咖啡酸二十二酯 | 50432-89-8

• 物质功能分类: 天然产物 - 苯丙素
• 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
• 中文名称: 咖啡酸二十二酯
• 英文名称: docosyl (3,4-dihydroxy)trans-cinnamate
• 英文别名: docosyl-3,4-dihydroxy-trans-cinnamate；docosyl-3,4-dihyroxy-trans-cinnamate；docosyl 3,4-dihydroxy-E-cinnamate；docosyl caffeate；docosyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 50432-89-8；28593-92-2
• 化学式: C₃₁H₅₂O₄
• 分子量: 488.751
• InChiKey: GUWHMEMJBCLEBP-WJTDDFOZSA-N

物化性质

• 沸点：
  604.0±45.0 °C(Predicted)
• 密度：
  0.989±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  13.3
• 重原子数：
  35
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  咖啡酸二十二酯 生成 二十二烷-1-醇
  参考文献：
  名称：

  IMAI, FUJIO;ITOH, KIKUO;KISHIBUCHI, NORIKO;KINOSHITA, TAKESHI;SANKAWA, US+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 119-123

  摘要：

  DOI：
• 作为产物：
  描述：

  二十二烷-1-醇 、 (E)-3-(3,4-dihydroxyphenyl)acryloyl chloride 生成 咖啡酸二十二酯
  参考文献：
  名称：

  Impact of Alkyl Esters of Caffeic and Ferulic Acids on Tumor Cell Proliferation, Cyclooxygenase Enzyme, and Lipid Peroxidation

  摘要：

  The antioxidant ferulic and caffeic acid phenolics are ubiquitous in plants and abundant in fruits and vegetables. We have synthesized a series of ferulic and caffeic acid esters and tested for tumor cell proliferation, cyclooxygenase enzymes (COX-1 and -2) and lipid peroxidation inhibitory activities in vitro. In the tumor cell proliferation assay, some of these esters showed excellent growth inhibition of colon cancer cells. Among the phenolics esters assayed, compounds 10 (C-12-caffeate), 11 (C-16-caffeate), 21 (C-8-ferulate), and 23 (C-12-ferulate) showed strong growth inhibition with IC50 values of 16.55, 13.46, 18.67, and 7.57 mu g/mL in a breast cancer cell line; 9.65, 7.45, 17.05, and 4.35 mu g/mL in a lung cancer cell line; 5.78, 3.5, 4.29, and 2.46 mu g/mL in a colon cancer cell line; 12.04, 12.21, 14.63, and 8.09 mu g/mL in a central nervous system cancer cell line; and 8.62, 7.76, 11.0, and 5.37 in a gastric cancer cell line. In COX enzyme inhibitory assays, ferulic and caffeic acid esters significantly inhibited both COX-1 and COX-2 enzymes. Caffeates 5-10 (C-4-C-12), inhibited COX-1 enzyme between 50% and 90% and COX-2 enzyme by about 70%, whereas ferulates 15-21 (C-3-C-8) inhibited COX-1 and COX-2 enzymes by 85-95% 25 mu g/mL. Long-chain caffeates 11-14 (C-16-C-22) and short-chain ferulates 15-20 (C-3-C-5) were the most active in lipid peroxidation inhibition and showed 6070% activity at 5 mu g/mL concentration.

  DOI：

  10.1021/jf060899p

文献信息

• [EN] COSMETIC TREATMENT PROCESS USING ORTHO-DIPHENOL DERIVATIVES, NOVEL COMPOUNDS AND COSMETIC COMPOSITION COMPRISING SAME<br/>[FR] PROCÉDÉ DE TRAITEMENT COSMÉTIQUE UTILISANT DES DÉRIVÉS D'ORTHODIPHÉNOL, NOUVEAUX COMPOSÉS, ET COMPOSITION COSMÉTIQUE LES COMPRENANT
  申请人：OREAL

  公开号：WO2012038334A1

  公开（公告）日：2012-03-29

  Cosmetic treatment process using ortho-diphenol derivatives, novel compounds and cosmetic composition comprising same The present invention relates to a cosmetic treatment process for keratin materials, in which a cosmetic composition comprising at least one compound of formula (I), or salts or solvates thereof, as defined hereinafter: is applied to said keratin materials. It is in particular a hair treatment process, in particular for damaged hair; preferably, it is a process for protecting and/or repairing the hair, in particular damaged hair. The invention also relates to certain novel compounds of formula (I) and to the cosmetic compositions comprising same.
• Impact of Alkyl Esters of Caffeic and Ferulic Acids on Tumor Cell Proliferation, Cyclooxygenase Enzyme, and Lipid Peroxidation
  作者：Bolleddula Jayaprakasam、Mulabagal Vanisree、Yanjun Zhang、David L. Dewitt、Muraleedharan G. Nair

  DOI：10.1021/jf060899p

  日期：2006.7.1

  The antioxidant ferulic and caffeic acid phenolics are ubiquitous in plants and abundant in fruits and vegetables. We have synthesized a series of ferulic and caffeic acid esters and tested for tumor cell proliferation, cyclooxygenase enzymes (COX-1 and -2) and lipid peroxidation inhibitory activities in vitro. In the tumor cell proliferation assay, some of these esters showed excellent growth inhibition of colon cancer cells. Among the phenolics esters assayed, compounds 10 (C-12-caffeate), 11 (C-16-caffeate), 21 (C-8-ferulate), and 23 (C-12-ferulate) showed strong growth inhibition with IC50 values of 16.55, 13.46, 18.67, and 7.57 mu g/mL in a breast cancer cell line; 9.65, 7.45, 17.05, and 4.35 mu g/mL in a lung cancer cell line; 5.78, 3.5, 4.29, and 2.46 mu g/mL in a colon cancer cell line; 12.04, 12.21, 14.63, and 8.09 mu g/mL in a central nervous system cancer cell line; and 8.62, 7.76, 11.0, and 5.37 in a gastric cancer cell line. In COX enzyme inhibitory assays, ferulic and caffeic acid esters significantly inhibited both COX-1 and COX-2 enzymes. Caffeates 5-10 (C-4-C-12), inhibited COX-1 enzyme between 50% and 90% and COX-2 enzyme by about 70%, whereas ferulates 15-21 (C-3-C-8) inhibited COX-1 and COX-2 enzymes by 85-95% 25 mu g/mL. Long-chain caffeates 11-14 (C-16-C-22) and short-chain ferulates 15-20 (C-3-C-5) were the most active in lipid peroxidation inhibition and showed 6070% activity at 5 mu g/mL concentration.
• IMAI, FUJIO;ITOH, KIKUO;KISHIBUCHI, NORIKO;KINOSHITA, TAKESHI;SANKAWA, US+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 119-123
  作者：IMAI, FUJIO、ITOH, KIKUO、KISHIBUCHI, NORIKO、KINOSHITA, TAKESHI、SANKAWA, US+

  DOI：——

  日期：——