acetate of (+)-catechin | 116935-88-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: acetate of (+)-catechin
• 英文别名: (-)-3-O-acetylcatechin；3-acetyl (+)-catechin；3-O-acetylcatechin；(2R)-3t-Acetoxy-2r-(3,4-dihydroxy-phenyl)-chroman-5,7-diol；((+)-Catechin)-monoacetat；[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] acetate
• CAS: 116935-88-7
• 化学式: C₁₇H₁₆O₇
• 分子量: 332.31
• InChiKey: CCTIBFOBERZTCX-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  acetate of (+)-catechin 在 吡啶 、 乙醇 作用下， 生成 (2R)-2r-(3,4-bis-methanesulfonyloxy-phenyl)-5,7-bis-methanesulfonyloxy-chroman-3t-ol
  参考文献：
  名称：

  Freudenberg et al., Justus Liebigs Annalen der Chemie, 1957, vol. 603, p. 177,178 Anm. 3

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(3,4-二乙酰氧基苯基)-3,4-二氢-2H-苯并吡喃-3,5,7-三基三乙酸酯 在 乙醇 、 potassium acetate 作用下， 生成 acetate of (+)-catechin
  参考文献：
  名称：

  Freudenberg; Boehme; Purrmann, Chemische Berichte, 1922, vol. 55, p. 1746

  摘要：

  DOI：

文献信息

• Enzyme-Mediated Regioprotection-Deprotection of Hydroxyl Groups in (+)-Catechin
  作者：Daniela Lambusta、Giovanni Nicolosi、Angela Patti、Mario Piattelli

  DOI：10.1055/s-1993-26019

  日期：——

  Several mono- and polyacetates of (+)-catechin [(2R,3S)-2-(3, 4-di-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol] have been synthesized by biocatalyzed reactions starting from (+)-catechin or (+)-catechin pentaacetate. In particular, 5-O-acetylcatechin and 7-O-acetylcatechin have been obtained by reaction of catechin with vinyl acetate in the presence of supported Pseudomonas cepacia lipase, while alcoholysis of catechin pentaacetate with 1-butanol catalyzed by the same enzyme yielded 3,3′,4′,5-O-tetraacetylcatechin and 3,3′,4′- O-triacetylcatechin and, under different experimental conditions, 3-O-acetylcatechin.

  以(+)-儿茶素或(+)-儿茶素五乙酸酯为起点，通过生物催化反应合成了多种(+)-儿茶素[(2R,3S)-2-(3,4-二羟基苯基)-3,4-二氢-2H-1-苯并吡喃-3,5,7-三醇]的单乙酸酯和多乙酸酯。特别是，在支持性头孢假单胞菌脂肪酶的作用下，儿茶素与乙酸乙烯酯发生反应，得到了 5-O-乙酰基儿茶素和 7-O-乙酰基儿茶素、而在同一种酶的催化下，儿茶素五乙酸酯与 1-丁醇发生醇解反应，可生成 3,3′,4′,5-O-四乙酰基儿茶素和 3,3′,4′- O-三乙酰基儿茶素，在不同的实验条件下，还可生成 3-O-乙酰基儿茶素。
• Carbon-13 nuclear magnetic resonance spectra of brominated catechin derivatives: Stereoelectronic effects on chemical shifts
  作者：E. Kiehlmann、A. S. Tracey

  DOI：10.1002/mrc.1260260306

  日期：1988.3

  been analysed in deuteriated acetone and chloroform. When a methoxy group is flanked by two bulky ortho substituents (6‐Br and C‐4), the MeO and ortho/para ring carbons (C‐4a, C‐6, C‐8) are deshielded owing to steric inhibition of resonance, which permits a distinction between 6‐ and 8‐substituted catechin methyl ethers. Hindered acetoxy groups do not give rise to this phenomenon.

  已在氘化丙酮和氯仿中分析了 21 种儿茶素衍生物在 C-6/C-8 处被溴和/或氢以及在氧处被甲基、乙酰基和/或氢取代的 13C NMR 光谱。当甲氧基侧接两个庞大的邻位取代基（6-Br 和 C-4）时，MeO 和邻位/对位环碳（C-4a、C-6、C-8）由于共振的空间抑制而被去屏蔽，这允许区分 6- 和 8- 取代的儿茶素甲基醚。受阻乙酰氧基不会引起这种现象。
• Freudenberg; Weinges, Justus Liebigs Annalen der Chemie, 1958, vol. 613, p. 61,67
  作者：Freudenberg、Weinges

  DOI：——

  日期：——
• Studies on the porcine liver esterase-catalyzed hydrolysis of pentaacetyl catechin and epicatechin: Application to the synthesis of novel dimers and trimers
  作者：Amit Basak、Sanket Das、Shrabani Bisai

  DOI：10.1016/j.bmcl.2008.07.058

  日期：2008.9

  Porcine liver esterase-catalyzed hydrolysis of 3,5,7,30,40-pentaacetylated catechin was studied. The selectivity of the enzyme in hydrolyzing the acetate moiety is time dependent. Careful control of the duration of hydrolysis makes it possible to isolate the differentially protected catechins. Similar result was also obtained in the epicatechin series. These results are important for elaboration of epicatechin or catechin into different derivatives with defined regiochemistry. These include novel dimeric and trimeric architectures. (C) 2008 Elsevier Ltd. All rights reserved.
• Regioselective hydrolysis of pentaacetyl catechin and epicatechin by porcine liver esterase
  作者：Amit Basak、Subrata Mandal、Saibal Bandyopadhyay

  DOI：10.1016/s0960-894x(03)00024-6

  日期：2003.3

  3,5,7,3',4'-Pentaacetyl catechin was selectively hydrolyzed to either 3,7,3',4-tetraacetyl catechin or 3-acetyl catechin depending upon the duration of hydrolysis. A similar result was also obtained in the epicatechin series. (C) 2003 Elsevier Science Ltd. All rights reserved.