香豆酸肉桂酯 | 115610-30-5

• 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: 香豆酸肉桂酯
• 英文名称: (E)-cinnamyl-(E)-4-coumarate
• 英文别名: cinnamyl p-coumarate；(E)-cinnamyl (E)-p-coumarate；p-coumaric cinnamyl ester；cinnamyl coumarate；3-(4-Hydroxyphenyl)propenoic acid 3-phenyl-2-propenyl ester；[(E)-3-phenylprop-2-enyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 115610-30-5
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: JDBSEUVQZVQSCN-NJPWYCGFSA-N

物化性质

• 沸点：
  484.8±33.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	3-phenylpropenyl 3-(4-methoxymethoxyphenyl)allylate	885703-06-0	C20H20O4	324.376
  ——	ethyl (E)-3-(4-(methoxymethoxy)phenyl)acrylate	847450-00-4	C13H16O4	236.268
  ——	(E)-3-(4-(methoxymethoxy)phenyl)acrylic acid	61844-66-4	C11H12O4	208.214
  肉桂酸	(E)-3-phenylacrylic acid	140-10-3	C9H8O2	148.161
  ——	α-chloroacetate de cinnamyle	104023-33-8	C11H11ClO2	210.66

反应信息

• 作为反应物：
  描述：

  香豆酸肉桂酯 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 3-Phenylpropyl 3-(4-hydroxyphenyl)propanoate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues

  摘要：

  Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on a-glucosidase.

  DOI：

  10.1021/np0496441
• 作为产物：
  描述：

  ethyl (E)-3-(4-(methoxymethoxy)phenyl)acrylate 在 盐酸 、 4-二甲氨基吡啶 、 氢氧化钾 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 香豆酸肉桂酯
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues

  摘要：

  Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on a-glucosidase.

  DOI：

  10.1021/np0496441

文献信息

• Mali; Papalkar, Journal of Chemical Research - Part S, 2001, # 10, p. 433 - 435
  作者：Mali、Papalkar

  DOI：——

  日期：——
• GREENAWAY, W.;MAY, J.;WHATLEY, F. R., J. CHROMATOGR., 472,(1989) N, C. 393-400
  作者：GREENAWAY, W.、MAY, J.、WHATLEY, F. R.

  DOI：——

  日期：——
• [EN] A METHOD FOR REGULATING BIOSYNTHESIS OF MONOLIGNOLS<br/>[FR] PROCÉDÉ DE RÉGULATION DE LA BIOSYNTHÈSE DE MONOLIGNOLS
  申请人：UNIV SAINS MALAYSIA

  公开号：WO2012158016A1

  公开（公告）日：2012-11-22

  A method for reducing the synthesis of monolignols in cytoplasm of the plant of Hevea brasiliensis, comprising the step of down-regulating expression of a nucleic acid template containing at least one nucleotide sequence set forth in SEQ ID NO. 1, SEQ ID NO. 2, SEQ ID NO. 3, SEQ ID NO. 4, SEQ ID NO. 5, SEQ ID NO. 6, SEQ ID NO. 7, SEQ ID NO. 8, SEQ ID NO. 9, SEQ ID NO. 10, SEQ ID NO. 1 1 or SEQ ID NO. 12 in at least one cell. Also claimed are nucleotide sequences encoding phenylalanine ammonia-lyase 1 (PALI), phenylalanine ammonia-lyase 2 (PAL2), cinnamate 4-hydroxylase (CH4), coumarate 3-hydroxylase 1 (C3H1), coumarate 3-hydroxylase 2 (C3H2), caffeic acid/5-hydroxyconiferaldehyde O-methyltransferase (COMT), Hydroxycinnamoyl-CoA:shikimate hydroxycinnamoyl transferase (HCT), ferulate 5-hydroxylase (F5H), 4-coumarate CoA ligase (4CL), 4-coumarate caffeoyl-CoA O-methyltransferase (CCoAOMT), 4-coumarate cinnamoyl coenzyme A reductase (CCRl), and 4-coumarate cinnamyl alcohol dehydrogenase (CAD) enzymes, all from Hevea brasiliensis.
• Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues
  作者：Li Hong Hu、Hong Bin Zou、Jing Xu Gong、Hai Bo Li、Lei Xiang Yang、Wei Cheng、Chang Xin Zhou、Hua Bai、Françoise Guéritte、Yu Zhao

  DOI：10.1021/np0496441

  日期：2005.3.1

  Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on a-glucosidase.