56-49-5 Usage
Uses
Used in Cancer Research:
3-Methylcholanthrene is used as a positive control in cancer research to induce specific forms of cytochrome P450. It is also used to assess its tumor initiation activity by Bhas 42 cell transformation assay.
Used in Biochemical Research:
3-Methylcholanthrene is used experimentally in biochemical research to induce specific forms of cytochrome P450, which are essential for the metabolism of drugs and other substances in the body.
Used as a Chemical Intermediate:
Although not a primary use, 3-Methylcholanthrene may serve as a possible chemical intermediate in the synthesis of other compounds.
Used in Coal Tar Products:
3-Methylcholanthrene is a component of coal tar products, which include coal tar, creosote, and coal tar pitch. These products are derived from the carbonization of bituminous coal and are known to contain carcinogenic components. Coal tar pitch, for example, is a black viscous liquid with an aromatic solvent odor, and it is used in various industrial applications.
Synthesis Reference(s)
The Journal of Organic Chemistry, 47, p. 2120, 1982 DOI: 10.1021/jo00132a026
Air & Water Reactions
Insoluble in water.
Reactivity Profile
3-METHYLCHOLANTHRENE can react with oxidizing materials. Ozone and chlorinating agents oxidize 3-METHYLCHOLANTHRENE.
Hazard
Powerful carcinogen.
Fire Hazard
Flash point data for 3-METHYLCHOLANTHRENE are not available; however, 3-METHYLCHOLANTHRENE is probably combustible.
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.
Safety Profile
Suspected carcinogen
with experimental carcinogenic,
neoplastigenic, and tumorigenic data. Poison
by intravenous and intraperitoneal routes.
Experimental teratogenic and reproductive
effects. Human mutation data reported.
When heated to decomposition it emits
acrid smoke and irritating fumes.
Potential Exposure
The coke-oven plant is the principal source of coal tar. The hot gases and vapors produced during the conversion of coal to coke are collected by means of a scrubber, which condenses the effluent into ammonia, water, crude tar, and other by-products. Crude tar is separated from the remainder of the condensate for refining and may undergo further processing. Employees may be exposed to pitch and creosote in metal and foundry operations; when installing electrical equipment; in construction, railway, utility; and briquette manufacturing.
Carcinogenicity
3-Methylcholanthrene is a rapid,
all-around neoplastic agent and a potent liver
tumorigen.
Environmental Fate
3-MC, when released to soil, adsorbs strongly to the soil and
does not leach. It does not biodegrade or hydrolyze significantly
but may evaporate from dry soil. If released to water, it is
expected to adsorb strongly to sediment and to bioconcentrate
in aquatic organisms. If released into the atmosphere, it may be
subject to direct photolysis because it absorbs strongly in the
ultraviolet (UV) spectrum of light. It may also react with peroxyl
radicals already present in the atmosphere. Its estimated
half-life in the atmosphere is 2.8 h. Considering an octanol/
water log concentration ratio of 6.42, a bioconcentration factor
of 45 000 has been estimated.
Shipping
UN1136 Coal tar distillates, flammable, Hazard Class: 3; Labels: 3-Flammable liquid
Toxicity evaluation
Metabolic activation of PAHs consists of oxidation of the rings
of unsubstituted PAHs. These oxidations are carried out by
mixed function oxidases of the liver, which contain cytochromes
P450 and P448 and require reduced nicotine adenine dinucleotide
and oxygen. In this oxidation, an epoxide intermediate is
formed that has been shown to have the requisite chemical
reactivity to bind covalently with DNA and histones and to serve
as the ultimate carcinogenic form of PAH. Administration of 3-
MC to rats increased hepatic nuclear proteins and caused
a turnover of protein of the endoplasmic reticulum. Studies of
14C amino acid incorporation showed that 3-MC causes
increased protein synthesis and reduced degradation of protein.
Incompatibilities
Incompatible with strong oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Phenols, such as creosote react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has pKa = 9.88). These materials are incompatible with strong reducing agents such as hydrides, nitrides, alkali metals, and sulfides. Flammable hydrogen gas is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (e.g., by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid
Waste Disposal
Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.
Check Digit Verification of cas no
The CAS Registry Mumber 56-49-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 6 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 56-49:
(4*5)+(3*6)+(2*4)+(1*9)=55
55 % 10 = 5
So 56-49-5 is a valid CAS Registry Number.
InChI:InChI=1/C21H16/c1-13-11-15-6-4-7-16-12-19-17-8-3-2-5-14(17)9-10-18(19)20(13)21(15)16/h2-10,12-13H,11H2,1H3
56-49-5Relevant articles and documents
A Highly Efficient Synthesis of 3-Methylcholanthrene
Gimisis, Thanasis,Koreeda, Masato
, p. 7158 - 7161 (2007/10/02)
A five-step synthesis of 3-methylcholanthrene (1) has been achieved starting from 5-methylhomophthalic anhydride and N,N-diethyl-1-naphthamide in 55percent overall yield.Treatment of a solution of the preformed lithium enolate of 5-methylhomophthalic anhydride (3) with an equimolar solution of 2-lithio-1-naphthamide (4), followed by acid hydrolysis, provides cleanly the spirobislactone 5 in 80percent overall yield.In addition, the synthesis features a unique, highly selective double Friedel-Crafts cyclization of the aryl diacid 2 with PPA to give rise, after acetylation, to keto acetate 6.
Synthesis of Polycyclic Aromatic Hydrocarbons via a Novel Annelation Method
Harvey, Ronald G.,Cortez, Cecilia,Jacobs, Stephen A.
, p. 2120 - 2125 (2007/10/02)
A new general synthetic approach to polycyclic aromatic hydrocarbons is described.The method is based on the convenient availability of o-lithioarylamides from regiospecific metalation of N,N-diethylarylamides with alkyllithium-amine reagents.Addition of the o-lithioarylamide to an aryl ketone or aldehyde affords a lactone.Reduction of the latter with zinc and alkali or HI generates the free acid which undergoes cyclization with ZnCl2 and Ac2O and reduction with zinc and alkali or HI to furnish the fully aromatic polyarene.Compounds synthesized via this route include 3-methylcholanthrene, benzanthracene, dibenzanthracene, dibenzanthracene, benzopyrene, and their methyl derivatives.Overall yields are generally good.Competitive enolate anion formation depresses the yield in the initial step in the reactions of enolizable ketones.However, this pathway can be suppressed with substantial improvement in yield through deuterium exchange of the hydrogens α to the carbonyl.The last three steps of the general method can be condensed to only one step through reductive cyclization of the lactone intermediates with hydriodic acid in acetic acid.While tertiary lactones are resistant to HI under these conditions, the corresponding free acids undergo reductive cyclization under similar conditions.
SYNTHESIS OF 3-METHYLCHOLANTHRENE
Jacobs, Stephen A.,Harvey, Ronald G.
, p. 1093 - 1096 (2007/10/02)
A novel synthesis of 3-methylcholanthrene is described which is operationally simpler than the method in current use and is potentially applicable to the synthesis of a wide range of other polycyclic hydrocarbons and their oxidized carcinogenic metabolites.
