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Benzoyl peroxide

Basic information Acne vulgaris Active Ingredients for Acne Medications Mode of action Side effects as Acne Treatment Other Uses Benzoyl peroxide and Pregnancy References Safety Related Supplier

Benzoyl peroxide Basic information

Product Name:
Benzoyl peroxide
CAS:
94-36-0
MF:
C14H10O4
MW:
242.23
EINECS:
202-327-6
Mol File:
94-36-0.mol
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Benzoyl peroxide Chemical Properties

Melting point:
105 °C(lit.)
Boiling point:
176°F
Density 
1.16 g/mL at 25 °C(lit.)
refractive index 
1.5430 (estimate)
Flash point:
>230 °F
storage temp. 
2-8°C
solubility 
0.35mg/l
form 
powder
color 
White
Water Solubility 
Insoluble
Merck 
14,1116
BRN 
984320
Exposure limits
TLV-TWA 5 mg/m3; IDLH 7000 mg/m3.
Stability:
Strong oxidizer. Highly flammable. Do not grind or subject to shock or friction. Incompatible with reducing agents, acids, bases, alcohols, metals, organic materials. Contact with combustible material, heating or friction may cause fire or explosion.
InChIKey
OMPJBNCRMGITSC-UHFFFAOYSA-N
CAS DataBase Reference
94-36-0(CAS DataBase Reference)
NIST Chemistry Reference
Benzoyl peroxide(94-36-0)
EPA Substance Registry System
Benzoyl peroxide (94-36-0)
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Safety Information

Hazard Codes 
O,Xn,N,Xi,E,T
Risk Statements 
8-36/37/38-43-36-2-7-1-51/53-21/22-62-50-61-3-39/23/24/25-40
Safety Statements 
53-17-26-36/37-45-60-36/37/39-3/7-14A-14-47-35-7-61-37/39-24
RIDADR 
UN 3108 5.2
WGK Germany 
2
RTECS 
DM8575000
Autoignition Temperature
176 °F
TSCA 
Yes
HazardClass 
5.2
PackingGroup 
II
HS Code 
29163200
Hazardous Substances Data
94-36-0(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 7710 mg/kg

MSDS

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Benzoyl peroxide Usage And Synthesis

Acne vulgaris

Although the precise cause of acne is unclear, it appears to be associated with at least four factors: increased sebum production, follicular keratinisation, bacterial colonisation and inflammation.
Study suggests the prevalent bacterium implicated in the clinical course of acne is Propionibacterium acnes (P acnes), a gram-positive anaerobe that normally inhabits the skin and is implicated in the inflammatory phase of acne.
Benzoyl peroxide is mainly indicated in the treatment of mild to moderate acne and is often prescribed in conjunction with oral antibiotics (erythromycin or clindamycin) in the treatment of moderate to severe acne.

Active Ingredients for Acne Medications

Benzoyl peroxide used in 2.5, 5, and 10 percent concentrations, depending on the acne severity. Usually these are in a gel spreading agent, but they can also be in a cream base or a drying paste. Benzoyl peroxide is a keratolytic, which means “keratin-dissolving” and works by loosening dead cells stuck in the follicles. It also releases oxygen in the follicle. Because acne bacteria are anaerobic, they cannot survive in the presence of oxygen. Benzoyl peroxide essentially works both as an interfollicular exfoliant and as an antibacterial.

Mode of action

Benzoyl peroxide is lipophilic that 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 oxidise proteins in bacterial cell membranes, exerting a bactericidal action. In addition, it has shown that benzoyl peroxide can reduce the free fatty acid content of sebum, which provides a useful marker for bacterial activity. Benzoyl peroxide has an anti-inflammatory action and 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 turnover rate of epithelial cells, thereby peeling the skin and promoting the resolution of comedones.

Side effects as Acne Treatment

Skin reactions such as peeling, itching, irritation, and reddened skin may occur, especially at the start of treatment. A very serious allergic reaction to this drug is rare. This medicine may be harmful if swallowed.

Other Uses


Benzoyl peroxide is used as a bleaching agent for certain foods, an oxidizing agent, a polymerizing initiator in the manufacture of plastics, a curing agent for silicone rubber, and an ingredient in various industrial processes.
Benzoyl peroxide, like most peroxides, is a powerful bleaching agent. It has a long history of use in the food industry as a bleaching agent added for flour, whey, and milk for cheese making. Contact with fabrics or hair can cause permanent color dampening almost immediately. Even secondary contact can cause bleaching.
Benzoyl peroxide is widely used as a catalyst in the polymerisation of molecules like styrene (phenylethene) to form polystyrene, which used to make many things from drinking cups to packaging material.

Benzoyl peroxide and Pregnancy

There are no studies looking at women who use topical benzoyl peroxide during pregnancy. When benzoyl peroxide is applied topically, only 5% is absorbed through the skin, and then it is completely metabolized to benzoic acid within the skin and excreted unchanged in the urine. It is not likely to increase risk for birth defects or cause problems for the baby. However, systemic effects on a pregnant woman and her child would not be expected and therefore use of this product during pregnancy would not be of concern.

References

https://medlineplus.gov/druginfo/meds/a601026.html
https://pubchem.ncbi.nlm.nih.gov/compound/benzoyl_peroxide#section=Drug-and-Medication-Information
http://www.chm.bris.ac.uk/motm/benzoyl-peroxide/benzoylh.htm
https://www.webmd.com/drugs/2/drug-1344/benzoyl-peroxide-topical/details
https://pubchem.ncbi.nlm.nih.gov/compound/benzoyl_peroxide#section=Top
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3114665/
https://mothertobaby.org/fact-sheets/topical-acne-treatments-pregnancy/pdf/

Chemical Properties

white powder or crystals

Chemical Properties

Benzoyl peroxide is an odorless, white or colorless crystalline powder.

Uses

benzoyl peroxide is an antibacterial ingredient commonly used in acne treatments. It functions by forcing an oxidant (peroxide in this case) into the philosebaceous orifice where it releases oxygen, thereby diminishing the P. acnes population. This reduces the level of free fatty acids and skin infection. Benzoyl peroxide may cause skin irritation in people with sensitive skin.

Uses

Benzoyl Peroxide is a colorless, crystalline solid with a faint odor of benzaldehyde resulting from the interaction of benzoyl chloride and a cooled sodium peroxide solution. it is insoluble in water. it is used in specified cheeses at 0.0002% of milk level. it is used for the bleaching of flour, slowly decomposing to exert its full bleaching action, which results in whiter flour and bread.

Uses

vitamin B complex

Uses

Benzoyl Peroxide is a widely used organic compound of the peroxide family. Benzoyl Peroxide is often used in acne treatments , bleaching and polymerizing polyester and many other uses.

Uses

Source of free radicals for industrial processes. Oxidizing agent in bleaching oils, flour, etc.; catalyst in the plastics industry; initiator in polymerization.

Uses

Benzoyl peroxide is used as a source offree radicals in many organic syntheses andto initiate polymerizations of styrene, vinylchloride, vinyl acetate, and acrylics; to curethermoset polyester resins and silicone rubbers;in medicine for treating acne; and forbleaching vegetable oil, cheese, flour, and fats.

Indications

Benzoyl peroxide is a potent oxidizing agent that has both antimicrobial and comedolytic properties; its primary use is in treating acne vulgaris. It is converted in the skin to benzoic acid; clearance of absorbed drug is rapid, and no systemic toxicity has been observed. The major toxicities are irritation and contact allergy. Outgrowth of bacteria resistant to topical antibiotics used to treat acne can be reduced by the addition of benzoyl peroxide in combination products such as erythromycin (Benzamycin) and clindamycin (Benzaclin).

brand name

Acne-Aid Cream (Stiefel); Benoxyl (Stiefel); Benzac (Galderma); Benzac W (Galderma); Brevoxyl (Stiefel); Clear By Design (SmithKline Beecham); Dry and Clear (Whitehall-Robins); Epi-Clear (Bristol-Myers Squibb); Fostex BPO Bar, Gel, and Wash (Bristol-Myers Products); Loroxide (Dermik); PanOxyl (Stiefel); Persa-Gel (Ortho Pharmaceutical); Vanoxide (Dermik);Altex.

World Health Organization (WHO)

Benzoyl peroxide slowly releases oxygen and hence is bactericidal. It is also keratolytic, antiseborrheic and irritant. It is used in the treatment of acne. Benzoyl peroxide is listed in the WHO Model List of Essential Drugs.

General Description

White, odorless powder, moderately toxic.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Benzoyl peroxide reacts exothermically withstrong acids, strong bases, amines, reducingagents, and sulfur compounds. Explosionshave been reported when it reacted withcarbon tetrachloride and ethylene (Bolt andJoyce 1947), lithium aluminum hydride(Sutton 1951), N,N-dimethyl aniline (Hornerand Betzel 1953), hot chloroform (NFPA1986), and methyl methacrylate (NFPA1986). Lappin (1948) reported an explosionwhen a bottle was opened. Organic matterentrapped in the threads of the bottleprobably reacted explosively with benzoylperoxide.

Hazard

Highly toxic via inhalation. May explode spontaneously when dry (<1% of water). Never mix unless at least 33% water is present. Skin and upper respiratory tract irritant. Questionable carcinogen.

Health Hazard

The health hazard from benzoyl peroxideis low. It can cause irritation of the skin,mucous membranes, and eyes. An intraperitonealinjection of 250 mg/kg was lethal toadult mice. Systemic toxicity in humans isnot known. It may be mild to moderatelytoxic on an acute basis. The oral LD50 valuein rats is 7710 mg/kg (NIOSH 1986). Itstoxicity from inhalation is low; an LC50 valueof 700 ppm in mice is suggested (ACGIH1986).
Benzoyl peroxide may cause gene damageand DNA inhibition. It has been foundto cause skin tumor. The evidence of its carcinogenicityin animals and humans is inadequate.

Fire Hazard

Benzoyl peroxide can cause a major fire and explosion hazard. It is highly flammable and a strong oxidizer; autoignition temperature 80°C (176°F). It ignites instantly. The rate and violence of decomposition and the potential ease of such ignition or decomposition have been experimentally measured by Noller et al. (1964). Lead pipe deformation (LPD), pressure vessel test (PVT), and self-accelerating decomposition test (SADT) have been performed to measure these explosive characteristics. Heating 5 g of benzoyl peroxide in an aluminum tester containing an aperture vent and 6-atm rupture disk, caused the disk to blow up in 95 seconds when the aperture vent area was less than 174.7 mm2. Redried material was more violent. The decomposition hazard was greatly reduced with wet and diluted benzoyl peroxide.
Noller et al. (1964) measured the SADT temperature at 82.2°C (180°F), above which the decomposition was self-accelerating, sudden, and produced smoke.
Benzoyl peroxide is a deflagrant, posing a severe explosion hazard. The compound is sensitive to heavy shock, such as impact or blows, as well as to friction and heat. Especially in the dry state, it is highly dangerous.
A water sprinkler should be used to extinguish fires. Water should be used to keep the containers cool.

Contact allergens

Benzoyl peroxide is an oxidizing agent widely employed in acne topical therapy. It is also used as a polymerization catalyst of dental or industrial plastics and as a decolorizing agent of flours, oils, fats, and waxes. Irritant or allergic dermatitis may affect workers in the electronics and plastics (epoxy resins and catalysts) industries, electricians, ceramic workers, dentists and dental technicians, laboratory technicians, bakers, and acne patients. As it was contained in candles, it also induced contact dermatitis in a sacristan. Patch tests may be irritant.

Potential Exposure

Used as polymerization initiator, curing agent, and cross-linking agent.

Veterinary Drugs and Treatments

Benzoyl peroxide products are used topically either as gels or in shampoos. Shampoos are generally used for seborrheas, greasy skin (seborrhea oleosa), or crusty pyodermas (such as seborrheic dermatitis/pyoderma commonly seen in Cocker Spaniels). Gels may be useful for treating recurrent localized skin infections (e.g., chin acne), localized Demodex lesions, superficial and deep pyodermas (adjunctive therapy), seborrhea oleosa, and Schnauzer comedo syndrome. Benzoyl peroxide possesses antimicrobial (especially antibacterial), keratolytic and antiseborrheic actions. It also is It has some mild antipruritic activity and wound healing effects, and is thought to increase follicular flushing. Benzoyl peroxide’s antimicrobial activity is due to the oxidative benzoyl peroxy radicals formed that disrupt cell membranes.

Carcinogenicity

When repeatedly applied to the skin of mice, BPO was not carcinogenic . However, benzoyl peroxide is a tumor promoter in mice and hamsters, but has shown no complete carcinogenic or tumor-initiating activity . There has been one controversial Japanese report that was interpreted as BPO being a complete carcinogen. However, when the data were critically evaluated, it was found consistent with BPO acting as a skin tumor promoter and not as a carcinogen. The International Agency for Research on Cancer (IARC) has evaluated the carcinogenicity of benzoyl peroxide. They classified it as Group 3. This means there is limited or inadequate evidence of carcinogenicity for animals and inadequate or absent information for humans. In addition, there are other animals and in vitro studies that continue to support the lack of carcinogenic or mutagenic properties for BPO .

storage

Benzoyl peroxide should be stored in acool and well-ventilated area, isolated fromother chemicals and free of heating andelectrical installations. Dry compound maybe shipped in polyethylene-lined paper bagsor fiber containers packed in wooden boxeso.

Shipping

UN3104 : Organic peroxide type C, solid, Hazard Class: 5.2; Labels: 5.2—Organic peroxide, Technical Name Required. UN3108 : Organic peroxide type E, solid, Hazard Class: 5.2; Labels: 5.2—Organic peroxide, Technical

Purification Methods

Dissolve benzoyl peroxide in CHCl3 at room temperature and precipitate it by adding an equal volume of MeOH or pet ether. Similarly it is precipitated from acetone by adding two volumes of distilled water. It has also been crystallised from 50% MeOH and from diethyl ether. Dry it under vacuum at room temperature for 24hours. Store it in a desiccator in the dark at 0o. When purifying in the absence of water it can be EXPLOSIVE, and operations should be done on a very small scale with adequate protection. Large amounts should be kept moist with water and stored in a refrigerator. [Kim et al. J Org Chem 52 3691 1987, Beilstein 9 IV 777.]

Incompatibilities

May explode when heated above melting point, 103 C. A strong oxidizer. Extremely explosionsensitive to heat, shock, friction, and concussion. May explode or cause fire on contact with reducing agents; combustible substances, organic substances, wood, paper, metal powders, lithium aluminum hydride. Violent reaction with alcohols, organic and inorganic acids, and amines.

Waste Disposal

Pretreatment involves decomposition with sodium hydroxide. The final solution of sodium benzoate, which is very biodegradable, may be flushed into the drain. Disposal of large quantities of solution may require pH adjustment before release into the sewer or controlled incineration after mixing with a noncombustible material.

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Benzoyl peroxideSupplierMore

Shanghai Aladdin Bio-Chem Technology Co.,LTD Gold
Tel:
021-20337333/400-620-6333
Email:
sale@aladdin-e.com
Products Intro:
Product Name:Benzoyl peroxide
CAS:94-36-0
Purity:AR Package:69.3RMB/250G
Hubei XinMingTai Chemical Co., Ltd. Gold
Tel:
027-62437337-
Email:
1228159977@qq.com
Products Intro:
Product Name:Benzoyl peroxide
CAS:94-36-0
Purity:98% HPLC Package:1KG;5KG;10KG;50KG;100KG
Foshan Daping Chemical Technology Co., Ltd Gold
Tel:
0757-26601217-
Email:
dxp6878@163.com
Products Intro:
Product Name:BPO
CAS:94-36-0
Purity:80
Tianjin Zhongxin Chemtech Co., Ltd.
Tel:
86(0)22-66880623
Email:
sales@tjzxchem.com
Products Intro:
Product Name:Benzoyl peroxide
Purity:74-77% Package:25kg drum
J & K SCIENTIFIC LTD.
Tel:
010-82848833- ;010-82848833-
Email:
jkinfo@jkchemical.com;market6@jkchemical.com
Products Intro:
Product Name:Benzoyl peroxide, 98%, wetted with ca. 25% H2O
CAS:94-36-0
Purity:98% Package:100G;25G;500G
Basic information Acne vulgaris Active Ingredients for Acne Medications Mode of action Side effects as Acne Treatment Other Uses Benzoyl peroxide and Pregnancy References Safety Related Supplier