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Merck

442388

3-Methylcholanthrene

analytical standard

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About This Item

Empirical Formula (Hill Notation):
C21H16
CAS Number:
56-49-5
Molecular Weight:
268.35
EC Number:
200-276-4
UNSPSC Code:
12352200
PubChem Substance ID:
24867823
Beilstein/REAXYS Number:
1913890
MDL number:
MFCD00003704
NACRES:
NA.24

Product Name

3-Methylcholanthrene, analytical standard

InChI key

PPQNQXQZIWHJRB-UHFFFAOYSA-N

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

SMILES string

Cc1ccc2cc3c(ccc4ccccc34)c5CCc1c25

grade

analytical standard

CofA

current certificate can be downloaded

packaging

ampule of 50 mg

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

bp

280 °C/80 mmHg (lit.)

mp

178-180 °C (lit.)

application(s)

environmental

format

neat

storage temp.

2-30°C

Quality Level

200

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

General description

3-Methylcholanthrene, a potent polycyclic aryl hydrocarbon receptor agonist, which is a carcinogen that can be obtained as a byproduct of combustion of various organic substances like coal, garbage, gas and oil. It suppresses the proliferation of human umbilical vascular endothelial cells.

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX3777
MKCW6709
MKCS1215
MKCN0004
MKCG5224

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Attenuation of polycyclic aromatic hydrocarbon (PAH)-mediated pulmonary carcinogenesis in mice by omega-3-fatty acids
Moorthy B, et al.
Faseb Journal, 31, 1067-1064 (2017)
Mechanism of p53-dependent apoptosis induced by 3-methylcholanthrene involvement of p53 phosphorylation and p38 MAPK
Kwon YW, et al.
The Journal of Biological Chemistry, 277, 1837-1844 (2002)
Molecular mechanisms of p21 and p27 induction by 3?methylcholanthrene, an aryl?hydrocarbon receptor agonist, involved in antiproliferation of human umbilical vascular endothelial cells
Pang P-H, et al.
Journal of Cellular Physiology, 215, 161-171 (2008)
3?Methylcholanthrene/Aryl?Hydrocarbon Receptor?Mediated Hypertension Through eNOS Inactivation
Chang C-C, et al.
Journal of Cellular Physiology, 232, 1020-1029 (2017)
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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