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Record Information
Version3.6
Creation Date2006-08-13 10:18:14 UTC
Update Date2016-02-11 01:06:33 UTC
HMDB IDHMDB04072
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Hydroxystyrene
Description4-hydroxystyrene occurs frequently in different ciders, wines, foods and berries, e.g. cloudberry. Styrene is a prohapten metabolized in the skin by aryl hydrocarbon hydroxylase (AHH, EC 1.14.14.1) to styrene epoxide acting as the true hapten. Styrene occurs in nature and as a synthetic product.(PMID: 6713846 ).
Structure
Thumb
Synonyms
ValueSource
4-VinylphenolChEBI
P-HydroxystyreneChEBI
P-VinylphenolChEBI
Chemical FormulaC8H8O
Average Molecular Weight120.1485
Monoisotopic Molecular Weight120.057514878
IUPAC Name4-ethenylphenol
Traditional Name4-vinylphenol
CAS Registry Number2628-17-3
SMILES
OC1=CC=C(C=C)C=C1
InChI Identifier
InChI=1S/C8H8O/c1-2-7-3-5-8(9)6-4-7/h2-6,9H,1H2
InChI KeyInChIKey=FUGYGGDSWSUORM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassStyrenes
Direct ParentStyrenes
Alternative Parents
Substituents
  • Styrene
  • Phenol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point73.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.4 mg/mLALOGPS
logP2.07ALOGPS
logP2.41ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)9.56ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.73 m3·mol-1ChemAxon
Polarizability13.15 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID706
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB010540
KNApSAcK IDNot Available
Chemspider ID56234
KEGG Compound IDC05627
BioCyc IDCPD-1075
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04072
Metagene LinkHMDB04072
METLIN ID7012
PubChem Compound62453
PDB IDNot Available
ChEBI ID1883
References
Synthesis ReferenceShuey, Steven W. Processes for conversion of tyrosine to p-hydroxystyrene and p-acetoxystyrene. PCT Int. Appl. (2007), 28 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Manini P, De Palma G, Mozzoni P, Andreoli R, Poli D, Bergamaschi E, Franchini I, Mutti A: GSTM1 polymorphism and styrene metabolism: insights from an acute accidental exposure. Toxicol Lett. 2002 Aug 5;134(1-3):201-8. [12191879 ]
  2. Manini P, Andreoli R, Poli D, De Palma G, Mutti A, Niessen WM: Liquid chromatography/electrospray tandem mass spectrometry characterization of styrene metabolism in man and in rat. Rapid Commun Mass Spectrom. 2002;16(24):2239-48. [12478566 ]
  3. Sjoborg S, Fregert S, Trulsson L: Contact allergy to styrene and related chemicals. Contact Dermatitis. 1984 Feb;10(2):94-6. [6713846 ]