3-acetoxy-2-methoxy-5-methyl-1,4-benzoquinone | 4346-28-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-acetoxy-2-methoxy-5-methyl-1,4-benzoquinone
• 英文别名: (2-Methoxy-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl) acetate
• CAS: 4346-28-5
• 化学式: C₁₀H₁₀O₅
• 分子量: 210.186
• InChiKey: IFINIBWQKGVDPI-UHFFFAOYSA-N

物化性质

• 沸点：
  334.2±42.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-acetoxy-2-methoxy-5-methyl-1,4-benzoquinone 在 三丁基氯化锡 、 potassium carbonate 、 magnesium 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.08h， 生成 5-demethoxy-5-hydroxyubiquinone
  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 vanadia sodium chlorate 、 sodium hydroxide 、 三氯化铝 、 硫酸 、 双氧水 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 10.08h， 生成 3-acetoxy-2-methoxy-5-methyl-1,4-benzoquinone
  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

文献信息

• DMSP-OLS estimation of tropical forest area impacted by surface fires in Roraima, Brazil: 1995 versus 1998
  作者：C. D. Elvidge、V. R. Hobson、K. E. Baugh、J. B. Dietz、Y. E. Shimabukuro、T. Krug、E. M. L. M. Novo、F. R. Echavarria

  DOI：10.1080/01431160120888

  日期：2001.1

  A procedure has been developed to locate and estimate the area of heavy forest burning based on the frequency of DMSP-OLS (US Air Force Defense Meteorological Satellite Program Operational Linescan System) fire detection from time series of observations across the fire season. A calibration was developed for Roraima, Brazil, using Landsat Thematic Mapper (TM) data acquired near the end of the 1998 burn season and analysed to identify unburnt, partially burnt and heavily burnt forest areas. A fire detection frequency threshold of five nights was used to map heavily burnt forest using the 3 months of DMSP-OLS observations. The threshold of five fire detections, which could occur anytime during the 3-month time period, was selected to constrain errors of commission involving unburnt forest to 10% of the total area for unburnt forest in the calibration area. At this threshold setting the DMSP-OLS estimate of heavily burnt forest area covered 79% of the Landsat measured area. It was found that 77% of the 1998 heavily burnt forest area was outside of the state's protected areas (national parks, reserves, indigenous areas). Two of the protected areas sustained a substantial increase in heavily burnt forest in 1998 relative to 1995 (Reserva Biologica Mucajai and Parque Indigena Yanomami). The 1998 forest burning in these two areas was concentrated in their eastern-most sections. The core of the Yanomami area did not sustain extensive burning in 1998. Protected areas in the north-eastern section of the state, where forests are mixed with cerrado, had moderate increases in heavily burnt forest in 1998. Other protected areas were largely free of the heavy forest burning, which was concentrated to the west of the state's primary cerrado zone.
• 122. Derivatives of 1 : 2 : 3 : 4-tetrahydroxybenzene. Part VII. The synthesis of fumigatin
  作者：Wilson Baker、H. Raistrick

  DOI：10.1039/jr9410000670

  日期：——
• 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.
• Synthesis and Spectroscopic Characterization of [1′-14C]Ubiquinone-2, [1′-14C]-5-Demethoxy-5-hydroxyubiquinone-2, and [1′-14C]-5-Demethoxyubiquinone-2
  作者：Anita van der Klei、Robertus L. P. de Jong、Johan Lugtenburg、Aloysius G. M. Tielens

  DOI：10.1002/1099-0690(200209)2002:17<3015::aid-ejoc3015>3.0.co;2-g

  日期：2002.9