Eugenol glucuronide | 95480-61-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Eugenol glucuronide
• 英文别名: eugenol-β-D-glucuronide；beta-D-Glucopyranosiduronic acid, 2-methoxy-4-(2-propen-1-yl)phenyl；(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-methoxy-4-prop-2-enylphenoxy)oxane-2-carboxylic acid
• CAS: 95480-61-8
• 化学式: C₁₆H₂₀O₈
• 分子量: 340.33
• InChiKey: MQXZRKSWEMEXCG-JHZZJYKESA-N

物化性质

• 沸点：
  573.7±50.0 °C(Predicted)
• 密度：
  1.426±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 4.0h， 以89.7%的产率得到Eugenol glucuronide
  参考文献：
  名称：

  阿司匹林丁香酚酯两种代谢产物及其制备方法

  摘要：

  本发明提供阿司匹林丁香酚酯两种代谢产物M1和M2，其化学结构式如下：M1通过丁香酚与氯磺酸反应，吡啶做缚碱剂和溶剂制得；M2通过丁香酚与2,3,4‑O‑三乙酰基‑β‑D‑葡萄糖醛酸甲酯三氯乙酰亚胺酯发生取代反应，然后在碱性条件下脱去乙酰基制得。阿司匹林丁香酚酯代谢产物M1和M2的制备方法合理，操作简便。

  公开号：

  CN108358981A

文献信息

• Synthesis of Four Eugenol Metabolites
  作者：Xixi Jia、Hao Zhou、Xiwang Liu、Jianyong Li

  DOI：10.2174/1570178617999200807213745

  日期：2021.5

  Four eugenol metabolites were concisely synthesized and their structures were confirmed by 1H-NMR, 13C-NMR and high-resolution mass (HR-MS). Among them, the synthesis of eugenol-β-Dglucuronide (3) and eugenol sulfate (4) was reported for the first time. The successful synthesis of the four eugenol metabolites provides a material basis for further metabolic study of prodrug aspirin eugenol ester (AEE)

  简明地合成了四种丁子香酚代谢物，并通过1H-NMR，13C-NMR和高分辨率质谱（HR-MS）确认了它们的结构。其中，首次报道了丁香酚-β-葡糖醛酸苷（3）和硫酸丁香酚（4）的合成。四种丁香酚代谢物的成功合成为前药阿司匹林丁香酚酯（AEE）的进一步代谢研究提供了物质基础。
• COMPOUNDS FOR A CONTROLLED RELEASE OF ACTIVE MOLECULES
  申请人：FIRMENICH SA

  公开号：US20160137952A1

  公开（公告）日：2016-05-19

  The present invention relates to the field of perfumery. More particularly, it concerns compounds comprising at least one β-glucuronide moiety capable of liberating a perfuming alcohol. The present invention concerns also the use of said compounds in perfumery as well as the perfuming compositions or perfumed articles, in particular deodorants or antiperspirants comprising the invention's compounds.

  本发明涉及香料领域，更具体地涉及包含至少一个β-葡萄糖醛酸酯基团的化合物，该基团能够释放出一种香料醇。本发明还涉及在香料领域中使用所述化合物以及包含本发明化合物的香料组合物或香料制品，特别是包括本发明化合物的除臭剂或抗汗剂。
• Compounds for a controlled release of active molecules
  申请人：FIRMENICH SA

  公开号：US10590365B2

  公开（公告）日：2020-03-17

  The present invention relates to the field of perfumery. More particularly, it concerns compounds comprising at least one β-glucuronide moiety capable of liberating a perfuming alcohol. The present invention concerns also the use of said compounds in perfumery as well as the perfuming compositions or perfumed articles, in particular deodorants or antiperspirants comprising the invention's compounds.

  本发明涉及香水领域。更具体地说，本发明涉及包含至少一个β-葡萄糖醛酸分子的化合物，该分子能够释放出香料醇。本发明还涉及上述化合物在香水中的应用，以及包含本发明化合物的香水组合物或香水制品，特别是除臭剂或止汗剂。
• o-Methoxy-4-alkylphenols That Form Quinone Methides of Intermediate Reactivity Are the Most Toxic in Rat Liver Slices
  作者：David C. Thompson、Kumar Perera、E. S. Krol、Judy L. Bolton

  DOI：10.1021/tx00045a001

  日期：1995.4

  The effects of p-alkyl substituents on the relative cytotoxicity of 4-alkyl-2 -methoxyphenols were investigated in isolated rat liver slices. The derivatives of 4-alkyl-2-methoxyphenol studied were 4-methyl- (creosol), 4-ethyl-, 4-propyl-, 4-isopropyl-, 4-allyl-2-methoxyphenol (eugenol), as well as 4-allyl-2,6-dimethoxyphenol. The data were correlated with previous microsomal experiments which showed that all of the 4-alkyl-2-methoxyphenols were converted to quinone methides (QMs; 4-methylene-2,5-cyclohexadien-1-ones) via a cytochrome P450-catalyzed process [Bolton, J. L., Comeau, E., and Vukomanovic, V. (1995) Chem.-Biol. Interact., in press]. The present investigation showed little correlation between the rate of QM formation in microsomes and the relative toxicities of the alkylphenols, unless the QMs formed were of similar reactivity. In contrast, a plot of-alkylphenol toxicity versus the relative hydrolysis rates of QMs derived from these phenols fit a parabolic equation with a minimum at the data for 4-isopropyl-2-methoxyphenol. These data suggest that in vivo oxidation of phenols to QMs which have lifetimes in the 10 s-10 min range results in cytotoxicity. QMs with reactivities outside this window are less toxic since the electrophile is either too stable for reaction with cellular nucleophiles or too reactive for nucleophilic cellular macromolecules to compete with solvent, These data suggest that a reactivity window exists for QMs which is a primary determinant of the extent of cytotoxic injury caused by these reactive electrophiles.
• EP3011000B1
  申请人：——

  公开号：EP3011000B1

  公开（公告）日：2017-08-09