1,2-dihydroxy-3,4-dimethoxy-6-methylbenzene | 54826-79-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,2-dihydroxy-3,4-dimethoxy-6-methylbenzene
• 英文别名: 2,3-dihydroxy-4,5-dimethoxytoluene；3,4-dihydroxy-1,2-dimethoxy-5-methylbenzene；3,4-dimethoxy-6-methyl-pyrocatechol；3,4-Dimethoxy-6-methyl-brenzcatechin；2,3-Dihydroxy-4,5-dimethoxy-toluol；3,4-Dimethoxy-6-methylpyrocatechol；3,4-dimethoxy-6-methylbenzene-1,2-diol
• CAS: 54826-79-8
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: DNTPARUYPAHKHN-UHFFFAOYSA-N

物化性质

• 熔点：
  101 °C
• 沸点：
  337.5±37.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-dihydroxy-3,4-dimethoxy-6-methylbenzene 在 vanadia sodium chlorate 、 硫酸 作用下， 以 水 为溶剂， 反应 6.0h， 以88%的产率得到烟曲霉醌
  参考文献：
  名称：

  Synthesis and Spectroscopic Characterization of [1′-14C]Ubiquinone-2, [1′-14C]-5-Demethoxy-5-hydroxyubiquinone-2, and [1′-14C]-5-Demethoxyubiquinone-2

  摘要：

  DOI：

  10.1002/1099-0690(200209)2002:17<3015::aid-ejoc3015>3.0.co;2-g
• 作为产物：
  描述：

  3,4,5-三甲氧基甲苯 在 sodium hydroxide 、 三氯化铝 、 乙醚 、 双氧水 作用下， 生成 1,2-dihydroxy-3,4-dimethoxy-6-methylbenzene
  参考文献：
  名称：

  122. 1：2：3：4-四羟基苯的衍生物。第七部分 熏蒸素的合成

  摘要：

  DOI：

  10.1039/jr9410000670

文献信息

• A Penicillium sp. F33 metabolite and its synthetic derivatives inhibit acetyl-CoA:1-O-alkyl-sn-glycero-3-phosphocholine acetyltransferase (a key enzyme in platelet-activating factor biosynthesis) and carrageenan-induced paw edema in mice
  作者：Yasuhiro Yamazaki、Kengo Yasuda、Tensei Matsuyama、Takuya Ishihara、Ryoko Higa、Taira Sawairi、Masahiko Yamaguchi、Masahiro Egi、Shuji Akai、Toshio Miyase、Akira Ikari、Masao Miwa、Junko Sugatani

  DOI：10.1016/j.bcp.2013.06.021

  日期：2013.9

  Acetyl-CoA:1-O-alkyl-sn-glycero-3-phosphocholine (lyso-PAF) acetyltransferase is a key enzyme in the biosynthesis of 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine (PAF) in inflammatory cells. Substances which inhibit this enzyme are of therapeutic interest. In this study, we screened for new inhibitors of lyso-PAF acetyltransferase with anti-inflammatory effects. In a metabolite from Penicillium sp. F33, we isolated an acetyltransferase inhibitor identified as dihydrofumigatin (2-methoxy-1,3,4-trihydroxy-5-methylbenzene) from high resolution mass spectrometer and NMR data. Dihydrofumigatin had strong acetyltransferase inhibitory activity, but was not stable in aqueous solution. Thus, we chemically synthesized its oxidized form fumigatin (3-hydroxy-2-methoxy-5-methyl-1,4-benzoquinone) and derivatives thereof, and evaluated their inhibitory effects. Strong inhibitory activity was observed for saturated fatty acid esters of fumigatin; the order of inhibition was 3-decanoyloxy-2-methoxy-5-methyl-1,4-benzoquinone (termed FUD-7, IC50 = 3 mu M) > 2-methoxy-5-methyl-3-tetradecanoyloxy-1,4-benzoquinone (termed FUD-8, IC50 = 20 mu M) > 3-hexanoyloxy-2-methoxy-5-methyl-1,4-benzoquinone (IC50 = 139 mu M). Interestingly, these compounds also significantly suppressed the gene expression of lyso-PAF acetyltransferase/LPCAT2 in mouse bone marrow-derived macrophages stimulated by lipopolysaccharide (LPS). We further evaluated the effect of these substances on anti-inflammatory activity in vivo using the carrageenan-induced mouse paw edema test. FUD-7 and FUD-8 at 2.5 mg/kg showed significant, 47.9-51.7%, inhibition stronger than that of prednisolone at 10 mg/kg (41.9%). These results suggest that FUD-7 and FUD-8 are potent inhibitors with anti-inflammatory activity. (C) 2013 Elsevier Inc. All rights reserved.
• 329. New synthesis of fumigatin, spinulosin monomethyl ethers, and aurantiogliocladin
  作者：T. R. Seshadri、G. B. Venkatasubramanian

  DOI：10.1039/jr9590001660

  日期：——
• Holton, Dolores M.; Murphy, David, Journal of the Chemical Society. Perkin transactions II, 1980, p. 1757 - 1760
  作者：Holton, Dolores M.、Murphy, David

  DOI：——

  日期：——
• Compositions and Methods With Enhanced Therapeutic Activity
  申请人：Chaplin David

  公开号：US20090137687A1

  公开（公告）日：2009-05-28

  This invention relates to novel tricyclic quinone and catechol compositions, compositions containing prodrugs of tricyclic quinone and catechol compositions, and methods of use for the treatment of solid tumor cancers and other vascular proliferative disorders. In certain aspects, the compositions of the invention are capable of generating both a vascular targeting effect and tumor cell cytotoxicity (e.g., by oxidative stress) in order to achieve an enhanced anti-tumor response in a patient.

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