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Identification
NameOxybenzone
Accession NumberDB01428
TypeSmall Molecule
GroupsApproved
Description

Oxybenzone 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.

Structure
Thumb
Synonyms
SynonymLanguageCode
(2-Hydroxy-4-methoxyphenyl)phenylmethanoneNot AvailableNot Available
2-Benzoyl-5-methoxyphenolNot AvailableNot Available
2-Hydroxy-4-methoxybenzophenoneNot AvailableNot Available
4-Methoxy-2-hydroxybenzophenoneNot AvailableNot Available
4-Methoxy-2-hydroxybenzophenone butyric acidNot AvailableNot Available
Benzophenone-3Not AvailableNot Available
OxibenzonaSpanishINN
OxybenzonumLatinINN
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Iman Skin Tone Evener Bb Spf 15cream7.5; 3 g/100mL; g/100mLtopicalImpala, Inc.2012-08-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Elf Super Glossy Lip Shine Spf 15cream7; 5 g/100g; g/100gtopicalHangzhou Facecare Cosmetics Co., Ltd.2010-12-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Elf Tinted Moisturizer Spf 15cream7; 5 g/100g; g/100gtopicalHangzhou Facecare Cosmetics Co., Ltd.2010-12-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Elf Lip Balm Spf 15cream5; 4.5 g/100g; g/100gtopicalHangzhou Facecare Cosmetics Co., Ltd.2010-12-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Moisturizing Sunscreen Spf15lotion1; 1 mL/200mL; mL/100mLtopicalShine & Pretty (USA), Corp.1996-02-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Elf Super Glossy Lip Shine Spf 15cream7.5; 6 g/100g; g/100gtopicalJ. A. Cosmetics U.S. INC2011-10-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Elf Tinted Moisturizer Spf 15cream7.5; 3.5 g/100g; g/100gtopicalJ. A. Cosmetics U.S. INC2011-10-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Elf Conditioning Lip Balm Spf 15cream7.5; 3 g/100g; g/100gtopicalJ. A. Cosmetics U.S. INC2011-10-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Elf Lip Balm Spf 15cream7.5; 5 g/100g; g/100gtopicalJ. A. Cosmetics U.S. INC2011-10-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Elf Lip Balm Spf 15 Colorcream7.5; 5 g/100g; g/100gtopicalJ. A. Cosmetics U.S. INC2011-10-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Elf Tinted Moisturizer Spf 20cream6; 3.5; 5 g/100g; g/100g; g/100gtopicalJ. A. Cosmetics U.S. INC2011-10-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number131-57-7
WeightAverage: 228.2433
Monoisotopic: 228.07864425
Chemical FormulaC14H12O3
InChI KeyDXGLGDHPHMLXJC-UHFFFAOYSA-N
InChI
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
IUPAC Name
2-benzoyl-5-methoxyphenol
SMILES
COC1=CC(O)=C(C=C1)C(=O)C1=CC=CC=C1
Taxonomy
DescriptionThis compound 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
  • Methoxyphenol
  • Acetophenone
  • Methoxybenzene
  • Aryl ketone
  • Phenol ether
  • Benzoyl
  • Anisole
  • Phenol
  • Alkyl aryl ether
  • Vinylogous acid
  • Ketone
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationUsed as an ingredient in sunscreen and other cosmetics.
PharmacodynamicsOxybenzone is an organic compound used in sunscreens. It is a derivative of benzophenone.
Mechanism of actionOxybenzone absorbs UV-A ultraviolet rays, preventing them from reaching the skin.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationIn vivo studies show oxybenzone is abosorbed transdermally (through the skin) and is excreted in the urine.
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9973
Blood Brain Barrier+0.8691
Caco-2 permeable+0.9258
P-glycoprotein substrateNon-substrate0.6198
P-glycoprotein inhibitor INon-inhibitor0.7188
P-glycoprotein inhibitor IINon-inhibitor0.8124
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.703
CYP450 2D6 substrateNon-substrate0.8915
CYP450 3A4 substrateNon-substrate0.6542
CYP450 1A2 substrateInhibitor0.911
CYP450 2C9 substrateNon-inhibitor0.907
CYP450 2D6 substrateNon-inhibitor0.9437
CYP450 2C19 substrateInhibitor0.8995
CYP450 3A4 substrateNon-inhibitor0.9258
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5
Ames testNon AMES toxic0.9098
CarcinogenicityNon-carcinogens0.8403
BiodegradationNot ready biodegradable0.6452
Rat acute toxicity1.6986 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9358
hERG inhibition (predictor II)Non-inhibitor0.9337
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Creamtopical5; 4.5 g/100g; g/100g
Creamtopical6; 3.5; 5 g/100g; g/100g; g/100g
Creamtopical7.5; 3 g/100g; g/100g
Creamtopical7.5; 3 g/100mL; g/100mL
Creamtopical7.5; 3.5 g/100g; g/100g
Creamtopical7.5; 5 g/100g; g/100g
Creamtopical7.5; 6 g/100g; g/100g
Creamtopical7; 5 g/100g; g/100g
Lotiontopical1; 1 mL/200mL; mL/100mL
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point65.5 °CPhysProp
boiling point155 °C at 5.00E+00 mm HgPhysProp
logP3.79CHEM INSPECT TEST INST (1992)
Predicted Properties
PropertyValueSource
Water Solubility0.128 mg/mLALOGPS
logP3.35ALOGPS
logP3.62ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)8.07ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity65.08 m3·mol-1ChemAxon
Polarizability23.96 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.57 KB)
SpectraMS1D NMR
References
Synthesis ReferenceNot Available
General Reference
  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
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.7 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on July 24, 2007 06:56 / Updated on September 16, 2013 17:14