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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:00 UTC
HMDB IDHMDB0015497
Secondary Accession Numbers
  • HMDB15497
Metabolite Identification
Common NameOxybenzone
DescriptionOxybenzone, also known as benzophenone-3 or oxibenzona, belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. Oxybenzone is a drug which is used as an ingredient in sunscreen and other cosmetics. Based on a literature review a significant number of articles have been published on Oxybenzone.
Structure
Data?1582753303
Synonyms
ValueSource
2-Benzoyl-5-methoxyphenolChEBI
2-Hydroxy-4-methoxybenzophenoneChEBI
4-Methoxy-2-hydroxybenzophenoneChEBI
Benzophenone-3ChEBI
OxibenzonaChEBI
OxybenzonumChEBI
Uvinul 40Kegg
(2-Hydroxy-4-methoxyphenyl)phenylmethanoneHMDB
4-Methoxy-2-hydroxybenzophenone butyric acidHMDB
HMBP CPDHMDB
SolbarHMDB
2-Hydroxy-4-methoxybenzoneHMDB
Eusolex 4360HMDB
Eusolex-4360HMDB
Chemical FormulaC14H12O3
Average Molecular Weight228.2433
Monoisotopic Molecular Weight228.07864425
IUPAC Name2-benzoyl-5-methoxyphenol
Traditional Nameoxybenzone
CAS Registry Number131-57-7
SMILES
COC1=CC(O)=C(C=C1)C(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C14H12O3/c1-17-11-7-8-12(13(15)9-11)14(16)10-5-3-2-4-6-10/h2-9,15H,1H3
InChI KeyDXGLGDHPHMLXJC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzophenones
Direct ParentBenzophenones
Alternative Parents
Substituents
  • Benzophenone
  • Diphenylmethane
  • Aryl-phenylketone
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Methoxybenzene
  • Benzoyl
  • Aryl ketone
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Vinylogous acid
  • Ketone
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point65.5 °CNot Available
Boiling Point370.00 to 371.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.13 g/LNot Available
LogP3.79CHEM INSPECT TEST INST (1992)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP3.35ALOGPS
logP3.62ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)7.07ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity65.08 m³·mol⁻¹ChemAxon
Polarizability23.96 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+152.81431661259
DarkChem[M-H]-155.20231661259
DeepCCS[M+H]+155.9830932474
DeepCCS[M-H]-153.58430932474
DeepCCS[M-2H]-186.53630932474
DeepCCS[M+Na]+162.03630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OxybenzoneCOC1=CC(O)=C(C=C1)C(=O)C1=CC=CC=C12951.0Standard polar33892256
OxybenzoneCOC1=CC(O)=C(C=C1)C(=O)C1=CC=CC=C11940.1Standard non polar33892256
OxybenzoneCOC1=CC(O)=C(C=C1)C(=O)C1=CC=CC=C12023.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oxybenzone,1TMS,isomer #1COC1=CC=C(C(=O)C2=CC=CC=C2)C(O[Si](C)(C)C)=C12044.4Semi standard non polar33892256
Oxybenzone,1TBDMS,isomer #1COC1=CC=C(C(=O)C2=CC=CC=C2)C(O[Si](C)(C)C(C)(C)C)=C12290.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Oxybenzone EI-B (Non-derivatized)splash10-004i-0390000000-d20281152dd02868f0f42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oxybenzone EI-B (Non-derivatized)splash10-004i-1190000000-c313f66363430324ce8e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oxybenzone EI-B (Non-derivatized)splash10-004i-0390000000-d20281152dd02868f0f42018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oxybenzone EI-B (Non-derivatized)splash10-004i-1190000000-c313f66363430324ce8e2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxybenzone GC-MS (Non-derivatized) - 70eV, Positivesplash10-116r-3940000000-a08f2fbf12b371790d682017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxybenzone GC-MS (1 TMS) - 70eV, Positivesplash10-05i9-7590000000-722f71d95a4db2587c752017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxybenzone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0fb9-5970000000-201ffa188f10c8981e9e2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-ITFT , positive-QTOFsplash10-0udi-0900000000-25520d89872ff52a3ed32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-ITFT , positive-QTOFsplash10-004i-0090000000-91e535fa71de15e790042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-ITFT , positive-QTOFsplash10-004i-0390000000-440768455ae7530c19092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-ITFT , positive-QTOFsplash10-0udi-0910000000-d7fdecc4ef3f7a7317492017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-ITFT , positive-QTOFsplash10-0udi-0900000000-e961d0acc366c6018be12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-ITFT , positive-QTOFsplash10-0udi-1900000000-7c8fdbbdfd111f438a022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-ITFT , positive-QTOFsplash10-0zfs-5900000000-daad8bf207afcb7e0b352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-ITFT , positive-QTOFsplash10-004i-0090000000-f005541a3bcdeecd4a502017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-ITFT , positive-QTOFsplash10-004i-0390000000-4d6d607f4d00d653af572017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-ITFT , positive-QTOFsplash10-0udi-0910000000-5bd3907cf283f3acd6962017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-ITFT , positive-QTOFsplash10-0udi-0900000000-2952f2aadcf45f405c212017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-ITFT , positive-QTOFsplash10-0udi-1900000000-d9d09a5a4ce6a4afa1f22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-ITFT , positive-QTOFsplash10-0zfs-5900000000-bd6b959b532a530b39062017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-ITFT , positive-QTOFsplash10-0udi-0900000000-c3d717596cccd924dc192017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-QTOF , positive-QTOFsplash10-004i-0590000000-4e2b5ecc7de18b3512522017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-QTOF , positive-QTOFsplash10-0udi-0900000000-465387cfd8d500df15162017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-QTOF , positive-QTOFsplash10-004j-9400000000-e9226c86961ff5d9d15b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-QFT , positive-QTOFsplash10-0ufr-0940000000-2a55f01ddfa3b0ff8f422017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxybenzone LC-ESI-QFT , positive-QTOFsplash10-0ufr-0950000000-1544559b42fcf578bf822017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybenzone 10V, Positive-QTOFsplash10-004i-0390000000-ef128eea7b7d7e7dbcdf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybenzone 20V, Positive-QTOFsplash10-0a4i-0920000000-97ee31aa08ce2b10ba9c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybenzone 40V, Positive-QTOFsplash10-0a4i-3900000000-ddc34f664246caca67e22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybenzone 10V, Negative-QTOFsplash10-004i-0190000000-1c88d49c7e5e54c22dd92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybenzone 20V, Negative-QTOFsplash10-004i-2590000000-9ca9837a82a21062e38b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxybenzone 40V, Negative-QTOFsplash10-002f-9600000000-41ed0c81cc277f1f44a12016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01428 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01428 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01428
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4471
KEGG Compound IDC14285
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxybenzone
METLIN IDNot Available
PubChem Compound4632
PDB IDNot Available
ChEBI ID34283
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1131411
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gonzalez H, Farbrot A, Larko O, Wennberg AM: Percutaneous absorption of the sunscreen benzophenone-3 after repeated whole-body applications, with and without ultraviolet irradiation. Br J Dermatol. 2006 Feb;154(2):337-40. [PubMed:16433806 ]