2-羟基-3-(4-羟基-3-甲氧基苯基)丙酸 | 2475-56-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: 2-羟基-3-(4-羟基-3-甲氧基苯基)丙酸
• 中文别名: N,N-二(2-乙基己基)-1H-苯并三唑-1-甲基胺
• 英文名称: 3-(4-hydroxy-3-methoxyphenyl)lactic acid
• 英文别名: vanillactic acid；tanshinol；β-(3-methoxy-4-hydroxyphenyl)-α-hydroxypropionic acid；Vanillomilchsaeure；Vanillactinsaeure；2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propanoic acid
• CAS: 2475-56-1
• 化学式: C₁₀H₁₂O₅
• mdl: MFCD00055232
• 分子量: 212.202
• InChiKey: SVYIZYRTOYHQRE-UHFFFAOYSA-N

物化性质

• 沸点：
  432.6±40.0 °C(Predicted)
• 密度：
  1.380±0.06 g/cm3(Predicted)
• 溶解度：
  甲醇（微溶）、水（微溶）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2918990090
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  2,2,2-三氟-N,N-二(三甲硅基)乙酰胺 、 2-羟基-3-(4-羟基-3-甲氧基苯基)丙酸 在 吡啶 作用下， 反应 0.5h， 生成 Benzenepropanoic acid, 3-methoxy-alpha,4-bis[(trimethylsilyl)oxy]-, trimethylsilyl ester
  参考文献：
  名称：

  Conversion of Dehydrodiferulic Acids by Human Intestinal Microbiota

  摘要：

  Plant cell wall associated dehydrodiferulic acids (DFA) are abundant components of cereal insoluble dietary fibers ingested by humans. The ability of human intestinal microbiota to convert DFA was studied in vitro by incubating 8-O-4- and 5-5-coupled DFA with fecal suspensions. 8-O-4-DFA was completely degraded by the intestinal microbiota of the majority of donors, yielding homovanillic acid, 3-(3,4-dihydroxyphenyl)propionic acid, and 3,4-dihydroxyphenylacetic acid as the main metabolites. The transient formation of ferulic acid and presumably 3-(3-hydroxy-4-methoxyphenyl)pyruvic acid suggests an initial cleavage of the ether bond. In contrast to 8-O-4-DFA, the 5-5-coupled DFA was not cleaved into monomers by any of the fecal suspensions. Only the side chains were hydrogenated and the methoxy groups were demethylated. The cleavage of DFA by human intestinal microbiota, which depended on their coupling type, may affect both the bioavailability of DFA and the degradability of DFA-coupled fiber in the gut.

  DOI：

  10.1021/jf900159h
• 作为产物：
  描述：

  (Z)-2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid 在 盐酸 、 汞 、 锌 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以73%的产率得到2-羟基-3-(4-羟基-3-甲氧基苯基)丙酸
  参考文献：
  名称：

  A Modified Synthesis of (±)-β-Aryllactic acids

  摘要：

  据报道，丹参中活性成分的外消旋形式，即（±）-ß-(3,4-二羟基苯基)乳酸[(±)-3-(3,4-二羟基苯基)-2-羟基丙酸]及其七种外消旋衍生物已成功合成。

  DOI：

  10.1055/s-1992-26228

文献信息

• 29Si and13C NMR spectra of 4-substituted 2-methoxytrimethylsiloxybenzenes. Factors determining the chemical shifts in models of lignin constituents
  作者：Jan Schraml、Magdalena Kvíčalová、Václav Chvalovský、Thomas Elder、Robert Brežný

  DOI：10.1002/mrc.1260281112

  日期：1990.11

  29Si and 13C NMR chemical shifts are reported for a series of twenty 4‐substituted 2‐methoxytrimethyl‐siloxybenzenes; the set of substituents incorporates a basic set of ten substituents differing in their relative polar and resonance effects and ten other substituents which model substituents encountered in lignins. The factors affecting the chemical shifts are discussed using a comparison with the

  报告了一系列 20 个 4-取代的 2-甲氧基三甲基-甲硅烷氧基苯的 29Si 和 13C NMR 化学位移；这组取代基包含一组基本的十个取代基，它们的相对极性和共振效应不同，以及十个模拟木质素中遇到的取代基的其他取代基。影响化学位移的因素通过与类似系列化合物的 NMR 数据进行比较、与取代基参数的相关性和通过量子化学方法计算的电子电荷（力场优化分子几何的 MNDO 计算）为基本集合进行讨论. 得出的结论是，在三甲基甲硅烷氧基的邻位上的甲氧基在其大部分时间里，甲基位于苯环平面内的构象，与呈垂直构象的三甲基甲硅烷氧基相反。在甲氧基和三甲基甲硅烷氧基上观察到的邻近去屏蔽效应受 4 位取代基的影响，这与这些效应是由于邻位氧原子或其未共享电子的相互作用的观点一致。29Si 化学位移对σpis 的依赖性基本上不受邻甲氧基存在的影响。这与这些效应是由于邻位氧原子或其未共享电子的相互作用的观点一致。29Si
• SUBSTITUTED BETA-PHENYL-ALPHA-HYDROXY-PROPANOIC ACID, SYNTHESIS METHOD AND USE THEREOF
  申请人：Zheng Xiaohui

  公开号：US20090131677A1

  公开（公告）日：2009-05-21

  The present invention relates to a compound of the formula (I), wherein R 1 , R 2 and R 3 are each independently selected from H, OH, F, Cl, Br, methoxy and ethoxy; or alternatively, R 1 and R 2 together form —OCH 2 O—, R 3 is selected from H, OH, methoxy, ethoxy and halogens; R 4 is OH or acyloxy; R 5 is cycloalkoxyl, amino and substituted amino, and when R 5 is selected from amino, at least one of R 1 , R 2 and R 3 is not H. The present invention further relates to a process for synthesizing a compound of the formula (I), and use of the compound of the formula (I) in the manufacture of a medicament for the prevention or treatment of cardiovascular or cerebrovascular diseases.

  本发明涉及公式（I）的化合物，其中R1、R2和R3各自独立地选自H、OH、F、Cl、Br、甲氧基和乙氧基；或者，R1和R2一起形成-OCH2O-，R3选自H、OH、甲氧基、乙氧基和卤素；R4为OH或酰氧基；R5为环烷氧基、氨基和取代氨基，当R5选自氨基时，至少有R1、R2和R3中的一个不是H。本发明还涉及合成公式（I）化合物的方法，以及使用公式（I）化合物制造用于预防或治疗心血管或脑血管疾病的药物。
• Isolated stromal cells for use in the tretment of diseases of the central nervous system
  申请人：MCP Hahnemann University

  公开号：EP1815862A1

  公开（公告）日：2007-08-08

  Methods of treating a human patient having a disease, disorder or condition of the central nervous system are disclosed. The methods include obtaining a bone marrow sample from a human donor, isolating stromal cells from the bone marrow sample, and administering the isolated stromal cells to the central nervous system of the human patient, wherein the presence of the isolated stromal cells in the brain effects treatment of the disease, disorder or condition. Stromal cells which are isolated may be cultured in vitro, they may be genetically engineered to produce therapeutic compounds, and/or they may be predifferentiated prior to administration into the central nervous system.

  本发明公开了治疗患有中枢神经系统疾病、失调或状况的人类患者的方法。这些方法包括从人类捐献者处获取骨髓样本，从骨髓样本中分离出基质细胞，并将分离出的基质细胞施用于人类患者的中枢神经系统，其中，分离出的基质细胞在大脑中的存在会对疾病、紊乱或病症产生治疗效果。分离出的基质细胞可以在体外培养，也可以通过基因工程产生治疗化合物，和/或在进入中枢神经系统前进行预分化。
• SUBSTITUTED BETA-PHENYL-ALPHA-HYDROXY PROPANOIC ACID, SYNTHESIS METHOD AND USE THEREOF
  申请人：Northwest University

  公开号：EP2019090A1

  公开（公告）日：2009-01-28

  The present invention relates to a compound of the formula (I), wherein R1, R2 and R3 are each independently selected from H, OH, F, Cl, Br, methoxy and ethoxy; or alternatively, R1 and R2 together form -OCH2O-, R3 is selected from H, OH, methoxy, ethoxy and halogens; R4 is OH or acyloxy; R5 is cycloalkoxyl, amino and substituted amino, and when R5 is selected from amino, at least one of R1, R2 and R3 is not H. The present invention further relates to a process for synthesizing a compound of the formula (I), and use of the compound of the formula (I) in the manufacture of a medicament for the prevention or treatment of cardiovascular or cerebrovascular diseases.

  本发明涉及一种式(I)化合物，其中R1、R2和R3各自独立地选自H、OH、F、Cl、Br、甲氧基和乙氧基；或者，R1和R2一起形成-OCH2O-，R3选自H、OH、甲氧基、乙氧基和卤素；R4是OH或酰氧基；R5是环烷氧基、氨基和取代氨基，当R5选自氨基时，R1、R2和R3中至少有一个不是H。本发明进一步涉及一种合成式（I）化合物的工艺，以及式（I）化合物在制造预防或治疗心脑血管疾病的药物中的用途。
• Substituted beta-phenyl-alpha-hydroxy propanoic acid, synthesis method and use thereof
  申请人：Northwest University

  公开号：EP2514739A1

  公开（公告）日：2012-10-24

  The present invention relates to a compound of the formula (I), wherein R1, R2 and R3 are each independently selected from H, OH, F, Cl, Br, methoxy and ethoxy; or alternatively, R1 and R2 together form -OCH2O-, R3 is selected from H, OH, methoxy, ethoxy and halogens; R4 is OH or acyloxy; R5 is cycloalkoxyl, amino and substituted amino, and when R5 is selected from amino, at least one of R1, R2 and R3 is not H. The present invention further relates to a process for synthesizing a compound of the formula (I), and use of the compound of the formula (I) in the manufacture of a medicament for the prevention or treatment of cardiovascular or cerebrovascular diseases.

  本发明涉及一种式(I)化合物，其中R1、R2和R3各自独立地选自H、OH、F、Cl、Br、甲氧基和乙氧基；或者，R1和R2一起形成-OCH2O-，R3选自H、OH、甲氧基、乙氧基和卤素；R4是OH或酰氧基；R5是环烷氧基、氨基和取代氨基，当R5选自氨基时，R1、R2和R3中至少有一个不是H。本发明进一步涉及一种合成式（I）化合物的工艺，以及式（I）化合物在制造预防或治疗心脑血管疾病的药物中的用途。