Benzoyl peroxide (CHEM004082)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 01:34:11 UTC
Update Date2016-10-28 10:01:52 UTC
Accession NumberCHEM004082
Identification
Common NameBenzoyl peroxide
ClassSmall Molecule
DescriptionBenzoyl peroxide is a commonly used drug in topical treatments for acne.[L33249,L33264,L33269,L33299,L33314] It has been formulated as products with either a single active ingredient,[L33249,L33299] or with [erythromycin],[L33264] [clindamycin],[L33269] or [adapalene].[L33314] After administration, the peroxide bond is cleaved, allowing benzoyloxy radicals to nonspecifically interact with proteins.[A18903,A233859] This treatment decreases keratin and sebum around follicles, as well as increasing turnover of epithelial cells.[A234059,A234064,A234069] Benzoyl peroxide, in combination with erythromycin, was granted FDA approval on 26 October 1984.[L33264]
Contaminant Sources
  • Clean Air Act Chemicals
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • OECD HPV Chemicals
  • OSHA Hazardous Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
BepioKegg
Abcat 40HMDB
Abcure S-40-25HMDB
AcetoxylHMDB
AcetOxyl 2.5 and 5HMDB
AcnegelHMDB
Akneroxid 5HMDB
Akneroxid LHMDB
Akneroxide LHMDB
Aksil 5HMDB
AsidopanHMDB
Aztec benzoyl peroxide-70-77HMDB
Aztec benzoyl peroxide-dryHMDB
Aztec bpoHMDB
Benbel cHMDB
Benox 50HMDB
BenoxylHMDB
Benoxyl (5&10) lotionHMDB
BenzacHMDB
Benzac WHMDB
BenzagelHMDB
Benzagel 10HMDB
BenzaknenHMDB
BenzaknewHMDB
BenzamycinHMDB
BenzashaveHMDB
Benzoic acid, peroxideHMDB
Benzol peroxideHMDB
BenzoperoxideHMDB
BenzoylHMDB
Benzoyl peroideHMDB
Benzoyl peroxide (luperox(R) a70S)HMDB
Benzoyl peroxide (luperox(R) a75)HMDB
Benzoyl peroxide (luperox(R) a75fp)HMDB
Benzoyl peroxide (luperox(R) a98)HMDB
Benzoyl peroxide(usan)HMDB
Benzoyl peroxide, blend in dibutyl phthalateHMDB
Benzoyl peroxide, blend in tricresyl phosphateHMDB
Benzoyl peroxide, usanHMDB
Benzoyl superoxideHMDB
BenzoylperoxidHMDB
BenzoylperoxydeHMDB
BPOHMDB
BrevoxylHMDB
Cadat bpoHMDB
CadetHMDB
Cadet bpo-70WHMDB
CadoxHMDB
Cadox 40EHMDB
Cadox bHMDB
Cadox b 40EHMDB
Cadox b 50PHMDB
Cadox b 70WHMDB
Cadox b-CH 50HMDB
Cadox bpo-w40HMDB
Cadox BSHMDB
Cadox btaHMDB
Cadox BTW-50HMDB
Chaloxyd BP 50FTHMDB
Clear by designHMDB
Clearasil antibacterial acne lotionHMDB
Clearasil benzoyl peroxide lotionHMDB
Clearasil BP acne treatmentHMDB
DebroxideHMDB
DermoxylHMDB
DesandenHMDB
Desquam eHMDB
Desquam XHMDB
Desquam-XHMDB
DibenzoylperoxidHMDB
DibenzoylperoxydeHMDB
Diphenylglyoxal peroxideHMDB
Diphenylglyoxal superoxideHMDB
DiphenylperoxyanhydrideHMDB
DRY and clearHMDB
Duresthin 5HMDB
EloxylHMDB
Epi clear antiseptic lotionHMDB
Epi-clearHMDB
FloroxHMDB
Fostex bpoHMDB
GaroxHMDB
IncidolHMDB
LoroxideHMDB
LucidolHMDB
Lucidol (peroxide)HMDB
Lucidol 50PHMDB
Lucidol 75fpHMDB
Lucidol b 50HMDB
Lucidol g 20HMDB
Lucidol GSHMDB
Lucidol KL 50HMDB
Lucidol RMHMDB
Lucidol-70HMDB
Lucidol-78HMDB
LuciliteHMDB
LucipalHMDB
LupercoHMDB
Luperco aHMDB
Luperco aaHMDB
Luperco acHMDB
Luperco afrHMDB
Luperco afr-250HMDB
Luperco astHMDB
Luperox a98HMDB
Luperox FLHMDB
LuzidolHMDB
Mixture OF dibenzoyl peroxide and calcium sulfateHMDB
Mixture OF dibenzoyl peroxide and calcium sulphateHMDB
MytolacHMDB
Nayper b and boHMDB
Nayper boHMDB
NericurHMDB
Norox BZP-250HMDB
Norox BZP-C-35HMDB
NovadeioxHMDB
NovadeloxHMDB
NSC 675HMDB
Oxy 5HMDB
Oxy washHMDB
Oxy-10 coverHMDB
Oxy-5HMDB
Oxy-LHMDB
OxyliteHMDB
PanoxylHMDB
PeriygelHMDB
Perossido di benzoileHMDB
Peroxide, benzoylHMDB
Peroxide, dibenzoylHMDB
Peroxyde de benzoyleHMDB
PeroxydermHMDB
PeroxydexHMDB
Persa-gelHMDB
PersadoxHMDB
Phisoac BPHMDB
PreoxydexHMDB
PresadoxHMDB
Quinolor compoundHMDB
Resdan akneHMDB
SanoxitHMDB
Silica hydrogelHMDB
Stri-dex b.pHMDB
Stri-dex b.p.HMDB
SulfoxylHMDB
SuperoxHMDB
Superox 744HMDB
Superoxide, benzoylHMDB
Superoxide, diphenylglyoxalHMDB
ThermadermHMDB
TopexHMDB
VanoxideHMDB
XeracHMDB
Xerac BPHMDB
Xerac BP 10HMDB
Xerac BP 5HMDB
Dibenzoyl peroxideHMDB
Chemical FormulaC14H10O4
Average Molecular Mass242.227 g/mol
Monoisotopic Mass242.058 g/mol
CAS Registry Number94-36-0
IUPAC Namebenzoyl benzenecarboperoxoate
Traditional Namefostex
SMILESO=C(OOC(=O)C1=CC=CC=C1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C14H10O4/c15-13(11-7-3-1-4-8-11)17-18-14(16)12-9-5-2-6-10-12/h1-10H
InChI KeyOMPJBNCRMGITSC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzoyl peroxides. These are organic compounds containing two benzoyl groups O-linked to each other via a peroxide group. Their skeleton has the general formula [C6H5C(O)]2O2.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoyl peroxides
Direct ParentBenzoyl peroxides
Alternative Parents
Substituents
  • Benzoyl peroxide
  • Peroxybenzoate
  • Benzoic acid or derivatives
  • Benzoyl
  • Dicarboxylic acid or derivatives
  • Peroxycarboxylic acid or derivatives
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.029 g/LALOGPS
logP2.75ALOGPS
logP3.95ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity64.77 m³·mol⁻¹ChemAxon
Polarizability24.16 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0900000000-423d9df6ef4f9ce5a079Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0390000000-50998e66fa2f7bef20e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0920000000-e7246fd3375ad32b63a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4900000000-584b69634dd12fe901d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-31279cde2ca79ff16285Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0290000000-9bcc1591e9874715a701Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-3930000000-ac2e3837cbd47bd6015dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0980000000-c0b8b681a6b292a33c25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-488d41e3a0b2e5a9eb49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2900000000-2602e3f446e8009ad5fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-871b46014990fc059dacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-c13c84561286f2b25014Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f83e28014dc1944fb49aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB09096
HMDB IDHMDB0032040
FooDB IDFDB008743
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBenzoyl peroxide
Chemspider ID6919
ChEBI IDNot Available
PubChem Compound ID7187
Kegg Compound IDC19346
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Welch SL: Oral toxicity of topical preparations. Vet Clin North Am Small Anim Pract. 2002 Mar;32(2):443-53, vii.
2. Nacht S, Gans EH, McGinley KJ, Kligman AM: Comparative activity of benzoyl peroxide and hexachlorophene. In vivo studies against propionibacterium acnes in humans. Arch Dermatol. 1983 Jul;119(7):577-9.
3. Angelini G, Vena GA, Meneghini CL: Allergic contact dermatitis to some medicaments. Contact Dermatitis. 1985 May;12(5):263-9.
4. Hegemann L, Toso SM, Kitay K, Webster GF: Anti-inflammatory actions of benzoyl peroxide: effects on the generation of reactive oxygen species by leucocytes and the activity of protein kinase C and calmodulin. Br J Dermatol. 1994 May;130(5):569-75.
5. Dreno B: Topical antibacterial therapy for acne vulgaris. Drugs. 2004;64(21):2389-97.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.