(+/-)-1-O-feruloylglycerol | 120601-69-6

• 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-feruloylglycerol
• 英文别名: 1(3)-feruloyl-sn-glycerol；monoferuloyl-sn-glycerol；1-feruloyl-sn-glycerol；1-monoferuloylglycerol；1-O-feruloyl glycerol；glyceryl monoferulate；Glyceryl ferulate；2,3-dihydroxypropyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 120601-69-6
• 化学式: C₁₃H₁₆O₆
• 分子量: 268.266
• InChiKey: QXRAHTFDPBQKIM-HWKANZROSA-N

物化性质

• 保留指数：
  2522.7

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

• 作为反应物：
  描述：

  (+/-)-1-O-feruloylglycerol 、 硬脂酸 在 Novozym 435 作用下， 80.0 ℃ 、90.0 kPa 条件下， 反应 12.0h， 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
• 作为产物：
  描述：

  阿魏酸 在 Amberlyst 15 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 52.0h， 生成 (+/-)-1-O-feruloylglycerol
  参考文献：
  名称：

  Batovska, Daniela I.; Kishimoto, Takao; Bankova, Vassya S., Molecules, 2005, vol. 10, # 3, p. 552 - 558

  摘要：

  DOI：

文献信息

• Studies on the chemical constituents of Lilium henryi BAKER.
  作者：HIROKO SHIMOMURA、YUTAKA SASHIDA、YOSHIHIRO MIMAKI、YOICHI IITAKA

  DOI：10.1248/cpb.36.2430

  日期：——

  New bitter phenolic glycosides and a steroid glucoside have been isolated from the fresh bulbs of Lilium Henryi. On the basis of spectroscopic data, chemical evidence and X-ray crystallographic analysis, their structures have been elucidated as (2S)-1-O-p-methoxycinnamoyl-3-O-β-D-glucopyranosylglycerol (methylregaloside A), (2S)-1-O-caffeoyl-3-O-β-D-glucopyranosylglycerol (regaloside C), 3-O-feruloyl-6'-O-(4-O-β-D-glucopyranosylferuloyl)sucrose, and (25R)-3β, 26-dihydroxy-5α-cholestane-6, 22-dione 3-O-β-D-glucopyranoside. Several known components have also been isolated and identified.

  从百合科植物百合的新鲜鳞茎中分离得到了2个新的苦味酚苷和1个甾体葡萄糖苷，通过波谱数据、化学证据及X射线单晶衍射分析确定了它们的结构，分别为：(2S)-1-O-对-甲氧基肉桂酰基-3-O-β-D-吡喃葡萄糖基甘油（甲基罗果苷A）、(2S)-1-O-咖啡酰基-3-O-β-D-吡喃葡萄糖基甘油（罗果苷C）、3-O-阿魏酰基-6'-O-(4-O-β-D-吡喃葡萄糖基阿魏酰基)蔗糖和(25R)-3β，26-二羟基-5α-胆甾烷-6，22-二酮3-O-β-D-吡喃葡萄糖苷，同时还分离并鉴定了几种已知成分。
• Suberin Structure in Potato Periderm:  Glycerol, Long-Chain Monomers, and Glyceryl and Feruloyl Dimers
  作者：José Graça、Helena Pereira

  DOI：10.1021/jf0006123

  日期：2000.11.1

  aliphatics. GC-MS analysis showed the presence of monomers, dimers, and trimers (87, 12, and 1% of identified compounds, respectively). A total of 26 dimers were identified by EIMS: monoacylglyceryl esters of alpha,omega-diacids, omega-hydroxyacids, and alkanoic acids (with predominance of the 1- and 2-isomers of the monoacylglyceryl ester of the octadec-9-enodioic acid), as well as feruloyl esters of omega-hydroxyacids

  在无提取物马铃薯皮层中的Suberin约占NaOCH（3）甲醇分解测定的25％。单体成分的特征是甘油（占单体的20％），长链α，ω-二酸，ω-羟基酸，链烷酸和alkan-1-ols，主要为十八烷基-9-烯二酸和18-羟基十八烷基- 9-烯酸（分别占长链单体的39％和15％）。还存在芳族羟基肉桂基单体（<1％）。使用Ca（OH）（2）催化的甲醇分解作用对马铃薯皮层素木素进行部分解聚可溶解约10％的木脂素脂族化合物。GC-MS分析表明存在单体，二聚体和三聚体（分别为所鉴定化合物的87％，12％和1％）。通过EIMS识别出总共26个二聚体：α，ω-二酸，ω-羟酸的单酰基甘油酯，和链烷酸（以十八烷基9-烯二酸的单酰基甘油酯的1和2异构体为主），以及ω-羟基酸和alkan-1-ol的阿魏酸酯和少量的单铁酰甘油。在讨论了木质素大分子结构之后，提出了在具有亚醇的细胞壁中，多脂族聚合物具有由甘油确保的三维
• [EN] USE OF COMPOUNDS RESULTING FROM A SUGAR POLYOL OR FROM A DEHYDROGENATED SUGAR POLYOL DERIVATIVE AS A UV-SCREENING AGENT; ANTISUN COMPOSITIONS CONTAINING SAME; AND NOVEL COMPOUNDS<br/>[FR] UTILISATION DES COMPOSÉS OBTENUS À PARTIR D'UN POLYOL DE TYPE SUCRE OU D'UN DÉRIVÉ DÉSHYDROGÉNÉ DE POLYOL DE TYPE SUCRE À TITRE D'AGENT DE FILTRATION UV ; COMPOSITIONS ANTISOLAIRES LES CONTENANT ; ET NOUVEAUX COMPOSÉS
  申请人：OREAL

  公开号：WO2012010554A1

  公开（公告）日：2012-01-26

  The present invention relates to the cosmetic use, as an agent for screening out UV radiation, of compounds resulting from a sugar polyol or from a dehydrogenated sugar polyol derivative of formula (I) or (II) in which A1 and A2 denote UV-screening groups; Z1 and Z2 a sugar polyol group or a dehydrogenated sugar polyol derivative such that the product of formula (I) has in its structure from 1 to 4 -OH groups remaining and optionally from 1 to 2 -COOH groups. The present invention also relates to a composition comprising, in a cosmetically acceptable medium, at least one compound of formula (I) or (II). The present invention also relates to novel compounds resulting from a sugar polyol or from a dehydrogenated sugar polyol derivative of formula (I) or (II).

  本发明涉及一种化妆品用途，即作为筛选紫外线辐射的剂量，使用公式（I）或（II）的糖多醇或去氢糖多醇衍生物所得化合物，其中A1和A2表示紫外线筛选基团；Z1和Z2表示糖多醇基团或去氢糖多醇衍生物，使得公式（I）的产物在其结构中具有1-4个-OH基团和可选的1-2个-COOH基团。本发明还涉及一种组合物，其中包含在化妆品可接受介质中的至少一种公式（I）或（II）的化合物。本发明还涉及由公式（I）或（II）的糖多醇或去氢糖多醇衍生物所得的新化合物。
• 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