Quick Search

PRODUCTS

BENZOPHENONE 4

Benzophenone-4

CAS NO : 4065-45-6

 4-Hydroxy-2-methoxy-5-(oxo-phenylmethyl)benzenesulfonic acid; Sulisobenzone; benzophenone-4; 2-benzoyl-5-methoxy-1-phenol-4-sulfonic acid

Benzophenone-4

CAS NO : 4065-45-6

SYNONYM : 4-Hydroxy-2-methoxy-5-(oxo-phenylmethyl)benzenesulfonic acid; Sulisobenzone; benzophenone-4; 2-benzoyl-5-methoxy-1-phenol-4-sulfonic acid; benzenesulfonic acid, 5-benzoyl-4-hydroxy-2-methoxy-; benzophenone 4; 5-benzoyl-4-hydroxy-2-methoxybenzene sulfonic acid; 5-benzoyl-4-hydroxy-2-methoxybenzenesulfonic acid; 3-benzoyl-4-hydroxy-6-methoxybenzenesulfonic acid; 2-benzoyl-5-methoxy-1-phenol-4-sulfonic acid; 4-hydroxy-2-methoxy-5-(phenylcarbonyl)benzenesulfonic acid; 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid; 2-hydroxy-4-methoxybenzophenone-5-sulfonicacid; 2-hydroxy-4-methoxybenzophenone-5-sulphonic acid; 1-phenol-4-sulfonic acid, 2-benzoyl-5-methoxy-; seesorb 101S; spectra-sorb UV 284; sulisobenzona; sulisobenzone; sulisobenzonum;sungard; syntase 230; uv absorber HMBS; uval; uvinuc MS 40; uvinul; Sulisobenzone; 4065-45-6; Benzophenone-4; 5-Benzoyl-4-hydroxy-2-methoxybenzenesulfonic acid; Sungard; 2-Hydroxy-4-methoxybenzophenone-5-sulfonic acid; Benzophenone 4; Uval; Benzenesulfonic acid, 5-benzoyl-4-hydroxy-2-methoxy-; Sulisobenzona; Sulisobenzonum; Syntase 230; Uvinul MS 40; Spectra-Sorb UV 284; Uvinuc ms 40; 2-HYDROXY-4-METHOXY-5-SULFOBENZOPHENONE; MS 40; Sulisobenzonum; Uvinul MS-40 substanz; EINECS 223-772-2; 1-Phenol-4-sulfonic acid, 2-benzoyl-5-methoxy-; 3-Benzoyl-4-hydroxy-6-methoxybenzenesulfonic acid; 5-Benzoyl-4-hydroxy-2-methoxybenzene sulfonic acid; Uval sodium salt; 1-PHENOL-4-SULFONIC ACID, 2-BENZOYL-5-METHOXY-; 1-PHENOL-4-SULFONIC ACID, 2-BENZOYL-5-METHOXY- (6CI); 2-BENZOYL-5-METHOXY- 1-PHENOL-4-SULFONIC ACID; 2-HYDROXY-4-METHOXYBENZOPHENONE- 5-SULFONIC ACID; 2-HYDROXY-4-METHOXYBENZOPHENONE-5-SULFONIC ACID; 5-BENZOYL-4-HYDROXY-2-METHOXY- BENZENESULFONIC ACID; 5-BENZOYL-4-HYDROXY-2-METHOXYBENESULFONIC ACID; 5-BENZOYL-4-HYDROXY-2-METHOXYBENZENE SULFONIC ACID; 5-BENZOYL-4-HYDROXY-2-METHOXYBENZENESULFONIC ACID; 5-BENZOYL-4-HYDROXY-2-METHOXYBENZOLSULFONSAEURE; B4; BENZENESULFONIC ACID; 5-BENZOYL-4-HYDROXY-2-METHOXY-; BENZENESULFONIC ACID; 5BENZOYL4HYDROXY2METHOXY; BENZOPHENONE 4; BENZOPHENONE-4; BRN 2889165; EINECS 223-772-2; MS 40; SEESORB 101S; SPECTRA-SORB UV 284; SULISOBENZONA; SULISOBENZONE; SULISOBENZONE (BENZOPHENONE-4); SULISOBENZONUM; SUNGARD; SYNTASE 230; UVAL; UVINUC MS 40; UVINUL; UVINUL MS 40; UVINUL MS-40 SUBSTANZ

Sulisobenzone (benzophenone-4) is an ingredient in some sunscreens which protects the skin from damage by UVB and UVA ultraviolet light.[2][3]

Its sodium salt, sulisobenzone sodium, is also referred to as benzophenone-5.

Identifiers
CAS Number: 4065-45-6 
3D model (JSmol): Interactive image
ChemSpider : 18829 
ECHA InfoCard :    100.021.612 
KEGG    :D05964 
PubChem CID:19988
UNII    : 1W6L629B4K 
CompTox Dashboard (EPA)    :DTXSID2042436 

Properties
Chemical formula    C14H12O6S
Molar mass    308.31 g/mol
Appearance    Light-tan powder
Melting point    145 °C (293 °F; 418 K)
Solubility in water    1 g per 4 mL

UVA+UVB filters :Bemotrizinol (Tinosorb S)Benzophenones 1–12DioxybenzoneDrometrizole trisiloxane (Mexoryl XL)Iscotrizinol (Uvasorb HEB)OctocryleneOxybenzone (Eusolex 4360)Sulisobenzonehybrid (chemical/physical): Bisoctrizole (Tinosorb M / Eversorb M)physical: Titanium dioxideZinc oxide

Description: Water-soluble UVA and UVB filter. Only short UVA (UVA-2, 290-360 nm) but not long UVA are filtered. Synonyms: Sulisobenzone, 1-phenol-4-sulfonic acid. Highly stable, does not degrade in sunlight but protects other UV blocking agents from UV-induced degradation. Benzophenone-4 is readily soluble in water, propylene glycol, glyerin, ethanol and isopropyl alcohol. Due to its high acidity (pH < 2.5 in a 1% solution), a neutralizing agent (e.g. triethanolamine) must be added to elevate the pH to >3.5. Yellow to beige powder.
CAS: 4065-45-6
INCI Name: Benzophenone-4
Benefits:
Water-soluble UVA & UVB filter. Used primrily as UVA filter
Should be combined with other sunscreens (e.g. octocrylene, homosalate, ethylhexyl salicylate, OM-cinnamate) for effective UVB protection. Benzophenone-4 provides inadequate UVB protection when used alone.
Does not penetrate the skin to a large degree, but enhances the ability of other ingredients to penetrate
Helps to stabilize UV sensitive formulations such as hair dyes, hair sprays and color enhanced formulations
Provides protection of colorants against fading and help stabilize fragrances and active ingredients against oxidation
Use: Incorporate into water phase (pH 1.2-2.2). Allowed use levels: USA 10% (when used alone; 5-10% when used in combination), Brazil 10%, Japan 10%, EU 5%. For external use only.
Applications: Sun care products, color cosmetics with sun protection, various cosmetics & fragrances for product protection.
Country of Origin: USA
Raw material source: Benzophenone-3
Manufacture: Benzophenone-4 is prepared via sulfonation of benzophenone-3. The product is then purified by precipitation from aqueous hydrochloric acid, isolated by centrifugation, washed with acidic water, and dried.
Animal Testing: Not animal tested
GMO: GMO free (does not contain plant-derived components)
Vegan: Does not contain animal-derived components
Regulatory Information: Sunscreens are registered as API (Active Pharmaceutical Ingredient) or OTC-drug with the FDA. This means that, if you want to sell products containing a sunscreen, your facility must be registered with the FDA and operate under cGMP guidelines. Further information about the FDA regulation of sunscreens can be found here.
Documents: SDS, Fact Sheet, Certificate of Analysis
For California Customers: Under California's Safe Drinking Water and Toxic Enforcement Act, better known as OEHHA Prop 65, we are required to place a warning to this product since the OEHHA believes that benzophenone (CAS 119-61-9), a substance used in the production of benzophenone-4, is cancerogenic.

2-Hydroxy-4-methoxybenzophenone-5-sulfonic acid Typical Properties

Test Items    Test Specification    Typical Test  Result
Appearance    Off-white or light yellow crystalline powder    Light yellow crystalline powder
Melting Point    ≥ 140°C    Conform
Specific Extinction(1%,1cm)    E285: ≥ 460    485
E325: ≥ 290    295
Loss on drying    ≤ 3.0%    0.26%
Gardner color    ≤ 2.0    1.2
Heavy metals    ≤ 5 ppm    2ppm
Turbidity    ≤ 4.0 EBC    2.6EBC
PH value    1.2~2.2    1.8
Assay    ≥ 99.0%    99.82%
 2-Hydroxy-4-methoxybenzophenone-5-sulfonic acid Usage

Mainly used for water soluble in cosmetics as a resistance to bask in sunscreen, can also be used in other water-soluble ink, paint, etc for uv absorber;As anti-ultraviolet finishing agent for cotton fabric, polyester fiber has good anti aging and softening effect.A broad-spectrum UV absorber, absorption with high efficiency, non-toxic side effects, no teratogenicity, optical, thermal stability is good wait for an advantage, it also can absorb uv-a and UV – B, is approved by the FDA Ⅰ kind of sunscreen, use frequency is higher in the United States and Europe, widely used in sun lotion, cream, honey, latex, oil and other sunscreen cosmetics as anti-ultraviolet finishing agent, the cotton fabric, polyester fiber has good anti aging and softening effect. Mainly used for water soluble in cosmetics as a resistance to bask in sunscreen, can also be used in other water-soluble ink, paint, etc for uv absorber.

Benzophenone-4 is a white or pale yellow powder. It is used in bath products, makeup products, hair products, sunscreens and skin care products to protect cosmetics and personal care products from deterioration by absorbing, reflecting, or scattering UV rays. When used as a sunscreen ingredient, Benzophenone-4 protects the skin from UV rays.
What Is It?
Benzophenone-1, -3, -4, -5, -9 and-11 are compounds made from 2-hydroxybenzophenone. These compounds are powders. In cosmetics and personal care products, Benzophenone-1 and Benzophenone-3 are used mostly in the formulation of nail polishes and enamels. These Benzophenone ingredients are also used in bath products, makeup products, hair products, sunscreens and skin care products.

Why is it used in cosmetics and personal care products?
Benzophenone-1, Benzophenone-3, Benzophenone-4, Benzophenone-5, Benzophenone-9 and Benzophenone-11 protect cosmetics and personal care products from deterioration by absorbing, reflecting, or scattering UV rays. When used as sunscreen ingredients, Benzophenone-3 and Benzophenone-4 protect the skin from UV rays.

Benzophenone-4 is an ingredient found in bath, makeup, hair, sunscreens, and skin care products.

What are some products that may contain benzophenone-4?
Cosmetics, Hair Care, Liquids, Sunscreens

UV Absorber
UV absorber (Ultraviolet light absorbers) are molecules used in organic materials such as:

Polymers
Paints
Coating
Rubber
UV Absorber
These absorbers to absorb UV light to reduce the UV degradation (photo-oxidation) of a material. Different UV absorbers are utilized depending upon the substrate, intended functional life, and sensitivity to UV degradation. They absorb UV light and convert it into heat.

Physical Description: DryPowder
Color/Form: Light-tan powder
Melting Point: 145.0 °C
Solubility  : 10 microgram/mL
Vapor Pressure : 1.3X10-11 mm Hg at 25 °C (est)
Stability/Shelf Life : Stable under recommended storage conditions.
Decomposition :When heated to decomposition it emits toxic vapors of /sulfur oxides/.

Drug Indication
Sunscreening agents are used to prevent sunburn, actinic keratosis, and premature skin aging and to reduce the incidence of skin cancer [L2664].

Therapeutic Uses
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/
Drug Warnings
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.

Pharmacology
Benzophenone sunscreens, applied topically, protect the skin from these harmful effects of ultraviolet light by chemically absorbing light energy (photons) [L2664]. 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 [L2665].

Absorption, Distribution and Excretion
Absorption
Does not penetrate the skin to a large degree, but enhances the ability of other chemicals to penetrate [L2665].
Route of Elimination
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 [L2663].
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-4'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 [L2663].

Mechanism of Action

A surface coating of benzophenone 4 decreases the amount of UV radiation absorbed by the skin by limiting the total amount of energy that reaches the skin [L2663]. 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 [L2669].
Benzophenone 4 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 ...

Use Classification
Cosmetics -> Uv absorber; Uv filter-- Benzophenone 4

Uses
Beverage, juice: Subcategory of beverage, food for human consumption
Decor, lawn garden:     Products used outside the home (includes outdoor toys such as sandboxes, canopies and shelters, garden statues, outdoor lighting and seating, outdoor power equipment, etc 
Drug:    Drug product, or related to the manufacturing of drugs; modified by veterinary, anim
Food:    Food for human consumption, does not include food additives (see food_additive); also includes manufacture of food, facilities related to food (with appropriate modifiers) 
Fragrance, consumer use    : Term applied when the only information the source indicates is 'consumer' or 'consumer product' ; also applied to terms that the source indicates are for consumer use, yet the descriptor term is ambivalent about usage (e.g., cleaning_washing products may be for industrial or consumer use, when the source indicates consumer use, the consumer_use term is also applied) - see appendix for full list of unambiguous consumer related terms plus ambiguous consumer related terms which if indicated are labeled with 'consumer_use
Manufacturing, chemical    : General term used only when the only information known from the source is 'chemical,' typically related to manufacturing of chemicals, or laboratory chemicals 
Personal care: hair conditioning treatment; spray: Hair conditioning and moisturizing treatments for occasional use (spray or aerosol formulation specified)
Personal care: hair styling; spray: Hair styling products for hold, shine, or texture (spray or aerosol formulation specified)
Personal care: hand/body lotion; spray    : Lotions and creams primarily for hands and body (spray or aerosol formulation specified)
Personal care: shaving cream; gel: Shaving creams, foams, balms and soaps (gel formulation specified)
Personal_care, cosmetics, shampoo, hair:    General products related to the hair (hair tools, hair salons, shampoo, conditioner, hair dye); more specific modifiers included when known
Personal_care, sunscreen: Sunscreen, used on the skin to protect skin from the sun's rays
Personal_care, soap, hand: Personal care products used on the hands, such as soaps, lotions, sanitizers (does not include handwear, i.e. gloves)
Raw_material, personal_care, cosmetics: Subcategory of personal_care, includes fragrances, shampoos, make-up, etc.; appropriate modifiers included when known
Toys:Toys (e.g. dress-up clothes, dolls, playground equipment, bath toys, etc); pet toys; includes additional modifiers when appropriate
Toys, child_use: Related to products specifically designed for children (e.g. toys, children's cosmetics, etc)
 Ultraviolet absorber for leather and textile fibers; in cosmetics and shampoos
Used as an ultraviolet absorber in US cosmetics at concentrations of 5-10%
Benzophenones-2, -3, -4, -6, -8, and -9 are used in suntan lotions and hair sprays because they protect the skin and hair from the harmful effects of the sun. These ingredients also photostabilize cosmetic dyes, creams, and lotion's.
Industry Uses :preservative

Methods of Manufacturing
Benzophenone-4 is prepared via sulfonation of Benzophenone-3. The product is purified by precipitation from aqueous HCl, isolated by centrifugation, washed with acidic water, and dried.

Formulations/Preparations
The maximum recommended levels of lead and arsenic impurities in Benzophenone-4 are /13 ppm and 1 ppm respectively/.

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.
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.

Analytic Laboratory Methods
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

Skin, Eye, and Respiratory Irritations    HelpNew Window
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.

Fire Fighting Procedures
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

Cleanup Methods
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.

Disposal Methods
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.

Preventive Measures
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).

Storage Conditions
Keep container tightly closed in a dry and well-ventilated place. Hygroscopic. Store under inert gas. Keep in a dry place.
Store below 40 °C (104 °F), preferably between 15 and 30 deg. C (59 and 86 deg. F), unless otherwise specified by manufacturer. /Sunscreen agents, topical/

Strong oxidizing agents.

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/
Acute oral toxicity (LD50): 3530 mg/kg [Rat]. This drug can cause skin and eye irritation [L2665]. 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 [L2664]. 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 [A32929]. 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 [F40].
/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/ ...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. If released to air, an estimated vapor pressure of 1.3X10-11 mm Hg at 25 °C indicates sulisobenzone will exist solely in the particulate phase in the atmosphere. Particulate-phase sulisobenzone will be removed from the atmosphere by wet and dry deposition. Sulisobenzone absorbs at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight. If released to soil, sulisobenzone is expected to have high mobility based upon an estimated Koc of 67. The estimated pKa values of the sulfonic acid are -2.4 and 7.6, 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. 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 based upon its vapor pressure. No relevant data were available to assess the importance of biodegradation in soil or water. If released into water, sulisobenzone is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected based upon the estimated pKa values. An estimated BCF of 3.2 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Sensitized photolysis may have some importance in natural waters exposed to sunlight. 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)
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).
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).

CAS number: 4065-45-6
 "Controversial / at risk" in all categories.
Origin(s): Synthetic
INCI name: BENZOPHENONE-4
Chemical name: 5-Benzoyl-4-hydroxy-2-methoxybenzenesulfonic acid
EINECS/ELINCS number: 223-772-2
Classification: Suspected endocrine disruptor, UV chemical filter, Regulated
Restriction in Europe: VI/22
The maximum permissible concentration in cosmetics is as follows: 5% (in acid).
Its functions (INCI)
Uv absorber : Protects the cosmetic product from the effects of UV-light
Uv filter : Filters certain UV rays to protect the skin or hair from the harmful effects of these rays.
This ingredient is present in 1.73% of cosmetics.
Shampoo colored hair / mixed (22.71%)
Styling mousse (14.48%)
Styling gel (13.72%)
Styling spray (10.88%)
Disentangling (9.47%)

Chemical ultraviolet (UV) filters have, over the last few decades, been increasingly used not only in conventional sunscreen products but also in many cosmetics and toiletries. Allergic contact dermatitis as well as photoallergic contact dermatitis reactions have been well documented as a consequence of such use. Over a 3-year period, we recorded the number of positive patch test reactions to a selection of chemical UV filters that we added to our usual cosmetics/facial series. Our objective was to investigate whether any of these filters produced significant numbers of positive patch test results in the absence of photostimulation. Our results show that not only did benzophenone 4 (2-hydroxy-4-methoxybenzophenone-5-sulphonic acid: sulisobenzone) produce significantly more positive patch test results than the other UV filters that were tested, but also it was the third most frequently positive result overall. Our findings would support the inclusion of benzophenone 4 when patch testing to investigate likely contact dermatitis from cosmetics and toiletries.


Benzophenone 4 is used in personal care products such as lip balm and nail polish to protect the products from UV light. Derivatives of benzophenone, such as benzophenone-2 (BP2) and oxybenzone (benzophenone-3 or BP3) are common ingredients in sunscreen. Benzophenone is persistent, bioaccumulative and toxic (PBT).[1] [2] These chemicals are linked to cancer, endocrine disruption, and organ system toxicity.

FOUND IN: Lip balm, nail polish, foundations, baby sunscreens, fragrance, shampoo, conditioner, hair spray, moisturizers, and foundation

WHAT TO LOOK FOR ON THE LABEL: Benzophenone, ingredients containing the word benzophenone (for example benzophenone-2), BP# (for example BP2), oxybenzone, sulisobenzone, sulisobenzone sodium

WHAT IS BENZOPHENONE 4?
Benzophenone 4 is widely used in household products, such as sunglasses, food packaging, laundry and cleaning products to protect from UV light.[5] MORE...

HEALTH CONCERNS: Cancer, endocrine disruption, developmental and reproductive toxicity,  organ system toxicity, irritation, ecotoxicity MORE...

VULNERABLE POPULATIONS: Women and infants

REGULATIONS: Benzophenone 4, benzophenone-2, benzophenone-3, benzophenone-4, and benzophenone-5 restricted in cosmetics in United States[3] and oxybenzone is restricted in cosmetics at up to 10% maximum concentration in the EU.[4]

HOW TO AVOID: Read labels and avoid products containing these chemicals. Choose sunscreens that rely on non-nanoized zinc oxide or titanium dioxide.

Chemical ultraviolet (UV) filters have, over the last few decades, been increasingly used not only in conventional sunscreen products but also in many cosmetics and toiletries. Allergic contact dermatitis as well as photoallergic contact dermatitis reactions have been well documented as a consequence of such use. Over a 3-year period, we recorded the number of positive patch test reactions to a selection of chemical UV filters that we added to our usual cosmetics/facial series. Our objective was to investigate whether any of these filters produced significant numbers of positive patch test results in the absence of photostimulation. Our results show that not only did benzophenone 4 (2-hydroxy-4-methoxybenzophenone-5-sulphonic acid: sulisobenzone) produce significantly more positive patch test results than the other UV filters that were tested, but also it was the third most frequently positive result overall. Our findings would support the inclusion of benzophenone 4 when patch testing to investigate likely contact dermatitis from cosmetics and toiletries.

A water-soluble, chemical sunscreen agent that is a secondary UVB absorber with some activity in the short UVA range as well. Being a secondary UV absorber means that its protection is weak and it has to be combined with other sunscreen filters for proper sun protection. 

More often than not, Benzophenone-4 is not used as a sunscreen agent but as a photoprotectant to extend product shelf life, or as a color-protectant for products in clear packages. 

A Contact Dermatitis article from 2007 names BP-4 as an emerging allergen, as it was the most frequently positive chemical UV filter and third most frequently positive ingredient overall among the 35 substances patch tested in the study (13 positives of 1693 people tested).

Sulisobenzone (benzophenone-4) is a sunscreen ingredient; can cause skin and eye irritation. Does not penetrate the skin to a large degree, but enhances the ability of other chemicals to penetrate.

Your patch testing results indicate that you have a contact allergy to "Deleted"
BENZOPHENONE-4. It is important that you familiarize yourself with this chemical and
take steps to avoid coming in contact with it.
What is "Deleted" BENZOPHENONE-4 and where is it found?
This chemical is used as a sunscreen in various products including moisturizers, nail
polishes, lipsticks, lip balms, textiles, plastics and paints. Further research may identify
additional product or industrial usages of this chemical.
What else is "Deleted" BENZOPHENONE-4 called?
This chemical can be identified by different names, including:
2-Hydroxy-4-methoxybenzophenone-5-sulfonic acid, Sulisobenzone, 3-Benzoyl-4-hydroxy-6-methoxybenzenesulfonic acid,
Sulsisobenzone, 5-Benzoyl-4-hydroxy-2-methoxybenzenesulfonic acid, Sungard, Benzophenone 4, Uval, Cyasorb UV 284,
Uvinul MS-40, Spectra-Sorb UV 284, Uvistat 1121
This may not be a complete list as manufacturers introduce and delete chemicals from their product lines.
THINGS YOU CAN DO TO HELP MANAGE YOUR CONTACT ALLERGY
 Be vigilant... read the product label. Always take the time to read the ingredient listing on product packages.
This should be your first step each time you purchase a product as manufacturers sometimes change product
ingredients. If you have any concerns ask your pharmacist or your doctor.
Test the product first. If you have purchased a new product you should test it on a small skin area to see if you
get a reaction before using the product on larger skin areas.
Advise people you obtain services from of your contact allergy. This should include people like your
pharmacist, doctor, hairdresser, florist, veterinarian, etc.
Inform your employer if the source of your contact allergy is work related. You should identify the specific
source of the chemical and take the necessary steps to avoid further exposure. Protective wear may be
adequate or you may need to make a change in your work activities. Both you and your employer benefit when
the cause of your occupational dermatitis is eliminated

Benzophenone-4 is also known as sulisobenzone and is typically an ingredient in most sunscreens. It is used as a skin protectant from damage by short-wave UVA ultraviolet light and UVB. Ungraded products supplied by Spectrum are indicative of a grade suitable for general industrial use or research purposes and typically are not suitable for human consumption or therapeutic use
Sulisobenzone is an ingredient in some sunscreens which protects the skin from damage by UVB and short-wave UVA ultraviolet light.

Chemical ultraviolet (UV) filters have, over the last few decades, been increasingly used not only in conventional sunscreen products but also in many cosmetics and toiletries. Allergic contact dermatitis as well as photoallergic contact dermatitis reactions have been well documented as a consequence of such use. Over a 3‐year period, we recorded the number of positive patch test reactions to a selection of chemical UV filters that we added to our usual cosmetics/facial series. Our objective was to investigate whether any of these filters produced significant numbers of positive patch test results in the absence of photostimulation. Our results show that not only did benzophenone 4 (2‐hydroxy‐4‐methoxybenzophenone‐5‐sulphonic acid: sulisobenzone) produce significantly more positive patch test results than the other UV filters that were tested, but also it was the third most frequently positive result overall. Our findings would support the inclusion of benzophenone 4 when patch testing to investigate likely contact dermatitis from cosmetics and toiletries.

The UV/chlorine process significantly facilitated the degradation of BP-4.
Mutual transformation between the chlorinated product P1 and BP-4 was observed.
The inhomogeneous charge distribution of Csingle bondCl bond led to dechlorination of P1.
A more complete toxicity evaluation system was established.
UV/chlorination showed lower ecotoxicity than chlorination in water treatment.


Abstract
This study investigated the degradation of benzophenone-4 (BP-4) in a UV/chlorine disinfection process, with chlorination and UV disinfection as comparisons. With a degradation efficiency of 80% after 10 s, the UV/chlorine process significantly enhanced the degradation of BP-4. However, a rebound of 36% of the initial concentration was observed in the UV/chlorine process ([free active chlorine (FAC)]0:[BP-4]0 = 1:1, pH = 7). The same tendency appeared under the addition of alkalinity, Cl−, and humic acid (HA). This work interpreted this interesting kinetic tendency from the perspective of mechanism. In fact, the transformation between the chlorinated product P1 and BP-4 was reversible under certain conditions. The inhomogeneous charge distribution of the Csingle bondCl bond in P1 led to the photolytic dechlorination of P1. This transformation caused an increase in BP-4 concentration. In addition, the increase in the UV light power promoted the photodecomposition of P1 under the experimental condition. In addition, this study evaluated the change in absorbable organic halogens (AOX) and three kinds of toxicity changes in the BP-4 solution after chlorination and the UV/chlorine process, including the acute toxicity of luminescent bacteria, endocrine disrupting effect and cytotoxicity. The UV/chlorine process exhibited lower ecotoxicity than chlorination in water treatment.

Chemical UVB sunscreen/sunblock: Benzophenone-3 (Oxybenzone), Benzophenone-4 (Sulisobenzone)
Generic name: Benzophenone-3 (Oxybenzone), Benzophenone-4 (Sulisobenzone)

Brand(s): Various

Type: Chemical

Range of UV spectrum covered: UVB, short UVA (UVA-2) but not long UVA

Wavelengths covered: 290-360 nm

Stability:
Highly stable, do not degrade in sunlight. Protect other UV blocking agents from UV-induced degradation.

Summary:
Benzophenone-3 (Oxybenzone) and Benzophenone-4 (Sulisobenzone) are chemical UV absorbers solid (powder) at normal temperature. Both cover UVB and short UVA (UVA-2) range but are relatively weak sunscreens, inadequate when used alone. They are both very stable and protect and augment other UV absorbers. Benzophenones are absorbed into the skin and have been shown in some studies to promote generation of potentially harmful free radicals. The health implications are unclear but some experts have raised concerns that warrant further research.

Details:
Benzophenones are weak chemical UV absorbers. Benzophenone-3 (Oxybenzone) and Benzophenone-4 (Sulisobenzone) are the benzophenones most commonly used is sunscreen products. They are chemicals solid (powder) at normal temperature. Oxybenzone is water insoluble. Sulisobenzone is water insoluble in its acid form, but can be dissolved in water if neutralized. Both cover UVB and short UVA (UVA-2) range but are relatively weak sunscreens, inadequate when used alone. They are both very stable and protect and augment other UV absorbers.

Benzophenones are relatively easily absorbed into the skin and have been shown in some studies to promote generation of potentially harmful free radicals. Implications of these finding for typical use are unknown but some experts have raised concerns that warrant further research. (See our article on possible risks of absorbable chemical sunscreens.)
Benzophenone-4 is used as a light protection agent in cosmetics. In combination with UV the substance may cause a light sensitization (photo contact allergy) (see photo allergy below).

 
Benzophenone-4: A photostabilizer and sunscreen agent used for its ability to absorb UV rays. It helps prevent the integrity of other cosmetic ingredients from deteriorating under the sun. Though it covers UVB and short UVA (UVA-2) range rays, it's an inadequate sunscreen agent when used alone. For this reason, it is often used in conjunction with other sun protecting ingredients. It’s used in a variety of personal care products like sunscreen, nail polish, lotion/cream and lipstick.

The benzophenone 4 are a group of aromatic ketones that have both pharmaceutical and industrial applications. They have UVB and some UVA absorbing properties and act like optical filters to block out harmful UV rays. They may be used in a sunscreen product to reduce skin damage and to retard photodegradation or extend shelf life in toiletries and plastic surface coatings.
Because they commonly cause contact allergic dermatitis, benzophenones were declared the Contact Allergen of the Year for 2014 by the American Contact Dermatitis Society (ACDS).

- Sunscreen UVB protection 

Benzophenone 4 is used as an ultraviolet curing agent, flavor ingredient, fragrance enhancer and perfume fixative, and as an additive for plastics, coatings and adhesive formulations. Benzophenone is also used as a screen to prevent ultraviolet light-induced damage to cosmetics. Benzophenone-4 provides inadequate UVB protection when used alone. Does not penetrate the skin to a large degree, but enhances the ability of other ingredients to penetrate. Helps to stabilize UV sensitive formulations such as hair dyes, hair sprays and color enhanced formulations.

Benzophenone-4 is a water soluble broad UV-filter. It has worldwide approval for skin protection and it is widely used in sun preparations. It can also offer protections of  colorants against fading and help stabilize fragrances and active ingredients against oxidation.

FORMULATING :

Benzophenone-4 is approved world, the maximum concentration in ready for use preparation various according to local legislation.
The sulfonic acid group makes Benzophenone-4 soluble in water, these acid group must be neutralized with one of the usual neutralizing agents,e.g.Na OH. The yellow color of benzopheonone-4 is intensified bu neutralization, this may change the coloration of the solution.
It should be noted that Benzophenone-4 is not compatible with magnesium salts.  

Benzophenone-4 (BZ4) was separated from surfactants, dyes, preservatives, and other components of hair shampoos by thin-layer chromatography on silica gel 60 stationary phase, with ethyl acetate-ethanol-water-pH 6 phosphate buffer (15 : 7 : 5 : 1 v/v/v/v) as mobile phase. Densitometry scanning of chromatograms was performed at 285 nm. The densitometric calibration curve for BZ4 was nonlinear (second-degree polynomial), with . The limits of detection and quantification were ca. 0.03 and ca. 0.1 μg spot−1, respectively. The results obtained by HPTLC-densitometry were compared to those obtained by zero and 2nd derivative UV spectrophotometry. In the case of spectrophotometric methods, calibration curves were linear with . The chromatographic method was fully validated.


Sulisobenzone (Benzophenone 4) is approved by the FDA in concentrations of up to 10% and in Canada, is approved by Health Canada at the same concentrations 14. It works to filter out both UVA and UVB rays, protecting the skin from sun UV damage 8.

The UV-filter substance, sulisobenzone (BP-4) is widely used an ingredient in sunscreens and other personal care products 1, 10. It falls under the drug category of benzophenones. The benzophenones are a group of aromatic ketones that have both pharmaceutical and industrial applications 13. Benzophenones may be found organically in fruits such as grapes 11.

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 12.

As a group, benzophenones may be used to delay photodegradation or extend shelf life in toiletries and plastic surface coatings 13.

Origins: Synthetic
CosIng functions:UV Absorber, UV Filter

  • Share !
E-NEWSLETTER