BENZOYL PEROXIDE
Benzoyl peroxide, also called dibenzoyl peroxide, is an organic peroxide with structural formula (C6H5−C(=O)O−)2, often abbreviated as (BzO)2.
Benzoyl peroxide molecule can be described as two benzoyl (C6H5−C(=O)−, Bz) groups connected by a peroxide (−O−O−).
Benzoyl peroxide is a white granular solid with a faint odor of benzaldehyde, poorly soluble in water but in acetone, ethanol, and many other organic solvents.
Benzoyl peroxide, also known as dibenzoyl peroxide, is a widely used organic compound of the peroxide family.
Benzoyl peroxide is an oxidizer which is principally used in producing polymers.
Benzoyl peroxide is an antibacterial and anti-inflammatory agent used for the symptomatic treatment of mild to moderate acne vulgaris and rosacea.
Benzoyl Peroxide is an organic compound with C14H10O4 as a structural or chemical formula.
The benzoyl chloride, sodium hydroxide, and hydrogen peroxide reaction manufactures benzoyl peroxide.
Benzoyl peroxide has antibacterial properties and is widely used in treating acne.
Benzoyl peroxide is a peroxide that involves keratolytic, comedolytic, irritant, and anti-inflammatory actions.
Synonyms: Dibenzoyl Peroxide, benzoperoxide, dibenzoyl peroxide (DBPO), BPO, Peroxide, dibenzoyl, BPO, DBPO, Benzoic Peroxyanhydride
CAS Number: 94-36-0
Formula: C14H10O4
Molar mass: 242.230 g·mol−1
Density: 1.334 g/cm3
Melting point: 103 to 105 °C (217 to 221 °F) decomposes
APPLICATIONS OF BENZOYL PEROXIDE:
In concentrations between 2.5% to 10%, this compound can be applied to human skin to treat acne.
Benzoyl peroxide can remove dye stains and ink from many playthings, such as vinyl dolls.
Benzoyl peroxide can also be used as a bleaching agent in cheese and bread.
Benzoyl peroxide is used in tooth whitening and cosmetic hair coloring.
In organic chemistry, benzoyl peroxide is a very convenient oxidant.
The polymerization process of resins can be initiated with the help of Benzoyl peroxide.
Benzoyl peroxide is also used as a catalyst in synthesizing thermosetting polyester resins.
Benzoyl Peroxide is used as a source of free radicals in many organic syntheses and to initiate polymerizations of styrene, vinyl chloride, vinyl acetate, and acrylics to cure thermoset polyester resins and silicone rubbers; in medicine for treating acne; and for bleaching vegetable oil, cheese, flour, and fats.
Benzoyl peroxide is mainly used in the production of plastics and for bleaching flour, hair, plastics, and textiles.
Product Type: Polymerization Initiators / Inhibitors / Catalysts > Polymerization initiators > Benzoyl peroxide
As a bleach, Benzoyl peroxide has been used as a medication and a water disinfectant.
As a medication, Benzoyl peroxide is mainly used to treat acne alone or in combination with other treatments.
Benzoyl peroxide is also used in dentistry for teeth whitening.
Benzoyl peroxide is mainly used as a radical initiator to induce chain-growth polymerization reactions, such as polyester and poly(methyl methacrylate) (PMMA) resins, dental cement, and restoratives.
Benzoyl peroxide is the most crucial organic peroxide used for this purpose, a relatively safe alternative to the much more hazardous methyl ethyl ketone peroxide.
Benzoyl peroxide is also used in rubber curing and as a finishing agent for some acetate yarns.
Benzoyl Peroxide is an organic solid in the peroxide family used to improve flour.
Benzoyl Peroxide is used to bleach flour, slowly decomposing to exert its full bleaching action, resulting in whiter flour and bread.
Luperox A75 by Arkema is benzoyl peroxide.
It is a 75% active grade of Benzoyl peroxide / BPO with the remainder water added for added safety.
It is used in bulk polymerizations.
Heavy metal or amine accelerators can achieve room temperature curing operations such as thermoset or acrylic composites.
Benzoyl peroxide is commonly used in organic chemistry as a radical initiator.
Benzoyl peroxide is an organic peroxide that readily undergoes homolysis to form free radicals.
The O-O bond in benzoyl peroxide is relatively weak and can undergo hemolysis when exposed to sufficient light or heat.
Other uses
Due to its strong antibacterial and anti-inflammatory effects on the skin, Benzoyl Peroxide has been recognized as a treatment for acne.
The antiseptic quality of the peroxide makes it adept at reducing bacteria on the skin's surface, as well as whiteheads and blackheads.
Another reason for Benzoyl Peroxide’s popularity amongst acne sufferers is that it is safe to use in conjunction with salicylic acid products.
Tube of a water-based 5% benzoyl peroxide preparation for the treatment of acne
Benzoyl peroxide is effective for treating acne lesions.
Benzoyl peroxide does not induce antibiotic resistance.
It may be combined with salicylic acid, sulfur, erythromycin clindamycin (antibiotics), or adapalene (a synthetic retinoid).
Two common combination drugs include benzoyl peroxide/clindamycin and adapalene/benzoyl peroxide, adapalene being a chemically stable retinoid that can be combined with benzoyl peroxide, unlike tazarotene and tretinoin.
Combination products such as benzoyl peroxide/clindamycin and benzoyl peroxide/salicylic acid appear slightly more effective than benzoyl peroxide alone for treating acne lesions.
The combination tretinoin/benzoyl peroxide was approved for medical use in the United States in 2021.
Benzoyl peroxide for acne treatment is typically applied to the affected areas in gel, cream, or liquid in concentrations of 2.5%, increasing through 5.0% and up to 10%.
No strong evidence supports the idea that higher concentrations of benzoyl peroxide are more effective than lower concentrations.
Benzoyl peroxide is potentially explosive, especially in pure form.
Benzoyl peroxide can cause a significant fire and explosion hazard.
It is highly flammable and a strong oxidizer; the autoignition temperature is 80°C (176°F).
It ignites instantly.
Mechanism of action
Benzoyl peroxide is lipophilic and can penetrate the stratum corneum and enter the pilosebaceous follicle.
It is rapidly broken down to benzoic acid and hydrogen peroxide and generates free radicals that oxidize proteins in bacterial cell membranes, exerting a bactericidal action.
In addition, it has been shown that benzoyl peroxide can reduce sebum's free fatty acid content, which provides a valuable marker for bacterial activity.
Benzoyl peroxide has an anti-inflammatory action, and in vitro studies suggest that this action arises from its ability to kill polymorphonuclear leukocytes (PMN cells) in the pilosebaceous follicles and so prevent their release of reactive oxygen species such as peroxides, which enhance tissue inflammation. Involving equation about this process:
C6H5C(O)O-OC(O)C6H5 + H2O 2 C6H5COOH + ½ O2
Moreover, due to its irritant effect, benzoyl peroxide increases the turnover rate of epithelial cells, thereby peeling the skin and promoting the resolution of comedones.
Benzoyl peroxide is metabolized in the skin (predominantly in the upper layers of the epidermis) to benzoic acid and free oxygen radicals.
The former lowers skin pH; the latter disrupts microbial cell membranes.
Benzoyl peroxide has broad-spectrum antimicrobial activity that persists for 48 hours, even when conditions for bacterial growth are optimal.
It has also been shown to be keratoplastic by inhibiting epidermal metabolism and DNA synthesis.
Side effects
Skin irritation due to benzoyl peroxide
Application of benzoyl peroxide to the skin may result in redness, burning, and irritation.
This side effect is dose-dependent.
Because of these possible side effects, starting with a low concentration and building up as appropriate is recommended as the skin gradually tolerates the medication. Skin sensitivity typically resolves after a few weeks of continuous use.
Irritation can also be reduced by avoiding harsh facial cleansers and wearing sunscreen before exposure to the sun.
One in 500 people experience hypersensitivity to benzoyl peroxide and are liable to experience burning, itching, crusting, and possibly swelling.
About one-third of people experience phototoxicity under exposure to ultraviolet (UVB) light.
Dosage
In the U.S., the typical concentration of benzoyl peroxide is 2.5% to 10% for prescription and over-the-counter drug preparations used to treat acne.
Other medical uses
Benzoyl peroxide is used in dentistry as a tooth-whitening product.
Safety
Explosion hazard
Benzoyl peroxide is potentially explosive 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 tiny 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.[34]
The carcinogenic potential of benzoyl peroxide has been investigated.
A 1981 study published in Science found that although benzoyl peroxide is not a carcinogen, it promotes cell growth when applied to an initiated tumor.
The study concluded, "Caution should be recommended in using this and other free radical-generating compounds."
A 1999 IARC review of carcinogenicity studies found no convincing evidence linking benzoyl peroxide acne medication to human skin cancers.
However, some animal studies found that the compound could act as a carcinogen and enhance the effect of known carcinogens.
Skin irritation
In a 1977 human maximization test study, 76% of subjects acquired a contact sensitization to benzoyl peroxide.
Formulations of 5% and 10% were used.
The U.S. National Institute for Occupational Safety and Health has developed criteria for a recommended standard for occupational exposure to benzoyl peroxide.
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 used to wash off benzoyl peroxide-containing hygiene products.
Translated names
dibensoylperoxid bensoylperoxid (sv)
dibensoüülperoksiid bensoüülperoksiid (et)
Dibentsoyyliperoksidi bentsoyyliperoksidi (fi)
dibenzoil peroksid benzoil peroksid (sl)
dibenzoil-peroxid benzoil-peroxid (hu)
Dibenzoilperoksidas benzoilperoksidas (lt)
dibenzoilperoksīds benzoilperoksīds (lv)
dibenzoylperoksid benzoylperoksid (no)
dibenzoylperoxid benzoylperoxid (da)
Dibenzoylperoxid Benzoylperoxid (de)
dibenzoylperoxid benzoylperoxid (sk)
dibenzoylperoxid dibenzoylperoxid (cs)
dibenzoylperoxide benzoylperoxide (nl)
nadtlenek dibenzoilowy nadtlenek benzoilowy (pl)
perossido di dibenzoile benzoile perossido (it)
peroxid de dibenzoil peroxid de benzoil (mt)
peroxid de dibenzoil peroxid de benzoil (ro)
peroxyde de dibenzoyle;peroxyde de benzoyle peroxyde de benzoyle (fr)
peróxido de dibenzoílo peróxido de benzoílo (es)
peróxido de dibenzoílo peróxido de benzoílo (pt)
Δδιβενζοϋλυπεροξείδιο Ββενζοϋλυπεροξείδιο (el)
дибензоил пероксид бензоил пероксид (bg)
IUPAC names
benzoyl benzenecarboperoxoate
benzoyl benzenecarboperoxoate (with 25% H2O)
BENZOYL PEROXIDE
Benzoyl peroxide
benzoyl peroxide
Benzoyl peroxide (BPO)
Benzoyl Peroxide (wetted with ca. 25% Water)
DIBENZOYL PEROXIDE
Dibenzoyl peroxide
dibenzoyl peroxide
Dibenzoyl Peroxide
dibenzoyl peroxide
dibenzoyl peroxide (upper limit: 77% w/w; typical concentration: 75% w/w)
dibenzoyl peroxide; benzoyl peroxide
Dibenzoylperoxide
diphenylperoxyanhydride
LUPEROX A75
Peroxide, dibenzoyl
Peroxide, dibenzoyl
Trade names
Benzoic acid, peroxide
Benzoperoxide
Benzoyl peroxide, remainder water
Benzoyl Superoxide
Dibenzoyl peroxide
dibenzoyl peroxide
NOVIPER BP
Perkadox L-W75
Peróxido de dibenzoilo
202-327-6 [EINECS]
94-36-0 [RN]
BENZAC
BENZACLIN
benzoyl benzenecarboperoxoate
Benzoyl peroxide [USP] [Wiki]
Benzoyl peroxide (usp)
Benzoylperoxid [German]
benzoylperoxide
BPO
Diacyl peroxide
dibenzoyl peroxide
Dibenzoylperoxid [German]
Diphenylperoxyanhydrid [German] [ACD/IUPAC Name]
Diphenylperoxyanhydride [ACD/IUPAC Name]
Diphénylperoxyanhydride [French] [ACD/IUPAC Name]
Luperox(R) A70S, Benzoyl peroxide
Luperox(R) A75, Benzoyl peroxide
Luperox(R) A98, Benzoyl peroxide
Luperox(R) ATC50, Benzoyl peroxide
MFCD00003071 [MDL number]
Oxy 5
Perossido di benzoile [Italian]
Peróxido de benzoílo [Spanish]
Peroxyde de benzoyle [French]
过氧化苯甲酰 [Chinese]
117989-71-6 [RN]
132323-44-5 [RN]
143928-58-9 [RN]
202-327-6MFCD00003071
2685-64-5 [RN]
37370-29-9 [RN]
50-31-7 [RN]
Abcure S-40-25
Acetoxyl
AcetOxyl 2.5 and 5
Acne-Aid Cream
Acnegel
Akneroxid 5
Akneroxid L
Akneroxide L
Aksil 5
Asidopan
Aztec benzoyl peroxide-70-77
Aztec benzoyl peroxide-DRY
Aztec BPO
B 75W
Benbel C
Benoxyl
Benzac W
Benzagel
Benzagel 10
Benzaknen
Benzaknew
benzamycin [Wiki]
Benzashave
benzenecarboperoxoic acid (oxo-phenylmethyl) ester
benzenecarboperoxoic acid benzoyl ester
Benzol peroxide
Benzoperoxide
benzoyl
Benzoyl peroide
Benzoyl peroxide blend with dicyclohexyl phthalate
Benzoyl peroxyde
Benzoyl superoxide
Benzoylperoxid
Benzoylperoxyde
Bepio
Brevoxyl [Wiki]
Cadat BPO
Cadet
Cadet BPO 78W
Cadet BPO-70W
Cadox
Cadox BPO-W40
Cadox bta
Cadox BTW-50
Chaloxyd BP 50FT
Clear By Design
Debroxide
Dermoxyl
Desanden
Desquam E
Desquam X
Desquam-X
Dibenzoylperoxid
Dibenzoylperoxide
Dibenzoylperoxyde
Diphenylglyoxal peroxide
Diphenylglyoxal superoxide
Dry and Clear
Duresthin 5
Eloxyl
Epi-Clear
Florox
Fostex [Trade name]
Fostex BPO
G20
Garox
Incidol
Loroxide
Lucidol
Lucidol GS
Lucidol RM
Lucidol-78
Lucilite
Lucipal
Luperco
Luperco a
Luperco ac
Luperco afr
Luperco AFR-250
Luzidol
Mytolac
Nayper B and BO
Nayper bo
nericur
Norox bzp-250
Norox bzp-C-35
Novadeiox
Novadelox
Nyper B
Nyper BMT
OXY WASH
Oxy-10 Cover
Oxy-5
Oxy-L
Oxylite
Panoxyl [Wiki]
Periygel
Perkadox 20S
Perossido di benzoile
Peroxyderm
peroxydex
Persadox
Persa-Gel
phenylcarbonyl benzenecarboperoxoate
pHisoAc BP
Preoxydex
Presadox
Resdan Akne
Sanoxit
Silica hydrogel
Stri-dex B.P
Stri-dex B.P.
Sulfoxyl
Superox
Superox 744
Superoxide, Benzoyl
Superoxide, diphenylglyoxal
TCBA
TheraDerm
Thermaderm
Topex
Triaz
TRIAZ, Dibenzoyl peroxide
Vanoxide
W 75
WLN: RVOOVR
Xerac
Xerac BP
Xerac BP 10
Xerac BP 5
