3-(3,4-diacetoxyphenyl)propanoic acid | 69914-80-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(3,4-diacetoxyphenyl)propanoic acid
• 英文别名: 3-(3.4-Diacetoxyphenyl)-propionsaeure；3-(3,4-Diacetyloxyphenyl)propanoic acid
• CAS: 69914-80-3
• 化学式: C₁₃H₁₄O₆
• 分子量: 266.251
• InChiKey: NWWYVWYCLMZXLU-UHFFFAOYSA-N

物化性质

• 沸点：
  402.1±40.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(3,4-diacetoxyphenyl)propanoic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 9.25h， 生成 S-((R)-3-methoxy-3-oxo-2-aminopropyl) 3-(3,4-diacetoxyphenyl)propanethioate
  参考文献：
  名称：

  The synthesis and biological evaluation of novel Danshensu–cysteine analog conjugates as cardiovascular-protective agents

  摘要：

  A series of novel amide and thioester conjugates between Danshensu and cysteine derivatives have been designed and synthesized based on the strategy of "medicinal chemical hybridization". Pharmacological evaluation indicated that the amide conjugates 3a/4a/17a and thioester conjugates 6a-d exhibited obvious protective effects on H2O2-induced human umbilical vein endothelial cells (HUVECs). Pretreated with these conjugates could increase glutathione (GSH) activity and decrease malondialdehyde (MDA) level. Further study on mechanism of compound 4a revealed that it was related to its mitochondrial-protective effect and regulation of apoptosis-related proteins expression (Bax, p53, PARP, caspase-3, caspase-9 and Bcl-2). These results indicate that these Danshensu-cysteine analog conjugates possess significant cardiovascular-protective effects and merit further investigation. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.016
• 作为产物：
  描述：

  2-乙酰氨基-3-(3,4-二乙酰氧基苯基)-2-丙烯酸 在 盐酸 、 10% Pd/C 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 20.0~100.0 ℃ 、1.52 MPa 条件下， 反应 30.0h， 生成 3-(3,4-diacetoxyphenyl)propanoic acid
  参考文献：
  名称：

  The synthesis and biological evaluation of novel Danshensu–cysteine analog conjugates as cardiovascular-protective agents

  摘要：

  A series of novel amide and thioester conjugates between Danshensu and cysteine derivatives have been designed and synthesized based on the strategy of "medicinal chemical hybridization". Pharmacological evaluation indicated that the amide conjugates 3a/4a/17a and thioester conjugates 6a-d exhibited obvious protective effects on H2O2-induced human umbilical vein endothelial cells (HUVECs). Pretreated with these conjugates could increase glutathione (GSH) activity and decrease malondialdehyde (MDA) level. Further study on mechanism of compound 4a revealed that it was related to its mitochondrial-protective effect and regulation of apoptosis-related proteins expression (Bax, p53, PARP, caspase-3, caspase-9 and Bcl-2). These results indicate that these Danshensu-cysteine analog conjugates possess significant cardiovascular-protective effects and merit further investigation. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.016

文献信息

• Oxidative Fragmentation of Aspalathin Leads to the Formation of Dihydrocaffeic Acid and the Related Lysine Amide Adduct
  作者：Nils Mertens、Thomas Heymann、Marcus A. Glomb

  DOI：10.1021/acs.jafc.9b07689

  日期：2020.11.18

  the present study, the degradation of C-glucosidic dihydrochalcone aspalathin as the major phenolic compound in rooibos (Aspalathus linearis) was investigated. Analyses by gas chromatography–mass spectrometry of aqueous aspalathin–lysine incubations after silylation showed the formation of dihydrocaffeic acid [3-(3,4-dihydroxyphenyl)-propionic acid] under oxidative conditions as a novel degradation

  在本研究中，C-葡糖苷二氢查尔酮阿斯帕拉丁的降解是如意宝中主要的酚类化合物（Aspalathus linearis））进行了调查。甲硅烷基化后，通过气相色谱-质谱法分析阿斯巴林水溶液-赖氨酸的温育结果表明，在氧化条件下，二氢咖啡酸[3-（3,4-二羟基苯基）-丙酸]的形成是一种新的降解产物，最高可达10 mol％。高效液相色谱分析显示同时形成了低约30倍浓度的二氢咖啡酸赖氨酸酰胺，这通过合成可靠的参考标准物得到了明确证实。酶解后，高效液相色谱-串联质谱分析还证实了酰胺在阿斯帕林蛋白温育中的作用。从而，首次证实了酚类植物化合物与蛋白质在温和条件下（环境温度和中性pH）的共价相互作用。酸和游离酰胺也可以在路易波士茶中定量，发酵品种的酸值明显更高。阐明形成机理是由单线态氧引发的，并且包括与1,2,3,5-四羟基苯为对应物的重排-断裂机理。
• Oral pharmaceutical formulation for weight loss, diabetes and related disorders
  申请人：Lee Tien-Li

  公开号：US10835505B2

  公开（公告）日：2020-11-17

  There is disclosed an oral pharmaceutical formulation of bitter compounds that are agonists of taste receptor type 2 (TAS2R) receptors for the function of appetite suppression for the treatment of obesity. More specifically, the present disclosure provides an anti-obesity oral formulation comprising a bitter agent selected from the group consisting of denatonium salts including benzoate (DB), chloride (DC), acetate (DA), citrate (DCl), saccharide (DS), tartarate (DT), maleate (DM), 3-caffeoylquinic-1,5-lactone (3-CQL), chlorogenic acids (CGA), combinations thereof, and pharmaceutical excipients to facilitate a sustained release during transit through the gastrointestinal (GI) tract. Preferably, the oral pharmaceutical formulation further comprises either or both a sweet antagonist selected from the group consisting of lactisole, gymnemic acid, ziziphin, hodulcine, and combinations thereof, and a sour organic acid.

  本发明公开了一种苦味化合物的口服药物制剂，这些苦味化合物是味觉受体2型（TAS2R）受体的激动剂，具有抑制食欲的功能，可用于治疗肥胖症。更具体地说，本公开提供了一种抗肥胖口服制剂，其包含的苦味剂选自包括苯甲酸盐 (DB)、氯化物 (DC)、醋酸盐 (DA)、柠檬酸盐 (DCl)、糖苷 (DS)、酒石酸盐 (DT)、马来酸盐 (DM)、3-咖啡酰奎宁-1,5-内酯 (3-CQL)、绿原酸 (CGA)、它们的组合，以及药用辅料，以促进在胃肠道转运过程中的持续释放。优选地，口服药物制剂进一步包含选自乳异唑、钩藤碱、紫草素、霍豆碱及其组合的甜味拮抗剂和酸味有机酸中的一种或两种。
• Daucane Phytoestrogens:  A Structure−Activity Study
  作者：Giovanni Appendino、Paola Spagliardi、Giancarlo Cravotto、Victoria Pocock、Stuart Milligan

  DOI：10.1021/np0201671

  日期：2002.11.1

  The estrogenic activity of a series of analogues of the daucane ester ferutinin (1a) modified at the acyl moiety was investigated in a yeast screen containing the human estrogen receptor a. Rather strict structure-activity relationships were observed. Thus, while the parent polvol (jaeschkeanadiol, 2a) was inactive, the presence of a p-hydroxybenzoyl moiety was necessary for activity in the yeast screen. Homologation and vinylation were both detrimental for activity, as were methylation of the p-hydroxyl substituent and the introduction of oxygen functions on the adjacent carbons.
• JPH02129193A
  申请人：——

  公开号：JPH02129193A

  公开（公告）日：1990-05-17