HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Dibenzoylperoxid
BPO · DIBENZOYL PEROXIDE · benzoic peroxyanhydride · Benzoyl · BENZOYL BENZENECARBOPEROXOATE · Benzoylperoxid · Benzoyl peroxide paste · Benzamycin
Identifikatoren & physikalische Daten
| CAS No. | 94-36-0 |
|---|---|
| Summenformel | C14H10O4 |
| Durchschnittliche Molmasse | 242,23 g/mol |
| Monoisotopische Masse | 242,0579088 g/mol |
| SMILES | O=C(OOC(=O)c1ccccc1)c1ccccc1 |
| InChIKey | OMPJBNCRMGITSC-UHFFFAOYSA-N |
| PubChem CID | 7187 |
| ChEMBL | CHEMBL1200370 |
| ChEBI | CHEBI:82405 |
| EC No. | 202-327-6 |
| DTXSID | DTXSID6024591 |
| Lokaler Name | Dibenzoylperoxid |
Chemische & physikalische Eigenschaften
| XLogP | 3,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 52,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 18 |
| Formalladung | 0 |
| Komplexität | 258 |
| Stoffklassen | Other Classes -> Peroxides, OrganicFlammable agents - 4th degree |
| Arzneimittel | PharmaceuticalsPharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Chemical shift |
| LogP (Verteilungskoeffizient) | log Kow = 3.46 |
| Geruch | Faint, benzaldehyde-like odor. |
| Geschmack | Tasteless |
| Lebensmittelzusatzstoffe | COLOR OR COLORING ADJUNCT, FLOUR TREATING AGENT -> FDA Substance added to food |
| Dichte | 1.334 at 59 °F (USCG, 1999) - Denser than waterwill sink1.3340 at 25 °C1.3 g/cm³1.334 @25 °C1.16 g/mL at 25 °C(lit.) |
| Color/Form | CrystalsWhite, granular crystalline solidOrthorhombic prisms from etherColorless to white crystals or a granular powder. |
| Löslichkeit | less than 1 mg/mL at 79 °F (NTP, 1992)<1%In water, 9.10 mg/L at 25 °CSparingly soluble in waterSlightly soluble in waterSparingly soluble in alcoholsoluble in benzene, chloroform, ether1 g dissolves in 40 mL carbon disulfide, in about 50 mL olive oil0.35mg/lInsoluble |
| Flammpunkt | 176 °F (NIOSH, 2024)80 °C>230 °F |
| Human Drugs | Breast FeedingLactationMilk, HumanDermatologic AgentsPeroxidesFDA approved drugs -> Active ingredientDermatological medicines > Medicines affecting skin differentiation and proliferation |
| Schmelzpunkt | 105 °C(lit.) |
| Siedepunkt | 176°F |
| Dampfdruck | 0.009Pa at 25℃ |
| Brechungsindex | 1.5430 (estimate) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | powder |
| Farbe | White |
| Geruch | odorless |
| Merck | 14,1116 |
| BRN | 984320 |
| Henry-Konstante | 2.8×100 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | 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. |
| Kosmetik-Inhaltsstoffe Funktionen | OXIDISING |
| 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 |
| InChIKey | OMPJBNCRMGITSC-UHFFFAOYSA-N |
| SMILES | O(OC(=O)c2ccccc2)C(=O)c1ccccc1 |
| LogP (Verteilungskoeffizient) | 3.2 at 20℃ |
| CAS Datenbank | 94-36-0(CAS DataBase Reference) |
| NIST chemische Informationen | Benzoyl peroxide(94-36-0) |
| EPA chemische Informationen | Benzoyl peroxide (94-36-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH241: Heating may cause a fire or explosion [Danger Self-reactive substances and mixturesOrganic peroxides]P210, P234, P235, P240, P261, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, P370+P380+P375[+P378], P391, P403, P410, P411, P420, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1679) of reports.H241 (99.6%): Heating may cause a fire or explosion [Danger Self-reactive substances and mixtures |
|---|---|
| Regulatorische Informationen | Chemical: Peroxide, dibenzoylPeroxide, dibenzoyl is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Peroxide, dibenzoyl are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 12-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15164Dibenzoyl peroxide: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Peroxide, dibenzoyl: Human health tier II assessment |
| DOT-Kennzeichnung | Organic Peroxide |
| Brandgefahren | Special Hazards of Combustion Products: Suffocating smoke evolvedMany reactions may cause fire or explosion. Risk of fire and explosion. Explosive. See Chemical Dangers. |
| Brandpotenzial | This chemical is a highly flammable liquid.Moderate fire hazard by spontaneous chemical reaction in contact with reducing agents. It ignites readily and burns rapidly. |
| Gesundheitsgefahren | CONTACT WITH EYES OR SKIN: irritates eyes. Prolonged contact may irritate skin. (USCG, 1999) |
| Gefahrenübersicht | Benzoyl peroxide is a skin irritant and infrequent sensitizer. It may cause allergic contact dermatitis in dentists using acrylate cements and in bakers handling bleached flour. [Marks, p. 188] If left on clothes, can cause reddening of the skin[CHRIS] A skin, eye, and respiratory tract irritant[ICSC] |
| FDA-Anforderungen | In accordance with section 184.1(b)(1), the ingredient is used in food with no limitation other than current good manufacturing practice. The affirmation of this ingredient as generally recognized as safe (GRAS) as a direct human food ingredient is based upon the following current good manufacturing practice conditions of use: (1) The ingredient is used as a bleaching agent in food. (2) The ingredient is used in the following foods at levels not to exceed current good manufacturing practice: flourmilk used for production of Asiago fresh and Asiago soft cheese (section 133.102), Asiago medium cheese (section 133.103), Asiago old cheese (section 133.104), Blue cheese (section 133.106), Caciocavallo siciliano chesse (section 133.111), Gorgonzola cheese (section 133.141), Parmesan and reggiano cheese (section 133.165), Provolone cheese (section 133.181), Romano cheese (section 133.183), and Swiss and emmentaler cheese (section 133.195) in part 133 of this chapterand annatto-colored whey, such that the final bleached product conforms to the descriptions and specifications for whey, concentrated whey, or dried whey in section 184.1979(a) (1), (2), or (3), respectively.The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including benzoyl peroxide, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.Benzoyl peroxide is an indirect food additive for use only as a component of adhesives. |
| Reaktive Gruppe | Peroxides, Organic |
| EG-Einstufung | Symbol: E, XiR: 2-36-43S: (1/2)-3/7-14-36/37/39 |
| UN-Einstufung | UN Hazard Class: 5.2UN Pack Group: II |
| Special Reports | Preliminary 2D Animation of Events Leading to 2017 Fire at Arkema Chemical Plant in Crosby, Texas.[U.S. Chemical Safety BoardPreliminary 2D Animation of Events Leading to 2017 Fire at Arkema Chemical Plant in Crosby, TexasAvailable from, as of November 27, 2017: http://www.csb.gov/videos/preliminary-2d-animation-of-events-leading-to-2017-fire-at-arkema-chemical-plant-in-crosby-texas/]WHO/International Programme on Chemical Safety (IPCS)Joint Expert Committee on Food Additives (JECFA), WHO Food Additives Series 54 (2006)[Available from, as of September 13, 2017: http://www.who.int/foodsafety/publications/monographs/en/]Lai DY, et alJ Environ Sci Hlth 14 (Pt C, 1): 63-80 (1986). Carcinogenic potential of organic peroxides prediction based structure activity relationships and mechanism based short term test. |
| Brandbekämpfung | Fire Extinguishing Agents Not to Be Used: Do not use hand extinguishersUse water in large amounts. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.Remove contaminated clothes. Rinse and then wash skin with water and soap.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention . |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.(General first aid procedures) |
| Sichere Lagerung | Fireproof. Separated from combustible substances and reducing agents. Store only in original packaging. See Chemical Dangers. |
| Firefighting Hazards | Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Storage containers and parts of containers may rocket great distances, in many directions. |
| Expositionsschutz und Persönliche Schutzausrüstung | 5.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)] |
| Brandbekämpfungsverfahren | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.Use water spray to cool unopened containers.Use water only. Do not use chemical or carbon dioxide extinguishers. ... If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. ... The only respirators recommended for firefighting are self-contained breathing apparatuses that have full face-pieces and are operated in a pressure-demand or other positive-pressure mode. Clean up and salvage operations after a fire should not be attempted until all of the peroxide has cooled completely.To fight fire, use water spray, foam. |
| Lagerbedingungen | Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510): Other explosive hazardous materials.All precautions must be taken to guard against fire and explosion hazards. Keep in a cool place, out of the direct rays of the sun, away from sparks, open flames, and other sources of heat, avoid shock, rough handling, friction from grinding, etc. Isolated storage is requiredkeep away from possible contact with acids, alcohols, ethers, or other reducing agents or polymerization catalysts such as dimethylaniline.Do not store in the same area as other flammable materials. Protect containers against physical damage. Isolate in well-detached, fire-resistive, cool and well-ventilated building with no other materials stored thereinprovide explosion venting in a safe direction and prohibit any electrical installation or heating facilities. Dibenzoyl peroxide should be stored in and used from original containers. |
| Reinigungsverfahren | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Sweep up and shovel. Contain spillage, and then collect with an electrically protected vacuum cleaner or by wetbrushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal. Contain spillage, pick up with an electrically protected vacuum cleaner or by wet-brushing and transfer to a container for disposal according to local regulations.Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Mix spilled material with water-wetted vermiculite, and deposit in sealed containers. Do not use spark-generating materials or materials made of paper or wood for sweeping or handling spilled benzoyl peroxide. Ventilate area of spill or leak after cleanup is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If materials or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. ... If employees are required to clean up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable./LABORATORY QUANTITIES/ Wear eye protection, laboratory coat, and nitrile rubber gloves. Cover the spill with a 1:1:1 mixture by weight of sodium carbonate or calcium carbonate, clay cat litter (bentonite), and sand. Dampen this mixture thoroughly with water, and then scoop into a beaker using a plastic or cardboard shovel. Treat as per waste disposal procedure. Wash the area of the spill thoroughly with soap and water. |
| Freisetung ohne Brand | Excerpt from ERG Guide 146 [Organic Peroxides (Heat, Contamination and Friction Sensitive)]: |
| Entsorgungsverfahren | SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this materialContaminated packaging: Dispose of as unused product.SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for 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 non-combustible material.Wear nitrile rubber gloves, laboratory coat, and eye protection. Work in the fume hood or behind safety shield. Stir the dampened benzoyl peroxide with 10% sodium hydroxide solution (10 mL for each 1 g of peroxide) for 24 hours. The resultant sodium benzoate may be poured into the drain with at least 50 times its volume of water. Alternatively, react the dampened benzoyl peroxide with a solution of sodium or potassium iodide in acid. Gradually, and while stirring, add 1.0 g of peroxide to a solution of sodium iodide (1.4 g) or potassium iodide (1.5 g) in 28 mL of glacial acetic acid. The solution darkens rapidly due to formation of iodine. Allow to stand for 30 minutes. Add solid sodium metabisulfite until the solution is colorless. Wash the solution into the drain. |
| Verschüttetes entsorgen | Evacuate danger area! Remove all ignition sources. Wash away remainder with plenty of water. Do NOT absorb in saw-dust or other combustible absorbents. |
| Wechselwirkungen | In this communication, we report that iron overload augments benzoyl peroxide (BPO)-mediated tumor promotion in 7,12-dimethylbenz[a]anthracene (DMBA)-initiated mouse skin. Female albino Swiss mice were overloaded with iron and tumors were initiated by applying a single topical application of DMBA. A week after the initiation, promoting agent, BPO, was applied three times/week for 46 weeks. The appearance of the first tumor (papilloma) and the number of tumors/mouse were recorded. When compared to the control group, the iron-overloaded mice showed an increased incidence of tumors at various time intervals. In iron-overloaded animals, tumors appeared earlier and also the number of tumors/mouse was significantly higher. These data could be correlated with the iron levels of mouse skin in the two groups. Further, BPO-mediated induction in ornithine decarboxylase (ODC) activity and [(3)H]thymidine incorporation in cutaneous DNA were higher in the iron overload group. In addition, in iron-overloaded mice, cutaneous lipid peroxidation (LPO) and xanthine oxidase (XOD) activities were higher, whereas catalase activity was reduced. Similar to papilloma induction, a significant increase in carcinoma yield and incidence was observed in iron-overloaded animals. Based on this study, we propose that iron overload significantly increases the tumor promotion and progression potential of BPO. We suggest that oxidative stress generated by iron overload is responsible for the augmentation of BPO-mediated cutaneous tumorigenesis.Dermatophyte infections can be polymicrobial. Topical antifungal therapies offer limited coverage of yeasts and Gram-positive and Gram-negative bacteria. Moreover, the increased usage of these topical antimicrobial agents has resulted in the development of resistant cases. Benzoyl peroxide (BP), used in concert with antimicrobial agents containing an accessible tertiary amine, has previously been shown to increase radical activity and biological effect. /The study objective was/ to determine the applicability of using the tertiary amine terbinafine in concert with BP in dermatophyte and mixed skin infections by means of in vitro testing. In this preliminary in vitro study, the effect of BP, alone and in combination with terbinafine, was tested against Candida albicans, Pseudomonas aeruginosa and Staphylococcus aureus isolates following a checkerboard modification of the National Committee for Clinical Laboratory Standards M27-A2 and M7-A6. The individual minimum inhibitory concentrations of terbinafine, BP, and the combination, were determined against each isolate. The combination of BP with terbinafine led to additive activities against the majority of Candida albicans isolates tested and additionally expanded the bacterial coverage of terbinafine. The combination of antifungal agents bearing a tertiary amine with BP may have benefit in polymicrobial infections, given its wider antimicrobial coverage. Further appreciation of this mechanism of catalysis of BP radical formation by certain antimicrobials and other tertiary amine-containing compounds may lead to the discovery of improved treatments for several dermatological conditions.The current study evaluates the efficacy of Balsamodendron mukul Hook ex. Stocks, an indigenous plant, in the modulation of benzoyl peroxide (BPO) treated and ultraviolet (UV) light irradiated tumor promotional events. BPO is a well-known tumor promoter while UV radiations are capable of acting as complete carcinogens. Treatment of the dorsal portions of the mice skins with BPO (20 mg/0.2 mL/animal) and subsequent UV irradiation (0.420 J/sq m/s) caused a significant depletion of reduced glutathione (GSH), it's metabolizing and phase II enzymes (p < 0.01). Also, down regulation of the activities of antioxidant enzymes and up regulation of ornithine decarboxylase activity and enhancement in the synthesis of DNA, malondialdehyde (MDA) and hydrogen peroxide (H(2)O(2)) was observed. However, topical pretreatment with the extract of B. mukul not only restored the content of GSH, MDA and H(2)O(2) but it also recovered the activities of above-mentioned enzymes (p < 0.05) and prevented synthesis of DNA (p < 0.05) significantly. Although the lower dose was not very effective, the higher dose showed promising results against oxidative stress and hyperproliferative response of BPO and UVB radiations. From the present data we conclude that B. mukul is potentially strong enough to modulate the events of skin tumor promotion.The chemopreventive potential of cycloartenol on benzoyl peroxide and UVB radiation-induced cutaneous tumor promotion markers and oxidative stress in murine skin is assessed. Benzoyl peroxide treatment (20 mg/animal/0.2 mL acetone) and UVB radiation (0.420 J/sq m/s) caused a decrease in the activities of cutaneous antioxidant enzymes namely, catalase, glutathione peroxidase, glutathione reductase, glucose-6-phosphate dehydrogenase, phase II metabolizing enzyme such as glutathione-S-transferase and quinone reductase and depletion in the level of cutaneous glutathione. There was also enhancement in cutaneous microsomal lipid peroxidation, xanthine oxidase activity, [(14)C]-ornithine decarboxylase activity and [(3)H]-thymidine incorporation into cutaneous DNA. Cycloartenol was topically applied prior to the application of benzoyl peroxide at dose levels of 0.2 mg and 0.4 mg/kg body weight in acetone, which resulted in significant inhibition of epidermal ornithine decarboxylase activity and DNA synthesis (P < 0.001). There was also significant reduction of lipid peroxidation and xanthine oxidase activity (P < 0.001). In addition, the depleted levels of glutathione, inhibited activities of antioxidant and phase II metabolizing enzymes, were also recovered to a significant level (P < 0.001). The data indicate that cycloartenol is an effective chemopreventive agent in skin carcinogenesis.For more Interactions (Complete) data for Dibenzoyl peroxide (20 total), please visit the HSDB record page. |
| Zielorgane | Eyes, skin, respiratory system |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 92(SRC), determined from a structure estimation method(2), indicates that dibenzoyl peroxide is expected to have high mobility in soil(SRC). Volatilization of dibenzoyl peroxide from moist soil surfaces is expected(SRC) given an estimated Henry's Law constant of 3.5X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Dibenzoyl peroxide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.0X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). A 84% of Theoretical BOD using activated sludge in the Japanese MITI test(3) suggests that biodegradation is an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 92(SRC), determined from a structure estimation method(2), indicates that dibenzoyl peroxide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.5X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 16 and 120 days, respectively(SRC). Dibenzoyl peroxide is expected to undergo hydrolysis rapidly with estimated half-lives of 2 minutes and 13 seconds at respective pH values of 7 and 8(2). According to a classification scheme(4), an estimated BCF of 89(SRC), from its log Kow of 3.46(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate. A 84% of Theoretical BOD using activated sludge in the Japanese MITI test(6) suggests that biodegradation is an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dibenzoyl peroxide, which has an estimated vapor pressure of 7.0X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dibenzoyl peroxide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 4.5 days(SRC), calculated from its rate constant of 3.6X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase dibenzoyl peroxide may be removed from the air by wet and dry deposition(SRC). Dibenzoyl peroxide, dissolved in dioxane, absorbs light at a maximum of 275 nm and absorption continues up to about 320 nm(3)therefore, the compound may be susceptible to direct photolysis by sunlight(SRC). |
| Unerwünschte Wirkungen | Skin Sensitizer - An agent that can induce an allergic reaction in the skin.The most common adverse effect of benzoyl peroxide is its bleaching quality, potentially causing the discoloration of colored fabrics and hair bleaching. At higher concentrations, topical benzoyl peroxide causes mild dryness, erythema, and scaling. There are also case reports of contact dermatitis in a small percentage of patients, which should arouse suspicion in patients who develop marked erythema and irritation at the treatment site. In such instances, the prudent course of action is stopping benzoyl peroxide. |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its aerosol.inhalation, ingestion, skin and/or eye contact |
| Toxizitätsübersicht | IDENTIFICATION AND USE: Benzoyl peroxide forms colorless to white crystals or a granular powder. It is used as a bleaching agent for flour, fats, oils, and waxespolymerization catalystdrying agent for unsaturated oilspharmaceutical and cosmetic purposesrubber vulcanization without sulfurburnout agent for acetate yarnsproduction of cheeseand embossing vinyl flooring (proprietary). Its principal medical use is in the treatment of mild acne vulgaris (in which it is comedolytic) and acne rosacea, but it also is used in the treatment of decubital and stasis ulcers. HUMAN STUDIES: The only complications were contact irritant dermatitis in 3% and contact allergic dermatitis in 2% of patients treated with benzoyl peroxide. Potential symptoms of overexposure are irritation of skin, eyes, and mucous membranes, and sensitization dermatitis. Concentrations of 12.2 mg/cu m of air and higher resulted in pronounced irritation of the nose and throat. In the occupational setting it has produced allergic contact dermatitis in bakers. Benzoyl peroxide and Cu(I) induced 8-oxo-7,8-dihydro-2'-deoxyguanosine (8-oxodG) formation in double-stranded DNA more effectively than that in single-stranded DNA. Furthermore, benzoyl peroxide increased the amount of 8-oxodG in human cultured cells. ANIMAL STUDIES: Benzoyl peroxide dust irritates the eyes of rabbits if not washed out within five minutes after being placed in the conjunctival sac. Application of a 10% solution of benzoyl peroxide in propylene glycol to the skin of guinea-pigs resulted in slight to moderate erythema. A single application of either 20 or 40 mg benzoyl peroxide to the skin of mice induced marked hyperplasia and a temporary increase in the number of dark basal keratinocytes. Groups of 25 male and 25 female mice were fed a diet containing different doses of a commercial powder containing 18% benzoyl peroxide (calculated doses of benzoyl peroxide: 0, 28, 280 and 2800 ppm), for 80 weeks, at which time the number of survivors was 3, 10, 0 and 2 male mice and 9, 11, 9, and 11 femalesall surviving animals were then killed. A few tumors at various sites were observed, but the overall tumor incidence did not differ significantly between treated and control groups. A group of 20 male rats received subcutaneous injections of 2.9 mg benzoyl peroxide into the right hind leg twice weekly for 12 weeks and were observed for 14 months, at which time all animals were still alive. No malignant tumor was found at the injection site or in internal organs. Benzoyl peroxide was not mutagenic in Salmonella typhimurium TA1535, TA1537, TA92, TA94, TA98 or TA100 either in the presence or absence of an exogenous metabolic system. Benzoyl peroxide did not induce polyploidy or chromosomal aberrations in cultured Chinese hamster lung cells. Benzoyl peroxide is a free radical generating compound that acts as a tumor promoter and progressor in mouse skin. Benzoyl peroxide at non-cytotoxic concentration undergoes copper dependent activation to a reactive product to generate 8-OHdG within cultured murine keratinocytes. Peroxides were tested for embryotoxicity in 3-day chicken embryos using the air-chamber method. All peroxides, including benzoyl peroxide, caused malformations at a moderate frequency. A comparison of the mechanism of action of benzoyl peroxide was studied in three different cell lines: NIH 3T3, HDCS and A431. Benzoyl peroxide was found to mediate its effect by inducing poly ADP-ribosylation in all the three cell types studied but to different extents, with histone H1 serving as a common acceptor for poly ADP-ribose. It also stimulated the activities of the antioxidant enzymes CuZn superoxide dismutase and catalase in NIH 3T3 and HDCS cells, but not in A431. Alterations in the expression of c-jun and c-fos were observed in NIH 3T3 and A431 cells. Benzoyl peroxide appeared to mediate its effect via genetic and epigenetic mechanisms.Topical benzoyl peroxide should not be taken by mouthindications are strictly limited to topical use. In case of ingestion, patients should call 911, contact the poison control center (1-800-222-1222), or report to the nearest emergency department. There are no known antidotes for this medication. |
| Signs and Symptoms | Cough. Sore throat.Redness.irritation eyes, skin, mucous membranesensitization dermatitis |
| Ongoing Test Status | EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPAICSS Dashboard ApplicationAvailable from, as of September 21, 2017: http://actor.epa.gov/dashboard/]The following link will take the user to the National Toxicology Program (NTP) Test Status of Agents Search page, which tabulates the results and current status of tests such as "Short-Term Toxicity Studies", "Long-term Carcinogenicity Studies", "Developmental Studies", "Genetic Toxicology Studies", etc., performed with this chemical. Testing status for benzoyl peroxide is available.[Available from, as of September 13, 2017: https://ntpsearch.niehs.nih.gov/?e=True&ContentType=Testing+Status] |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of dibenzoyl peroxide can be estimated to be 92(SRC). According to a classification scheme(2), this estimated Koc value suggests that dibenzoyl peroxide is expected to have high mobility in soil. |
| Natural Pollution Sources | Dibenzoyl peroxide is of anthropogenic origin(SRC), and is not known to occur as a natural product(1). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ Benzoyl peroxide (BPO) as an anti-acne medication is not yet approved in Japan. This study evaluated the efficacy and safety of a once-daily topical application of BPO 3% gel versus an inert vehicle gel in Japanese acne patients. Three hundred and sixty patients were randomized to receive BPO 3% or vehicle for 12 weeks. The primary efficacy end-point was absolute change in number of total lesions (TL) from baseline to week 12 to demonstrate the superiority of BPO 3% versus vehicle. Secondary efficacy end-points were absolute and percent change in TL, inflammatory lesions (IL), non-inflammatory lesions (non-IL) and Investigator's Static Global Assessment (ISGA). Change in TL counts from baseline to week 12 for BPO 3% was superior to vehicle (difference, -21.0P < 0.001). Absolute and percent reductions in TL, IL and non-IL counts were greater for BPO 3% at all study visits. The proportion of patients with improvement in ISGA scores was significantly higher with BPO 3% than with vehicle from week 2. All adverse events were mild or moderate. Adverse drug-related reactions were higher for BPO 3% (30%) than with vehicle (5%). Local tolerability scores of grade 1 or more (slight to moderate) were more frequent with BPO 3% than vehicle with the most significant differences observed in dryness (56% vs 27% at week 1-4), peeling (19% vs 9% at week 1-2) and burning/stinging (58% vs 15% at week 1-12). These results indicate that BPO 3% is effective while maintaining a favorable safety and tolerability profile in Japanese acne patients./HUMAN EXPOSURE STUDIES/ Contact hypersensitivity is observed in 1% to 3% of patients under conditions of recommended use. ... And, in one study in volunteers, a reaction occurred in 70% of subjects after use of occlusive patches containing a 5% or 10% concentration./HUMAN EXPOSURE STUDIES/ 272 children up to the age of 14 years were patch tested during a 10-year period (1982-1991). 101 children (37.1%) gave positive reactions to 1 or more allergens. Of these, 54.4% (57/101), were considered relevant. The main allergens were, in order of frequency: nickel, rubber compounds, mercuric chloride, cobalt salts, thimerosal, benzoyl peroxide and fragrance mix./HUMAN EXPOSURE STUDIES/ 791 patients, among them 59 dental technicians and 732 other patients, were tested with the denture material series (DMS) recommended by the German Contact Dermatitis Research Group (DKG) in the hospitals of the Information Network of Departments of Dermatology (IVDK) between January 1990 and July 1993. Most frequently, positive reactions occurred to cadmium chloride in both groups. However, there was no evidence at all for relevance of these reactions. Benzoyl peroxide (BPO) ranked 2nd in patch test positivity. Although not statistically significant, reactions were more frequent in dental technicians, who might be exposed to BPO the in working environment. Methyl methacrylate (MMA) and triethylene glycol dimethacrylate (TEGDMA) were common sensitizers in dental technicians but not in other patients. This finding, too, has its explanation in the working process of manufacturing dental prostheses.For more Human Toxicity Excerpts (Complete) data for Dibenzoyl peroxide (21 total), please visit the HSDB record page. |
| Artificial Pollution Sources | Dibenzoyl peroxide's production and use as an initiator for polymerization of acrylates (including dental cements and restoratives) and other polymersas a bleaching agent for flour, fats, oils, waxes and milk used in the preparation of certain cheesesin medications for the topical treatment of acnein rubber curingand as a finishing agent for some acetate yarns(1) may result in its release to the environment through various waste streams(SRC). |
| Berufliche Expositionsstufe (OEB) | B |
| Arbeitsplatzgrenzwert (OEL) | TWA: 5 mg/m3 |
| Wassergefährdungsklasse (WGK) | 2 |
| Sofort lebensgefährliche Konzentration | 1,500 mg/m3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3108 5.2 |
| Zollcode | 29163200 |
| RTECS-Nr. | DM8575000 |
| R-Sätze (R) | 8-36/37/38-43-36-2-7-1-51/53-21/22-62-50-61-3-39/23/24/25-40 |
| Toxizität | LD50 orally in Rabbit: 7710 mg/kg |
| Gefahrensymbole | O,Xn,N,Xi,E,T |
| Sicherheitshinweise (S) | 53-17-26-36/37-45-60-36/37/39-3/7-14A-14-47-35-7-61-37/39-24 |
| Gefahrenklasse | 5.2Aquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Org. Perox. CSkin Sens. 1A |
| Verpackungsgruppe | II |
| Lagerklasse | 4.1A - Other explosive hazardous materials |
| Gefahrstoffdaten | 94-36-0(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 176 °F |
Anwendungen & Verwendung
Beschreibung
Benzoyl Peroxide may affect workers in the electronics and plastics (epoxy resins and catalysts) industries, electricians, ceramic workers, dentists and dental technicians, laboratory technicians and bakers. As it was contained in candles, it also induced contact dermatitis in a sacristan. However, some positive tests are of unknown occupational relevance.
Verwenden
Benzoyl Peroxide is a widely used organic compound of the peroxide family. It 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.