2-isopropyl-5-methylcyclohexyl 3,4,5-trihydroxybenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-isopropyl-5-methylcyclohexyl 3,4,5-trihydroxybenzoate
• 英文别名: Menthyl gallate；(5-methyl-2-propan-2-ylcyclohexyl) 3,4,5-trihydroxybenzoate
• 化学式: C₁₇H₂₄O₅
• 分子量: 308.375
• InChiKey: FCUPVWYUMCJPKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  薄荷脑 、 没食子酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 以46%的产率得到2-isopropyl-5-methylcyclohexyl 3,4,5-trihydroxybenzoate
  参考文献：
  名称：

  Molecular design of multifunctional antibacterial agents against methicillin resistant Staphylococcus aureus (MRSA)

  摘要：

  Antibacterial activity of a series of alkyl gallates (3,4,5-trihydroxybenzoates) against Gram-positive bacteria, especially methicillin resistant Staphylococcus aureus (MRSA) strains was evaluated. Gram-positive bacteria are all susceptible to alkyl gallates. Dodecyl gallate was the most effective against MRSA ATCC 33591 strain with the minimum bactericidal concentration (MBC) of 25 mug/mL (74 muM). The time-kill curve study showed that dodecyl gallate was bactericidal against this MRSA strain at any growth stage. This activity was observed even in the chloramphenicol-treated cells, but the rate of decrease of cell number was slower than that in the exponentially growing cells. The bactericidal activity of medium-chain alkyl gallates was noted in combination with their ability to disrupt the native membrane-associated function nonspecifically as surface-active agents (surfactants) and to inhibit the respiratory electron transport. Subsequently, the same series of alkyl protocatechuates (3,4-dihydroxybenzoates) were studied and the results obtained are similar to those found for alkyl gallates. The length of the alkyl chain is not a major contributor but is related to the activity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00433-4

文献信息

• Design, Synthesis, and Antifungal Activity of Alkyl Gallates Against Plant Pathogenic Fungi In Vitro and In Vivo
  作者：Xiao-Long Zhao、Chun-Qing Li、Xiao-Mei Song、Shuang-Mei Yan、Du-Qiang Luo

  DOI：10.1007/s10600-021-03276-3

  日期：2021.1

  A series of alkyl gallates was synthesized by reacting gallic acid with the corresponding alcohols. Their structures were determined on the basis of spectroscopic data, including NMR and MS. The antifungal activities of these compounds against plant pathogenic fungi in vitro and in vivo were assessed.

  通过没食子酸与相应的醇反应，合成了一系列没食子酸烷基酯。根据 NMR 和 MS 等光谱数据确定了这些化合物的结构。评估了这些化合物在体外和体内对植物病原真菌的抗真菌活性。
• TOPICAL ANTIVIRAL COMPOSITIONS
  申请人：Topical Remedy, LLC

  公开号：EP3344265A1

  公开（公告）日：2018-07-11
• [EN] GALLIC ACID ESTERS AND COMPOSITIONS COMPRISING THEREOF<br/>[FR] ESTERS D'ACIDE GALLIQUE ET COMPOSITIONS COMPRENANT CEUX-CI
  申请人：GHISALBERTI CARLO

  公开号：WO2008065527A2

  公开（公告）日：2008-06-05

  [EN] Gallates formed by condensation of gallic acid with a hydroxyl-containing fragrance for the use in a composition suitable for disinfecting and seboregulating purposes.
  [FR] L'invention concerne des gallates formés par condensation d'acide gallique avec une fragrance contenant un groupe hydroxyle, destinés à être utilisés dans une composition désinfectante et séborégulatrice.
• [EN] TOPICAL ANTIVIRAL COMPOSITIONS<br/>[FR] COMPOSITIONS ANTIVIRALES TOPIQUES
  申请人：TOPICAL REMEDY LLC

  公开号：WO2017040844A1

  公开（公告）日：2017-03-09

  In various embodiments compositions that inactivates a virus or inhibit replication of a virus are provided where the compositions comprise a C1-C10 alcohol; an acid selected from the group consisting of gallic acid, methyl gallate, 3, 4-dihydroxy benzoic acid, p-hydroxy benzoic acid, vanillic acid, p-coumaric acid, ferulic acid, syringic acid, salicylic acid, luteic acid, and eudesmic acid; and a pharmaceutically acceptable carrier; where the pH of said composition is pH 4.5 or lower. In certain embodiments the alcohol comprises one or more alcohols selected from the group consisting of ethanol, ethanol, 2-propanol, 1-propanol, 2,3-butanediol, 1,2-butanediol, 1,3-butanediol, and 1,4-butanediol, butyl alcohol (including n-butanol, sec-butanol, isobutanol, tert-butanol), pentanol, hexadecan-1-ol, ethane-1,2-diol, propane-1,2-diol, propane-1,2,3-triol, butane-1,2,3,4-tetraol, pentane-1,2,3,4,5-pentol, hexane-1,2,3,4,5,6-hexol, heptane-1,2,3,4,5,6,7-heptol, prop-2-ene-1-ol, 3,7-dimethylocta-2,6-dien-1-ol, prop-2-in-1-ol, cyclohexane-1,2,3,4,5,6-hexol, and 2-(2-propyl)-5-methyl-cyclohexane-1-ol.
• Molecular design of multifunctional antibacterial agents against methicillin resistant Staphylococcus aureus (MRSA)
  作者：I Kubo

  DOI：10.1016/s0968-0896(03)00433-4

  日期：2003.9.15

  Antibacterial activity of a series of alkyl gallates (3,4,5-trihydroxybenzoates) against Gram-positive bacteria, especially methicillin resistant Staphylococcus aureus (MRSA) strains was evaluated. Gram-positive bacteria are all susceptible to alkyl gallates. Dodecyl gallate was the most effective against MRSA ATCC 33591 strain with the minimum bactericidal concentration (MBC) of 25 mug/mL (74 muM). The time-kill curve study showed that dodecyl gallate was bactericidal against this MRSA strain at any growth stage. This activity was observed even in the chloramphenicol-treated cells, but the rate of decrease of cell number was slower than that in the exponentially growing cells. The bactericidal activity of medium-chain alkyl gallates was noted in combination with their ability to disrupt the native membrane-associated function nonspecifically as surface-active agents (surfactants) and to inhibit the respiratory electron transport. Subsequently, the same series of alkyl protocatechuates (3,4-dihydroxybenzoates) were studied and the results obtained are similar to those found for alkyl gallates. The length of the alkyl chain is not a major contributor but is related to the activity. (C) 2003 Elsevier Ltd. All rights reserved.