3-Methylcholanthrene

Base Information

• Chemical Name: 3-Methylcholanthrene
• CAS No.: 56-49-5
• Deprecated CAS: 345299-31-2
• Molecular Formula: C21H16
• Molecular Weight: 268.358
• Hs Code.: 2902909090
• European Community (EC) Number: 200-276-4
• NSC Number: 21970
• UN Number: 3077
• UNII: 214U33M1RL
• DSSTox Substance ID: DTXSID0020862
• Nikkaji Number: J2.319A
• Wikipedia: Methylcholanthrene
• Wikidata: Q223099
• NCI Thesaurus Code: C29795
• Pharos Ligand ID: 9FCXVLUZKG5N
• Metabolomics Workbench ID: 54967
• ChEMBL ID: CHEMBL40583
• Mol file: 56-49-5.mol

Synonyms:20 Methylcholanthrene;20-Methylcholanthrene;3 Methylcholanthrene;3-Methylcholanthrene;Methylcholanthrene

Chemical Property of 3-Methylcholanthrene

Chemical Property:

• Appearance/Colour: yellow crystalline solid
• Vapor Pressure: 2.16E-09mmHg at 25°C
• Melting Point: 178-180ºC
• Refractive Index: 1.4664 (estimate)
• Boiling Point: 280 ºC 80 mm Hg(lit.)
• Flash Point: -5ºC
• PSA: 0.00000
• Density: 1.223 g/cm³
• LogP: 5.55320
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility.: 2.9ug/L(25 oC)
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 268.125200510
• Heavy Atom Count: 21
• Complexity: 399

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Methylcholanthrene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Powerful carcinogen.
• Hazard Codes: T,Xn,F
• Statements: 45-36-20/21/22-11-53
• Safety Statements: 53-36/37/39-45-36-26-16-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: CC1=C2CCC3=C2C(=CC4=C3C=CC5=CC=CC=C54)C=C1
• Recent ClinicalTrials: Autologous Dendritic Cells Loaded With Autologous Tumor Associated Antigens for Treatment of Advanced Epithelial Ovarian Carcinomas
• Description: 3-Methylcholanthrene (3-MC) is a member of the polycyclic aromatic hydrocarbon (PAH) family and is used as an experimental cancer research chemical. As other PAHs, 3-MC might be found in trace quantities in coal tar and heavy-end petroleum hydrocarbons.
• Uses: A carcinogen 3-MC is used experimentally as a positive control in cancer research and in biochemical research to induce specific forms of cytochrome P450. Other than this, there is no particular use for this chemical except as a possible chemical intermediate. 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.

Technology Process of 3-Methylcholanthrene

There total 36 articles about 3-Methylcholanthrene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

6-acetoxy-3-methylcholanthrene (78606-95-8) → methylcholanthrene (56-49-5)

Guidance literature:

With hydrogen iodide; hypophosphorous acid; In propionic acid; for 0.166667h; Heating;

DOI:10.1016/S0040-4039(01)90245-X DOI:10.1021/jo00132a026

Reference yield: 89.0%

C23H16O3 → methylcholanthrene (56-49-5)

Guidance literature:

With zinc; In acetic acid; for 15h; Heating;

DOI:10.1021/jo00077a045

Reference yield:

3-methyl-1,2,2a,3,4,5-hexahydro-benz[j]aceanthrylene (100260-10-4) → methylcholanthrene (56-49-5)

Guidance literature:

With selenium; at 320 - 340 ℃;

DOI:10.1021/ja01287a502

upstream raw materials:

3ξ-(2-amino-phenyl)-2-(8-methyl-acenaphthen-3-yl)-acrylic acid

3α,7α-diacetoxy-12-one-5β-cholan-24-oic acid

3-methyl-2,2a,3,4-tetrahydro-1H-benz[j]aceanthrylen-5-one

3α,7α-dihydroxy-12-oxo-5β-cholan-24-oic acid

Downstream raw materials:

3-methyl-11,12-dihydrocholanthrene

3-methyl-1,2,6,7,8,9,10,12b-octahydro-benz[j]aceanthrylene

3-Methyl-cholanthren-1-on

acetic acid-(3-methyl-cholanthren-1-yl ester)

Refernces

• 1、 Gimisis, Thanasis,Koreeda, Masato. "A Highly Efficient Synthesis of 3-Methylcholanthrene". . p. 7158 - 7161. Retrieved 2007/10/02.
• 2、 Jacobs, Stephen A.,Harvey, Ronald G.. "SYNTHESIS OF 3-METHYLCHOLANTHRENE". . p. 1093 - 1096. Retrieved 2007/10/02.