十八烷基对香豆酸盐 | 72943-88-5

• 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: 十八烷基对香豆酸盐
• 英文名称: octadecanyl-3-[4-hydroxyphenyl]-prop-2-enoate
• 英文别名: (E)-octadecyl 3-(4-hydroxyphenyl)propenoate；n-octadecyl-4-hydroxycinnamate；(E)-octadecyl p-coumarate；octadecyl (E)-p-coumarate；octadecyl (E)-p-cumarate；octadecyl p-coumarate；octadecyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 72943-88-5
• 化学式: C₂₇H₄₄O₃
• 分子量: 416.645
• InChiKey: SXXOKKBSVARFFB-BSYVCWPDSA-N

物化性质

• 熔点：
  84-87 °C
• 沸点：
  529.5±25.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

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

• 作为反应物：
  描述：

  十八烷基对香豆酸盐 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 6.0h， 以93%的产率得到3-(4-Hydroxyphenyl)-propionsaeurestearylester
  参考文献：
  名称：

  对-香豆酸烷基酯及相关化合物的合成及DNA聚合酶的α和β抑制活性。

  摘要：

  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。

  DOI：

  10.1248/cpb.57.476
• 作为产物：
  描述：

  p-acetoxycinnamoyl chloride 在 吡啶 、 四亚甲基二胺 作用下， 以 氯仿 为溶剂， 生成 十八烷基对香豆酸盐
  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

• Long Chain Alkyl Esters of Hydroxycinnamic Acids as Promising Anticancer Agents: Selective Induction of Apoptosis in Cancer Cells
  作者：José C. J. M. D. S. Menezes、Najmeh Edraki、Shrivallabh P. Kamat、Mahsima Khoshneviszadeh、Zahra Kayani、Hossein Hadavand Mirzaei、Ramin Miri、Nasrollah Erfani、Maryam Nejati、José A. S. Cavaleiro、Tiago Silva、Luciano Saso、Fernanda Borges、Omidreza Firuzi

  DOI：10.1021/acs.jafc.7b01388

  日期：2017.8.23

  alkyl esters may possess enhanced biological activities. We evaluated C4, C14, C16, and C18 alkyl esters of p-coumaric, ferulic, sinapic, and caffeic acids (19 compounds) for their cytotoxic activity against four human cancer cells and also examined their effect on cell cycle alteration and apoptosis induction. The tetradecyl (1c) and hexadecyl (1d) esters of p-coumaric acid and tetradecyl ester of caffeic

  癌症是全世界发病率和死亡率的主要原因。羟基肉桂酸（HCA）是天然存在的化合物，其烷基酯可能具有增强的生物活性。我们评估了对香豆酸，阿魏酸，芥子酸和咖啡酸（19种化合物）的C4，C14，C16和C18烷基酯对四种人类癌细胞的细胞毒活性，并且还研究了它们对细胞周期改变和凋亡诱导的影响。对香豆酸的十四烷基（1c）和十六烷基（1d）和咖啡酸（4c）的十四烷基酯（而非亲本的HCA）具有IC 50对MOLT-4（人淋巴细胞白血病）细胞的选择性作用。分别为0.123±0.012、0.301±0.069和1.0±0.1μM。化合物1c，1d和4c显着增加了亚G1期的凋亡细胞，并激活了MOLT-4细胞中的caspase-3酶。化合物1c对抗药性MES-SA-DX5子宫肉瘤细胞的效力分别比阿霉素和顺铂高15.4倍和23.6倍。这些对香豆酸酯对NIH / 3T3成纤维细胞的功效要低好几倍。对接研究表明1c可能通
• 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。
• 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.