7,12-Dimethylbenz[a]anthracene - ≥95% , CAS No.57-97-6

CAS: 57-97-6 Cat. No.: D113432 Molecular Weight: 256.34 Beilstein Registry Number: 1912135 EC Number: 200-359-5

GRADE & PURITY ≥95%

Synonyms

DMBA | 7,12-Dimethylbenz[a]anthracene, >=95% | 9,10-Dimethyl-1,2-benzanthracene | 7,12-Dimethylbenz[a]anthracene, >=98% | 9,10-DIMETHYL-1,2-BENZANTHRACENE [MI] | Dimethylbenzanthrene | EINECS 200-359-5 | NCGC00091518-05 | 9,2-benzanthracene | 9,2-benzanth

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

7,12-Dimethylbenz[a]anthracene has been used to induce skin cancer in mice, buccal pouch carcinogenesis in syrian golden hamsters and breast cancer in rats.

7,12-Dimethylbenz[a]anthracene is a polycyclic aromatic hydrocarbon. It is used in cancer research. It is a carcinogenic organic pollutant generated from the incomplete combustion of gasoline and coal.

Specifications

Synonyms

DMBA | 7, 12-Dimethylbenz[a]anthracene, >=95% | 9, 10-Dimethyl-1, 2-benzanthracene | 7, 12-Dimethylbenz[a]anthracene, >=98% | 9, 10-DIMETHYL-1, 2-BENZANTHRACENE [MI] | Dimethylbenzanthrene | EINECS 200-359-5 | NCGC00091518-05 | 9, 2-benzanthracene | 9, 2-benzanth

Specifications & Purity

≥95%

Biochemical and Physiological Mechanisms

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 leukem

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 488179984
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488179984
• Canonical Smiles: CC1=C2C=CC3=CC=CC=C3C2=C(C4=CC=CC=C14)C
• IUPAC Name: 7,12-dimethylbenzo[a]anthracene
• InChIKey: ARSRBNBHOADGJU-UHFFFAOYSA-N
• INCHI: 1S/C20H16/c1-13-16-8-5-6-9-17(16)14(2)20-18(13)12-11-15-7-3-4-10-19(15)20/h3-12H,1-2H3
• Isomeric SMILES: CC1=C2C=CC3=CC=CC=C3C2=C(C4=CC=CC=C14)C
• WGK Germany: 3
• RTECS: CW3850000
• Molecular Weight: 256.34
• Beilstein: 1912135
• Reaxy-Rn: 1912135
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1912135&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Phenanthrenes and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Phenanthrenes and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenanthrenes and derivatives
• Alternative Parents: Anthracenes Aromatic hydrocarbons Polycyclic hydrocarbons Unsaturated hydrocarbons
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Phenanthrene - Anthracene - Aromatic hydrocarbon - Polycyclic hydrocarbon - Unsaturated hydrocarbon - Hydrocarbon - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.
• External Descriptors: tetraphenes - ortho-fused polycyclic arene

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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VDR Tclin Vitamin D receptor (26531 Activities)

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TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

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PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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PTH1R Tclin Parathyroid hormone receptor (47172 Activities)

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THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

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RXRA Tclin Retinoid X receptor alpha (3637 Activities)

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AHR Tclin Aryl hydrocarbon receptor (1071 Activities)

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GBA1 Tclin Beta-glucocerebrosidase (14647 Activities)

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NR1H4 Tclin Bile acid receptor FXR (6228 Activities)

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NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)

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SMPD1 Tchem Sphingomyelin phosphodiesterase (13561 Activities)

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CASP1 Tchem Caspase-1 (6235 Activities)

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CASP7 Tchem Caspase-7 (3146 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

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ATM Tchem Serine-protein kinase ATM (4198 Activities)

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Lymphoblastoid cell (5959 Activities)

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HIF1A Tchem Hypoxia-inducible factor 1 alpha (6027 Activities)

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HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)

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KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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L3MBTL1 Tchem Lethal(3)malignant brain tumor-like protein 1 (14536 Activities)

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HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)

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GMNN Tbio Geminin (128009 Activities)

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RAB9A Tbio Ras-related protein Rab-9A (22488 Activities)

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

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ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)

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BAZ2B Tchem Bromodomain adjacent to zinc finger domain protein 2B (56204 Activities)

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Associated Targets(non-human)

ampC Beta-lactamase AmpC (62480 Activities)

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Cruzipain (33337 Activities)

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Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

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Salmonella typhimurium (15756 Activities)

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Plasmodium falciparum (966862 Activities)

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Luciferin 4-monooxygenase (66902 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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Nr1i2 Nuclear receptor subfamily 1 group I member 2 (14 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility in Toluene almost transparency
• Melt Point(°C): 122-125°C
• Molecular Weight: 256.300 g/mol
• XLogP3: 5.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 256.125 Da
• Monoisotopic Mass: 256.125 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 346.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yin Xuan, Zhang Bowen, Luo Yunjun.  (2018)  Preparation and Characterization of Efficient Flame-Retardant and Thermostability Two-Component Aqueous Varnish Coatings.  POLYMER SCIENCE SERIES B,  59  (6): (697-707).  [PMID:] [10.1134/S1560090417060094]