Oxybenzone (CHEM003764)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (6)XML
Record Information
Version1.0
Creation Date2014-09-11 05:17:27 UTC
Update Date2026-05-14 17:00:21 UTC
Accession NumberCHEM003764
Identification
Common NameOxybenzone
ClassSmall Molecule
DescriptionOxybenzone is an organic compound used in sunscreens. It is a derivative of benzophenone. It forms colorless crystals that are readily soluble in most organic solvents. It is used as an ingredient in sunscreen and other cosmetics because it absorbs UV-A ultraviolet rays.
Contaminant Sources
  • Cosmetic Chemicals
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • Suspected Compounds - Waste Water
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Drug
  • Ester
  • Ether
  • Household Toxin
  • Metabolite
  • Organic Compound
  • Sunscreening Agent
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass228.243 g/mol
Monoisotopic Mass228.079 g/mol
CAS Registry Number131-57-7
IUPAC Name2-benzoyl-5-methoxyphenol
Traditional Nameoxybenzone
SMILESCOC1=CC(O)=C(C=C1)C(=O)C1=CC=CC=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point65.5°C
Boiling Point155°C at 5.00E+00 mm Hg
SolubilityNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0390000000-d20281152dd02868f0f4Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-1190000000-c313f66363430324ce8eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0390000000-d20281152dd02868f0f4Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-1190000000-c313f66363430324ce8eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-116r-3940000000-a08f2fbf12b371790d68Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05i9-7590000000-722f71d95a4db2587c75Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-25520d89872ff52a3ed3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-91e535fa71de15e79004Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0390000000-440768455ae7530c1909Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0910000000-d7fdecc4ef3f7a731749Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-e961d0acc366c6018be1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-1900000000-7c8fdbbdfd111f438a02Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0zfs-5900000000-daad8bf207afcb7e0b35Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-f005541a3bcdeecd4a50Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0390000000-4d6d607f4d00d653af57Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0910000000-5bd3907cf283f3acd696Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-2952f2aadcf45f405c21Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-1900000000-d9d09a5a4ce6a4afa1f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0zfs-5900000000-bd6b959b532a530b3906Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-c3d717596cccd924dc19Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0590000000-4e2b5ecc7de18b351252Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-465387cfd8d500df1516Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004j-9400000000-e9226c86961ff5d9d15bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0ufr-0940000000-2a55f01ddfa3b0ff8f42Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0ufr-0950000000-1544559b42fcf578bf82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0390000000-ef128eea7b7d7e7dbcdfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0920000000-97ee31aa08ce2b10ba9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-ddc34f664246caca67e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-1c88d49c7e5e54c22dd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2590000000-9ca9837a82a21062e38bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9600000000-41ed0c81cc277f1f44a1Spectrum
MSMass Spectrum (Electron Ionization)splash10-0fb9-5970000000-201ffa188f10c8981e9eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityOxybenzone absorbs UV-A ultraviolet rays, preventing them from reaching the skin.
MetabolismRoute of Elimination: In vivo studies show oxybenzone is abosorbed transdermally (through the skin) and is excreted in the urine.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed as an ingredient in sunscreen and other cosmetics.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01428
HMDB IDHMDB0015497
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkOxybenzone
Chemspider ID4471
ChEBI ID34283
PubChem Compound ID4632
Kegg Compound IDC14285
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11169173
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22721600
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=26118430
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=26167727
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=26295590
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=26487337
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26589946
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=26686077
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=26736174
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=27085067
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=27544106
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=27796700
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=28192168
14. 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.