5-Hydroxyeugenol | 4055-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-Hydroxyeugenol
• 英文别名: 2-hydroxy-3-methoxy-5-(2-propenyl)-phenol；3-methoxy-5-allyl-1,2-benzene-diol；3-methoxy-5-allyl-1,2-benzenediol；5-allyl-3-methoxybenzene-1,2-diol；5-allyl-2,3-dihydroxyanisole；5-hydroxy-eugenol；3-Methoxy-5-(prop-2-en-1-yl)benzene-1,2-diol；3-methoxy-5-prop-2-enylbenzene-1,2-diol
• CAS: 4055-72-5
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: BHIIRUKUMCZDIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

5-烯丙基-1-甲氧基-2,3-二羟基苯是人类可知的肉豆蔻醚的代谢物。

5-allyl-1-methoxy-2,3-dihydroxybenzene is a known human metabolite of myristicin.

来源:NORMAN Suspect List Exchange

安全信息

• 海关编码：
  2909500000

反应信息

• 作为反应物：
  描述：

  5-Hydroxyeugenol 在 吡啶 、 氢氧化钾 、 lithium aluminium tetrahydride 、 三氯化铝 、 selenium(IV) oxide 、 碳酸氢钠 、 palladium dichloride 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 60.0h， 生成 (+/-)-Eusiderin M
  参考文献：
  名称：

  (±)-Eusiderin G 和 (±)-Eusiderin M 的全合成

  摘要：

  (±)-Eusiderin G 和 (±)-Eusiderin M 首先由连苯三酚合成，其中 Claisen 重排用于提供两个重要的 C6-C3 单元。

  DOI：

  10.1002/jccs.200100011
• 作为产物：
  描述：

  5-hydroxyconiferyl alcohol 在 Larrea tridentata cinnamyl alcohol acyltransferase-1 、 propenylphenol synthase from Larrea tridentata 、 还原型辅酶Ⅰ 作用下， 以 aq. buffer 为溶剂， 反应 0.5h， 生成 5-Hydroxyeugenol
  参考文献：
  名称：

  Allyl/propenyl phenol synthases from the creosote bush and engineering production of specialty/commodity chemicals, eugenol/isoeugenol, in Escherichia coli

  摘要：

  The creosote bush (Larrea tridentata) harbors members of the monolignol acyltransferase, allylphenol synthase, and propenylphenol synthase gene families, whose products together are able to catalyze distinct regiospecific conversions of various monolignols into their corresponding allyl- and propenyl-phenols, respectively. In this study, co-expression of a monolignol acyltransferase with either substrate versatile allylphenol or propenylphenol synthases in Escherichia coli established that various monolignol substrates were efficiently converted into their corresponding allyl/propenyl phenols, as well as providing proof of concept for efficacious conversion in a bacterial platform. This capability thus potentially provides an alternate source to these important plant phytochemicals, whether for flavor/fragrance and fine chemicals, or ultimately as commodities, e.g., for renewable energy or other intermediate chemical purposes. Previous reports had indicated that specific and highly conserved amino acid residues 84 (Phe or Val) and 87 (Ile or Tyr) of two highly homologous allyl/propenyl phenol synthases (circa 96% identity) from a Clarkia species mainly dictate their distinct regiospecific catalyzed conversions to afford either allyior propenyl-phenols, respectively. However, several other allyl/propenyl phenol synthase homologs isolated by us have established that the two corresponding amino acid 84 and 87 residues are not, in fact, conserved. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.abb.2013.10.019

文献信息

• Total Synthesis of Six Natural Products of Benzodioxane Neolignans
  作者：Xiao-Bi Jing、Li Wang、Ying Han、Yao-Cheng Shi、Yong-Hong Liu、Jing Sun

  DOI：10.1002/jccs.200400149

  日期：2004.10

  (′)-Eusiderin E, (′)-Eusiderin F, (′)-Eusiderin K, (′)-Eusiderin J, (′)-Eusiderin M and (′)-Eusiderin G were first synthesized from pyrogallol, in which the Claisen Rearrangement was used to afford two important C6- C 3 units.

  (')-Eusiderin E、(')-Eusiderin F、(')-Eusiderin K、(')-Eusiderin J、(')-Eusiderin M 和 (')-Eusiderin G 首先由连苯三酚合成，其中Claisen 重排用于提供两个重要的 C6-C 3 单元。
• TOTAL SYNTHESIS OF (±)-EUSIDERIN K AND (±)-EUSIDERIN J
  作者：Xiaobi Jing、Wenxin Gu、Pingyan Bie、Xinfeng Ren、Xinfu Pan

  DOI：10.1081/scc-100103321

  日期：2001.1

  (±)-Eusiderin K and (±)-Eusiderin J were first synthesized from pyrogallol, in which the Claisen Rearrangement was used to afford two important C6-C3 units.

  (±)-Eusiderin K 和 (±)-Eusiderin J 首先由连苯三酚合成，其中使用克莱森重排提供两个重要的 C6-C3 单元。
• DDQ-Mediated Oxidation of Allylarenes: Expedient Access to Cinnamaldehyde-Containing Phenylpropanoids
  作者：Tao-Shan Jiang、Yongping Cai、Qingqing Zhang、Guohui Li、Xi Cheng

  DOI：10.1055/s-0037-1609554

  日期：2018.12

  Phenylpropanoid natural products containing a cinnamaldehyde motif were easily synthesized from allylarenes mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation. Representative examples described herein are five types of 4-hydroxycinnamaldehyde derivatives from monolignols biosynthesis, Boropinal C, and 7-methoxywutaifuranal from plant extracts. Especially, simple synthesis of 7-methoxywutaifuranal was exploited through selective mono-oxidation and subsequent isomerization–ring-closing-metathesis strategy.

  含有肉桂醛基团的苯丙烯类天然产物可以通过2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）氧化介导的烯丙基芳烃轻松合成。本文描述的代表性示例包括来自单木质素生物合成的五种4-羟基肉桂醛衍生物、来自植物提取物的Boropinal C和7-甲氧基乌太呋醛。特别是，通过选择性单氧化和随后的异构化-环闭合-鲁米诺烯交换策略，实现了对7-甲氧基乌太呋醛的简单合成。
• 一种4-羟基肉桂醛类化合物的合成方法
  申请人：安徽农业大学

  公开号：CN107573226A

  公开（公告）日：2018-01-12

  本发明申请涉及有机合成与农业化学领域，具体公开了一种合成式II所示4‑羟基肉桂醛类化合物的合成方法，该方法以4‑羟基烯丙基苯为原料，首先进行羟基保护，然后利用2,3‑二氯‑5,6‑二氰基‑1,4‑苯醌(DDQ)为氧化剂，水(H2O)为亲核试剂，在较温和条件下氧化烯丙基为α,β‑不饱和醛(即肉桂醛结构)，最后脱保护得到目标产物。本发明阐述了一种4‑羟基肉桂醛类化合物的合成新方法，具有无过渡金属的参与，反应条件简单温和，产物收率高等特点，在农业化学特别是植物科学和生物能源转化领域有广泛的应用前景。
• [EN] SYNTHESIS OF ELEMICIN AND TOPICAL ANALGESIC COMPOSITIONS<br/>[FR] SYNTHÈSE D'ÉLÉMICINE ET COMPOSITIONS ANALGÉSIQUES TOPIQUES
  申请人：LA GRANGE MARTIN JAMES

  公开号：WO2013133723A1

  公开（公告）日：2013-09-12

  The present invention is directed to the synthesis of elemicin and its isomeric form, and their use in topical analgesic formulations, including for dental and veterinary use. Various compositions include gels, films, dressings, cavity filling gels, having analgesic and/or antifungal properties.

  本发明涉及对艾利美辛及其异构形式的合成，以及它们在局部止痛制剂中的应用，包括用于牙科和兽医用途。各种组合包括凝胶、膜、敷料、蛀牙填充凝胶，具有止痛和/或抗真菌特性。