ContaminantDB: Phenanthrene

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:21 UTC

Update Date

2026-03-31 17:46:26 UTC

Accession Number

CHEM000215

Identification

Common Name

Phenanthrene

Class

Small Molecule

Description

Phenanthrene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are chemicals that are formed during the incomplete burning of 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
HPV EPA Chemicals
IARC Carcinogens Group 3
My Exposome Chemicals
STOFF IDENT Compounds
Suspected Compounds – Schymanski Project
T3DB toxins
Tobacco Smoke Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Food Toxin
Industrial By-product/Pollutant
Industrial/Workplace Toxin
Natural Compound
Organic Compound
Pollutant
Polycyclic Aromatic Hydrocarbon

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Phenanthracene	ChEBI
Phenanthren	ChEBI

Chemical Formula

C₁₄H₁₀

Average Molecular Mass

178.229 g/mol

Monoisotopic Mass

178.078 g/mol

CAS Registry Number

85-01-8

IUPAC Name

phenanthrene

Traditional Name

phenanthrene

SMILES

C1=CC=C2C(C=CC3=CC=CC=C23)=C1

InChI Identifier

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

InChI Key

YNPNZTXNASCQKK-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Naphthalene
Aromatic hydrocarbon
Polycyclic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

phenanthrenes (CHEBI:28851 )
ortho-fused polycyclic arene (CHEBI:28851 )
ortho-fused tricyclic hydrocarbon (CHEBI:28851 )
a ring (PHENANTHRENE-RING )

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

environmental contaminant

Physical Properties

State

Solid

Appearance

Colorless solid.

Experimental Properties

Property	Value
Melting Point	99.2°C
Boiling Point	Not Available
Solubility	0.00115 mg/mL at 25 °C [SCHWARZ,FP (1977)]

Predicted Properties

Property	Value	Source
Water Solubility	0.00034 g/L	ALOGPS
logP	4.55	ALOGPS
logP	3.95	ChemAxon
logS	-5.7	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	20.43 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-0900000000-73152ac8902a46a51b0e	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-0900000000-9b7fcb41bcf755cbca82	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-e07754c44a96c14bf7b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-0900000000-fcb3480d5ef5e6c5c5c9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-309955037ba0840b44e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-309955037ba0840b44e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-de91208ace0944a1f046	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-3900000000-2c8c905707eff1036da1	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: 700 mg/kg (Oral, Mouse) (7) LD50: 700 mg/kg (Intraperitoneal, Mouse) (7) LD50: 56 mg/kg (Intravenous, 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 volcanic 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 known antidote for PAHs. Exposure is usually handled with symptomatic treatment. (4)

Concentrations