇和商业谷维素合成的硬脂酸阿魏酸酯用于通过ABTS +自由基脱色测定，大豆油的氧化稳定性指数（OSI）以及通过分析抗氧化活性来更好地了解结构特征如何影响体外抗氧化活性油炸。阿魏酸硬脂酸酯可抑制ABTS +自由基的浓度为6.5–56.6％，具体取决于它们的浓度，但效果不如阿魏酸，尤其是在较低浓度下。阿魏酸和阿魏酸酯不起作用，或根据浓度降低大豆油的OSI达25％。在其作为煎炸油抗氧化剂的评估中，具有饱和固醇基的甾醇阿魏酸酯具有最佳的抗氧化活性，其次是在C5位具有一个双键的固醇。结果表明，在谷维素中发现的C4处的二甲基基团以及C9，C19环丙烷基团会对煎炸油中的抗氧化活性产生负面影响。

  DOI：

  10.1016/j.foodchem.2014.07.119

文献信息

• Synthesis of steryl ferulates with various sterol structures and comparison of their antioxidant activity
  作者：Jill K. Winkler-Moser、Hong-Sik Hwang、Erica L. Bakota、Debra A. Palmquist

  DOI：10.1016/j.foodchem.2014.07.119

  日期：2015.2

  vitro by the ABTS+ radical decolorization assay, by oxidative stability index (OSI) of soybean oil, and by analysis of antioxidant activity during frying. Steryl ferulates inhibited the ABTS+ radical by 6.5–56.6%, depending on their concentration, but were less effective, especially at lower concentrations, than ferulic acid. Ferulic acid and steryl ferulates had either no effect, or lowered the OSI

  由商业固醇和商业谷维素合成的硬脂酸阿魏酸酯用于通过ABTS +自由基脱色测定，大豆油的氧化稳定性指数（OSI）以及通过分析抗氧化活性来更好地了解结构特征如何影响体外抗氧化活性油炸。阿魏酸硬脂酸酯可抑制ABTS +自由基的浓度为6.5–56.6％，具体取决于它们的浓度，但效果不如阿魏酸，尤其是在较低浓度下。阿魏酸和阿魏酸酯不起作用，或根据浓度降低大豆油的OSI达25％。在其作为煎炸油抗氧化剂的评估中，具有饱和固醇基的甾醇阿魏酸酯具有最佳的抗氧化活性，其次是在C5位具有一个双键的固醇。结果表明，在谷维素中发现的C4处的二甲基基团以及C9，C19环丙烷基团会对煎炸油中的抗氧化活性产生负面影响。
• 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.