4-羟基-3-甲氧基苯甲酸辛酯 | 5438-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-羟基-3-甲氧基苯甲酸辛酯
• 英文名称: octyl 4-hydroxy-3-methoxybenzoate
• 英文别名: octyl vanillate；LINS03016；4-hydroxy-3-methoxy-benzoic acid octyl ester；4-Hydroxy-3-methoxy-benzoesaeure-octylester；Octyl 4-hydroxy-3-methoxy-benzoate
• CAS: 5438-62-0
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: CITHDNJMIRGMHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 水 作用下， 生成 4-羟基-3-甲氧基苯甲酸辛酯
  参考文献：
  名称：

  Reactions of Vanillin and its Derived Compounds. XIII.¹ A New Synthesis of Vanillic Acid Esters^2,3

  摘要：

  DOI：

  10.1021/ja01153a011

文献信息

• Structure–activity relationships of vanillic acid ester analogs in inhibitory effect of antigen-mediated degranulation in rat basophilic leukemia RBL-2H3 cells
  作者：Nao Ishimata、Hideyuki Ito、Akihiro Tai

  DOI：10.1016/j.bmcl.2016.06.028

  日期：2016.8

  Methyl vanillate (1) showed strong degranulation inhibitory activity among vanillin derivatives tested. In order to find structure–activity relationships for developing anti-allergic agents with simple structures and potent activity, we synthesized several vanillic acid (VA) ester derivatives with C1–C4 and C8 alkyl chains and evaluated their degranulation inhibitory activities. The most active compound

  在测试的香兰素衍生物中，香草酸甲酯（1）表现出较强的脱粒抑制活性。为了找到具有简单结构和有效活性的抗过敏药的结构-活性关系，我们合成了几种具有C 1 -C 4和C 8烷基链的香草酸（VA）酯衍生物，并评估了它们的脱粒抑制活性。VA酯衍生物的最活跃的化合物是衍生物5与C 4直链烷基链，和衍生物5表现出大约三倍比的更大抑制活性1。此外，我们根据参照图5，我们发现有效的脱粒抑制活性的最小结构要求苯环上的丁酯部分与苯环上的至少一个羟基直接连接。丁基间位或对位的羟基苯甲酸酯（10或11）具有比的简单的结构5和表现出比的更有效的脱颗粒抑制活性5。
• Antifungal activity of octyl gallate: structural criteria and mode of action
  作者：Isao Kubo、Ping Xiao、Ken'ichi Fujita

  DOI：10.1016/s0960-894x(00)00656-9

  日期：2001.2

  Octyl gallate (3,4,5-trihydroxybenzoate) was found to possess antifungal activity against Saccharomyces cerevisiae and Zygosaccharomyces bailii, in addition to its potent antioxidant activity. Catechol moiety is essential to elicit this activity. The primary fungicidal activity of octyl gallate comes from its ability to act as a nonionic surface-active agent (surfactant). The length of the alkyl chain is not a major contributor but plays an important role in eliciting the activity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Antiparasitic activity of new gibbilimbol analogues and SAR analysis through efficiency and statistical methods
  作者：Marina T. Varela、Maiara M. Romaneli、Marta L. Lima、Samanta E.T. Borborema、Andre G. Tempone、João P.S. Fernandes

  DOI：10.1016/j.ejps.2018.06.023

  日期：2018.9

  Chagas' disease and leishmaniasis are parasitic infections enrolled among the neglected tropical diseases, which urge for new treatments. In the search for new chemical entities as prototypes, gibbilimbols A/B have shown antiparasitic activity against Trypanosoma cruzi and Leishmania infantum, and then a set of analogues (LINS03 series) of this natural product were synthesized and evaluated in vitro against the parasites. In the present paper we reported five new compounds with activity against these protozoan parasites, and quite low cytotoxicity. Moreover, the interference of plasma membrane permeability of these analogues were also evaluated. We found that [(4-methoxyphenyl) methyl] octylamine (4) was noteworthy due to its high activity against the amastigote form of both parasites (IC50 1.3-5.8 mu M) and good selectivity index. In order to unveil the SAR for this chemotype, we also presented a group efficiency analysis and PCA and HCA study, which indicated that the methoxyl provides good activity with lower cytotoxicity to mammalian cells. The results from SAR analyses suggest different mechanisms of action between the neutral and basic compounds. In summary, the analogues represent important activity against these parasites and must be prototypes for further exploitation.