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Record Information
Version4.0
Creation Date2009-05-06 10:25:57 UTC
Update Date2017-09-27 08:26:59 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
Thumb
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-labeledMeSH
2-Naphthol, magnesium saltMeSH
2-Naphthol, potassium saltMeSH
2-Naphthol, titanium(4+) saltMeSH
2-Naphthol, 7-(14)C-labeledMeSH
2-Naphthol, (1+)MeSH
2-Naphthol, 1,4,5,8-(14)C4-labeledMeSH
2-Naphthol, sodium saltMeSH
2-Naphthol, bismuth saltMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassNaphthalenes
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

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-2900000000-59876f73d937e3fff0c1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-7b3aeb4e0f86148dab68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-a5c6a08b3ea484ba1d0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-2900000000-ecd1849d7a9f7a9bcac8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-e1a1f37ba96a4bf71d70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-e1a1f37ba96a4bf71d70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-019880a3b2ccbcc83a87View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00kf-3900000000-9ba2c98085c1cfb979aeView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    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
    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. [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 ]