2,6-Dimethoxybenzoquinone

2,6-Dimethoxybenzoquinone
Chemical structure of 2,6-dimethoxybenzoquinone
Names
IUPAC name
2,6-Dimethoxycyclohexa-2,5-diene-1,4-dione
Other names
2,6-Dimethoxy-1,4-benzoquinone; 2,6-DMBQ
Identifiers
530-55-2 N=
3D model (Jmol) Interactive image
ChEMBL ChEMBL448515 YesY
ChemSpider 61560 YesY
ECHA InfoCard 100.007.714
PubChem 68262
Properties
C8H8O4
Molar mass 168.15 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

2,6-Dimethoxybenzoquinone (2,6-DMBQ) is a benzoquinone, a chemical compound found in Rauvolfia vomitoria[1] and in Tibouchina pulchra.[2]

Toxicity

2,6-DMBQ is mutagenic,[3][4] cytotoxic,[4] genotoxic,[5] and hepatotoxic.[6][7][8]

References

  1. ↑ A note on the occurrence of 2,6-dimethoxybenzoquinone in Rauwolfia vomitoria. S. Morris Kupchan and Mang E. Obasi, Journal of the American Pharmaceutical Association, Volume 49, Issue 4, pages 257–258, April 1960, doi:10.1002/jps.3030490421
  2. ↑ Plant anticancer agents. XI. 2,6-dimethoxybenzoquinone as a cytotoxic constituent of Tibouchina pulchra. Jones E., Ekundayo O. and Kingston D.G.I., Journal of natural products, Jul-Aug 1981, doi:10.1021/np50016a019
  3. ↑ 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), 61-8
  4. 1 2 Brambilla 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
  5. ↑ 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
  6. ↑ 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.
  7. ↑ 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), 148-159
  8. ↑ Chan, 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.
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