1-O-feruloyl glycerol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-O-feruloyl glycerol
• 英文别名: 1-O-feruloylglycerol；1-glyceryl ferulate；1-feruloylglycerol；feruloyl glycerol；1-FG；2,3-Dihydroxypropyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• 化学式: C₁₃H₁₆O₆
• 分子量: 268.266
• InChiKey: QXRAHTFDPBQKIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  阿魏酸甲酯 、 甘油 在 氢氧化钾 作用下， 以18%的产率得到1-O-feruloyl glycerol
  参考文献：
  名称：

  Synthesis of α-monoglycerides of aromatic acids

  摘要：

  The synthesis of alpha-monoglycerides of aromatic acids has been performed by the transesterification of the methyl esters of the corresponding acids with glycerol. The structures of the compounds obtained have been confirmed by their IR, UV, and H-1 and C-13 NMR spectra.

  DOI：

  10.1007/bf02282504

文献信息

• Ultrasonic-promoted enzymatic preparation, identification and multi-active studies of nature-identical phenolic acid glycerol derivatives
  作者：Teng Sun、Haiping Zhang、Zhe Dong、Zengshe Liu、Mingming Zheng

  DOI：10.1039/c9ra09830e

  日期：——

  Phenolic acid glycerols (PAGs) are a group of rare phytochemicals found from potato periderm, which show great potential in the food, cosmetic and pharmaceutical industries. In this study, seven PAGs were enzymatically synthesized via transesterification of ethyl phenates (EPs) with glycerol by ultrasonic promotion. The conversions of 88.1–98.5% could be obtained in 1–9 h. Compared with the conventional

  酚酸甘油 (PAGs) 是从马铃薯外皮中发现的一组稀有植物化学物质，在食品、化妆品和制药行业中显示出巨大的潜力。在这项研究中，通过超声波促进酚乙酯 (EPs) 与甘油的酯交换酶促合成了七种 PAG 。88.1-98.5% 的转化率可以在 1-9 小时内获得。与传统搅拌方法相比，超声辅助催化效率显着提高了11.0-44.0倍。与母体酚酸 (PA) 相比，脂质过氧化抑制活性增加了 8.1 倍和 14.4 倍。此外，咖啡酰甘油和阿魏酰甘油对大肠杆菌表现出优异的抗菌活性与相应的 PA 相比，最小抑制浓度 (MIC) 降低了 4-16 倍。与相应的 PA 相比，PAG 还可以吸收更广泛和更高量的有害 UV-B 射线。目前用于简便合成多功能 PAG 的策略为天然植物化学物质和新型成分的开发和应用铺平了道路。
• Feruloylated Products from Coconut Oil and Shea Butter
  作者：David L. Compton、John R. Goodell、Mark A. Berhow、James A. Kenar、Steven C. Cermak、Kervin O. Evans

  DOI：10.1007/s11746-017-2953-7

  日期：2017.3

  medium chain triacylglycerol (TAG) standards, C8–C14. The feruloylated vegetable oils possessed an ultra violet (UV) absorbing λmax 328 nm, making them good UVAII absorbers, as defined by the U.S. Food and Drug Administration. The feruloylated coconut oil possessed a 17.5% higher absorption capacity than feruloylated shea butter on a per weight basis. All the feruloylated vegetable oils possessed rapid

  阿魏酸酯化椰子油和阿魏酸酯化乳木果油的合成以0.5-L规模，摇动的间歇反应进行了演示。在存在假丝酵母的情况下，阿魏酸乙酯和植物油/脂肪的摩尔比为1.0：1.3脂肪酶B在60°C下固定在丙烯酸树脂（Novozym 435）上。阿魏酸乙酯与椰子油和乳木果油的酯交换反应在22天后分别达到63％和70％的平衡转化率，乳木果油酯交换反应产生白色沉淀，这在椰子油酯交换反应中没有观察到。乳木果油中存在的二和单酰基甘油（DAG和MAG）显示出更快的酯交换速率，平衡转化率和白色沉淀。阿魏酸乙酯和椰子油的酯交换反应也在连续的酶促填充床生物反应器中进行了测试，使用Novozym 435在60°C的条件下，在4.5个月内每天生产0.5至0.9千克阿魏酸酯化的椰子油。通过LC-MS分析阿魏酸乙酯与中链三酰基甘油（TAG）标准品C8-C14的酯交换反应，鉴定出阿魏酸酯化的椰子油酰基甘油种类。阿魏酸酯化植物油具有紫外线
• Glycerol acyl-transfer kinetics of a circular permutated Candida antarctica lipase B
  作者：Joseph A. Laszlo、Ying Yu、Stefan Lutz、David L. Compton

  DOI：10.1016/j.molcatb.2011.06.002

  日期：2011.11

  Triacylglycerols containing a high abundance of unusual fatty acids, such as gamma-linolenic acid, or novel arylaliphatic acids, such as ferulic acid, are useful in pharmaceutical and cosmeceutical applications. Candida antarctica lipase B (CALB) is quite often used for non-aqueous synthesis, although the wildtype enzyme can be rather slow with bulky and sterically hindered acyl donor substrates. The catalytic performance of a circularly permutated variant of CALB, cp283, with various acyl donors and glycerol was examined. In comparison to wild-type CALB, butyl oleate and ethyl gamma-linolenate glycerolysis rates were 2.2- and 4.0-fold greater, respectively. Cp283 showed substrate inhibition by glycerol, which was not the case with the wild-type version. With either ethyl ferulate or vinyl ferulate acyl donors, cp283 matched the performance of wild-type CALB. Changes in active site accessibility resulting from circular permutation led to increased catalytic rates for bulky fatty acid esters but did not overcome the steric hindrance or energetic limitations experienced by arylaliphatic esters. Published by Elsevier B.V.
• Solvent-Free Enzymatic Preparation of Feruloylated Monoacylglycerols Optimized by Response Surface Methodology
  作者：Shang-De Sun、Liang Shan、Yuan-Fa Liu、Qing-Zhe Jin、Li-Xia Zhang、Xing-Guo Wang

  DOI：10.1021/jf0728911

  日期：2008.1.1

  The ability of immobilized lipase B from Candida antarctica (Novozym 435) to catalyze the direct esterification of glyceryl ferulate (FG) and oleic acid for feruloylated monoacylglycerols (FMAG) preparation in a solvent-free system was investigated. Enzyme screening and the effect of glycerol on the initial reaction rate of esterification were also investigated. Response surface methodology (RSM) was used to optimize the effects of the reaction temperature (55-65 degrees C), the enzyme load (8-14%; relative to the weight of total substrates), oleic acid/(FG + glycerol) (6:1-9:1; w/w), and the reaction time (1-2 h) on the conversion of FG and yield of FMAG. Validation of the RSM model was verified by the good agreement between the experimental and the predicted values of FG conversion and FMAG yield. The optimum preparation conditions were as follows: temperature, 60 degrees C enzyme load, 8.2%; substrate ratio, 8.65:1 (oleic acid/(FG + glycerol), w/w); and reaction time, 1.8 h. Under these conditions, the conversion of FG and yield of FMAG are 96.7 +/- 1.0% and 87.6 +/- 1.2%, respectively.
• Synthesis of α-monoglycerides of aromatic acids
  作者：A. F. Artamonov、F. S. Nigmatullina、M. T. Aldabergenova、B. Zh. Dzhiembaev

  DOI：10.1007/bf02282504

  日期：1999.7

  The synthesis of alpha-monoglycerides of aromatic acids has been performed by the transesterification of the methyl esters of the corresponding acids with glycerol. The structures of the compounds obtained have been confirmed by their IR, UV, and H-1 and C-13 NMR spectra.