4-acetyl-3-methoxy-5-methylbenzoic acid | 100507-74-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetyl-3-methoxy-5-methylbenzoic acid
• 英文别名: macrophomic acid
• CAS: 100507-74-2
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: GWSISRLRTQOQNE-UHFFFAOYSA-N

物化性质

• 沸点：
  385.3±42.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-acetoxy-5-acetyl-6-methyl-2-pyrone 在 dipotassium hydrogenphosphate 、 sodium dihydrogenphosphate 作用下， 以 乙醇 、 水 为溶剂， 反应 480.0h， 生成 4-acetyl-3-methoxy-5-methylbenzoic acid
  参考文献：
  名称：

  Sakurai, Ikuo; Miyajima, Hisae; Akiyama, Katsuyoshi, Chemical and pharmaceutical bulletin, 1988, vol. 36, p. 2003 - 2011

  摘要：

  DOI：

文献信息

• Substrate Diversity of Macrophomate Synthase Catalyzing an Unusual Multistep Transformation from 2-Pyrones to Benzoates
  作者：Kenji WATANABE、Takashi MIE、Akitami ICHIHARA、Hideaki OIKAWA、Mamoru HONMA

  DOI：10.1271/bbb.64.530

  日期：2000.1

  Macrophomate synthase, which we have recently purified, catalyzes an unusual multistep transformation from 5-acetyl-4-methoxy-6-methyl-2-pyrone to 4-acetyl-3-methoxy-5-methyl-benzoic acid (macrophomic acid). To investigate the substrate diversity of the enzyme, 40 analogs of 2-pyrone were prepared and their relative efficiency was examined in the enzymatic conversions. The experimental results reveal the structural requirements of the substrates and the rough size of the enzyme active site, and eliminate the ambiguity caused by contamination by other enzymes in the whole-cell experiments.

  我们最近纯化了一种名为黑腐醇合酶的酶，它催化一种不寻常的多步转化过程，从5-乙酰基-4-甲氧基-6-甲基-2-吡営转变为4-乙酰基-3-甲氧基-5-甲基苯甲酸（黑腐酸）。为了研究该酶的底物多样性，我们制备了40种2-吡喃酮的类似物，并考察了它们在酶促转化中的相对效率。实验结果揭示了底物的结构要求和酶活性位点的大致尺寸，并消除了全细胞实验中因其他酶污染导致的模糊性。
• Active site mutagenesis of the putative Diels–Alderase macrophomate synthase
  作者：Jörg M. Serafimov、Hans Christian Lehmann、Hideaki Oikawa、Donald Hilvert

  DOI：10.1039/b703177g

  日期：——

  Although the macrophomate synthase active site is rich in potential functional groups, site-directed mutagenesis shows that only three residues are absolutely required for catalysis of oxaloacetate decarboxylation and trapping of the resulting enolate with a 2-pyrone; the other residues that line the binding pocket are surprisingly tolerant to substitution.

  虽然巨噬细胞酸合成酶的活性位点富含潜在的功能基团，但定点突变显示，只有三个残基是催化草酰乙酸脱羧和用 2-吡喃酮捕获所产生的烯醇酮所绝对必需的；而位于结合口袋的其他残基对取代的耐受性令人惊讶。
• Sakurai, Ikuo; Suzuki, Harumi; Shimizu, Sakae, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 11, p. 5141 - 5143
  作者：Sakurai, Ikuo、Suzuki, Harumi、Shimizu, Sakae、Yamamoto, Yuzuru

  DOI：——

  日期：——
• Ichihara, Akitami; Murakami, Kazuo; Sakamura, Sadao, Agricultural and Biological Chemistry, 1984, vol. 48, # 3, p. 833 - 834
  作者：Ichihara, Akitami、Murakami, Kazuo、Sakamura, Sadao

  DOI：——

  日期：——
• Macrophomate synthase: unusual enzyme catalyzing multiple reactions from pyrones to benzoates
  作者：Hideaki Oikawa、Kenji Watanabe、Kenji Yagi、Satoshi Ohashi、Takashi Mie、Akitami Ichihara、Mamoru Honma

  DOI：10.1016/s0040-4039(99)01441-0

  日期：1999.9

  Macrophomate synthase which catalyzes unusual multiple reactions from 2-pyrone (3) to macrophomic acid (1) has been purified in a homogenous state. The macrophomate synthase is a dimeric enzyme which requires Mg2+ as a co-factor and whose molecular mass is 40 kDa. Study on substrate specificity showed that the enzyme is capable of converting various 2-pyrones to the corresponding benzoates. (C) 1999 Elsevier Science Ltd. All rights reserved.