Benzophenone 4
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Benzophenone 4
structure -
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CAS No:
4065-45-6
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Formula:
C14H12O6S
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Chemical Name:
Benzophenone 4
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Synonyms:
Benzenesulfonic acid,5-benzoyl-4-hydroxy-2-methoxy-;1-Phenol-4-sulfonic acid,2-benzoyl-5-methoxy-;5-Benzoyl-4-hydroxy-2-methoxybenzenesulfonic acid;MS 40;3-Benzoyl-4-hydroxy-6-methoxybenzenesulfonic acid;2-Hydroxy-4-methoxybenzophenone-5-sulfonic acid;Spectra-Sorb UV 284;Sulisobenzone;Uval;Uvinul MS 40;2-Hydroxy-4-methoxy-5-sulfobenzophenone;2-Methoxy-4-hydroxy-5-benzoylbenzenesulfonic acid;Syntase 230;Benzophenone 4;Seesorb 101S;Uvasorb S 5;Sungard;NSC 60584;Uvinul D 5030;Viosorb 111;Escalol 577;UV 284;BP 4;Kemisorb 11S;62121-63-5;197923-35-6
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CAS No:
Description
Sulisobenzone is an ingredient in some sunscreens which protects the skin from damage by UVB and short-wave UVA ultraviolet light.
DryPowder
Sulisobenzone is a member of benzophenones.|Sulisobenzone is approved by the FDA in concentrations of up to 10% and in Canada, is approved by Health Canada at the same concentrations. It works to filter out both UVA and UVB rays, protecting the skin from sun UV damage. The UV-filter substance, sulisobenzone (BP-4) is widely used an ingredient in sunscreens and other personal care products,. It falls under the drug category of benzophenones. The benzophenones are a group of aromatic ketones that have both pharmaceutical and industrial applications. Benzophenones may be found organically in fruits such as grapes. Benzophenones are used as photoinitiators, fragrance enhancers, ultraviolet curing agents, and, occasionally, as flavor ingredients; they are also used in the manufacture of insecticides, agricultural chemicals, and pharmaceuticals and as an additive for plastics, coatings, and adhesives. As a group, benzophenones may be used to delay photodegradation or extend shelf life in toiletries and plastic surface coatings.
Benzophenone 4 Basic Attributes
308.31
308.31
2889165
223-772-2
1W6L629B4K
DTXSID2042436
Light-tan powder
2914399090
Characteristics
109
2.2
DryPowder
1.4±0.1 g/cm3
145 °C
491 °C
0°C
1.617
1 g dissolves in 2 mL methanol, 3.3 mL ethanol, 4 mL water, 100 mL ethyl acetate.
-20°C
1.3X10-11 mm Hg at 25 deg C (est)
Henry's Law constant = 7X10-15 atm-cu m/mole at 25 °C (est)
pKa1 = -2.4 (sulfonic acid); pKa2 = 7.6 (hydroxyl)
168.59 Ų [M-H]-
Hydroxyl radical reaction rate constant: 7.5X10-11 cu cm/molecule sec at 25 °C (est)
Safety Information
NONH for all modes of transport
1
36/37/38
26-36-37/39-36/37/39-27
DB5044300
Xi
Stable under recommended storage conditions.
P261-P305 + P351 + P338
H315-H319-H335
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Strong oxidizing agents.
Sunscreen active ingredients. The active ingredient of the product consists of any of the following, within the concentration specified for each ingredient, and the finished product provides a minimum SPF value of not less than 2 as measured by the testing procedures established in subpart D of this part: Sulisobenzone up to 10 percent is included on this list.
|Danger|H315 (94.39%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 552 companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Not flammable or combustible.
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Wear self contained breathing apparatus for fire fighting if necessary.
Hazardous decomposition products formed under fire conditions. - Carbon oxides, Sulphur oxides
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Do not let product enter drains. Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Derivatives of PABA, benzophenone, cinnamic acid, and salicylate and 2-phenylbenzimidazole-5-sulfonic acid have caused skin irritation including burning, stinging, pruritus, and erythema on rare occasions. /Sunscreens/|... Benzophenones-4 and -11 were irritating to four and two subjects, respectively.
Toxicity
Acute oral toxicity (LD50): 3530 mg/kg [Rat]. This drug can cause skin and eye irritation. Drug-induced phototoxicity is a non-immunological inflammatory skin reaction, caused by concurrent topical or systemic exposure to a specific molecule and ultraviolet radiation. Most of the phototoxic compounds absorb energy particularly from UVA light leading to activated derivatives, which can induce cellular damage. Benzophenones are ultraviolet light filters that have been documented to cause a variety of adverse skin reactions, including contact and photocontact dermatitis, contact and photocontact urticaria, and anaphylaxis. Recently, they have become especially well known for their ability to induce allergy and photoallergy. Topical sunscreens and other cosmetics are the sources of these allergens in the majority of patients, however reports of reactions secondary to use of industrial products also exist. Benzophenones as a group have been named the American Contact Dermatitis Society's Allergen of the Year for 2014 to raise awareness of both allergy and photoallergy to these ubiquitous agents. The liver is the main target organ of benzophenone toxicity in rats and mice, based on elevations n liver weights, hepatocellular hypertrophy, clinical chemistry changes, and induction of liver microsomal cytochrome P450 2B isomer. The kidney was also identified as a target organ of benzophenone toxicity in rats only, which was based on exposure concentration-related increases in kidney weights and microscopic changes.
Agricultural workers are encouraged to use sunscreen to decrease the risk of UV-related skin cancer. Our previous studies have shown certain commercial sunscreens to be penetration enhancers. The focus of this project is to determine whether active ingredients in sunscreen formulations (i.e., the UV absorbing components and insect repellants for the sunscreen/bug repellant combinations) also act as dermal penetration enhancers for herbicides in vitro. The total percentages of 2,4-dichlorophenoxyacetic acid (2,4-D) penetrating through hairless mouse skin in 24 h ranged from 54.9 +/- 4.7 for the no sunscreen control to 86.9 +/- 2.5 for padimate-o. Of the active ingredients tested (7.5% octyl methoxycinnamate, 7% octocrylene, 0.6% oxybenzone, 5% homosalate, 5% octyl salicylate, 8% padimate-o, 10% sulisobenzone, and 9.5% and 19% N,N-diethyl-m-toluamide [DEET]), all but octocrylene led to a significant increase in total 2,4-D penetration as compared to the control (P < 0.05), and only octocrylene and oxybenzone did not significantly decrease the corresponding lag time. Octyl salicylate (P < 0.01) and octyl methoxycinnimate (P < 0.05) significantly increased the 3H2O penetration across mouse skin, indicating physical damage to the stratum corneum. Additional studies demonstrated that the penetration enhancement seen across hairless mouse skin also occurred with human skin. Thus, the active ingredients of sunscreen formulations enhance dermal penetration of the moderately lipophilic herbicide 2,4-D.|Diminish the penetration of ultraviolet (UV) light through the epidermis by absorbing UV radiation within a specific wavelength range. The amount and wavelength of UV radiation absorbed are affected by the molecular structure of the sunscreen agent. /Sunscreen agents, topical/
LD50 Rat oral 3530 mg/kg
/AQUATIC SPECIES/ In this work, /the authors/ evaluate whether in vitro systems are good predictors for in vivo estrogenic activity in fish. /Investigators/ focus on UV filters being used in sunscreens and in UV stabilization of materials. First, /investigators/ determined the estrogenic activity of 23 UV filters and one UV filter metabolite employing a recombinant yeast carrying the estrogen receptor of rainbow trout (rtERalpha) and made comparisons with yeast carrying the human hERalpha for receptor specificity. Benzophenone-1 (BP1), benzophenone-2 (BP2), 4,4-dihydroxybenzophenone, 4-hydroxybenzophenone, 2,4,4-trihydroxy-benzophenone, and phenylsalicylate showed full dose-response curves with maximal responses of 81-115%, whereas 3-benzylidene camphor (3BC), octylsalicylate, benzylsalicylate, benzophenone-3, and benzophenone-4 displayed lower maximal responses of 15-74%. Whereas the activity of 17beta-estradiol was lower in the rtERalpha than the hERalpha assay, the activities of UV filters were similar or relatively higher in rtERalpha, indicating different relative binding activities of both ER. Subsequently, /investigators/ analyzed whether the in vitro estrogenicity of eight UV filters is also displayed in vivo in fathead minnows by the induction potential of vitellogenin after 14 days of aqueous exposure. Of the three active compounds in vivo, 3BC induced vitellogenin at lower concentrations (435 ug/L) than BP1 (4919 ug/L) and BP2 (8783 ug/L). The study shows, for the first time, estrogenic activities of UV filters in fish both in vitro and in vivo. Thus /investigators/ propose that receptor-based assays should be used for in vitro screening prior to in vivo testing, leading to environmental risk assessments based on combined, complementary, and appropriate species-related assays for hormonal activity.|/AQUATIC SPECIES/ ... Here /the authors/ report on acute and chronic effects of UV-filters 3-(4-methylbenzylidene-camphor) (4MBC), 2-ethyl-hexyl-4-trimethoxycinnamate (EHMC), benzophenone-3 (BP3) and benzophenone-4 (BP4) on Daphnia magna. The acute toxicity increased with log Pow of the compound. The LC50 values (48 hr) of 4MBC, EHMC, BP3 and BP4 were 0.56, 0.29, 1.9 and 50 mg/L, respectively. A tentative preliminary environmental risk assessment (ERA) based on a limited set of data indicates that individual UV-filters should undergo further ecotoxicological analysis, as an environmental risk cannot be ruled out. Consequently new data on the environmental occurrence and the effects of UV-filters are needed for a more accurate ERA. When regarded as a mixture occurring in surface waters they may pose a risk for sensitive aquatic organisms.|/AQUATIC SPECIES/ ...In this study, /investigators/ evaluate the effects of benzophenone-4 (BP-4) in eleuthero-embryos and in the liver, testis and brain of adult male fish on the transcriptional level by focusing on target genes involved in hormonal pathways to provide a more complete toxicological profile of this important UV-absorber. Eleuthero-embryos and males of zebrafish were exposed up to 3 days after hatching and for 14 days, respectively, to BP-4 concentrations between 30 and 3000 ug/L. In eleuthero-embryos transcripts of vtg1, vtg3, esr1, esr2b, hsd17beta3, cyp19b cyp19a, hhex and pax8 were induced at 3000 ug/L BP-4, which points to a low estrogenic activity and interference with early thyroid development, respectively. In adult males BP-4 displayed multiple effects on gene expression in different tissues. In the liver vtg1, vtg3, esr1 and esr2b were down-regulated, while in the brain, vtg1, vtg3 and cyp19b transcripts were up-regulated. In conclusion, the transcription profile revealed that BP-4 interferes with the expression of genes involved in hormonal pathways and steroidogenesis. The effects of BP-4 differ in life stages and adult tissues and point to an estrogenic activity in eleuthero-embryos and adult brain, and an antiestrogenic activity in the liver. The results indicate that BP-4 interferes with the sex hormone system of fish, which is important for the risk assessment of this UV-absorber.
Because the absorptive characteristics of skin of children younger than 6 months of age may differ from those of adults and because the immaturity of metabolic and excretory pathways of these children may limit their ability to eliminate any percutaneously absorbed sunscreen agent, sunscreen products should be used in children younger than 6 months of age only as directed by a clinician. It is possible that the characteristics of geriatric skin also differ from those of skin in younger adults, but these characteristics and the need for special considerations regarding use of sunscreen preparations in this age group are poorly understood. /Sunscreens/
Sulisobenzone's production and use as an ultraviolet absorber in cosmetics, sunscreens and shampoos and in leather and textile fabrics(1,2) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 67(SRC), determined from a structure estimation method(2), indicates that sulisobenzone is expected to have high mobility in soil(SRC). The estimated pKa values of sulisobenzone are -2.4 and 7.6(3), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize. Sulisobenzone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). No relevant data were available to assess the importance of biodegradation in the environment(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 67(SRC), determined from a structure estimation method(2), indicates that sulisobenzone is not expected to adsorb to suspended solids and sediment(SRC). Estimated pKa values of -2.4 and 7.6(3) indicate sulisobenzone will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from an estimated log Kow of 0.37(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Sulisobenzone is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(5). Sulisobenzone absorbs at wavelengths >290(6) nm and therefore may be susceptible to direct photolysis by sunlight(SRC). Phenols are susceptible to sensitized photolysis in natural waters exposed to sunlight through reaction with hydroxy and peroxy radicals(7); therefore sensitized photolysis may have some importance in the environment(SRC). No relevant data were available to assess the importance of biodegradation in the environment(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sulisobenzone, which has an estimated vapor pressure of 1.3X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase sulisobenzone may be removed from the air by wet and dry deposition(SRC). Sulisobenzone absorbs at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of sulisobenzone with photochemically-produced hydroxyl radicals has been estimated as 7.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5.2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Sulisobenzone is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). Sulisobenzone absorbs at wavelengths >290(3) nm and therefore may be susceptible to direct photolysis by sunlight(SRC). Phenols are susceptible to sensitized photolysis in natural waters exposed to sunlight through reaction with hydroxy and peroxy radicals(4); therefore sensitized photolysis may have some importance in the environment(SRC).
An estimated BCF of 3 was calculated for sulisobenzone(SRC), using an estimated log Kow of 0.37(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of sulisobenzone can be estimated to be 67(SRC). According to a classification scheme(2), this estimated Koc value suggests that sulisobenzone is expected to have high mobility in soil. The estimated pKa values of sulisobenzone are -2.4 and 7.6(3), indicating that this compound will exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).
The estimated pKa values of -2.4 and 7.6(1) indicate sulisobenzone will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water and moist soil surfaces is not expected to be an important fate process. Sulisobenzone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-11 mm Hg(SRC), determined from a fragment constant method(2).
SURFACE WATER: In surface seawater samples collected from Folly Beach, South Carolina in the summer of 2010, sulisobenzone was not detected in any samples from four sites (detection limit 1 ng/L) while other UV filter compounds (avobenzone, octocrylene, octinoxate, and padimate-O) were detected at concentrations ranging from 10 to 2013 ng/L(1).
According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of sulisobenzone is 1 to 99; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 91,292 workers (38,820 of these were female) were potentially exposed to sulisobenzone in the US(1). Occupational exposure to sulisobenzone may occur through dermal contact with this compound at workplaces where sulisobenzone is produced or used. The general population may be exposed to sulisobenzone via dermal contact with this compound in consumer products, such as sunscreens and cosmetics, containing sulisobenzone(SRC).
Drug Information
Sunscreening agents are used to prevent sunburn, actinic keratosis, and premature skin aging and to reduce the incidence of skin cancer.
Daily use of a sunscreen with a high SPF (greater than 15) on usually exposed skin is recommended for residents of areas of high ... /solar radiation/ who work outdoors or ... /enjoy/ regular outdoor recreation. Daily use of a sunscreen can reduce the cumulative ... /solar/ exposure that causes actinic keratoses and squamous-cell carcinoma.|Sunscreen agents are indicated for the prevention of sunburn. In addition to limiting the skin's exposure to the sun, using sunscreen agents regularly when in the sun may help reduce long-term sun damage such as premature aging of the skin and skin cancer. /Sunscreen agents, topical; Included in US product labeling/
The manufacturers of sunscreen preparations with propellants warn that concentrating and subsequently inhaling the fumes from these preparations may be harmful or fatal. /Propellants/|Because the absorptive characteristics of skin of children younger than 6 months of age may differ from those of adults and because the immaturity of metabolic and excretory pathways of these children may limit their ability to eliminate any percutaneously absorbed sunscreen agent, sunscreen products should be used in children younger than 6 months of age only as directed by a clinician. It is possible that the characteristics of geriatric skin also differ from those of skin in younger adults, but these characteristics and the need for special considerations regarding use of sunscreen preparations in this age group are poorly understood. /Sunscreens/|Little information is available regarding the safety of chronic sunscreen usage, but commercially available physical and chemical sunscreens appear to have a low incidence of adverse effects. Derivatives of PABA, benzophenone, cinnamic acid, and salicylate and 2-phenylbenzimidazole-5-sulfonic acid have caused skin irritation including burning, stinging, pruritus, and erythema on rare occasions. /Sunscreens/|Sunscreens should not be used as a means of extending the duration of solar exposure, such as prolonging sunbathing, and should not be used as a substitute for clothing on usually unexposed sites, such as the trunk and buttocks. /Sunscreens/|For more Drug Warnings (Complete) data for SULISOBENZONE (11 total), please visit the HSDB record page.
Benzophenone sunscreens, applied topically, protect the skin from these harmful effects of ultraviolet light by chemically absorbing light energy (photons). Correct use of sunscreens serves to reduce the risk of sunburn. Sunscreen agents prevent the occurrence of squamous-cell carcinoma of the skin when used mainly during unintentional sun exposure. No conclusion can be drawn about the cancer-preventive activity of topical use of sunscreens against both basal-cell carcinoma and cutaneous melanoma. Use of sunscreens can extend the duration of intentional sun exposure, such as bathing in the sun.
Does not penetrate the skin to a large degree, but enhances the ability of other chemicals to penetrate.|This drug's main metabolite is excreted in urine conjugated with glucuronic acid. No p-hydroxybenzohydrol was detected in urine or feces, in a study of pharmacokinetics in rats.|Solvents used in sunscreen products affect the stability and binding of the drug to the skin; in general, alcoholic solvents allow for the most rapid and deepest epidermal penetration of sunscreens. It appears that sunscreen agents are absorbed by the intact epidermis to varying degrees. /Sunscreens/
Benzophenone's main metabolic pathway in the rabbit is by reduction to benzhydrol. A small amount (1%) is converted to p-hydroxybenzophenone following oral administration to rats.
A surface coating of benzophenones decreases the amount of UV radiation absorbed by the skin by limiting the total amount of energy that reaches the skin. Benzophenone sunscreens, applied topically, protect the skin from these harmful effects of ultraviolet light by chemically absorbing light energy (photons). As this occurs, the benzophenone molecule becomes activated to higher energy levels. As the excited molecule returns to its ground state, the energy is released in the form of thermal energy. The hydroxyl group in the ortho position to the carbonyl group is believed to be a structural requirement for the benzophenones' absorption of UV light. This structural arrangement also contributes to the electronic stability of the molecule. Benzophenones absorb energy throughout the UV range, although the maximum UV absorbance is between 284 and 287 nm for the 2-hydroxybenzophenones.|Benzophenone sunscreens, applied topically, protect the skin from these harmful effects of ultraviolet light by chemically absorbing light energy (photons). As this occurs, the Benzophenone molecule becomes excited to higher energy levels. As the excited molecule returns to its ground state, the energy is released in the form of thermal energy. The hydroxyl group in the ortho position to the carbonyl group is believed to be a structural requirement for the Benzophenones' absorption of UV light. This structural arrangement also contributes to the electronic stability of the molecule. Thus, a surface coating of Benzophenones decreases the amount of UV radiation absorbed by the skin by limiting the total amount of energy that reaches the skin. Benzophenones absorb energy throughout the UV range, though maximum absorbance is between 284 and 287 nm for the 2-hydroxybenzophenones ...|Diminish the penetration of ultraviolet (UV) light through the epidermis by absorbing UV radiation within a specific wavelength range. The amount and wavelength of UV radiation absorbed are affected by the molecular structure of the sunscreen agent. /Sunscreen agents, topical/
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/HUMAN EXPOSURE STUDIES/ ...To determine the frequency of irritant reactions to 19 organic sunscreen filters in current use. Ninety-four healthy volunteers were photopatch tested using the European consensus methodology to three different concentrations (2%, 5%, and 10%) of 19 organic sunscreen filters at the Photobiology Unit in Dundee, UK. Of the 94 subjects recruited, 80 were analyzed after withdrawals and exclusions. Of the 19 organic sunscreen filters studied, only 2 compounds led to irritant reactions in > or =5% subjects. Five per cent and 10% benzophenone-4 led to irritant reactions in four and six subjects, respectively. Five per cent methylene bis-benzotriazolyl tetramethylbutylphenol led to irritant reactions in six subjects, but unlike benzophenone-4, this was not in a dose-dependent fashion. When performing photopatch testing according to the European consensus methodology with these 19 organic sunscreen filters, a 10% concentration is suitable for all filters, except benzophenone-4, which should be tested at a concentration of 2%.|/HUMAN EXPOSURE STUDIES/ Cosmetic products containing Benzophenones-2, -3, or -4 (0.l%-3.5%) were tested for phototoxicity in humans. In each study, the test material was applied under occlusion to the subject's skin for 24 hours. Sites were then scored, exposed to UV radiation, and then scored daily for up to seven days. Nonirradiated/treated and nontreated/irradiated controls were frequently used. Products containing Benzophenones-2, -3, and -4 were nonphototoxic in all studies; however, a number of subjects experienced slight irritation (usually a 1+ response) to the test material.|/HUMAN EXPOSURE STUDIES/ /Investigators/ tested the potential irritancy of Benzophenone-4 on six adult white humans. Patches containing 1% or 10% Benzophenone-4 in alcohol were applied to the subjects for 24 hours, after which time the patches were removed, the sites scored, and fresh patches applied. This procedure was repeated every other day, three days per week for seven weeks, until a total of 21 patches had been made. The mean cumulative irritation scores for 1% and 10% solutions were 8.6 and 53.1, respectively (maximum score = 84). The latter value is indicative of a primary irritant.|/HUMAN EXPOSURE STUDIES/ Benzophenones-4 and -11 were tested for potential skin irritation in separate single insult patch tests. Each ingredient was applied at concentrations of 16, 8, and 4% in DMP /dimethyl phthalate/ and in petrolatum to the skin of each of 14 subjects. At a concentration of 16% in either base, Benzophenones-4 and -11 were irritating to four and two subjects, respectively. Neither ingredient was irritating at concentrations of 4% or 8% in either vehicle.|For more Human Toxicity Excerpts (Complete) data for SULISOBENZONE (8 total), please visit the HSDB record page.
2-hydroxy-4-methoxybenzophenone-5-sulfonic acid
Benzophenone 4 Use and Manufacturing
Synthesis of Xylene Dimethyl Ether 350 kg of water was added to the reactor and 150 kg of NaOH was added with stirring. After dissolving, the temperature was lowered to 10 ℃, 110 kg of resorcinol was added, and dissolved by stirring. Then, 126 kg of dimethyl sulfate was slowly added and reacted at 26-30 ℃ for 2 h. Dilute with water, separate the oil layer, and wash the oil layer to neutral with water. Removal of low Buddha point, distillation to collect 215 ~ 220 ℃ distillate, that is m-xylylene ether. Synthesis of 2-hydroxy-4-methoxybenzophenone First, 300 kg of chlorobenzene was added to the condensation kettle, with stirring, the catalyst AlCl3 350 kg and isophthalic ether 120 kg were added. Heat to about 80 ℃, slowly add 320 kg of benzoyl chloride. Reflux for 4 to 6 hours, cool, hydrolyze, distill off the solvent, cool, crystallize, and dry to obtain 2-hydroxy-4-methoxybenzophenone. Synthesis of 2-hydroxy-4-methoxy-5-sulfonated diphenylacetone First add 93% sulfuric acid to the sulfonation kettle, slowly add 2-hydroxy-4-methoxydibenzoyl under stirring Ketones are reacted at about 110 ℃ for 4 to 6 hours, cooled, crystallized, dried, and recrystallized to be the finished product.
As an anti-ultraviolet finishing agent, it has good anti-aging and softening effects on cotton fabrics and polyester fibers. It is widely used in sunscreen creams, creams, honey, lotions, oils and other cosmetics; it is a broad-spectrum ultraviolet absorber with high absorption efficiency, non-toxic, no teratogenic side effects, and good light and heat stability. It can absorb UV-A and UV-B at the same time. It is a class I sunscreen approved by the U.S. FDA. It is used more frequently in the U.S. and Europe. It is widely used in sunscreen cosmetics such as sunscreen creams, creams, honey, lotions, oils, etc. Ultraviolet finishing agent has good anti-aging and softening effects on cotton fabrics and polyester fibers. Mainly used as sunscreen and sunscreen in water-soluble cosmetics, as well as UV absorber in other water-soluble inks and coatings; mainly used as sunscreen and sunscreen in water-soluble cosmetics, and also in other water-soluble inks Used as UV absorber in paint, etc.
preservative
Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#7094]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Benzenesulfonic acid, 5-benzoyl-4-hydroxy-2-methoxy-. Aggregated National Production Volume: < 500,000 pounds.|Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Benzenesulfonic acid, 5-benzoyl-4-hydroxy-2-methoxy-. National Production Volume: Withheld.
The maximum recommended levels of lead and arsenic impurities in Benzophenone-4 are /13 ppm and 1 ppm respectively/.
All other chemical product and preparation manufacturing|Benzenesulfonic acid, 5-benzoyl-4-hydroxy-2-methoxy-: ACTIVE|The FDA Panel on Review of Topical Analgesics has proposed that Benzophenones-3, -4, and -8 are safe and effective as active ingredients in sunscreens for over-the-counter (OTC) use at the following concentrations: Benzophenone-3, 2%-6%; Benzophenone-4, 5%-10%; and Benzophenone-8, 3%. The Panel proposed these concentration limits on a combined safety and efficacy basis (a concentration limit may reflect maximum efficacy and not necessarily an indication of toxicity at a higher concentration).|Sunscreens are available in a variety of dosage forms and formulations. ... Because these formulations frequently change and the manufacturers often are reluctant to reveal specific ingredients in their formulations, a listing of commercially available sunscreens is not included in this monograph. /Sunscreens/
Analyte: sulisobenzone; matrix: chemical identification; procedure: ultraviolet absorption spectrophotometry with comparison to standards|Analyte: sulisobenzone; matrix: chemical purity; procedure: dissolution in water; addition of dehydrated isopropyl alcohol; potentiometric titration with tetrabutylammonium hydroxide to two endpoints
Cosmetics -> Uv absorber; Uv filter
Computed Properties
Molecular Weight:308.31
XLogP3:2.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:308.03545927
Monoisotopic Mass:308.03545927
Topological Polar Surface Area:109
Heavy Atom Count:21
Complexity:462
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
UV absorber, photoprotective agent to stabilize formulations against light degradation
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