4-hydroxy-3-methoxybenzyl undec-10-enoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxy-3-methoxybenzyl undec-10-enoate
• 英文别名: 10-undecylenic acid vanillyl ester；(4-Hydroxy-3-methoxyphenyl)methyl undec-10-enoate
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: DYFBQSXOOQAJLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  10-十一碳烯基氯酸 、 4-羟基-3-甲氧基苄醇 在 吡啶 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 4-hydroxy-3-methoxybenzyl undec-10-enoate
  参考文献：
  名称：

  WO2008/72072

  摘要：

  公开号：

文献信息

• Chemoselective Esterification of Phenolic Acids and Alcohols
  作者：Giovanni Appendino、Alberto Minassi、Nives Daddario、Federica Bianchi、Gian Cesare Tron

  DOI：10.1021/ol0266471

  日期：2002.10.1

  [formula: see text] The Mitsunobu reaction can distinguish between alcohol and phenol hydroxyls in esterification reactions, providing an expeditious and broadly applicable entry into various phenolics and polyphenolics of biomedical and nutritional relevance.

  Mitsunobu反应可以区分酯化反应中的醇羟基和酚羟基，为生物医学和营养相关的各种酚类和多酚类化合物提供了快速而广泛适用的入口。
• Evaluation of the Antioxidant Activity of Capsiate Analogues in Polar, Nonpolar, and Micellar Media
  作者：Kunduru K. Reddy、Thumu Ravinder、Rachapudi B. N. Prasad、Sanjit Kanjilal

  DOI：10.1021/jf104244m

  日期：2011.1.26

  Synthesis of 10 capsiate analogues was conducted by lipase-mediated (Novozyme 435) esterification of vanillyl alcohol with different fatty acids. The antioxidant activity of the synthesized capsiates was evaluated using three in vitro assays: DPPH radical scavenging assay (polar medium), Rancimat assay (nonpolar medium), and autoxidation of linoleic acid (micellar medium). The objective of this study is to find the influence of structural characteristics of the alkyl chain of capsiate analogues on their antioxidant activity. In these assays, BHT and alpha-tocopherol were used as reference compounds. Both DPPH and Rancimat assays did not show any specific trend of antioxidant activity with the increase in lipophilicity and also with the type of fatty acids grafted to the phenolic moiety. In the Tween 20 micellar system for the inhibition of autoxidation of linoleic acid, vanillyl ester attached to a C18 alkyl chain (vanillyl stearate, oleate and ricinoleate) exhibited maximum inhibition of autoxidation of linoleic acid.
• [EN] TERMINALLY UNSATURATED VANILLOIDS AND MEDICINAL APPLICATION THEREOF<br/>[FR] VANILLOÏDES À TERMINAISON INSATURÉE ET LEUR APPLICATION MEDICINALE
  申请人：GHISALBERTI CARLO

  公开号：WO2008072072A1

  公开（公告）日：2008-06-19

  [EN] Terminally unsaturated vanilloids for the manufacturing of a medicinal composition to treat capsaicin-responsive conditions. Said vanilloids are devoided of the disadvantage of capsaicin and analogs, namely the discomforting pungency, while retaining several of the their biological and clinically useful properties.
  [FR] La présente invention concerne des vanilloïdes à terminaison insaturée pour la fabrication d'une composition médicinale pour traiter des conditions réactives à la capsaïcine. Lesdits vanilloïdes sont exempts des effets désagréables de la capsaïcine et analogues, notamment l'âcreté, tout en préservant plusieurs de leurs propriétés biologiques et cliniques bénéfiques.