2,6-다이메톡시벤조퀴논

위키백과, 우리 모두의 백과사전.

2,6-다이메톡시벤조퀴논
Chemical structure of 2,6-dimethoxybenzoquinone
이름
우선명 (PIN)
2,6-dimethoxycyclohexa-2,5-diene-1,4-dione
별칭
2,6-dimethoxy-1,4-benzoquinone,
2,6-DMBQ
식별자
3D 모델 (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.714
UNII
  • InChI=1S/C8H8O4/c1-11-6-3-5(9)4-7(12-2)8(6)10/h3-4H,1-2H3 예예
    Key: OLBNOBQOQZRLMP-UHFFFAOYSA-N 예예
  • O=C1C(/OC)=C\C(=O)\C=C1\OC
성질
C8H8O4
몰 질량 168.148 g·mol−1
달리 명시된 경우를 제외하면, 표준상태(25 °C [77 °F], 100 kPa)에서 물질의 정보가 제공됨.
아니오아니오 확인 (관련 정보 예예아니오아니오 ?)

2,6-다이메톡시벤조퀴논(영어: 2,6-dimethoxybenzoquinone, 2,6-DMBQ)은 라우볼피아 보미토리아(Rauvolfia vomitoria)[1] 및 티보우키나 풀크라(Tibouchina pulchra)[2]에서 발견되는 벤조퀴논으로 분류되는 화합물이다.

독성[편집]

생리학적 농도에서 2,6-다이메톡시벤조퀴논은 항균 물질이다.[3] 더 높은 농도에서는 돌연변이,[4][5] 세포독성,[5] 유전독성,[6] 간독성[7][8][9]이 있다는 증거가 있다. 일부 보고서는 2,6-다이메톡시벤조퀴논의 돌연변이 유발성에 이의를 제기했고,[10] 다른 보고서에서는 그러한 가능성을 배제했다.[11]

같이 보기[편집]

각주[편집]

  1. ↑ Morris Kupchan, S.; Obasi, Mang E. (1960). “A Note on the Occurrence of 2,6-Dimethoxybenzoquinone in Rauwolfia vomitoria”. 《Journal of the American Pharmaceutical Association (Scientific Ed.)》 49 (4): 257–258. doi:10.1002/jps.3030490421. PMID 13853494. 
  2. ↑ Jones, Ellery; Ekundayo, Olusegun; Kingston, David G. I. (1981). “Plant Anticancer Agents. XI. 2,6-Dimethoxybenzoquinone as a Cytotoxic Constituent of Tibouchina pulchra”. 《Journal of Natural Products》 44 (4): 493–494. doi:10.1021/np50016a019. 
  3. ↑ Nishina, Atsuyoshi; Hasegawa, Kinichi; Uchibori, Tsuyoshi; Seino, Hajime; Osawa, Toshihiko (1991). “2,6-Dimethoxy-p-benzoquinone as an antibacterial substance in the bark of Phyllostachys heterocycla var. Pubescens, a species of thick-stemmed bamboo”. 《Journal of Agricultural and Food Chemistry》 39 (2): 266–269. doi:10.1021/jf00002a009. 
  4. ↑ 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
  5. ↑ 가 나 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
  6. ↑ 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
  7. ↑ 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.
  8. ↑ 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
  9. ↑ 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.
  10. ↑ Non-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)
  11. ↑ 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
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