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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 10:18:14 UTC
Update Date2020-02-26 21:24:56 UTC
HMDB IDHMDB0004072
Secondary Accession Numbers
  • HMDB04072
Metabolite Identification
Common Name4-Hydroxystyrene
Description4-Hydroxystyrene, also known as 4-vinylphenol, belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. 4-Hydroxystyrene is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Hydroxystyrene exists in all eukaryotes, ranging from yeast to humans. 4-Hydroxystyrene is a sweet, almond shell, and chemical tasting compound. Outside of the human body, 4-Hydroxystyrene is found, on average, in the highest concentration within a few different foods, such as white wines, beers, and corns and in a lower concentration in taco, bilberries, and tortilla. 4-Hydroxystyrene has also been detected, but not quantified in, several different foods, such as asparagus, cauliflowers, evergreen blackberries, tea, and tortilla chips. This could make 4-hydroxystyrene a potential biomarker for the consumption of these foods. Styrene is a prohapten metabolized in the skin by aryl hydrocarbon hydroxylase (AHH, EC1.14.14.1) to styrene epoxide acting as the true hapten. Styrene occurs in nature and as a synthetic product. 4-hydroxystyrene occurs frequently in different ciders, wines, foods and berries, e.g. cloudberry.
Structure
Data?1582752296
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 KeyFUGYGGDSWSUORM-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point73.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility8.4 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.73 m³·mol⁻¹ChemAxon
Polarizability13.15 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+123.96831661259
DarkChem[M-H]-121.4531661259
DeepCCS[M+H]+125.81630932474
DeepCCS[M-H]-122.30930932474
DeepCCS[M-2H]-159.39630932474
DeepCCS[M+Na]+134.69630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-HydroxystyreneOC1=CC=C(C=C)C=C12366.6Standard polar33892256
4-HydroxystyreneOC1=CC=C(C=C)C=C11147.7Standard non polar33892256
4-HydroxystyreneOC1=CC=C(C=C)C=C11207.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxystyrene,1TMS,isomer #1C=CC1=CC=C(O[Si](C)(C)C)C=C11258.1Semi standard non polar33892256
4-Hydroxystyrene,1TBDMS,isomer #1C=CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C11506.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Hydroxystyrene GC-EI-TOF (Non-derivatized)splash10-0006-0900000000-78e97f8689a1bddce8d12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxystyrene GC-EI-TOF (Non-derivatized)splash10-004l-1900000000-aabb90db206495e1949c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxystyrene GC-EI-TOF (Non-derivatized)splash10-0006-0900000000-78e97f8689a1bddce8d12018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxystyrene GC-EI-TOF (Non-derivatized)splash10-004l-1900000000-aabb90db206495e1949c2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxystyrene GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6900000000-e4b2ae72210dba8376c52016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxystyrene GC-MS (1 TMS) - 70eV, Positivesplash10-00fu-8900000000-96525d05990bd44a73e62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxystyrene 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-Hydroxystyrene LC-ESI-QFT , negative-QTOFsplash10-014i-0900000000-4748791daa3cc6db33cb2020-07-21HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxystyrene 10V, Positive-QTOFsplash10-00di-0900000000-b529604eb0086ce7d85a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxystyrene 20V, Positive-QTOFsplash10-00di-2900000000-cc4e2accb5dbfca1223a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxystyrene 40V, Positive-QTOFsplash10-0udi-9300000000-1a680f497983265f70002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxystyrene 10V, Negative-QTOFsplash10-014i-0900000000-992515c0effcfff517392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxystyrene 20V, Negative-QTOFsplash10-014i-0900000000-adf06e57ffef41aa20d02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxystyrene 40V, Negative-QTOFsplash10-014r-9600000000-7855fd6420cc0a980f562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxystyrene 10V, Positive-QTOFsplash10-00di-0900000000-2c381eb3871f5dbd6a942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxystyrene 20V, Positive-QTOFsplash10-00xr-9800000000-e2093cd31e1a5d12f8252021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxystyrene 40V, Positive-QTOFsplash10-0v00-9000000000-dd7dfadb6034e83a56c02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxystyrene 10V, Negative-QTOFsplash10-014i-0900000000-972f865a96261dcb891a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxystyrene 20V, Negative-QTOFsplash10-014i-3900000000-cc2986e6d45482e40a362021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxystyrene 40V, Negative-QTOFsplash10-0i2d-9000000000-6a5b5c88ab894e1f72332021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDNot Available
Phenol Explorer Compound ID706
FooDB IDFDB010540
KNApSAcK IDNot Available
Chemspider ID56234
KEGG Compound IDC05627
BioCyc IDCPD-1075
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7012
PubChem Compound62453
PDB IDNot Available
ChEBI ID1883
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed: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. [PubMed:12478566 ]
  3. Sjoborg S, Fregert S, Trulsson L: Contact allergy to styrene and related chemicals. Contact Dermatitis. 1984 Feb;10(2):94-6. [PubMed:6713846 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
4-Hydroxystyrene → 6-(4-ethenylphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
4-Hydroxystyrene → 4-Vinylphenol sulfatedetails