(2R)-2-(对羟基苄基)苹果酸 | 60449-48-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: (2R)-2-(对羟基苄基)苹果酸
• 英文名称: (2R)-2-(p-hydroxybenzyl)malic acid
• 英文别名: (-)-(R)-eucomic acid；(R)-eucomic acid；eucomic acid；2-(p-hydroxybenzyl)malic acid；Eucominsaeure；Eucomic acid, (-)-；(2R)-2-hydroxy-2-[(4-hydroxyphenyl)methyl]butanedioic acid
• CAS: 60449-48-1
• 化学式: C₁₁H₁₂O₆
• 分子量: 240.213
• InChiKey: XLGKDRSWPCQYAB-LLVKDONJSA-N

物化性质

• 沸点：
  444.3±45.0 °C(Predicted)
• 密度：
  1.529±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R)-2-(对羟基苄基)苹果酸 在 potassium carbonate 作用下， 以 乙醚 、 丙酮 为溶剂， 生成 (R)-2-Hydroxy-2-(4-methoxy-benzyl)-succinic acid dimethyl ester
  参考文献：
  名称：

  Isolierung，Konstitution和Synthese der（R）-（-）-Eucominsäure †

  摘要：

  来自杜仲（Eucomis punctata L'Hérit）的鳞茎。（百合科）和迄今未定义的杜仲属物种中，分离了新的光学活性酚羧酸杜仲酸。结构1是根据化学和光谱证据分配的。杜仲酸的绝对构型由其与二十碳二烯酸（（2 R，3 S）-2-（4'-羟基苄基）-酒石酸）的相关性决定（8）。因此，杜仲酸为（R）-（-）-2-（4'-羟基苄基）-苹果酸（1）。对于立体定向合成，甲基顺-对-甲氧基亚苄基-琥珀酸（22）转化为γ-内酯24，通过催化氢解反应生成（±）-2-（4'-羟基苄基）-苹果酸1-甲酯（27）。（-）-奎宁的拆分导致对映体酸29和30。左旋对映异构体30的甲酯与4'-O-甲基-杜仲酸的二甲酯3相同。

  DOI：

  10.1002/hlca.19740570628
• 作为产物：
  描述：

  4-(4-β-D-glucopyranosyloxybenzyl) (2R)-2-(p-hydroxybenzyl)-maleate 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 6.0h， 以40%的产率得到(2R)-2-(对羟基苄基)苹果酸
  参考文献：
  名称：

  Glucopyranosyloxybenzyl derivatives of (R)-2-benzylmalic acid and (R)-eucomic acid, and an aromatic glucoside from the pseudobulbs of Grammatophyllum speciosum

  摘要：

  Three new glucosyloxybenzyl derivatives of (R)-2-benzylmalic acid and of (R)-eucomic acid, grammatophyllosides A C, and a new phenolic glucoside, grammatophylloside D, were isolated from the pseudobulbs of Grammatophyllum speciosum along with cronupapine, vandateroside II, gastodin, vanilloloside, orcinol glucoside, and isovitexin. The structure elucidations of these compounds were based on analyses of physical and spectroscopic data, as well as chemical evidence. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.082

文献信息

• Two novel aromatic glucosides, marylaurencinosides D and E, from the fresh flowers of Cymbidium Great Flower ‘Marylaurencin’
  作者：Kazuko Yoshikawa、Mariko Okahuji、Kanako Iseki、Takuya Ito、Yoshinori Asakawa、Sachiko Kawano、Toshihiro Hashimoto

  DOI：10.1007/s11418-013-0814-8

  日期：2014.4

  Two novel aromatic glucosides, named marylaurencinosides D (1) and E (2), were isolated from the fresh flowers of Cymbidium Great Flower ‘Marylaurencin’. In addition, eight known aromatic compounds (3–10) were isolated. These structures were determined on the basis of NMR experiments as well as chemical evidence.

  从蕙兰大花“Marylaurencin”的鲜花中分离出两种新型芳香糖苷，命名为 Marylaurencinosides D (1) 和 E (2)。此外，还分离出了八种已知的芳香族化合物 (3-10)。这些结构是根据核磁共振实验和化学证据确定的。
• Determination of Eucomic Acid in Chinese Hawthorn Fruit and Products by Gas Chromatography-Mass Spectrometry
  作者：Zhe Gao、Rong-Fang Wang、Xiao-Hu Kang、Ai-Xia Qin、Ya-Nan Jia、Tong-Sen He、Yu-Lei Pan、Tong Cui

  DOI：10.14233/ajchem.2014.16312

  日期：——

  An analytical method for determination of eucomic acid in Chinese hawthorn fruit and its products by gas chromatography-mass spectrometry (GC-MS) was developed. The sample was extracted by ethanol, esterificated with sulphuric acid-methanol solution and then extracted with dichloromethane. The final analysis was performed by GC-MS using the fragment ions m/z 107 under selected ion monitoring (SIM) for the content of eucomic acid. External standard method was used for quantification. Under optimum conditions, there was a good linearity within the range of 2-500 μg/g. The limit of detection was 0.35 μg/g, the recoveries were in the range 87-102 %, the relative standard deviation (RSD) was 3.1-5.6 %. This method was applied to determine the eucomic acid in hawthorn fruit and its products. The content is between 5.1-255 μg/g.

  建立了山楂及其制品中杜仲酸的气相色谱-质谱联用分析方法。样品用乙醇提取，用硫酸-甲醇溶液酯化，然后用二氯甲烷提取。最终通过 GC-MS 使用 m/z 107 碎片离子在选择离子监测 (SIM) 下进行杜仲酸含量分析。采用外标法进行定量。在最佳条件下,在2~500 μg/g范围内具有良好的线性关系。检出限为0.35 μg/g，回收率为87-102%，相对标准偏差(RSD)为3.1-5.6%。该方法适用于山楂及其制品中杜仲酸的测定。含量在5.1-255μg/g之间。
• CRYSTAL OF EUCOMIC ACID NON-SOLVATE AND PRODUCTION METHOD THEREFOR
  申请人：Kyowa Hakko Bio Co., Ltd.

  公开号：EP3822249A1

  公开（公告）日：2021-05-19

  An object of the present invention is to provide a non-solvate crystal of eucomic acid having a low methanol content and excellent fluidity, and a method for producing the same. The present invention can provide a non-solvate crystal of eucomic acid having a low methanol content and excellent fluidity by drying a methanol solvate crystal of eucomic acid.

  本发明的目的是提供一种甲醇含量低、流动性好的非溶解性优可酸晶体，以及生产这种晶体的方法。本发明可以通过干燥优可酸的甲醇溶物晶体，提供甲醇含量低、流动性好的优可酸非溶物晶体。
• Non-solvate crystal of eucomic acid and method for producing same
  申请人：KYOWA HAKKO BIO CO., LTD.

  公开号：US11365170B2

  公开（公告）日：2022-06-21

  An object of the present invention is to provide a non-solvate crystal of eucomic acid having a low methanol content and excellent fluidity, and a method for producing the same. The present invention can provide a non-solvate crystal of eucomic acid having a low methanol content and excellent fluidity by drying a methanol solvate crystal of eucomic acid.

  本发明的目的是提供一种甲醇含量低、流动性好的非溶解性优可酸晶体，以及生产这种晶体的方法。本发明可以通过干燥优可酸的甲醇溶物晶体，提供甲醇含量低、流动性好的优可酸非溶物晶体。
• (R)-Eucomic acid, a leaf-opening factor of the model organism, Lotus japonicus
  作者：Masahiro Okada、Sungwook Park、Takahiro Koshizawa、Minoru Ueda

  DOI：10.1016/j.tet.2008.11.097

  日期：2009.3

  In the post-genomic era, the biological activity of endogenous metabolites can be linked to genomic information via its target protein. Consequently, studies concerned with the identification of endogenous bioactive metabolites from model organisms should be undertaken. (R)-Eucomic acid (1) was identified as an endogenous metabolite concerning leaf movement in the model legume, Lotus japonicus. Absolute stereochemistry was investigated by comparison of physical characteristics of natural and synthetic enantiomers of 1. Identification of endogenous metabolites in a model legume would be particularly advantageous for further studies on the chemical biology of this biologically intriguing phenomenon. (C) 2008 Elsevier Ltd. All rights reserved.