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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:32:24 UTC
Update Date2020-02-26 21:44:19 UTC
HMDB IDHMDB0029751
Secondary Accession Numbers
  • HMDB29751
Metabolite Identification
Common NameNaphthalene
DescriptionNaphthalene, also known as naftaleno or albocarbon, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Naphthalene is possibly neutral. Naphthalene is a dry, pungent, and tar tasting compound. Outside of the human body, Naphthalene is found, on average, in the highest concentration within a few different foods, such as black walnuts, corns, and cloves. Naphthalene has also been detected, but not quantified in, several different foods, such as green bell peppers, orange bell peppers, rices, yellow bell peppers, and red bell peppers. This could make naphthalene a potential biomarker for the consumption of these foods. Naphthalene was once the primary ingredient in mothballs, though its use has largely been replaced in favor of alternatives such as 1,4-dichlorobenzene. Naphthalene is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Inhalation of naphthalene vapor has been associated with headaches, nausea, vomiting and dizziness. Naphthalene is the most abundant single component of coal tar so most of it is now industrially derived from coal tar.
Structure
Data?1582753459
Synonyms
ValueSource
NaftalenoChEBI
NaftalinaChEBI
NaphtaleneChEBI
NaphtalineChEBI
NaphthalenChEBI
NaphthalinChEBI
AlbocarbonHMDB
Camphor tarHMDB
Moth ballsHMDB
Moth flakesHMDB
MothballsHMDB
NaftalenHMDB
NaphthalineHMDB
NaphtheneHMDB
Tar camphorHMDB
TolboxaneHMDB
White tarHMDB
Chemical FormulaC10H8
Average Molecular Weight128.1705
Monoisotopic Molecular Weight128.062600256
IUPAC Namenaphthalene
Traditional Namenaphthalene
CAS Registry Number91-20-3
SMILES
C1=CC2=CC=CC=C2C=C1
InChI Identifier
InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
InChI KeyUFWIBTONFRDIAS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Indirect biological role:

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point80.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.031 mg/mL at 25 °CNot Available
LogP3.30Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.066 g/LALOGPS
logP3.33ALOGPS
logP2.96ChemAxon
logS-3.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.51 m³·mol⁻¹ChemAxon
Polarizability14.56 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-28274068093bf0319e30Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-10810744223497787156Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-f640b15d5ebd285008e9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-2900000000-837afe39d2806871be73Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-5900000000-262e4b8e72f3d3fa0593Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-3900000000-0e32d0a2d4bb6373bea3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-34ade0e20ab7aa4d4e7fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-c780f74ca6838fbab7d8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4900000000-b2e474b4d7508faeddc3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-7900000000-43781a61560faeff786dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0900000000-7a87251d344c519a4335Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-004i-0900000000-0532459557fd0c543587Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-1900000000-5a22b095f0a190f1b978Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-28274068093bf0319e30Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-10810744223497787156Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-f640b15d5ebd285008e9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-2900000000-837afe39d2806871be73Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-5900000000-262e4b8e72f3d3fa0593Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-3900000000-0e32d0a2d4bb6373bea3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-34ade0e20ab7aa4d4e7fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-c780f74ca6838fbab7d8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4900000000-b2e474b4d7508faeddc3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-7900000000-43781a61560faeff786dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0900000000-7a87251d344c519a4335Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-1900000000-35bf92cf7a210b27759bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-9058dd9b60d558e52773Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-9058dd9b60d558e52773Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1900000000-91e4df79f1f59e0c0465Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8575b97da509996b8151Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-8575b97da509996b8151Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-ff7fd755c09159064a33Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-2900000000-1f03568d4331683921b4Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Breath
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAsthma details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
Associated Disorders and Diseases
Disease References
Asthma
  1. van de Kant KD, van Berkel JJ, Jobsis Q, Lima Passos V, Klaassen EM, van der Sande L, van Schayck OC, de Jongste JC, van Schooten FJ, Derks E, Dompeling E, Dallinga JW: Exhaled breath profiling in diagnosing wheezy preschool children. Eur Respir J. 2013 Jan;41(1):183-8. doi: 10.1183/09031936.00122411. [PubMed:23277518 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000954
KNApSAcK IDC00001259
Chemspider ID906
KEGG Compound IDC00829
BioCyc IDNAPHTHALENE
BiGG IDNot Available
Wikipedia LinkNaphthalene
METLIN IDNot Available
PubChem Compound931
PDB IDNPY
ChEBI ID16482
Food Biomarker OntologyNot Available
VMH IDNPTHL
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Pandya U, Saini MK, Jin GF, Awasthi S, Godley BF, Awasthi YC: Dietary curcumin prevents ocular toxicity of naphthalene in rats. Toxicol Lett. 2000 Jun 5;115(3):195-204. [PubMed:10814889 ]
  2. Yen KM, Serdar CM: Genetics of naphthalene catabolism in pseudomonads. Crit Rev Microbiol. 1988;15(3):247-68. [PubMed:3288442 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .