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4-Hydroxybenzyl alcohol (M2MDB001852)

Record Information
Version2.0
Creation Date2012-08-09 09:16:18 -0600
Update Date2015-09-13 12:56:17 -0600
Secondary Accession Numbers
  • ECMDB21457
Identification
Name:4-Hydroxybenzyl alcohol
Description4-hydroxybenzyl alcohol is the cleavage product produced during the biosynthesis of the thiazole moiety of thiamine from tyrosine as part of the thiamine biosynthesis pathway. (PMID 369616, EcoCyc)
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • 4-(Hydroxymethyl)phenol
  • 4-(hydroxymethyl)phenol (ACD/Name 4.0)
  • 4-hydroxybenzenemethanol
  • 4-Hydroxybenzylalcohol
  • 4-Methylolphenol
  • 4-Methylophenol
  • A-hydroxy-p-cresol
  • Alpha-hydroxy-p-cresol
  • B4-hydroxy-enzenemethanol
  • Gastrodigenin
  • P-(hydroxymethyl)phenol
  • P-hydroxy-Benzyl alcohol
  • P-Hydroxybenzyl alcohol
  • P-Methylolphenol
  • Para-Hydroxybenzyl alcohol
  • α-Hydroxy-P-cresol
Chemical Formula:C7H8O2
Weight:Average: 124.1372
Monoisotopic: 124.0524295
InChI Key:BVJSUAQZOZWCKN-UHFFFAOYSA-N
InChI:InChI=1S/C7H8O2/c8-5-6-1-3-7(9)4-2-6/h1-4,8-9H,5H2
CAS number:623-05-2
IUPAC Name:4-(hydroxymethyl)phenol
Traditional IUPAC Name:P-hydroxybenzyl alcohol
SMILES:OCC1=CC=C(O)C=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzyl alcohols
Direct ParentBenzyl alcohols
Alternative Parents
Substituents
  • Benzyl alcohol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:124.5 °C
Experimental Properties:
PropertyValueSource
LogP:0.25 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility59.8 g/LALOGPS
logP0.53ALOGPS
logP0.9ChemAxon
logS-0.32ALOGPS
pKa (Strongest Acidic)9.48ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.85 m³·mol⁻¹ChemAxon
Polarizability12.86 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i1-9400000000-f08047b4457dc23151d9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gdi-0970000000-2415f3f14aceb1b2477bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00os-1930000000-4cb3e427ccd00fb05cefView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004j-1930000000-8da8f2d1a4cd6945c0d2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00os-0930000000-fb426d5a8be1daafc38cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9830000000-37513a80b983842a093dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i1-9400000000-f08047b4457dc23151d9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gdi-0970000000-2415f3f14aceb1b2477bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00os-1930000000-4cb3e427ccd00fb05cefView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004j-1930000000-8da8f2d1a4cd6945c0d2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00os-0930000000-fb426d5a8be1daafc38cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9830000000-37513a80b983842a093dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fv-9700000000-75343ed1558a8215cd86View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fmi-8930000000-dc7e6a9414fca90c09ffView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0900000000-e86139fcdae517d0dd50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-23d9f02bc9bfae1b0404View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9500000000-ef57e905020db4322452View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1900000000-08d6d0fac3014c21f4e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-5900000000-a615d3a76cf31c5305cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-e8119b2a0a6f66edc346View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-1900000000-14e2a5a869f98931316eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9200000000-3f2037d44894ccf1af87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9100000000-5896e65cef551a4d404fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006x-9600000000-2e7ed49ef552bb91252dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9500000000-39119700dc572f82fda6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-ade1ec5c4dc45647bb63View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Nair B: Final report on the safety assessment of Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate. Int J Toxicol. 2001;20 Suppl 3:23-50. Pubmed: 11766131
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • White, R. H. (1979). "4-Hydroxybenzyl alcohol. A metabolite produced during the biosynthesis of thiamine in Escherichia coli." Biochim Biophys Acta 583:55-62. Pubmed: 369616
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID67410
HMDB IDHMDB11724
Pubchem Compound ID125
Kegg IDC17467
ChemSpider ID122
Wikipedia IDGastrodigenin
BioCyc ID4-HYDROXY-BENZYL-ALCOHOL
EcoCyc ID4-HYDROXY-BENZYL-ALCOHOL

Enzymes

Protein Details
1. Dehydroglycine synthase
General function:
Involved in catalytic activity
Specific function:
Catalyzes the radical-mediated cleavage of tyrosine to dehydroglycine and p-cresol
Gene Name:
thiH
Uniprot ID:
P30140
Molecular weight:
43320
Reactions
L-tyrosine + S-adenosyl-L-methionine + reduced acceptor = 2-iminoacetate + 4-methylphenol + 5'-deoxyadenosine + L-methionine + acceptor + 2 H(+).