Acenaphthylene (CHEM000550)

Record Information
Version1.0
Creation Date2009-03-06 18:59:14 UTC
Update Date2026-03-31 19:20:40 UTC
Accession NumberCHEM000550
Identification
Common NameAcenaphthylene
ClassSmall Molecule
Description
Acenaphthylene 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
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Food Toxin
  • Natural Compound
  • Organic Compound
  • Pollutant
  • Polycyclic Aromatic Hydrocarbon
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Cyclopenta[de]naphthaleneChEBI
Acenaphthylene, radical ion (1-)HMDB
Chemical FormulaC12H8
Average Molecular Mass152.192 g/mol
Monoisotopic Mass152.063 g/mol
CAS Registry Number208-96-8
IUPAC Nameacenaphthylene
Traditional Nameacenaphthylene
SMILESC1=CC2=C3C1=CC=CC3=CC=C2
InChI IdentifierInChI=1S/C12H8/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-8H
InChI KeyHXGDTGSAIMULJN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acenaphthylenes. These are aromatic polycyclic compounds containing an acenaphthylene moiety. Acenaphthylene is a carbotricyclic compound, consisting of a naphthalene with positions C1 and C8 connected by an ethylene bridge.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAcenaphthylenes
Sub ClassNot Available
Direct ParentAcenaphthylenes
Alternative Parents
Substituents
  • Acenaphthylene
  • Naphthalene
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated hydrocarbon
  • Olefin
  • 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 Point92.5°C
Boiling PointNot Available
Solubility0.0161 mg/mL at 25°C [WALTERS,RW & LUTHY,RG (1984A)]
Predicted Properties
PropertyValueSource
Water Solubility0.0015 g/LALOGPS
logP3.9ALOGPS
logP3.33ChemAxon
logS-5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity51.9 m³·mol⁻¹ChemAxon
Polarizability17.1 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
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: 1700 mg/kg (Intraperitoneal, Rat) (7) LD50: 1760 mg/kg (Oral, Mouse) (7)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Acenaphthylene is found in creosotes, which are probably carcinogenic to humans (Group 2A). (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 vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (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 know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (4)
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0247900
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAcenaphthylene
Chemspider ID8807
ChEBI ID33081
PubChem Compound ID9161
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17824537
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24631927
3. 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.