Chrysene (CHEM000127)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (5)XML
Record Information
Version1.0
Creation Date2009-03-06 18:58:09 UTC
Update Date2026-03-31 19:21:31 UTC
Accession NumberCHEM000127
Identification
Common NameChrysene
ClassSmall Molecule
DescriptionChrysene 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 2B
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • 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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2,5,6-DibenzonaphthaleneChEBI
1,2-BenzophenanthreneChEBI
Benz[a]phenanthreneChEBI
Benzo[a]phenanthreneChEBI
ChrysenChEBI
Chemical FormulaC18H12
Average Molecular Mass228.288 g/mol
Monoisotopic Mass228.094 g/mol
CAS Registry Number218-01-9
IUPAC Namechrysene
Traditional Namechrysene
SMILESC1=CC=C2C(C=CC3=C2C=CC2=CC=CC=C32)=C1
InChI IdentifierInChI=1S/C18H12/c1-3-7-15-13(5-1)9-11-18-16-8-4-2-6-14(16)10-12-17(15)18/h1-12H
InChI KeyWDECIBYCCFPHNR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as chrysenes. Chrysenes are compounds containing the polyaromatic chrysene moiety, which consists of a benzene ring fused to a phenanthrene ring system to form Benzo[a]phenanthrene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassChrysenes
Direct ParentChrysenes
Alternative Parents
Substituents
  • Chrysene
  • Naphthalene
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceColorless solid.
Experimental Properties
PropertyValue
Melting Point258.2°C
Boiling PointNot Available
Solubility2e-06 mg/mL at 25 °C [MILLER,MM et al. (1985)]
Predicted Properties
PropertyValueSource
Water Solubility5.0e-06 g/LALOGPS
logP5.71ALOGPS
logP4.94ChemAxon
logS-7.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity75.41 m³·mol⁻¹ChemAxon
Polarizability26.55 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0190000000-feb74c065b2ddee5d227Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-b7159ca7c08c3b71bd95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-d6a81f78e33eddf5f623Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-0090000000-0ac1df0c431c6c822036Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-3a53674e8156110b1bedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-3a53674e8156110b1bedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090000000-b07df02ba42d33808729Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-1345c9a6e6eae7276959Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-1345c9a6e6eae7276959Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0090000000-96fab4943b7ee18d243fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-21ab23fa1007795bd0daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-21ab23fa1007795bd0daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090000000-8062207992d5862f74bbSpectrum
MSMass Spectrum (Electron Ionization)splash10-004i-0090000000-008c5314ed8ae5725e3aSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4)
Mechanism of ToxicityThe 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)
MetabolismPAH 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 ValuesLD50: >320 mg/kg (Intraperitoneal, Mouse) (7)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (6)
Uses/SourcesPAHs 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. Chrysene is also used in the manufacture of some wood preservatives and dyes. (4)
Minimum Risk LevelNot Available
Health EffectsPAHs 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)
SymptomsAcute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (1)
TreatmentThere is no known antidote for PAHs. Exposure is usually handled with symptomatic treatment. (4)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0250216
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-13772
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkChrysene
Chemspider ID8817
ChEBI ID51687
PubChem Compound ID9171
Kegg Compound IDC14222
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24128549
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24382467
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24519633