ContaminantDB: Anthracene

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:59:14 UTC

Update Date

2026-03-31 19:20:43 UTC

Accession Number

CHEM000551

Identification

Common Name

Anthracene

Class

Small Molecule

Description

Anthracene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are chemicals that are formed during the incomplete burning organic substances, such as fossil fuels. They are usually found as a mixture containing two or more of these compounds. (4)

Contaminant Sources

Clean Air Act Chemicals
ECHA Carcinogen
ECHA PBT
FooDB Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 3
My Exposome Chemicals
OECD HPV Chemicals
STOFF IDENT Compounds
Suspected Compounds – Schymanski Project
T3DB toxins
Tobacco Smoke Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Food Toxin
Natural Compound
Organic Compound
Pollutant
Polycyclic Aromatic Hydrocarbon

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Anthrazen	ChEBI
Anthracene, sodium salt, ion (1-)	HMDB

Chemical Formula

C₁₄H₁₀

Average Molecular Mass

178.229 g/mol

Monoisotopic Mass

178.078 g/mol

CAS Registry Number

120-12-7

IUPAC Name

anthracene

Traditional Name

anthracene

SMILES

C1=CC2=CC3=CC=CC=C3C=C2C=C1

InChI Identifier

InChI=1S/C14H10/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-10H

InChI Key

MWPLVEDNUUSJAV-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Not Available

Direct Parent

Anthracenes

Alternative Parents

Substituents

Anthracene
Aromatic hydrocarbon
Polycyclic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

anthracenes (CHEBI:35298 )
acene (CHEBI:35298 )
ortho-fused tricyclic hydrocarbon (CHEBI:35298 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Colorless solid.

Experimental Properties

Property	Value
Melting Point	215.0°C
Boiling Point	Not Available
Solubility	4.34e-05 mg/mL at 24°C [MAY,WE et al. (1983)]

Predicted Properties

Property	Value	Source
Water Solubility	0.00048 g/L	ALOGPS
logP	4.56	ALOGPS
logP	3.95	ChemAxon
logS	-5.6	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	58.96 m³·mol⁻¹	ChemAxon
Polarizability	20.61 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0900000000-d3d9e217ff8f2666316b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-57a407595d8d4d4f8360	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-57a407595d8d4d4f8360	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-1900000000-7b27938dfa3a7a68eaf4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-1441cd503a5c1f7bffa7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-1441cd503a5c1f7bffa7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-d151e8f9f566ca0e402f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-2afa14fa908f69024c44	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-2afa14fa908f69024c44	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0900000000-86e8a779c98b6b6a02ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-a5c7c61e51665431ac9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-a5c7c61e51665431ac9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-a5c7c61e51665431ac9b	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-2900000000-675a19db0c1732536f9c	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (4) ; inhalation (4)

Mechanism of Toxicity

The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (4, 5, 2, 3)

Metabolism

PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (4)

Toxicity Values

LD50: 1470-2440 mg/kg (Oral, Mouse) (7) LD50: 430 mg/kg (Intraperitoneal, Mouse) (7)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (6)

Uses/Sources

PAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (4)

Minimum Risk Level

Not Available

Health Effects

PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (4)

Symptoms

Acute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (1)

Treatment

There is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (4)

Concentrations

Status	Value	Unit	Sample Location	Reference

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0248460

FooDB ID

FDB006967

Phenol Explorer ID

Not Available

KNApSAcK ID

C00002864

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Lucien E. Bourson, Serge Y. Delavarenne, Pierre Tellier, “1,2,3,4,4a,9a-Hexahydro-9,10-anthracene-dione, its preparation and its application to the delignification of lignocellulosic materials.” U.S. Patent US4235666, issued June, 1929.

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17257678

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18565569

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19162536

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=7561049

5. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.

Anthracene (CHEM000551)

Structure for CHEM000551: Anthracene