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1,4-Benzoquinone (CAS 106-51-4)

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Alternate Names:
Quinone; 1,4-Cyclohexadienedione
Application:
1,4-Benzoquinone is a major metabolite of benzene that is found to induce apoptosis
CAS Number:
106-51-4
Purity:
≥99%
Molecular Weight:
108.09
Molecular Formula:
C6H4O2
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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1,4-Benzoquinone, also referred to as para-benzoquinone or PBQ, emerges as an organic compound boasting the molecular formula C6H4O2. With its distinct yellow crystalline structure, it exudes a potent aroma and boasts high solubility in organic solvents. This compound plays a pivotal role as an intermediary in organic compound synthesis, holding diverse applications within the chemical sector. Notably, it serves as a vital building block in the creation of polymers and dyes. Extensive exploration of 1,4-Benzoquinone has unfolded across the realms of organic chemistry and biochemistry. In the domain of organic chemistry, it takes center stage as a synthetic intermediate facilitating the production of a spectrum of organic compounds, encompassing dyes and polymers. Meanwhile, within biochemistry, it has assumed the role of a model compound, offering insights into the intricacies of enzyme-mediated oxidation processes concerning aromatic compounds. The mechanism underpinning the action of 1,4-benzoquinone is intricate, involving a sequence of discrete steps. The initial phase entails an oxidation reaction, wherein the compound reacts with an oxidizing agent like oxygen or air, culminating in the genesis of a quinone. Subsequently, this quinone undergoes further oxidation, metamorphosing into a hydroquinone. Ultimately, this hydroquinone undergoes reduction, giving rise once more to 1,4-benzoquinone. 1,4-Benzoquinone is a major metabolite of benzene. It has been found to generate H2O2 in cells. It has been suggested that the peroxide reacts with Cu(I) to produce an active species that induces internucleosomal DNA fragmentation.


1,4-Benzoquinone (CAS 106-51-4) References

  1. 1,4-Benzoquinone (para-quinone).  |  . 1999. IARC Monogr Eval Carcinog Risks Hum. 71 Pt 3: 1245-50. PMID: 10476391
  2. 1,4-benzoquinone attracts males of Rhizotrogus vernus Germ.  |  Imrei, Z., et al. 2002. Z Naturforsch C J Biosci. 57: 177-81. PMID: 11926532
  3. 1,4-Benzoquinone is a topoisomerase II poison.  |  Lindsey, RH., et al. 2004. Biochemistry. 43: 7563-74. PMID: 15182198
  4. 1,4-Benzoquinone-based electrophoretic assay for glucose oxidase.  |  Urban, PL., et al. 2006. Anal Biochem. 359: 35-9. PMID: 17027609
  5. Neuroprotection by small molecule activators of the nerve growth factor receptor.  |  Lin, B., et al. 2007. J Pharmacol Exp Ther. 322: 59-69. PMID: 17468299
  6. Amperometric carbon paste enzyme electrodes with Fe(3)O(4) nanoparticles and 1,4-benzoquinone for glucose determination.  |  Erden, PE., et al. 2013. Artif Cells Nanomed Biotechnol. 41: 165-71. PMID: 22889252
  7. Stimulation of nerve growth factor synthesis/secretion by 1,4-benzoquinone and its derivatives in cultured mouse astroglial cells.  |  Takeuchi, R., et al. 1990. FEBS Lett. 261: 63-6. PMID: 2307236
  8. Inactivation of urease by 1,4-benzoquinone: chemistry at the protein surface.  |  Mazzei, L., et al. 2016. Dalton Trans. 45: 5455-9. PMID: 26961812
  9. A mechanism for 1,4-Benzoquinone-induced genotoxicity.  |  Son, MY., et al. 2016. Oncotarget. 7: 46433-46447. PMID: 27340773
  10. Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits-Synthesis and Antitumor Activity.  |  Kadela-Tomanek, M., et al. 2017. Molecules. 22: PMID: 28287461
  11. PINK1/Parkin-mediated mitophagy was activated against 1,4-Benzoquinone-induced apoptosis in HL-60 cells.  |  Zhang, C., et al. 2018. Toxicol In Vitro. 50: 217-224. PMID: 29567065
  12. 1,4-Benzoquinone antimicrobial agents against Staphylococcus aureus and Mycobacterium tuberculosis derived from scorpion venom.  |  Carcamo-Noriega, EN., et al. 2019. Proc Natl Acad Sci U S A. 116: 12642-12647. PMID: 31182590
  13. l-Carnitine protects against 1,4-benzoquinone-induced apoptosis and DNA damage by suppressing oxidative stress and promoting fatty acid oxidation in K562 cells.  |  Sun, R., et al. 2020. Environ Toxicol. 35: 1033-1042. PMID: 32478940
  14. 1,4-Benzoquinone reductase from basidiomycete Phanerochaete chrysosporium: spectral and kinetic analysis.  |  Brock, BJ. and Gold, MH. 1996. Arch Biochem Biophys. 331: 31-40. PMID: 8660680
  15. Oxidative DNA damage and apoptosis induced by benzene metabolites.  |  Hiraku, Y. and Kawanishi, S. 1996. Cancer Res. 56: 5172-8. PMID: 8912853

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

1,4-Benzoquinone, 5 g

sc-202873B
5 g
$20.00

1,4-Benzoquinone, 25 g

sc-202873C
25 g
$29.00

1,4-Benzoquinone, 100 g

sc-202873
100 g
$56.00

1,4-Benzoquinone, 250 g

sc-202873D
250 g
$80.00

1,4-Benzoquinone, 500 g

sc-202873A
500 g
$110.00

What is the appearance of the compound?

Asked by: two2igm05
Thank you for your question. The appearance of this compound is a golden prismatic crystal.
Answered by: Technical Support
Date published: 2017-01-18
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Rated 5 out of 5 by from ChowChow, PW. et al. (PubMed 25645895) investigated the mechanism linking benzene exposure to targeting hematopoietic stem cells (HSCs) and hematopoietic progenitor cells (HPCs) using phenotypic and clonogenic analyses. Mouse bone marrow (BM) cells were exposed ex vivo to the benzene metabolite, 1,4-benzoquinone (1,4-BQ), for 24h. 1,4-BQ caused lineage-related cytotoxicity in mouse HPCs, demonstrating greater toxicity in single-lineage progenitors than in those of multi-lineage. -SCBT Publication Review
Date published: 2015-05-29
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1,4-Benzoquinone is rated 5.0 out of 5 by 1.
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