1,3-O-diferuloylglycerol | 83008-46-2

• 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: 1,3-O-diferuloylglycerol
• 英文别名: 1,3-diferuloyl-sn-glycerol；Glyceryl 1,3-diferulate；[2-hydroxy-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxypropyl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 83008-46-2
• 化学式: C₂₃H₂₄O₉
• 分子量: 444.438
• InChiKey: PATJZXBBUQEFOY-NXZHAISVSA-N

物化性质

• 熔点：
  47-56 °C
• 沸点：
  634.4±55.0 °C(Predicted)
• 密度：
  1.340±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  ethyl 4-hydroxy-3-methoxycinnamate 在 Novozym 435 作用下， 80.0 ℃ 、95.0 kPa 条件下， 反应 17.0h， 生成 1,3-O-diferuloylglycerol
  参考文献：
  名称：

  Comparative Study of Soybean Oil and the Mixed Fatty Acids as Acyl Donors for Enzymatic Preparation of Feruloylated Acylglycerols in Ionic Liquids

  摘要：

  Feruloylated acylglycerols (FAGs) are the lipophilic derivatives of ferulic acid. In this work, soybean oil (SBO) and the mixed fatty acids (MFA) were selected as fatty acyl donors, and reacted with glyceryl monoferulate (GMF) to prepare FAGs in ionic liquids (ILs). Effect of various reaction parameters (time, temperature, enzyme concentration, and substrate ratio) and ILs on the GMF conversion and the reaction selectivity for FAGs formation were investigated. Response surface methodology (RSM) based on a 3-level-4-factor Box-Behnken experimental design was employed to evaluate the inactive effect of reaction parameters. For the esterification of GMF with MFA, the maximum GMF conversion (98.9 +/- 0.9%) and FAG yield (88.9 +/- 0.6%) were achieved in [C(10)mim]PF6. However, for the transesterification of GMF with SBO, the maximum GMF conversion (94.3 +/- 0.7%) and FAG yield (83.8 +/- 1.0%) were obtained in [C(12)mim]PF6. High FAG selectivities (similar to 0.90) were also obtained using SBO or MFA as acyl donors.

  DOI：

  10.1021/acs.jafc.5b03479

文献信息

• Identification and quantification of feruloylated mono-, di-, and triacylglycerols from vegetable oils
  作者：David L. Compton、Joseph A. Laszlo、Mark A. Berhow

  DOI：10.1007/s11746-006-5010-5

  日期：2006.9

  AbstractThe use of HPLC‐MS to separate and identify the feruloylated acylglycerols formed during the transesterification of ethyl ferulate with TAG was examined. Novozym 435 (Candida antarctica lipase B)‐catalyzed transesterifications of ethyl ferulate and soybean oil resulted in a mixture of feruloylated MAG, DAG, and TAG and diferuloylated DAG and TAG. These feruloylated acylglycerols have recently garnered much interest as cosmeceutical ingredients. The ratio of the various feruloylated acylglycerol species in the resultant oils is presumed to affect the oil's cosmetic efficacy as well as its physical (formulation) properties. Thus, it was desirable to develop an analytical method to separate, identify, and quantify the individual feruloylated acylglycerols to determine their relative ratios. The feruloylated acylglycerols were successfully separated and identified by HPLC‐MS using a phenyl‐hexyl reversed‐phase column developed with a water/methanol/1‐butanol gradient. The chromatograms of the feruloylated acylglycerols from soybean oil were convoluted by myriad fatty acids; therefore, feruloylated acylglycerols from triolein were studied as a model reaction. Hydrolysis of the feruloylated acylglycerols from triolein catalyzed by Lipase PS‐C “Amano” I (Burkholderia cepacia), which showed no hydrolysis reactivity toward ethyl ferulate, allowed for the chromatographic assignment of the feruloyl acylglycerol positional isomers.
• COMPOSITIONS COMPRISING A UV-ABSORBING CHROMOPHORE AND METHODS OF MAKING AND USING SAME
  申请人：BIOTECHNOLOGY RESEARCH AND DEVELOPMENT CORPORATION

  公开号：EP1948318A1

  公开（公告）日：2008-07-30
• METHODS OF MAKING COMPOSITIONS COMPRISING A UV-ABSORBING CHROMOPHORE
  申请人：Laszlo A. Joseph

  公开号：US20070077636A1

  公开（公告）日：2007-04-05

  A method of making a compound having the structural formula: wherein at least two of R 1 , R 2 , and R 3 are non-fatty acid carboxylates, and the other of R 1 , R 2 , and R 3 are each either a C 2 -C 24 fatty acid moiety, OH, or a non-fatty acid carboxylate, wherein the first and second non-fatty acid carboxylates, when present, are the same or different, comprising (a) partially deacylating a triacylglycerol so as to provide a mono- or diacylglycerol, (b) reacting in a reaction mixture an acyl ester of the phytochemical with said mono- or diacylglycerol in the presence of a esterase catalyst under conditions that permit transesterification of said ester with said mono- or diacylglycerol, and (c) recovering said compound from said reaction mixture.
• COMPOSITIONS COMPRISING A UV-ABSORBING CHROMOPHORE
  申请人：Laszlo A. Joseph

  公开号：US20070077214A1

  公开（公告）日：2007-04-05

  A chemical composition comprising a linker agent and a compound comprising at least one UV-absorbing chromophore, wherein the linker agent is characterized by the general formula: wherein X 1 and X 2 are the same or different, and at least one of X 1 or X 2 is a functional group that bonds with the compound comprising at least one UV-absorbing chromophore, and b+f≧2, Y comprises an 0, N, or S that is substituted or unsubstituted, each a, b, c, e and f is ≧0 and a+b+c+e+f≧2, d is 0 or 1, n1 and n2 represent the number of hydrogen atoms required to complete the undesignated valencies, and m ranges from 1 to about 100 and each individual m unit may be the same or different.
• Compositions comprising a UV-absorbing chromophore
  申请人：Laszlo Joseph A.

  公开号：US20100215600A1

  公开（公告）日：2010-08-26

  A chemical composition comprising a linker agent and a compound comprising at least one UV-absorbing chromophore, wherein the linker agent is characterized by the general formula: wherein X 1 and X 2 are the same or different, and at least one of X 1 or X 2 is a functional group that bonds with the compound comprising at least one UV-absorbing chromophore, and b+f≧2, Y comprises an 0, N, or S that is substituted or unsubstituted, each a, b, c, e and f is ≧0 and a+b+c+e+f≧2, d is 0 or 1, n1 and n2 represent the number of hydrogen atoms required to complete the undesignated valencies, and m ranges from 1 to about 100 and each individual m unit may be the same or different.