D3254
Sigma

7,12-Dimethylbenz[a]anthracene

≥95%

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Synonym

1,4-Dimethyl-2,3-benzophenanthrene

9,10-Dimethyl-1,2-benzanthracene

DMBA

Molecular Formula

C₂₀H₁₆

Molecular Weight

256.34

CAS Number

57-97-6

Beilstein Registry Number

1912135

MDL number

MFCD00003600

PubChem Substance ID

24893738

EG/EC Number

200-359-5

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Descriptions

Biochem/physiol Actions

The oxidation of DMBA by P450 enzymes produces metabolites that form covalent adducts with DNA and the formation within DNA of depurinated abasic sites. It is most commonly used to induce skin or mammary tumors in animals, though it also can induce leukemias and tumors at other sites.

Properties

assay

≥95%

122-123 °C(lit.)

References

Reference

Devanesan, P.D., et al., Identification and quantitation of 7,12-dimethylbenz[a]anthracene-DNA adducts formed in mouse skin. Chem. Res. Toxicol. 6, 364-371, (1993) abstract

Chow, L.W., et al., A rat cell line derived from DMBA-induced mammary carcinoma. Life Sci. 73, 27-40, (2003) abstract

Ishikawa, T., et al., Inhibition of skin cancer by IP6 in vivo: initiation-promotion model. Anticancer Res. 19, 3749-3752, (1999) abstract

Sugiyama, T., et al., 7,12-DMBA-induced rat leukemia: a review with insights into future research. Leuk. Res. 26, 1053-1068, (2002) abstract

Kleiner, H.E., et al., Role of cytochrome p4501 family members in the metabolic activation of polycyclic aromatic hydrocarbons in mouse epidermis. Chem. Res. Toxicol. 17, 1667-1674, (2004) abstract

Merck

Merck 13,3262

Beilstein

Beil. 5,IV,2587

reference

Aldrich MSDS 1, 754:D / Corp MSDS 1 (1), 1352:C / FT-IR 2 (2), 1672:A / FT-IR 1 (1), 966:B / FT-NMR 1 (2), 54:B / IR-Spectra (3), 582:A / NMR-Reference 2 (1), 769:D / RegBook 1 (1), 1155:G / Sax 6, 1135 / Sigma FT-IR 1 (2), 497:C / Structure Index 1, 178:A:4

Safety

Hazard Codes

Risk Statements

45-22

Safety Statements

53-36/37-45

RIDADR

UN 3077 9/PG 3

WGK Germany

RTECS

CW3850000