Benzoyl peroxide

Benzoyl peroxide is a chemical compound (specifically, an organic peroxide) with structural formula (C6H5−C(=O)O−)2, often abbreviated as (BzO)2. In terms of its structure, the molecule can be described as two benzoyl (C6H5−C(=O)−, Bz) groups connected by a peroxide (−O−O−). It is a white granular solid with a faint odour of benzaldehyde, poorly soluble in water but soluble in acetone, ethanol, and many other organic solvents. Benzoyl peroxide is an oxidizer, but it is principally used as in the production of polymers.[4]

Benzoyl peroxide
Clinical data
Trade namesBenzac, Panoxyl, others
Other namesbenzoperoxide, dibenzoyl peroxide (DBPO)
AHFS/Drugs.comProfessional Drug Facts
MedlinePlusa601026
License data
Routes of
administration		Topical
ATC code
Legal status
Legal status
Identifiers
IUPAC name
  • benzoic peroxyanhydride[3]
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.002.116
Chemical and physical data
FormulaC14H10O4
Molar mass242.230 g·mol−1
3D model (JSmol)
Density1.334 g/cm3
Melting point103 to 105 °C (217 to 221 °F) decomposes
Solubility in waterpoor mg/mL (20 °C)
SMILES
  • c1ccc(cc1)C(=O)OOC(=O)c2ccccc2
InChI
  • InChI=1S/C14H10O4/c15-13(11-7-3-1-4-8-11)17-18-14(16)12-9-5-2-6-10-12/h1-10H Y
  • Key:OMPJBNCRMGITSC-UHFFFAOYSA-N
Data page
Benzoyl peroxide (data page)

Benzoyl peroxide is mainly used in production of plastics[5][6]

Because of these possible side effects, it is recommended to start with a low concentration and build up as appropriate, as the skin gradually develops tolerance to the medication. Skin sensitivity typically resolves after a few weeks of continuous use.[7][8] Irritation can also be reduced by avoiding harsh facial cleansers and wearing sunscreen prior to sun exposure.[8]

One in 500 people experience hypersensitivity to BPO and are liable to experience burning, itching, crusting, and possibly swelling.[9][10] About one-third of people experience phototoxicity under exposure to ultraviolet (UVB) light.[11]

Other uses

As a bleach, it has been used as a medication and a water disinfectant.[12][13] In specialized contexts, the name may be abbreviated as BPO.

Benzoyl peroxide is used in dentistry as a tooth whitening product.

Explosion hazard

Benzoyl peroxide is potentially explosive[14] like other organic peroxides, and can cause fires without external ignition. The hazard is acute for the pure material, so the compound is generally used as a solution or a paste. For example, cosmetics contain only a small percentage of benzoyl peroxide and pose no explosion risk.

Toxicity

Benzoyl peroxide breaks down in contact with skin, producing benzoic acid and oxygen, neither of which is very toxic.[15]

With regards to BPO's carcinogenic potential, one study concluded, "caution should be recommended in the use of this and other free radical-generating compounds".[16] A 1999 IARC review of carcinogenicity studies found no evidence linking BPO acne medication to skin cancers in humans. However, some animal studies found that the compound could act as a carcinogen and enhance the effect of known carcinogens.[17]

Skin irritation

In a 1977 study using a human maximization test, 76% of subjects acquired a contact sensitization to benzoyl peroxide. Formulations of 5% and 10% were used.[18]

The U.S. National Institute for Occupational Safety and Health has developed criteria for a recommended standard for occupational exposure to benzoyl peroxide.[19]

Cloth staining
A bleached fabric stain caused by contact with benzoyl peroxide

Contact with fabrics or hair, such as from still-moist acne medication, can cause permanent color dampening almost immediately. Even secondary contact can cause bleaching, for example, contact with a towel that has been used to wash off benzoyl peroxide-containing hygiene products.[20]

References
  1. "Epsolay- benzoyl peroxide cream". DailyMed. 25 April 2022. Archived from the original on 16 May 2022. Retrieved 15 May 2022.
  2. "Epsolay- benzoyl peroxide cream". DailyMed. 5 May 2022. Archived from the original on 20 June 2022. Retrieved 19 June 2022.
  3. IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-65.7.5". In Favre HA, Powell WH (eds.). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPAC–RSC. ISBN 978-0-85404-182-4.
  8. Alldredge BK, Koda-Kimble MA, Young LY, eds. (2013). Applied Therapeutics: The Clinical Use of Drugs (10th ed.). Baltimore: Wolters Kluwer Health/Lippincott Williams & Wilkins. p. 949. ISBN 978-1609137137.
  9. Cunliffe WJ, Burke B (1 January 1982). "Benzoyl peroxide: lack of sensitization". Acta Dermato-Venereologica. 62 (5): 458–9. doi:10.2340/00015555462458459 (inactive 31 July 2022). PMID 6183909. Archived from the original on 27 February 2021. Retrieved 17 July 2020.{{cite journal}}: CS1 maint: DOI inactive as of July 2022 (link)
  10. "Benzoyl peroxide". Mayo Clinic. 1 January 2016. Archived from the original on 18 July 2016.
  11. Jeanmougin M, Pedreiro J, Bouchet J, Civatte J (1 January 1983). "[Phototoxic activity of 5% benzoyl peroxide in man. Use of a new methodology]". Dermatologica. 167 (1): 19–23. doi:10.1159/000249739. PMID 6628794.
  12. Stellman JM (1998). Encyclopaedia of Occupational Health and Safety: Guides, indexes, directory. International Labour Organization. p. 104. ISBN 9789221098171. Archived from the original on 18 September 2017.
  14. Cartwright H (17 March 2005). "Chemical Safety Data: Benzoyl peroxide". Oxford University. Archived from the original on 12 October 2010. Retrieved 13 August 2011.
  15. Benzoyl peroxide (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, April 2004
  16. Slaga TJ, Klein-Szanto AJ, Triplett LL, Yotti LP, Trosko KE (August 1981). "Skin tumor-promoting activity of benzoyl peroxide, a widely used free radical-generating compound". Science. 213 (4511): 1023–5. Bibcode:1981Sci...213.1023S. doi:10.1126/science.6791284. PMID 6791284.
  17. International Agency for Research on Cancer (1999): "Benzoyl peroxide". in Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide Archived 15 July 2020 at the Wayback Machine. Monographs on the Evaluation of Carcinogenic Risks to Humans, number 71, pages 345–358. ISBN 92-832-1271-1
  18. Leyden JJ, Kligman AM (October 1977). "Contact sensitization to benzoyl peroxide". Contact Dermatitis. 3 (5): 273–5. doi:10.1111/j.1600-0536.1977.tb03674.x. PMID 145346. S2CID 33553359.
  19. "Criteria for a Recommended Standard: Occupational Exposure to Benzoyl Peroxide (77-166)". CDC - NIOSH Publications and Products. 6 June 2014. doi:10.26616/NIOSHPUB76128. Archived from the original on 9 August 2016. Retrieved 15 July 2016.
  20. Bojar RA, Cunliffe WJ, Holland KT (February 1995). "The short-term treatment of acne vulgaris with benzoyl peroxide: effects on the surface and follicular cutaneous microflora". The British Journal of Dermatology. 132 (2): 204–8. doi:10.1111/j.1365-2133.1995.tb05014.x. PMID 7888356. S2CID 22468429.
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