Showing Compound Card for 2-Naphthol (CDB005036)

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Record Information
Version1.0
Created at2020-04-17 19:02:49 UTC
Updated at2021-01-04 18:48:58 UTC
CannabisDB IDCDB005036
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2-Naphthol
Description2-Naphthol, also known as beta-naphthol, 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. 2-Naphthol exists as a colorless crystalline solid and has a faint, phenol-like odor. It is 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. Industrially, 2-Naphthol is used in the production of 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 polycyclic aromatic hydrocarbons (PAHs) and pesticides such as chlorpyrifos (PMID 24093754 ). PAH exposures may include exposure to naphthalene in older types of mothballs, fires that produce polyaromatic hydrocarbons (PAHs), and tobacco smoke. Beta-Naphthol is one of several phenolic compounds found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight144.17
Monoisotopic Molecular Weight144.0575
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00kf-3900000000-9ba2c98085c1cfb979ae2014-09-20View Spectrum
GC-MS2-Naphthol, non-derivatized, GC-MS Spectrumsplash10-0006-2900000000-59876f73d937e3fff0c1Spectrum
GC-MS2-Naphthol, non-derivatized, GC-MS Spectrumsplash10-0006-2900000000-59876f73d937e3fff0c1Spectrum
Predicted GC-MS2-Naphthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-0900000000-2b4afdf032e4268cf0dbSpectrum
Predicted GC-MS2-Naphthol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fk9-8950000000-be69afc3a0e419124c04Spectrum
Predicted GC-MS2-Naphthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Naphthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0002-0900000000-150b753c58953122f7a02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0002-0900000000-3ed11eab13f522e296d02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0002-0900000000-76ad2ee08369a5c727272020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-014j-0900000000-668149fa5169e936b8cc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-014i-0900000000-818a664d833b009956ca2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-014i-1900000000-cfdbc5ded35ac6d127e82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-016u-3900000000-7581b81c891ce2121e302020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-016u-6900000000-ecc855690e59bfdd55982020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-016u-9800000000-68d9b962e8fe933361262020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-016r-9400000000-9eeb688197da71b8a3bc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-0900000000-820d3a81dfc9463584eb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-000i-9000000000-41143d019e9e3192e3a92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-014i-0900000000-8a33e2a4035f1d5db4c62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-00kf-0900000000-b57369b32440fe60da1d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0006-0900000000-95369892ad06085feeaa2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0006-0900000000-4359d09beb852a6b4d8d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-014j-1900000000-3f45d855eafad75b3a672021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-014j-2900000000-949ec470c0e3ac2ca5b22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0006-0900000000-ec57dc12ddf60a2741f02021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-7b3aeb4e0f86148dab682016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-a5c6a08b3ea484ba1d0d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-2900000000-ecd1849d7a9f7a9bcac82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-e1a1f37ba96a4bf71d702016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-e1a1f37ba96a4bf71d702016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-019880a3b2ccbcc83a872016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0012322
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Sreekanth R, Prasanthkumar KP, Sunil Paul MM, Aravind UK, Aravindakumar CT: Oxidation reactions of 1- and 2-naphthols: an experimental and theoretical study. J Phys Chem A. 2013 Nov 7;117(44):11261-70. doi: 10.1021/jp4081355. Epub 2013 Oct 29. [PubMed:24093754 ]