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MedKoo Cat#: 581255 | Name: Dibenz[a,h]anthracene
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dibenz[a,h]anthracene is a fused five ringed, cyclopenta, PAHs compound which is common as a pollutant of smoke and oils. It is white to light yellow crystalline solid. It has induced DNA damage and gene mutations in bacteria as well as gene mutations and transformation in several types of mammalian cell cultures.

Chemical Structure

Dibenz[a,h]anthracene
Dibenz[a,h]anthracene
CAS#53-70-3

Theoretical Analysis

MedKoo Cat#: 581255

Name: Dibenz[a,h]anthracene

CAS#: 53-70-3

Chemical Formula: C22H14

Exact Mass: 278.1096

Molecular Weight: 278.35

Elemental Analysis: C, 94.93; H, 5.07

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
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Related CAS #
No Data
Synonym
Dibenz[a,h]anthracene; DB(a,h)A; benzo[k]tetraphene; 1,2:5,6-Dibenzanthracene; NSC 22433; NSC22433; NSC-22433;
IUPAC/Chemical Name
1,2:5,6-Dibenzanthracene
InChi Key
LHRCREOYAASXPZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H14/c1-3-7-19-15(5-1)9-11-17-14-22-18(13-21(17)19)12-10-16-6-2-4-8-20(16)22/h1-14H
SMILES Code
C12=CC=CC=C1C=CC3=CC4=C5C(C=CC=C5)=CC=C4C=C32
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 278.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Padilla-Chavarría HI, Guizado TR, Pimentel AS. Molecular dynamics of dibenz[a,h]anthracene and its metabolite interacting with lung surfactant phospholipid bilayers. Phys Chem Chem Phys. 2015 Aug 28;17(32):20912-22. doi: 10.1039/c5cp01443c. Epub 2015 Jul 27. PubMed PMID: 26214736. 2: Chang RL, Wood AW, Huang MT, Xie JG, Cui XX, Reuhl KR, Boyd DR, Lin Y, Shih WJ, Balani SK, Yagi H, Jerina DM, Conney AH. Mutagenicity and tumorigenicity of the four enantiopure bay-region 3,4-diol-1,2-epoxide isomers of dibenz[a,h]anthracene. Carcinogenesis. 2013 Sep;34(9):2184-91. doi: 10.1093/carcin/bgt164. Epub 2013 May 13. PubMed PMID: 23671133; PubMed Central PMCID: PMC3765047. 3: Malik AI, Rowan-Carroll A, Williams A, Lemieux CL, Long AS, Arlt VM, Phillips DH, White PA, Yauk CL. Hepatic genotoxicity and toxicogenomic responses in Muta™Mouse males treated with dibenz[a,h]anthracene. Mutagenesis. 2013 Sep;28(5):543-54. doi: 10.1093/mutage/get031. Epub 2013 Jun 21. PubMed PMID: 23793610. 4: Kim JH, Kim WK. Use of the Integrated Biomarker Response to Measure the Effect of Short-term Exposure to Dibenz[a,h]anthracene in Common carp (Cyprinus carpio). Bull Environ Contam Toxicol. 2016 Apr;96(4):496-501. doi: 10.1007/s00128-015-1726-y. Epub 2016 Jan 7. PubMed PMID: 26744022. 5: Mannes PZ, Onyango EO, Gribble GW. Triple Benzannulation of Naphthalene via a 1,3,6-Naphthotriyne Synthetic Equivalent. Synthesis of Dibenz[a,c]anthracene. J Org Chem. 2015 Nov 6;80(21):11189-92. doi: 10.1021/acs.joc.5b01972. Epub 2015 Oct 20. Erratum in: J Org Chem. 2015 Dec 18;80(24):12746. PubMed PMID: 26452053. 6: Juhasz AL, Stanley GA, Britz ML. Metabolite repression inhibits degradation of benzo[a]pyrene and dibenz[a,h]anthracene by Stenotrophomonas maltophilia VUN 10,003. J Ind Microbiol Biotechnol. 2002 Feb;28(2):88-96. PubMed PMID: 12074057. 7: Lubet RA, Connolly GM, Nebert DW, Kouri RE. Dibenz[a,h]anthracene-induced subcutaneous tumors in mice. Strain sensitivity and the role of carcinogen metabolism. Carcinogenesis. 1983;4(5):513-7. PubMed PMID: 6850980. 8: Paquette JA, Yardley CJ, Psutka KM, Cochran MA, Calderon O, Williams VE, Maly KE. Dibenz[a,c]anthracene derivatives exhibiting columnar mesophases over broad temperature ranges. Chem Commun (Camb). 2012 Aug 25;48(66):8210-2. doi: 10.1039/c2cc33407k. Epub 2012 Jul 11. PubMed PMID: 22781447. 9: Dibenz[a,h]anthracene. IARC Monogr Eval Carcinog Risk Chem Hum. 1983 Dec;32:299-308. PubMed PMID: 6586661. 10: Koizumi TA, Hariu T, Sei Y. Crystal structure of 1,13,14-tri-aza-dibenz[a,j]anthracene 1,1,2,2-tetra-chloro-ethane monosolvate. Acta Crystallogr E Crystallogr Commun. 2015 May 23;71(Pt 6):681-3. doi: 10.1107/S2056989015009263. eCollection 2015 Jun 1. PubMed PMID: 26090149; PubMed Central PMCID: PMC4459339. 11: National Toxicology Program. Polycyclic aromatic hydrocarbons: 15 Listings - benz[a]anthracene, benzo[b]fluoranthene, benzo[j]fluoranthene, benzo[k]fluoranthene, benzo[a]pyrene, dibenz[a,h]acridine, dibenz[a,j]acridine, dibenz[a,h]anthracene, 7H-dibenzo[c,g]carbazole, dibenzo[a,e]pyrene, dibenzo[a,h]pyrene, dibenzo[a,i]pyrene, dibenzo[a,l]pyrene, indeno[1,2,3-cd]pyrene, 5-methylchrysene. Rep Carcinog. 2011;12:353-61. PubMed PMID: 21863085. 12: VANDUUREN BL. THE METABOLISM OF DIBENZ(A,H)ANTHRACENE. Acta Unio Int Contra Cancrum. 1963;19:524-7. PubMed PMID: 14050597. 13: AR FFMANN E, CHRISTENSEN BC. Studies on the newt test for carcinogenicity. 1. Benzo[a]pyrene, dibenz[a,h] anthracene and 3-methylcholanthrene. Acta Pathol Microbiol Scand. 1961;52:330-42. PubMed PMID: 14036848. 14: Duncan ME, Brookes P. Metabolism and macromolecular binding of dibenz(a,c)anthracene and dibenz(a,h)anthracene by mouse embryo cells in culture. Int J Cancer. 1972 Mar 15;9(2):349-52. PubMed PMID: 5064938. 15: LIJINSKY W, CEFIS F, GARCIA H, SAFFIOTTI U. SKIN TUMORIGENESIS BY DIBENZ(A,H)ANTHRACENE MODIFIED BY ITS HYDROGENATED DERIVATIVES. J Natl Cancer Inst. 1965 Jan;34:7-12. PubMed PMID: 14287284. 16: Slaga TJ, Viaje A, Buty SG, Bracken WM. Dibenz[a,c]anthracene: a potent inhibitor of skin-tumor initiation by 7,12-dimethylbenz[a]anthracene. Res Commun Chem Pathol Pharmacol. 1978 Mar;19(3):477-83. PubMed PMID: 418469. 17: MacNicoll AD, Burden PM, Rattle H, Grover PL, Sims P. The formation of dihydrodiols in the chemical or enzymic oxidation of dibenz[a,c]anthracene, dibenz[a,h]-anthracene and chrysene. Chem Biol Interact. 1979 Oct;27(2-3):365-79. PubMed PMID: 115599. 18: Fuchs J, Mlcoch J, Oesch F, Platt KL. Characterization of highly polar DNA adducts derived from dibenz[A,H]anthracene (DBA), 3,4-dihydroxy-3,4-dihydro-DBA, and 3,4,10,11-tetrahydroxy-3,4,10,11-tetrahydro-DBA. Toxicol Ind Health. 1993 May-Jun;9(3):503-9. PubMed PMID: 8367889. 19: Mannes PZ, Onyango EO, Gribble GW. Correction to "Triple Benzannulation of Naphthalene via a 1,3,6-Naphthotriyne Synthetic Equivalent. Synthesis of Dibenz[a,c]anthracene". J Org Chem. 2015 Dec 18;80(24):12746. doi: 10.1021/acs.joc.5b02627. Epub 2015 Nov 24. PubMed PMID: 26600209. 20: Frank H, Funk M, Oesch F, Platt KL. Synthesis, absolute configuration, and bacterial mutagenicity of the 8 stereoisomeric vicinal diol epoxides at the terminal benzo ring of carcinogenic dibenz[a,h]anthracene. Chem Res Toxicol. 2011 Dec 19;24(12):2258-68. doi: 10.1021/tx200398b. Epub 2011 Nov 16. PubMed PMID: 22087540.