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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-05-06 10:25:57 UTC
Update Date2020-10-09 21:09:11 UTC
HMDB IDHMDB0012322
Secondary Accession Numbers
  • HMDB12322
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
Data?1582753041
Synonyms
ValueSource
2-HydroxynaphthaleneChEBI
2-NaphthalenolChEBI
beta-HydroxynaphthaleneChEBI
beta-NaphtholChEBI
b-HydroxynaphthaleneGenerator
Β-hydroxynaphthaleneGenerator
b-NaphtholGenerator
Β-naphtholGenerator
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
2-Naphthol, 8-(14)C-labeledHMDB
2-Naphthol, magnesium saltHMDB
2-Naphthol, potassium saltHMDB
2-Naphthol, titanium(4+) saltHMDB
2-Naphthol, 7-(14)C-labeledHMDB
2-Naphthol, (1+)HMDB
2-Naphthol, 1,4,5,8-(14)C4-labeledHMDB
2-Naphthol, sodium saltHMDB
2-Naphthol, bismuth saltHMDB
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 KeyJWAZRIHNYRIHIV-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • 1-hydroxy-2-unsubstituted benzenoid
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Indirect biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.49 m³·mol⁻¹ChemAxon
Polarizability15.56 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)splash10-0006-2900000000-59876f73d937e3fff0c1Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-2900000000-59876f73d937e3fff0c1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0900000000-2b4afdf032e4268cf0dbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-8950000000-be69afc3a0e419124c04Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0002-0900000000-150b753c58953122f7a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0002-0900000000-3ed11eab13f522e296d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0002-0900000000-76ad2ee08369a5c72727Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-014j-0900000000-668149fa5169e936b8ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-014i-0900000000-818a664d833b009956caSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-014i-1900000000-cfdbc5ded35ac6d127e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-016u-3900000000-7581b81c891ce2121e30Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-016u-6900000000-ecc855690e59bfdd5598Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-016u-9800000000-68d9b962e8fe93336126Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-016r-9400000000-9eeb688197da71b8a3bcSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-0900000000-820d3a81dfc9463584ebSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-000i-9000000000-41143d019e9e3192e3a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-7b3aeb4e0f86148dab68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-a5c6a08b3ea484ba1d0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-2900000000-ecd1849d7a9f7a9bcac8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-e1a1f37ba96a4bf71d70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-e1a1f37ba96a4bf71d70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-019880a3b2ccbcc83a87Spectrum
MSMass Spectrum (Electron Ionization)splash10-00kf-3900000000-9ba2c98085c1cfb979aeSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Phenol Explorer Compound IDNot Available
FooDB IDFDB000877
KNApSAcK IDNot Available
Chemspider ID8341
KEGG Compound IDC11713
BioCyc IDCPD-8131
BiGG IDNot Available
Wikipedia Link2-Naphthol
METLIN IDNot Available
PubChem Compound8663
PDB ID03V
ChEBI ID10432
Food Biomarker OntologyNot Available
VMH IDM00668
MarkerDB IDMDB00029788
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. [PubMed: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. [PubMed: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. [PubMed:18856458 ]