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Record Information
Version3.6
Creation Date2009-05-06 10:25:57 UTC
Update Date2016-02-11 01:24:18 UTC
HMDB IDHMDB12322
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Naphthol
Description2-Naphthol is a colorless crystalline solid and an isomer of 1-naphthol, differing by the location of the hydroxyl group on naphthalene. The naphthols are naphthalene homologues of phenol, with the hydroxyl group being more reactive than in the phenols. 2-Naphthol has several different uses including dyes, pigments, fats, oils, insecticides, pharmaceuticals, perfumes, antiseptics, synthesis of fungicides, and antioxidants for rubber. Detection of 2-Naphthol in urine usually results from long-term persistent exposure to pesticides such as chlorpyrifos, but also due to exposure to naphthalene in older types of mothballs, fires that produce polyaromatic hydrocarbons (PAHs), and tobacco smoke.
Structure
Thumb
Synonyms
ValueSource
2-NaphthalenolChEBI
beta-HydroxynaphthaleneChEBI
beta-NaphtholChEBI
b-HydroxynaphthaleneGenerator
β-hydroxynaphthaleneGenerator
b-NaphtholGenerator
β-naphtholGenerator
2-HydroxynaphthaleneHMDB
2-NaftolHMDB
2-NaftoloHMDB
2-NaphtolHMDB
Antioxygene BNHMDB
Azogen developer aHMDB
beta-MonoxynaphthaleneHMDB
beta-NaftolHMDB
beta-NaftoloHMDB
beta-Naphthyl alcoholHMDB
beta-Naphthyl hydroxideHMDB
beta-NaphtolHMDB
beta-NaptholHMDB
Beta.-hydroxynaphthaleneHMDB
BetanaphtholHMDB
Developer BNHMDB
HydronaphtholHMDB
IsonaphtholHMDB
Naphthol bHMDB
TrimetinHMDB
Chemical FormulaC10H8O
Average Molecular Weight144.1699
Monoisotopic Molecular Weight144.057514878
IUPAC Namenaphthalen-2-ol
Traditional Nameβ naphthol
CAS Registry Number135-19-3
SMILES
OC1=CC2=CC=CC=C2C=C1
InChI Identifier
InChI=1S/C10H8O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11H
InChI KeyInChIKey=JWAZRIHNYRIHIV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthols and derivatives
Direct ParentNaphthols and derivatives
Alternative Parents
Substituents
  • 2-naphthol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point123 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.70HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.72 mg/mLALOGPS
logP2.93ALOGPS
logP2.66ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)9.78ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.49 m3·mol-1ChemAxon
Polarizability15.56 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-00kf-3900000000-9ba2c98085c1cfb979aeView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified0.00183 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.00183 umol/mmol creatinineAdult (>18 years old)MaleRoofers (post shift) details
UrineDetected and Quantified0.0028 (0.0025-0.0031) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.00315 (0.00278-0.00357) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
UrineDetected and Quantified0.00259 (0.00234-0.00293) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.0032 (0.0029-0.0038) umol/mmol creatinineAdult (>18 years old)MaleIdiopathic infertility details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000877
KNApSAcK IDNot Available
Chemspider ID8341
KEGG Compound IDC11713
BioCyc IDCPD-8131
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12322
Metagene LinkHMDB12322
METLIN IDNot Available
PubChem Compound8663
PDB ID03V
ChEBI ID10432
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. COLOMB D, TISSOT A: [2nd Case of dermatitis from betanaphthol with reticular reactions]. Lyon Med. 1956 Nov 4;88(45):423-4. [13386410 ]
  2. PATTERSON SJ, LERRIGO AF: Betanaphthol in gelatin capsules; its use as a preservative, with a method for its determination. Q J Pharm Pharmacol. 1947 Apr-Jun;20(2):83-6. [20260560 ]
  3. VORONEOV II: [Effect of temperature in the sulphonating of betanaphtol for production of 2,6,8-naphtaldisulphonic acid]. Zhurnal Prikl Him. 1947 May;20(5):464-6. [18856458 ]