2,6-Dimethoxybenzoquinone

changed changed 456498687 2,6-Dimethoxybenzoquinone 2,6-Dimethoxy-1,4-benzoquinone.svg Chemical structure of 2,6-dimethoxybenzoquinone Chemical structure of 2,6-dimethoxybenzoquinone 2,6-Dimethoxycyclohexa-2,5-diene-1,4-dione 2,6-Dimethoxy-1,4-benzoquinone; 2,6-DMBQ 530-55-2 correct CAS correct FDA 1Z701W789S correct EBI 448515 68262 correct chemspider 61560 correct chemspider OLBNOBQOQZRLMP-UHFFFAOYSA-N O=C1C(/OC)=C\C(=O)\C=C1\OC correct chemspider 1S/C8H8O4/c1-11-6-3-5(9)4-7(12-2)8(6)10/h3-4H,1-2H3 8 8 4 2,6-Dimethoxybenzoquinone (2,6-DMBQ) is a chemical compound, classified as a benzoquinone, that has been found in Rauvolfia vomitoria 10.1002/jps.3030490421 A Note on the Occurrence of 2,6-Dimethoxybenzoquinone in Rauwolfia vomitoria 1960 Morris Kupchan S. Obasi Mang E. Journal of the American Pharmaceutical Association (Scientific Ed.) 49 4 257–258 13853494 and in Tibouchina pulchra. 10.1021/np50016a019 Plant Anticancer Agents. XI. 2,6-Dimethoxybenzoquinone as a Cytotoxic Constituent of Tibouchina pulchra 1981 Jones Ellery Ekundayo Olusegun Kingston David G. I. Journal of Natural Products 44 4 493–494 Toxicity At physiological concentrations 2,6-dimethoxybenzoquinone is an antibacterial substance. 10.1021/jf00002a009 2,6-Dimethoxy-p-benzoquinone as an antibacterial substance in the bark of Phyllostachys heterocycla var. Pubescens, a species of thick-stemmed bamboo 1991 Nishina Atsuyoshi Hasegawa Kinichi Uchibori Tsuyoshi Seino Hajime Osawa Toshihiko Journal of Agricultural and Food Chemistry 39 2 266–269 At higher concentrations there is evidence that it is mutagenic,Canonero R; Poggi C Mutagenic activity of 2,6-dimethoxy-1,4-benzoquinone, produced during the nitrosation of dimethophrine, in V 79 cells. Bollettino della Societa italiana di biologia sperimentale (1988), 64(1), 61-8Brambilla G; Robbiano L; Cajelli E; Martelli A; Turmolini F; Mazzei M Cytotoxic, DNA-damaging and mutagenic properties of 2,6-dimethoxy-1,4-benzoquinone, formed by dimethophrine-nitrite interaction. The Journal of Pharmacology and Experimental Therapeutics (1988), 244(3), 1011-5 cytotoxic, genotoxic,Mazzei M; Roma G; Balbi A; Sottofattori E; Robbiano L Formation of 2,6-dimethoxy-1,4-benzoquinone, a highly genotoxic compound, from the reaction of sodium nitrite with the sympathomimetic drug dimethophrine in acidic aqueous solution. Il Farmaco; edizione scientifica (1988), 43(6), 523-38 and hepatotoxic.Moore, Gregory A.; Rossi, Luisa; Nicotera, Pierluigi; Orrenius, Sten; O'Brien, Peter J. Quinone toxicity in hepatocytes: studies on mitochondrial calcium release induced by benzoquinone derivatives. Archives of Biochemistry and Biophysics (1987), 259(2), 283-95.Siraki, Arno G.; Chan, Tom S.; O'Brien, Peter J. Application of Quantitative Structure-Toxicity Relationships for the Comparison of the Cytotoxicity of 14 p-Benzoquinone Congeners in Primary Cultured Rat Hepatocytes Versus PC12 Cells. Toxicological Sciences (2004), 81(1), 148-159Chan, Katie; Jensen, Neil; O'Brien, Peter J. Structure-activity relationships for thiol reactivity and rat or human hepatocyte toxicity induced by substituted p-benzoquinone compounds. Journal of Applied Toxicology (2008), 28(5), 608-620. Some reports have challenged its mutagenicityNon-mutagenicity of some wood-related compounds in the bacterial/microsome plate incorporation and microsuspension assays. Mohtashamipur, E., Norpoth, K. International archives of occupational and environmental health. (1984) and others exclude such a possibility.International Journal of Toxicology, 26:253–259, Safety Studies Regarding a Standardized Extract of Fermented Wheat Germ James T. Heimbach JHeimbach LLC, Port Royal, Virginia, USA Gyula Sebestyen Department of Public Health, Faculty of Medicine, Semmelweis University, Budapest, Hungary Gabor Semjen Department of Pharmacology and Toxicology, Faculty of Veterinary Science, Szent Istvan University, Budapest, Hungary Elke Kennepohl Write-Tox Consulting, Spruce Grove, Alberta, Canada References Category:1,4-Benzoquinones Category:Enol ethers