出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/10/18 00:15:14」(JST)
| Names | |
|---|---|
| IUPAC name
dibenzoyl peroxide
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| Other names
Benzoyl peroxide (BPO)
Benzoperoxide |
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| Identifiers | |
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CAS Number
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94-36-0 Y |
| ChEMBL | ChEMBL1200370 N |
| ChemSpider | 6919 Y |
| ECHA InfoCard | 100.002.116 |
| EC Number | 202-327-6 |
| Jmol 3D model | Interactive image |
| KEGG | D03093 Y |
| PubChem | 7187 |
| RTECS number | DM8575000 |
| UNII | W9WZN9A0GM Y |
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InChI
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SMILES
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| Properties | |
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Chemical formula
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C14H10O4 |
| Molar mass | 242.23 g·mol−1 |
| Appearance | colourless solid |
| Density | 1.334 g/cm3 |
| Melting point | 103 to 105 °C (217 to 221 °F; 376 to 378 K) decomposes |
|
Solubility in water
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poor |
| Pharmacology | |
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ATC code
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D10AE01 (WHO) QD11AX90 (WHO) |
| Hazards | |
| Main hazards | irritant, explosive[1] |
| Safety data sheet | See: data page |
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EU classification (DSD)
|
E (E) Xi (Xi) |
| R-phrases | R3, R7, R36, R43 |
| S-phrases | (S2), S3/7, S14, S36/37/39 |
| NFPA 704 |
1
3
3
OX
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| Flash point | 80 °C; 176 °F; 353 K[1] |
|
Autoignition
temperature |
80 °C (176 °F; 353 K) |
| Lethal dose or concentration (LD, LC): | |
|
LD50 (median dose)
|
7710 mg/kg (mouse, oral)[2] |
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LC50 (median concentration)
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7000 mg/m3 (mouse, 4 hr)[2] |
| US health exposure limits (NIOSH): | |
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PEL (Permissible)
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TWA 5 mg/m3[1] |
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REL (Recommended)
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TWA 5 mg/m3[1] |
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IDLH (Immediate danger)
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1500 mg/m3[1] |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| N verify (what is YN ?) | |
| Infobox references | |
Benzoyl peroxide (BPO) is an organic compound in the peroxide family. It consists of two benzoyl groups bridged by a peroxide link. Its structural formula is (C6H5CO)2O2. It is one of the most important organic peroxides in terms of applications and the scale of its production. Benzoyl peroxide is used as an acne treatment, for bleaching flour, hair and teeth, for cross-linking polyester resins, and for many other purposes.
It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.[3]
Most benzoyl peroxide is used as a radical initiator to induce polymerizations.[4] Other major applications include its antiseptic and bleaching properties.
Benzoyl peroxide (BPO) is effective for reducing the number and severity of acne lesions. BPO has a bactericidal effect on Propionibacterium acnes bacteria associated with acne and does not induce antibiotic resistance.[5][6] It may be combined with salicylic acid, sulfur, erythromycin or clindamycin (antibiotics), or adapalene (a synthetic retinoid). Two common combination drugs include benzoyl peroxide/clindamycin and adapalene/benzoyl peroxide, an unusual formulation considering most retinoids are deactivated by peroxides. Combination products such as benzoyl peroxide/clindamycin and benzoyl peroxide/salicylic acid appear to be slightly more effective than benzoyl peroxide alone for the treatment of acne lesions.[6]
Benzoyl peroxide for acne treatment is typically applied to the affected areas in gel or cream form, in concentrations of 2.5% increasing through 5.0%, and up to 10%.[5] No strong evidence supports the idea that higher concentrations of benzoyl peroxide are more effective than lower concentrations.[5]
Benzoyl peroxide commonly causes initial dryness and sometimes irritation, although the skin develops tolerance after a week or so. A small percentage of people are much more sensitive to it and liable to suffer burning, itching, crusting, and possibly swelling.[7] It is sensible to apply the lowest concentration and build up as appropriate. Once tolerance is achieved, increasing the quantity or concentration and gaining tolerance at a higher level may give better subsequent acne clearance.[8] Irritation can also be reduced by avoiding harsh facial cleansers and wearing sunscreen prior to sun exposure.[8]
Other common uses for benzoyl peroxide include
In the U.S., the typical concentration for benzoyl peroxide is 2.5% to 10% for both prescription and over-the-counter drug preparations that are used in treatment for acne. Higher concentrations are used for hair bleach and teeth whitening. Benzoyl peroxide, like most peroxides, is a powerful bleaching agent. Contact with fabrics or hair 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.[11]
Concentrated benzoyl peroxide is potentially explosive[12] 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 percent of benzoyl peroxide and pose no explosion risk.
The carcinogenic potential of benzoyl peroxide has been investigated. A 1981 study published in the journal Science found that although benzoyl peroxide is not a carcinogen, it does promote cell growth when applied to an initiated tumor. The study concluded, "caution should be recommended in the use of this and other free radical-generating compounds".[13]
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.[14]
The U.S. National Institute for Occupational Safety and Health has developed criteria for a recommended standard for occupational exposure to benzoyl peroxide.[15]
Skin irritation due to benzoyl peroxide
A bleached fabric stain caused by contact with benzoyl peroxide.
Benzoyl peroxide was the first organic peroxide prepared by intentional synthesis. It was prepared by treating benzoyl chloride with barium peroxide,[16] a reaction that probably follows this equation:
Benzoyl peroxide is usually prepared by treating hydrogen peroxide with benzoyl chloride.
The oxygen–oxygen bond in peroxides is weak. Thus benzoyl peroxide readily undergoes homolysis (symmetrical fission), forming free radicals:
The symbol • indicates that the products are radicals; i.e., they contain at least one unpaired electron. Such species are highly reactive. The homolysis is usually induced by heating. The half-life of benzoyl peroxide is one hour at 92 °C. At 131 °C, the half-life is one minute.[17]
Benzoyl peroxide breaks down in contact with skin, producing benzoic acid and oxygen, neither of which is significantly toxic.[18]
E numbers
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Acne-treating agents (D10)
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| Antibacterial |
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| Keratolytic |
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| Anti-inflammatory |
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| Antibiotics |
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| Hormonal |
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| Retinoids |
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| Other |
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| Combinations |
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| 関連記事 | 「peroxide」 |