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Molecular structure of trans-7,8-Dihydroxy-7,8-dihydrobenzo[a]pyrene, CAS Number: 57404-88-3
trans-7,8-Dihydroxy-7,8-dihydrobenzo[a]pyrene (CAS 57404-88-3)
Alternate Names:
(±)-trans-7,8-Dihydroxy-7,8-dihydrobenzo[a]pyrene; Benzo[a]pyrene-trans-7,8-dihydrodiol; trans-7,8-Dihydro-7,8-dihydroxybenzo[a]pyrene
CAS Number:
57404-88-3
Molecular Weight:
286.32
Molecular Formula:
C20H14O2
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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SDS & Certificate of Analysis
trans-7,8-Dihydroxy-7,8-dihydrobenzo[a]pyrene is a compound of interest primarily in the field of environmental chemistry and toxicology research. As an oxidized metabolite of benzo[a]pyrene, it is studied for its role in understanding the metabolic activation of polycyclic aromatic hydrocarbons (PAHs) and their subsequent interactions with biological macromolecules. Research often focuses on its binding affinity to DNA, which has implications for mutagenesis and carcinogenesis studies. Additionally, the compound′s hydroxyl groups are key functional groups that researchers may target in enzymatic studies, particularly those involving phase II metabolic enzymes. In analytical chemistry, it serves as a standard for calibrating equipment used to detect and quantify PAHs in environmental samples.
trans-7,8-Dihydroxy-7,8-dihydrobenzo[a]pyrene (CAS 57404-88-3) References
- Metabolism of benzo[a]pyrene to trans-7,8-dihydroxy-7, 8-dihydrobenzo[a]pyrene by recombinant human cytochrome P450 1B1 and purified liver epoxide hydrolase. | Shimada, T., et al. 1999. Chem Res Toxicol. 12: 623-9. PMID: 10409402
- Metabolism of benzo[a]pyrene: conversion of (+/-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene to highly mutagenic 7,8-diol-9,10-epoxides. | Thakker, DR., et al. 1976. Proc Natl Acad Sci U S A. 73: 3381-5. PMID: 1068451
- (+/-)-trans-7,8-dihydroxy-7,8-dihydrobenzo (a)pyrene: a potent skin carcinogen when applied topically to mice. | Levin, W., et al. 1976. Proc Natl Acad Sci U S A. 73: 3867-71. PMID: 1069271
- Myeloperoxidase-enhanced formation of (+-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene-DNA adducts in lung tissue in vitro: a role of pulmonary inflammation in the bioactivation of a procarcinogen. | Petruska, JM., et al. 1992. Carcinogenesis. 13: 1075-81. PMID: 1322250
- Contribution of dihydrodiol dehydrogenase to the metabolism of (+/-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene in fortified rat liver subcellular fractions. | Shou, M., et al. 1992. Carcinogenesis. 13: 1575-82. PMID: 1394842
- Comparisons of (+/-)-benzo[a]pyrene-trans-7,8-dihydrodiol activation by human cytochrome P450 and aldo-keto reductase enzymes: effect of redox state and expression levels. | Quinn, AM. and Penning, TM. 2008. Chem Res Toxicol. 21: 1086-94. PMID: 18402469
- In vivo formation and persistence of DNA adducts in mouse and rat skin exposed to (+/-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene and (+/-)-7 beta,8 alpha-dihydroxy-9 alpha,10 alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene. | Rojas, M. and Alexandrov, K. 1986. Carcinogenesis. 7: 1553-60. PMID: 3091285
- Oxene transfer, electron abstraction, and cooxidation in the epoxidation of stilbene and 7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene by hemoglobin. | Catalano, CE. and Ortiz de Montellano, PR. 1987. Biochemistry. 26: 8373-80. PMID: 3442662
- Epoxidation of (+/-)-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene during (bi)sulfite autoxidation: activation of a procarcinogen by a cocarcinogen. | Reed, GA., et al. 1986. Proc Natl Acad Sci U S A. 83: 7499-502. PMID: 3463979
- Prostaglandin endoperoxide synthetase-dependent cooxidation of (+/-)-trans-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene in C3H/10T 1/2 clone 8 cells. | Boyd, JA., et al. 1982. Cancer Res. 42: 2628-32. PMID: 6805944
- Metabolism of (+/-)-trans-7,8-dihydroxy-7,8-dihydro-benzo[a]pyrene in mouse liver microsomes and the effect of 2(3)-tert-butyl-4-hydroxy-anisole. | Dock, L., et al. 1982. Carcinogenesis. 3: 697-701. PMID: 6889472
- On the effect of cellular nucleophiles on the binding of metabolites of 7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene and 9-hydroxybenzo(a)pyrene to nuclear DNA. | Guenthner, TM., et al. 1980. Carcinogenesis. 1: 407-18. PMID: 7196808
- Identification of benzo[a]pyrene-7,8-dione as an authentic metabolite of (+/-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene in isolated rat hepatocytes. | Flowers-Geary, L., et al. 1995. Carcinogenesis. 16: 2707-15. PMID: 7586190
- Expression and characterization of four recombinant human dihydrodiol dehydrogenase isoforms: oxidation of trans-7, 8-dihydroxy-7,8-dihydrobenzo[a]pyrene to the activated o-quinone metabolite benzo[a]pyrene-7,8-dione. | Burczynski, ME., et al. 1998. Biochemistry. 37: 6781-90. PMID: 9578563
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
trans-7,8-Dihydroxy-7,8-dihydrobenzo[a]pyrene, 2.5 mg | sc-498583 | 2.5 mg | $401.00 |