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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-05-06 10:25:57 UTC
Update Date2021-10-13 05:35:01 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-NaftolChEBI
2-NaftoloChEBI
2-NaphthalenolChEBI
2-NaphtolChEBI
Antioxygene BNChEBI
Azogen developer aChEBI
beta-HydroxynaphthaleneChEBI
beta-NaftolChEBI
beta-NaftoloChEBI
beta-NaphtholChEBI
beta-Naphthyl alcoholChEBI
beta-Naphthyl hydroxideChEBI
beta-NaphtolChEBI
C.I. azoic coupling component 1ChEBI
C.I. developer 5ChEBI
Developer aChEBI
Developer amsChEBI
Developer BNChEBI
IsonaphtholChEBI
b-HydroxynaphthaleneGenerator
Β-hydroxynaphthaleneGenerator
b-NaftolGenerator
Β-naftolGenerator
b-NaftoloGenerator
Β-naftoloGenerator
b-NaphtholGenerator
Β-naphtholGenerator
b-Naphthyl alcoholGenerator
Β-naphthyl alcoholGenerator
b-Naphthyl hydroxideGenerator
Β-naphthyl hydroxideGenerator
b-NaphtolGenerator
Β-naphtolGenerator
beta-MonoxynaphthaleneHMDB
beta-NaptholHMDB
Beta.-hydroxynaphthaleneHMDB
BetanaphtholHMDB
HydronaphtholHMDB
Naphthol bHMDB
TrimetinHMDB
2-Naphthol, 8-(14)C-labeledMeSH, HMDB
2-Naphthol, magnesium saltMeSH, HMDB
2-Naphthol, potassium saltMeSH, HMDB
2-Naphthol, titanium(4+) saltMeSH, HMDB
2-Naphthol, 7-(14)C-labeledMeSH, HMDB
2-Naphthol, (1+)MeSH, HMDB
2-Naphthol, 1,4,5,8-(14)C4-labeledMeSH, HMDB
2-Naphthol, sodium saltMeSH, HMDB
2-Naphthol, bismuth saltMeSH, HMDB
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

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point123 °CNot Available
Boiling Point285.00 to 286.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility755 mg/L @ 25 °C (exp)The Good Scents Company Information System
LogP2.70HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.0631661259
DarkChem[M-H]-127.17431661259
DeepCCS[M+H]+128.45230932474
DeepCCS[M-H]-125.56530932474
DeepCCS[M-2H]-162.11930932474
DeepCCS[M+Na]+137.53230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-NaphtholOC1=CC2=CC=CC=C2C=C12834.2Standard polar33892256
2-NaphtholOC1=CC2=CC=CC=C2C=C11502.8Standard non polar33892256
2-NaphtholOC1=CC2=CC=CC=C2C=C11520.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Naphthol,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2C=CC=CC2=C11537.1Semi standard non polar33892256
2-Naphthol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C=CC=CC2=C11816.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Naphthol EI-B (Non-derivatized)splash10-0006-2900000000-59876f73d937e3fff0c12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Naphthol EI-B (Non-derivatized)splash10-0006-2900000000-59876f73d937e3fff0c12018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Naphthol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0900000000-2b4afdf032e4268cf0db2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Naphthol GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-8950000000-be69afc3a0e419124c042017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Naphthol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Naphthol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00kf-3900000000-9ba2c98085c1cfb979ae2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol Orbitrap 2V, positive-QTOFsplash10-0002-0900000000-150b753c58953122f7a02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol Orbitrap 3V, positive-QTOFsplash10-0002-0900000000-3ed11eab13f522e296d02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol Orbitrap 4V, positive-QTOFsplash10-0002-0900000000-76ad2ee08369a5c727272020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol Orbitrap 5V, positive-QTOFsplash10-014j-0900000000-668149fa5169e936b8cc2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol Orbitrap 6V, positive-QTOFsplash10-014i-0900000000-818a664d833b009956ca2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol Orbitrap 7V, positive-QTOFsplash10-014i-1900000000-cfdbc5ded35ac6d127e82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol Orbitrap 8V, positive-QTOFsplash10-016u-3900000000-7581b81c891ce2121e302020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol Orbitrap 10V, positive-QTOFsplash10-016u-6900000000-ecc855690e59bfdd55982020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol Orbitrap 12V, positive-QTOFsplash10-016u-9800000000-68d9b962e8fe933361262020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol Orbitrap 14V, positive-QTOFsplash10-016r-9400000000-9eeb688197da71b8a3bc2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol n/a 10V, positive-QTOFsplash10-014i-0900000000-820d3a81dfc9463584eb2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol n/a 10V, positive-QTOFsplash10-000i-9000000000-41143d019e9e3192e3a92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol 90V, Negative-QTOFsplash10-014i-0900000000-8a33e2a4035f1d5db4c62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol 75V, Negative-QTOFsplash10-00kf-0900000000-b57369b32440fe60da1d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol 45V, Negative-QTOFsplash10-0006-0900000000-95369892ad06085feeaa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol 60V, Negative-QTOFsplash10-0006-0900000000-4359d09beb852a6b4d8d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol 75V, Positive-QTOFsplash10-014j-1900000000-3f45d855eafad75b3a672021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol 90V, Positive-QTOFsplash10-014j-2900000000-949ec470c0e3ac2ca5b22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Naphthol 15V, Negative-QTOFsplash10-0006-0900000000-ec57dc12ddf60a2741f02021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Naphthol 10V, Positive-QTOFsplash10-0002-0900000000-7b3aeb4e0f86148dab682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Naphthol 20V, Positive-QTOFsplash10-0002-0900000000-a5c6a08b3ea484ba1d0d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Naphthol 40V, Positive-QTOFsplash10-014j-2900000000-ecd1849d7a9f7a9bcac82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Naphthol 10V, Negative-QTOFsplash10-0006-0900000000-e1a1f37ba96a4bf71d702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Naphthol 20V, Negative-QTOFsplash10-0006-0900000000-e1a1f37ba96a4bf71d702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Naphthol 40V, Negative-QTOFsplash10-0006-0900000000-019880a3b2ccbcc83a872016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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 IDC00052877
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
Good Scents IDrw1057991
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 ]