3-O-(trans-4-feruloyl)-β-sitostanol | 106774-76-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-O-(trans-4-feruloyl)-β-sitostanol
• 英文别名: 3-O-(trans-4-feruloyl)stigmastanol；stigmastanol trans-ferulate；trans-feruloyl stigmastanol；sigmastanol trans-ferulate；trans-sitostanyl ferulate；stigmastanol ferulate；Sitostanyl ferulate；[(3S,5S,8R,9S,10S,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 106774-76-9；115587-24-1；117857-72-4；117857-70-2
• 化学式: C₃₉H₆₀O₄
• 分子量: 592.903
• InChiKey: RAKOKKNCCBUUMP-HNBUMGCJSA-N

物化性质

• 沸点：
  652.3±40.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-O-(trans-4-feruloyl)-β-sitostanol 以 氯仿 为溶剂， 反应 3.0h， 以25%的产率得到cis-feruloyl stigmastanol
  参考文献：
  名称：

  Isolation of ovulatory-active substances from crops of Job's tears(Coix lacryma-jobi L. var. ma-yuen Stapf.).

  摘要：

  在正常周期雌性金仓鼠输卵管的显微镜观察指导下，从Jpb的眼泪（Coix lacryma-jobi L. var. ma-yuen STAPF. Gramineae）作物中分离出排卵活性物质。通过化学和光谱手段，这些化合物被确定为反式阿魏酰基豆甾醇和反式阿魏酰基菜甾醇（1）的9:1混合物，以及它们的几何异构体（2）的9:1混合物。还进行了反式和顺式阿魏酰基豆甾醇的合成。物质1和200微克/天的合成反式阿魏酰基豆甾醇在雌性金仓鼠中表现出诱导排卵和刺激卵巢卵泡生长的作用。

  DOI：

  10.1248/cpb.36.3147
• 作为产物：
  描述：

  阿魏酸 在 哌嗪 、 吡啶 、 4-二甲氨基吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.5h， 生成 3-O-(trans-4-feruloyl)-β-sitostanol
  参考文献：
  名称：

  谷物中游离植物甾醇/植物甾烷醇和完整植物甾醇/植物甾烷醇脂肪酸和酚酸酯的同时分析

  摘要：

  开发了一种基于固相萃取的方法，可从谷物脂质中有效分离出游离的植物甾醇/植物甾烷醇以及植物甾醇/植物甾烷醇脂肪酸和酚酸酯。借助于毛细管气相色谱法分析完整形式的酯缀合物。除游离固醇和甾烷醇外，还通过气相色谱-质谱法在四种谷物中鉴定出多达33种不同的脂肪酸和酚酸酯。大部分（52-57％）的固醇和甾烷醇以脂肪酸酯的形式存在。在玉米中，确定了三种基于谷粒干物质的甾醇和甾烷醇的最高含量，而黑麦的油提取物的脂肪酸酯和游离甾醇/甾烷醇的含量分别是玉米油的1.7和1.6倍。结果表明，与黑麦，小麦和斯佩尔特小麦相比，从玉米中获得的甾醇/甾烷醇及其酯类和含量存在相当大的差异。所提出的方法可用于定量各种游离的植物甾醇/植物甾烷醇和完整的植物甾醇/植物甾烷酸酯，以表征不同类型的谷物。

  DOI：

  10.1021/jf300878h

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.
• Improved Method for the Synthesis of <i>trans</i>-Feruloyl-β-sitostanol
  作者：Anthony M. Condo,、David C. Baker、Robert A. Moreau、Kevin B. Hicks

  DOI：10.1021/jf010703f

  日期：2001.10.1

  Phytosterols and phytostanols are known to lower low-density lipoprotein-cholesterol (LDL-C) levels in humans by up to 15%, and at least two products, Benecol and Take Control, are now on the market as naturally derived fatty acid esters of phytostanols (stanol esters) and phytosterols (sterol esters), respectively. A synthetic process was developed to synthesize gram quantities of trans-feruloyl-beta-sitostanol from ferulic acid and beta-sitostanol, with high purity and yields of approximately 60%. The process involves (a) condensation of trans-4-O-acetylferulic acid with the appropriate phytostanol or phytostanol mixture in the presence of N,N-dicyclohexylcarbodiimide and 4-(dimethylamino)pyridine, (b) separation of the trans-4-O-acetylferuloyl products by preparative liquid chromatography, (c) selective deacetylation of the feruloyl acetate, and (d) chromatographic purification of the feruloylated phytostanols. The process was successfully applied to synthesize stanol trans-feruloyl esters from "Vegetable Stanols", a mixture of approximately 70:30 beta-sitostanol and beta-campestanol, in comparable purity and yield.
• KONDO, JOSIKADZU;SUDZUKI, AKIEHTSU;KUBOYAMA, MORIO
  作者：KONDO, JOSIKADZU、SUDZUKI, AKIEHTSU、KUBOYAMA, MORIO

  DOI：——

  日期：——
• Simultaneous Analysis of Free Phytosterols/Phytostanols and Intact Phytosteryl/Phytostanyl Fatty Acid and Phenolic Acid Esters in Cereals
  作者：Rebecca Esche、Andreas Barnsteiner、Birgit Scholz、Karl-Heinz Engel

  DOI：10.1021/jf300878h

  日期：2012.5.30

  acid esters from cereal lipids was developed. The ester conjugates were analyzed in their intact form by means of capillary gas chromatography. Besides free sterols and stanols, up to 33 different fatty acid and phenolic acid esters were identified in four different cereal grains via gas chromatography–mass spectrometry. The majority (52–57%) of the sterols and stanols were present as fatty acid esters

  开发了一种基于固相萃取的方法，可从谷物脂质中有效分离出游离的植物甾醇/植物甾烷醇以及植物甾醇/植物甾烷醇脂肪酸和酚酸酯。借助于毛细管气相色谱法分析完整形式的酯缀合物。除游离固醇和甾烷醇外，还通过气相色谱-质谱法在四种谷物中鉴定出多达33种不同的脂肪酸和酚酸酯。大部分（52-57％）的固醇和甾烷醇以脂肪酸酯的形式存在。在玉米中，确定了三种基于谷粒干物质的甾醇和甾烷醇的最高含量，而黑麦的油提取物的脂肪酸酯和游离甾醇/甾烷醇的含量分别是玉米油的1.7和1.6倍。结果表明，与黑麦，小麦和斯佩尔特小麦相比，从玉米中获得的甾醇/甾烷醇及其酯类和含量存在相当大的差异。所提出的方法可用于定量各种游离的植物甾醇/植物甾烷醇和完整的植物甾醇/植物甾烷酸酯，以表征不同类型的谷物。