isopropyl 2,4-dihydroxy-6-methylbenzoate | 31489-29-9

• 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: isopropyl 2,4-dihydroxy-6-methylbenzoate
• 英文别名: Isopropyl 2,4-hydroxy-6-methylbenzoate；propan-2-yl 2,4-dihydroxy-6-methylbenzoate
• CAS: 31489-29-9
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: KOOFBAZCFXMKFF-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C
• 沸点：
  353.5±22.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  isopropyl 2,4-dihydroxy-6-methylbenzoate 在 sodium hydroxide 、 乙醚 、 双氧水 作用下， 生成 2,3,4-trihydroxy-6-methyl-benzoic acid isopropyl ester
  参考文献：
  名称：

  A mechanism for restriction of the activation-zone propagation for a hemostasis system (A mathematical model)

  摘要：

  DOI：

  10.1134/1.1342454
• 作为产物：
  描述：

  i-Propyl-3,5-dibrom-2,4-dihydroxy-6-methyl-benzoat 以78%的产率得到isopropyl 2,4-dihydroxy-6-methylbenzoate
  参考文献：
  名称：

  Dornhagen, Juergen; Scharf, Hans-Dieter, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1985, vol. 40, # 11, p. 1541 - 1549

  摘要：

  DOI：

文献信息

• Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth, 2. Novel analogues of obtusatic acid
  作者：S Kumar KC

  DOI：10.1016/s0223-5234(00)00132-x

  日期：2000.4

  acid analogues has been synthesized and evaluated as inhibitors of leukotriene B(4) (LTB(4)) biosynthesis and as antiproliferative agents. The 4-O-benzylated and the 4-O-demethylated congeners were the most potent inhibitors of LTB(4) production of the depside class of compounds, with IC(50) values in the submicromolar range. Furthermore, these compounds do not function as redox-based inhibitors because

  已合成了一系列的tus酸类似物，并被评估为白三烯B（4）（LTB（4））生物合成的抑制剂和抗增殖剂。4-O-苄基化和4-O-去甲基化同类物是最有效的Lpp（4）产生的深度类化合物的抑制剂，IC（50）值在亚微摩尔范围内。此外，这些化合物不能用作基于氧化还原的抑制剂，因为它们对稳定的自由基2,2,2-二苯基-1-吡啶并肼基不具有反应性，并且不产生可观量的脱氧核糖降解（作为衡量其生成潜力的量度）羟基自由基。一些钝化酸同源物也是角质形成细胞生长的有效抑制剂。生长抑制不是通过破坏细胞膜来介导的，
• Inhibition of Mushroom Tyrosinase Activity by Orsellinates
  作者：Thiago Inácio Barros Lopes、Roberta Gomes Coelho、Neli Kika Honda

  DOI：10.1248/cpb.c17-00502

  日期：——

  This study evaluated the tyrosinase-related activity of resorcinol (1), orcinol (2) lecanoric acid (3), and derivatives of this acid (4-15). Subjected to alcoholysis, lecanoric acid (3), a depside isolated from the lichen Parmotrema tinctorum, produces orsellinic acid (2,4-dihydroxy-6-methylbenzoic acid) (4) and orsellinates (2,4-dihydroxy-6-methyl benzoates) (5-15). At 0.50 mM, methyl (5), ethyl (6)

  已经提出了酪氨酸酶抑制剂在制药，食品生物加工和环境工业中的几种应用。但是，已知只有少数化合物可作为有效的酪氨酸酶抑制剂。这项研究评估了间苯二酚（1），蓖麻酚（2）柠檬酸（3）和该酸的衍生物（4-15）的酪氨酸酶相关活性。从酒精中分离出来的lecanoric acid（3）是从地衣Parmotrema tinctorum中分离得到的一种生成物，生成奥来酸（2,4-dihydroxy-6-methylbenzoic acid）（4）和奥山酸酯（2,4-dihydroxy-6-methyl benzoates） ）（5-15）。在0.50 mM时，甲基（5），乙基（6），正丙基（7），叔丁基（11）和正十六烷基山梨酸酯（15）充当酪氨酸酶激活剂，而正丁基（8）则是酪氨酸酶激活剂。丙基（9），仲丁基（10），正戊基（12），正己基（13）和山梨酸正辛酯（14）充当抑制剂。
• Zearalenone Mimics: Synthesis of (E)-6-(1-Alkenyl)-substituted <font>β</font>-Resorcylic Acid Esters
  作者：Hannes Mikula、Christian Hametner、Johannes Fröhlich

  DOI：10.1080/00397911.2012.681827

  日期：2013.7.18

  the synthesis of mimics of the Fusarium mycotoxin zearalenone (1) have been developed. Optimized preparation of (E)-6-(1-alkenyl) substituted β-resorcylic acid esters was realized via ortho-directed lithiation of variable substrates combined with allylation/isomerization or via formylation/Schlosser–Wittig olefination using different protective group patterns. Spontaneous decarboxylation of (E)-6-(1-alkenyl)

  摘要 已经开发了两种用于合成镰刀菌毒素玉米赤霉烯酮 (1) 模拟物的通用策略。(E)-6-(1-烯基)取代的β-间苯二甲酸酯的优化制备是通过可变底物的邻位锂化结合烯丙基化/异构化或通过使用不同保护基团模式的甲酰化/Schlosser-Wittig烯化来实现的。(E)-6-(1-烯基) 取代的 β-间苯二酸的自发脱羧表明该取代基对这些化合物的化学行为的影响。这些模拟物已用于开发用于合成 ZEN 的 II 期代谢物（葡萄糖苷、葡萄糖醛酸苷）的优化标准方案，进一步的应用（即硫酸盐偶联物）仍在研究中。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• Radical-Scavenging Activity of Orsellinates
  作者：Thiago Inácio Barros Lopes、Roberta Gomes Coelho、Nídia Cristiane Yoshida、Neli Kika Honda

  DOI：10.1248/cpb.56.1551

  日期：——

  Lichens are an important source of phenolic compounds and have been intensively investigated for their biological and pharmacological activities. Lecanoric acid (1), a lichen depside, was isolated from a Parmotrema tinctorum specimen and treated with alcohols to produce orsellinic acid (2) and orsellinates (3) to (9) (2,4-dihydroxy-6-n-methyl benzoates). Free radical scavenging activity of methyl (3), ethyl (4), n-propyl (5), n-butyl (6), iso-propyl (7), sec-butyl (8), tert-butyl (9) orsellinates was evaluated using 2,2′-diphenyl-1-picrylhydrazyl (DPPH) method. Results showed that chain elongation of methyl (3) to n-butyl (6) causes a rise in the antioxidant activity. However, iso-propyl (7) and tert-butyl (9) were more active than the correspondent linear compounds, although sec-butyl (8) was less active among the chain ramified compounds. All the orsellinates were less active than lecanoric acid (1) and orsellinic acid (2). Orcinol (10) and resorcinol (11) were also determined for comparison with activities of orsellinates. Gallic acid (12) was used as control.

  地衣是酚类化合物的重要来源，人们对其生物和药理活性进行了深入研究。从 Parmotrema tinctorum 标本中分离出地衣苷酸 Lecanoric acid (1)，并用醇处理生成 orsellinic acid (2) 和 orsellinates (3) 至 (9)（2,4-二羟基-6-正甲基苯甲酸酯）。采用 2,2′-二苯基-1-苦基肼（DPPH）法评估了橙皮苷酸甲酯（3）、乙酯（4）、正丙酯（5）、正丁酯（6）、异丙酯（7）、仲丁酯（8）和叔丁酯（9）的自由基清除活性。结果表明，甲基（3）链延长为正丁基（6）会导致抗氧化活性上升。不过，异丙基（7）和叔丁基（9）的活性高于相应的线性化合物，但仲丁基（8）的活性在链延伸化合物中较低。所有橙皮苷酸的活性都低于柠檬酸（1）和橙皮苷酸（2）。此外，还测定了 Orcinol (10) 和 resorcinol (11)，以便与 orsellinates 的活性进行比较。没食子酸（12）用作对照。
• Antimycobacterial activity of lichen substances
  作者：N.K. Honda、F.R. Pavan、R.G. Coelho、S.R. de Andrade Leite、A.C. Micheletti、T.I.B. Lopes、M.Y. Misutsu、A. Beatriz、R.L. Brum、C.Q.F. Leite

  DOI：10.1016/j.phymed.2009.07.018

  日期：2010.4

  We describe here the extraction and identification of several classes of phenolic compounds from the lichens Parmotrema dilatatum (Vain.) Hale, Parmotrema tinctorum (Nyl.) Hale, Pseudoparmelia sphaerospora (Nyl.) Hale and Usnea subcavata (Motyka) and determined their anti-tubercular activity. The depsides (atranorin, diffractaic and lecanoric acids), depsidones (protocetraric, salazinic, hypostictic and norstictic acids), xanthones (lichexanthone and secalonic acid), and usnic acid, as well seven orsellinic acid esters, five salazinic acid 8',9'-O-alkyl derivatives and four lichexanthone derivatives, were evaluated for their activity against Mycobacterium tuberculosis. Diffractaic acid was the most active compound (MIC value 15.6 mu g/ml, 41.6 mu M), followed by norstictic acid (MIC value 62.5 mu g/ml, 168 mu M) and usnic acid (MIC value 62.5 mu g/ml, 182 mu M). Hypostictic acid (MIC value 94.0 mu g/ml, 251 mu M) and protocetraric acid (MIC value 125 mu g/ml, 334 mu M) showed moderate inhibitory activity. The other compounds showed lower inhibitory activity on the growth of M. tuberculosis, varying from MIC values of 250 to 1370 mu M. (C) 2009 Elsevier GmbH. All rights reserved.