octadecyl (E)-o-coumarate

• 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: octadecyl (E)-o-coumarate
• 英文别名: octadecyl o-coumarate；octadecyl (E)-3-(2-hydroxyphenyl)prop-2-enoate
• 化学式: C₂₇H₄₄O₃
• 分子量: 416.645
• InChiKey: KJNLKABHSOUUFQ-GHVJWSGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  30
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  硬脂醇 在 吡啶 、 四亚甲基二胺 作用下， 以 氯仿 为溶剂， 生成 octadecyl (E)-o-coumarate
  参考文献：
  名称：

  Characterization and quantitation of hexadecyl, octadecyl, and eicosyl esters of p-coumaric acid in the vine and root latex of sweetpotato [Ipomoea batatas (L.) Lam.]

  摘要：

  Methanol extracts of vine latex of four cultivars of sweetpotato [Ipomoea batatas (L.) Lam.] were analyzed for their chemical phenolic composition by reversed-phase HPLC. Major components were identified as hexadecyl, octadecyl, and eicosyl p-coumarates by an evaluation of data from UV spectra, hydrolysis, synthesis, and GC/MS of their trimethylsilyl derivatives. Both Z- and E-isomers of the phenolic acid were found, with the latter predominating. Trace quantities of hexadecyl (Z)- and (E)-ferulates were also identified in ester concentrates. Levels of octadecyl (E)-p-coumarate ranged from 0.7% fresh weight in cv. Resisto to almost 2% in cv. Jewel, while the hexadecyl ester levels were only 1/4 to 1/3 these values. Levels of the Z-esters were 1/10 to 1/20 of the levels of the corresponding E-isomers. Levels of the esters in cv. Jewel sweetpotato root latex were 2-10-fold the levels in the vine latex, while the ratio of E-esters to Z-esters was found to be 7-14-fold. The concentration of Z-esters among the sweetpotato cultivars tested correlated closely with the leaf feeding index for the sweetpotato weevil (Cylas formicarius) (R(2): C-20 = 0.96; C-18 = 0.98; C-16 = 0.71). The results indicate a possible relationship between latex chemistry and insect resistance that might be exploited via plant breeding.

  DOI：

  10.1021/jf00047a041

文献信息

• Synthesis and DNA Polymerase .ALPHA. and .BETA. Inhibitory Activity of Alkyl p-Coumarates and Related Compounds
  作者：Katsumi Nishimura、Yukiko Takenaka、Manami Kishi、Takao Tanahashi、Hiromi Yoshida、Chiaki Okuda、Yoshiyuki Mizushina

  DOI：10.1248/cpb.57.476

  日期：——

  trans- and cis-Icosyl, docosyl, and tetracosyl p-coumarates, constituents of Artemisia annua L., and their structurally-related compounds were synthesized and evaluated for inhibitory activity on DNA polymerases alpha and beta. Among 30 compounds synthesized, octadecyl trans- and cis-p-coumarates and octadecyl p-hydroxyphenylpropiolate showed strong inhibitory activity on DNA polymerases alpha and

  合成了Artemisia annua L.的组成部分的反式和顺式-二十烷基，二十二烷基和十四烷基对-香豆酸酯及其结构相关的化合物，并评估了它们对DNA聚合酶α和β的抑制活性。在合成的30种化合物中，十八烷基反式和顺式对-香豆酸酯和十八烷基对羟基苯丙酸酯显示出对DNA聚合酶α和β的强抑制活性。
• [EN] COMPOSITIONS FOR TOPICAL DELIVERY OF A PHARMACEUTICALLY ACTIVE AGENT HAVING REDUCED OXIDATION<br/>[FR] COMPOSITIONS A OXYDATION REDUITE UTILISEES POUR L'ADMINISTRATION LOCALE D'UN AGENT ACTIF SUR LE PLAN PHARMACEUTIQUE
  申请人：PROCTER & GAMBLE

  公开号：WO2001060337A1

  公开（公告）日：2001-08-23

  The present invention relates to compositions for the topical delivery of at least one pharmaceutically active agent comprising from about 1% to about 50% by weight of at least one phospholipid, from about 0.01% to about 10% of at least one pharmaceutically active agent, from about 0.01% to about 0.5% by weight of at least one chelating agent, and at least one suitable carrier material selected from components used in compositions for topical application. The at least one chelating agent prevents or reduces the oxidation of the topical compositions of the present invention.
• [EN] COMPOSITIONS FOR TOPICAL DELIVERY OF A PHARMACEUTICALLY ACTIVE AGENT HAVING REDUCED SKIN IRRITATION<br/>[FR] COMPOSITIONS REDUISANT L'IRRITATION CUTANEE UTILISEES POUR L'ADMINISTRATION LOCALE D'UN AGENT ACTIF SUR LE PLAN PHARMACEUTIQUE
  申请人：PROCTER & GAMBLE

  公开号：WO2001060336A1

  公开（公告）日：2001-08-23

  The present invention relates to compositions for the topical delivery of at least one pharmaceutically active agent comprising from about 1 % to about 50 % by weight of at least one phospholipid and from about 0.1 % to about 50 % by weight of at least one skin conditioning agent. The at least one skin conditioning agent prevents or reduces the drying, irritation, and/or itching of the skin of animals and/or humans caused by the continuous or repetitive application of topical compositions to the skin of animals and/or humans, which contain high levels of phospholipids.
• Characterization and quantitation of hexadecyl, octadecyl, and eicosyl esters of p-coumaric acid in the vine and root latex of sweetpotato [Ipomoea batatas (L.) Lam.]
  作者：Maurice E. Snook、Emma S. Data、Stanley J. Kays

  DOI：10.1021/jf00047a041

  日期：1994.11

  Methanol extracts of vine latex of four cultivars of sweetpotato [Ipomoea batatas (L.) Lam.] were analyzed for their chemical phenolic composition by reversed-phase HPLC. Major components were identified as hexadecyl, octadecyl, and eicosyl p-coumarates by an evaluation of data from UV spectra, hydrolysis, synthesis, and GC/MS of their trimethylsilyl derivatives. Both Z- and E-isomers of the phenolic acid were found, with the latter predominating. Trace quantities of hexadecyl (Z)- and (E)-ferulates were also identified in ester concentrates. Levels of octadecyl (E)-p-coumarate ranged from 0.7% fresh weight in cv. Resisto to almost 2% in cv. Jewel, while the hexadecyl ester levels were only 1/4 to 1/3 these values. Levels of the Z-esters were 1/10 to 1/20 of the levels of the corresponding E-isomers. Levels of the esters in cv. Jewel sweetpotato root latex were 2-10-fold the levels in the vine latex, while the ratio of E-esters to Z-esters was found to be 7-14-fold. The concentration of Z-esters among the sweetpotato cultivars tested correlated closely with the leaf feeding index for the sweetpotato weevil (Cylas formicarius) (R(2): C-20 = 0.96; C-18 = 0.98; C-16 = 0.71). The results indicate a possible relationship between latex chemistry and insect resistance that might be exploited via plant breeding.