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Showing Compound 2-Naphthol (FDB000877)

Record Information
Version1.0
Creation date2010-04-08 22:04:45 UTC
Update date2018-05-28 22:36:45 UTC
Primary IDFDB000877
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Naphthol
DescriptionTrace constituent of essential oils 2-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.; 2-Naphthol, or ?-naphthol, is a colorless crystalline solid with the formula C10H7OH. 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. Both isomers are soluble in simple alcohols, ethers, and chloroform. They can be used in the production of dyes and in organic synthesis. For example, 2-naphthol reacts to form BINOL.
CAS Number135-19-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
β-hydroxynaphthalenebiospider
β-monoxynaphthalenebiospider
β-naftolbiospider
β-naftolobiospider
β-naphtholbiospider
β-naphthyl alcoholbiospider
β-naphthyl hydroxidebiospider
β-naphtolbiospider
β-naphtol(german)biospider
β-naptholbiospider
βnaphtholbiospider
2-Naphthalenol, 9CIdb_source
2-naphthol, (1+)biospider
2-naphthol, 1,4,5,8-(14)C4-labeledbiospider
2-naphthol, 7-(14)C-labeledbiospider
2-naphthol, 8-(14)C-labeledbiospider
2-naphthol, bismuth saltbiospider
2-naphthol, magnesium saltbiospider
2-naphthol, potassium saltbiospider
2-naphthol, sodium saltbiospider
2-naphthol, titanium(4+) saltbiospider
2-Napththolbiospider
Beta-hydroxynaphthalenebiospider
Beta-monoxynaphthalenebiospider
Beta-naftolbiospider
Beta-naftolobiospider
Beta-naphtholbiospider
Beta-naphthyl alcoholbiospider
Beta-naphthyl hydroxidebiospider
Beta-naphtolbiospider
Beta-naptholbiospider
C.I. Developer 5biospider
Developer sodiumbiospider
naphthalen-2-olbiospider
Naphthalenolbiospider
Naphthol, βbiospider
Naphthol, betabiospider
β-hydroxynaphthaleneGenerator
β-naphtholGenerator
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
Chemical FormulaC10H8O
IUPAC namenaphthalen-2-ol
InChI IdentifierInChI=1S/C10H8O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11H
InChI KeyJWAZRIHNYRIHIV-UHFFFAOYSA-N
Isomeric SMILESOC1=CC2=CC=CC=C2C=C1
Average Molecular Weight144.1699
Monoisotopic Molecular Weight144.057514878
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 83.31%; H 5.59%; O 11.10%DFC
Melting PointMp 123°DFC
Boiling PointBp 285-286°DFC
Experimental Water Solubility0.755 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP2.70HANSCH,C ET AL. (1995)
Experimental pKa9.51
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00kf-3900000000-9ba2c98085c1cfb979aeSpectrum
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, positivesplash10-0002-0900000000-150b753c58953122f7a0Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0002-0900000000-3ed11eab13f522e296d0Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0002-0900000000-76ad2ee08369a5c72727Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-014j-0900000000-668149fa5169e936b8ccSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-014i-0900000000-818a664d833b009956caSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-014i-1900000000-cfdbc5ded35ac6d127e8Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-016u-3900000000-7581b81c891ce2121e30Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-016u-6900000000-ecc855690e59bfdd5598Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-016u-9800000000-68d9b962e8fe93336126Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-016r-9400000000-9eeb688197da71b8a3bcSpectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-0900000000-820d3a81dfc9463584ebSpectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-000i-9000000000-41143d019e9e3192e3a9Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-014i-0900000000-8a33e2a4035f1d5db4c6Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-00kf-0900000000-b57369b32440fe60da1dSpectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0006-0900000000-95369892ad06085feeaaSpectrum
MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0006-0900000000-4359d09beb852a6b4d8dSpectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-014j-1900000000-3f45d855eafad75b3a67Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-014j-2900000000-949ec470c0e3ac2ca5b2Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0006-0900000000-ec57dc12ddf60a2741f0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-7b3aeb4e0f86148dab68Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-a5c6a08b3ea484ba1d0dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-2900000000-ecd1849d7a9f7a9bcac8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-e1a1f37ba96a4bf71d70Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-e1a1f37ba96a4bf71d70Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-019880a3b2ccbcc83a87Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
ChemSpider ID8341
ChEMBL IDCHEMBL14126
KEGG Compound IDC11713
Pubchem Compound ID8663
Pubchem Substance IDNot Available
ChEBI ID10432
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12322
CRC / DFC (Dictionary of Food Compounds) IDBLN50-J:BLN50-J
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID03V
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID2-Naphthol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference