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Identification
Name Oxybenzone
Accession Number DB01428
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
(2-Hydroxy-4-methoxyphenyl)phenylmethanone
2-Benzoyl-5-methoxyphenol
2-Hydroxy-4-methoxybenzophenone
4-Methoxy-2-hydroxybenzophenone
4-Methoxy-2-hydroxybenzophenone butyric acid
Oxibenzona [inn-spanish]
Oxybenzonum [inn-latin]
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories
  • Sunscreening Agents
CAS number 131-57-7
Weight Average: 228.2433
Monoisotopic: 228.07864425
Chemical Formula C14H12O3
InChI Key InChIKey=DXGLGDHPHMLXJC-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
Plain Text
IUPAC Name
2-benzoyl-5-methoxyphenol
SMILES
COC1=CC(O)=C(C=C1)C(=O)C1=CC=CC=C1
Plain Text
Mass Spec show (8.57 KB)
Taxonomy
Kingdom Organic
Classes
  • Benzophenones
Substructures
  • Hydroxy Compounds
  • Phenols and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Methoxyphenols
  • Aromatic compounds
  • Anisoles
  • Benzophenones
  • Benzoyl Derivatives
  • Phenyl Esters
  • Ketones
Pharmacology
Indication Used as an ingredient in sunscreen and other cosmetics.
Pharmacodynamics Oxybenzone is an organic compound used in sunscreens. It is a derivative of benzophenone.
Mechanism of action Oxybenzone absorbs UV-A ultraviolet rays, preventing them from reaching the skin.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination In vivo studies show oxybenzone is abosorbed transdermally (through the skin) and is excreted in the urine.
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms
Form Route Strength
Lotion Topical
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 65.5 °C PhysProp
boiling point 155 °C at 5.00E+00 mm Hg PhysProp
logP 3.79 CHEM INSPECT TEST INST (1992)
Predicted Properties
Property Value Source
water solubility 1.28e-01 g/l ALOGPS
logP 3.35 ALOGPS
logP 3.62 ChemAxon
logS -3.2 ALOGPS
pKa (strongest acidic) 8.07 ChemAxon
pKa (strongest basic) -4.8 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 46.53 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 65.08 ChemAxon
polarizability 23.96 ChemAxon
References
Synthesis Reference Not 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
Resource Link
KEGG Drug D05309 Link_out
KEGG Compound C14285 Link_out
PubChem Compound 4632 Link_out
PubChem Substance 46508419 Link_out
ChemSpider 4471 Link_out
BindingDB 50253134 Link_out
PharmGKB PA164742933 Link_out
Wikipedia http://en.wikipedia.org/wiki/Oxybenzone Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (73.7 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Comments
Drug created on July 24, 2007 06:56 / Updated on February 08, 2013 16:20