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213942

Sigma-Aldrich

3-Methylcholanthrene

98%

Synonym(s):

20-Methylcholanthrene, Methylcholanthrene

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About This Item

Empirical Formula (Hill Notation):
C21H16
CAS Number:
56-49-5
Molecular Weight:
268.35
Beilstein/REAXYS Number:
1913890
EC Number:
200-276-4
MDL number:
MFCD00003704
UNSPSC Code:
12352005
PubChem Substance ID:
57647926
NACRES:
NA.25

assay

98%

form

solid

bp

280 °C/80 mmHg (lit.)

mp

178-180 °C (lit.)

SMILES string

Cc1ccc2cc3c(ccc4ccccc34)c5CCc1c25

InChI

1S/C21H16/c1-13-6-7-15-12-20-17-5-3-2-4-14(17)8-9-18(20)19-11-10-16(13)21(15)19/h2-9,12H,10-11H2,1H3

InChI key

PPQNQXQZIWHJRB-UHFFFAOYSA-N

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Application

3-Methylcholanthrene has been used to assess its tumor initiation activity by Bhas 42 cell transformation assay. It has also been used to induce the activity of cytochrome P450.

Biochem/physiol Actions

3-Methylcholanthrene is a carcinogen used to induce transformation of cultured cells. It is also used to induce fibrosarcomas and skin carcinomas in laboratory animals. 3-methylcholanthrene is a potent aryl hydrocarbon receptor agonist.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H350,H413

Hazard Classifications

Aquatic Chronic 4 - Carc. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Nadine Y Crowe et al.
The Journal of experimental medicine, 196(1), 119-127 (2002-07-03)
Natural killer (NK) T cells initiate potent antitumor responses when stimulated by exogenous factors such as interleukin (IL)-12 or alpha-galactosylceramide (alpha-GalCer), however, it is not clear whether this reflects a physiological role for these cells in tumor immunity. Through adoptive
A high-throughput Bhas 42 cell transformation assay for the determination of the carcinogenicity of three herbal extracts
Pu J, et al.
Fundamental Toxicological Sciences, 3(4), 157-166 (2016)
Simple machine perfusion significantly enhances hepatocyte yields of ischemic and fresh rat livers
Izamis ML, et al.
Cell medicine, 4(3), 109-123 (2013)
Aryl Hydrocarbon Receptor: A New Player of Pathogenesis and Therapy in Cardiovascular Diseases
Yi T, et al.
BioMed Research International, 1-11 (2018)
Elin Swedenborg et al.
Molecular and cellular endocrinology, 362(1-2), 39-47 (2012-05-29)
The two estrogen receptor isoforms ERα and ERβ mediate biological effects of estrogens, but are also targets for endocrine disruptive chemicals (EDCs), compounds that interfere with hormonal signaling. 3-Methylcholanthrene (3-MC) and dioxin (TCDD) are EDCs and prototypical aryl hydrocarbon receptor
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