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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:12 UTC
Update Date2023-02-21 17:21:27 UTC
HMDB IDHMDB0032012
Secondary Accession Numbers
  • HMDB32012
Metabolite Identification
Common Name4-Hydroxy-3-methoxybenzenemethanol
Description4-Hydroxy-3-methoxybenzenemethanol, also known as 4-hydroxy-3-methoxybenzyl alcohol or 3-methoxy-4-hydroxybenzyl alcohol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 4-Hydroxy-3-methoxybenzenemethanol is a drug. 4-Hydroxy-3-methoxybenzenemethanol is a sweet, anise, and balsam tasting compound. 4-hydroxy-3-methoxybenzenemethanol has been detected, but not quantified, in fruits and herbs and spices. This could make 4-hydroxy-3-methoxybenzenemethanol a potential biomarker for the consumption of these foods.
Structure
Data?1677000087
Synonyms
ValueSource
4-Hydroxy-3-methoxy-benzenemethanolChEBI
4-Hydroxy-3-methoxybenzyl alcoholChEBI
3-Methoxy-4-hydroxybenzyl alcoholHMDB
4-(Hydroxymethyl)-2-methoxyphenolHMDB
4-HYDROXY-3-methoxy-benzyl alcoholHMDB
4-Hydroxy-3-methoxybenzenemethanol, 9ciHMDB
4-Hydroxy-3-methoxyphenyl methanolHMDB
4-Hydroxy-3-methoxyphenylmethanolHMDB
a,4-Dihydroxy-3-methoxytolueneHMDB
FEMA 3737HMDB
V 0018 (Alcohol)HMDB
Vanillic alcoholHMDB
Vanillin alcoholHMDB
VanillolHMDB
Vanillyl alcoholHMDB
Vanillyl-alcoholHMDB
4-Hydroxy-3-methoxybenzenemethanolChEBI
Chemical FormulaC8H10O3
Average Molecular Weight154.1632
Monoisotopic Molecular Weight154.062994186
IUPAC Name4-(hydroxymethyl)-2-methoxyphenol
Traditional Namevanillyl alcohol
CAS Registry Number498-00-0
SMILES
COC1=CC(CO)=CC=C1O
InChI Identifier
InChI=1S/C8H10O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-4,9-10H,5H2,1H3
InChI KeyZENOXNGFMSCLLL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Benzyl alcohol
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Primary alcohol
  • Aromatic alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point114 - 115 °CNot Available
Boiling Point312.00 to 313.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2 mg/mL at 20 °CNot Available
LogP0.420The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility29.4 g/LALOGPS
logP0.5ALOGPS
logP0.74ChemAxon
logS-0.72ALOGPS
pKa (Strongest Acidic)9.92ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.32 m³·mol⁻¹ChemAxon
Polarizability15.74 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.78131661259
DarkChem[M-H]-130.2731661259
DeepCCS[M+H]+140.0430932474
DeepCCS[M-H]-136.21230932474
DeepCCS[M-2H]-173.73430932474
DeepCCS[M+Na]+149.27330932474
AllCCS[M+H]+132.932859911
AllCCS[M+H-H2O]+128.432859911
AllCCS[M+NH4]+137.132859911
AllCCS[M+Na]+138.432859911
AllCCS[M-H]-130.832859911
AllCCS[M+Na-2H]-132.232859911
AllCCS[M+HCOO]-133.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-3-methoxybenzenemethanolCOC1=C(O)C=CC(CO)=C12741.8Standard polar33892256
4-Hydroxy-3-methoxybenzenemethanolCOC1=C(O)C=CC(CO)=C11419.0Standard non polar33892256
4-Hydroxy-3-methoxybenzenemethanolCOC1=C(O)C=CC(CO)=C11481.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-3-methoxybenzenemethanol,1TMS,isomer #1COC1=CC(CO)=CC=C1O[Si](C)(C)C1551.4Semi standard non polar33892256
4-Hydroxy-3-methoxybenzenemethanol,1TMS,isomer #2COC1=CC(CO[Si](C)(C)C)=CC=C1O1564.4Semi standard non polar33892256
4-Hydroxy-3-methoxybenzenemethanol,2TMS,isomer #1COC1=CC(CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C1623.9Semi standard non polar33892256
4-Hydroxy-3-methoxybenzenemethanol,1TBDMS,isomer #1COC1=CC(CO)=CC=C1O[Si](C)(C)C(C)(C)C1795.2Semi standard non polar33892256
4-Hydroxy-3-methoxybenzenemethanol,1TBDMS,isomer #2COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O1788.3Semi standard non polar33892256
4-Hydroxy-3-methoxybenzenemethanol,2TBDMS,isomer #1COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2078.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol GC-EI-TOF (Non-derivatized)splash10-05ot-1980000000-90c0d7b9d5ab2ad49ebd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol GC-EI-TOF (Non-derivatized)splash10-05ot-1980000000-90c0d7b9d5ab2ad49ebd2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-1900000000-4bfb638326b97e8c9eeb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol GC-MS (2 TMS) - 70eV, Positivesplash10-00gi-7390000000-dfd8ee944e68b10e25142017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol DI-ESI-qTof , Negative-QTOFsplash10-0udr-0900000000-cae1bb4557de8c5c425e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol DI-ESI-qTof , Negative-QTOFsplash10-0udi-0900000000-a953d3d5aa4c7a4bbb1d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 10V, Positive-QTOFsplash10-0a4r-0900000000-8cec776a8684a3c300ba2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 20V, Positive-QTOFsplash10-000i-0900000000-c5e19bc7f2c583cdd9d12015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 40V, Positive-QTOFsplash10-052r-5900000000-5795c57b2d2294956f782015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 10V, Negative-QTOFsplash10-0udi-0900000000-da35d09bba9c4f0150c12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 20V, Negative-QTOFsplash10-0uki-1900000000-bddb6a9312eb8cd5304d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 40V, Negative-QTOFsplash10-0a4i-9800000000-8b1a492cf5623f10508d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 10V, Negative-QTOFsplash10-0udi-0900000000-55caab0c9e31716e1c832021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 20V, Negative-QTOFsplash10-0zmr-0900000000-622397e9193433d156222021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 40V, Negative-QTOFsplash10-0zfr-9500000000-e4dfb45f82af81f401b12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 10V, Positive-QTOFsplash10-00di-2900000000-01d9f9426f095b48367d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 20V, Positive-QTOFsplash10-0a4r-1900000000-97c5e5bea153c9d796512021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxybenzenemethanol 40V, Positive-QTOFsplash10-0pc0-9300000000-7d51ed335759aaf044c42021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12087
Phenol Explorer Compound IDNot Available
FooDB IDFDB008710
KNApSAcK IDC00058122
Chemspider ID56139
KEGG Compound IDC06317
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVanillyl_alcohol
METLIN IDNot Available
PubChem Compound62348
PDB IDNot Available
ChEBI ID18353
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1037781
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .