Compendium of the most significant studies with reference to properties, intake, effects.

Beel R, Lütke Eversloh C, Ternes TA. Biotransformation of the UV-filter sulisobenzone: challenges for the identification of transformation products. Environ Sci Technol. 2013 Jul 2;47(13):6819-28. doi: 10.1021/es400451w. 

Abstract. The UV-filter substance Sulisobenzone (BP-4) is widely employed in sunscreens and other personal care products. In the current study, its behavior during biological wastewater treatment was investigated.

Frikeche J, Couteau C, Roussakis C, Coiffard LJ. Research on the immunosuppressive activity of ingredients contained in sunscreens. Arch Dermatol Res. 2015 Apr;307(3):211-8. doi: 10.1007/s00403-014-1528-9.

Abstract. The immunosuppressive properties of Benzophenone-4, an UV-filter and three ingredients, Allantoin, Bisabolol and Enoxolon used in sunscreen formulation, previously characterized as anti-inflammatory compounds, are studied. The results of this study demonstrate that four tested molecules have effects on DCs and T cells which are the most important cells of the immune system. The impact is also visible on keratinocyte cells which are in the direct contact with skin sunscreens. Each ingredient should be used with caution at reduced doses or even removed from some cosmetic preparations, such as sunscreens.

Jia X, Jin J, Gao R, Feng T, Huang Y, Zhou Q, Li A. Degradation of benzophenone-4 in a UV/chlorine disinfection process: Mechanism and toxicity evaluation. Chemosphere. 2019 May;222:494-502. doi: 10.1016/j.chemosphere.2019.01.186.

Abstract. This study investigated the degradation of benzophenone-4 (BP-4) in a UV/chlorine disinfection process, with chlorination and UV disinfection as comparisons. 

Molins-Delgado D, Díaz-Cruz MS, Barceló D. Ecological risk assessment associated to the removal of endocrine-disrupting parabens and benzophenone-4 in wastewater treatment. J Hazard Mater. 2016 Jun 5;310:143-51. doi: 10.1016/j.jhazmat.2016.02.030.

Abstract. The occurrence of four widely used and endocrine disrupting parabens (PBs) (methylparaben, propylparaben, butylparaben and benzylparaben) and a polar UV filter (benzophenone-4) were determined in influent and effluent wastewater from the 19 major wastewater treatment plants (WWTPs) of Catalonia, Spain.

Sherwood VF, Kennedy S, Zhang H, Purser GH, Sheaff RJ. Altered UV absorbance and cytotoxicity of chlorinated sunscreen agents. Cutan Ocul Toxicol. 2012 Dec;31(4):273-9. doi: 10.3109/15569527.2011.647181. 

Abstract. Sunscreens are widely utilized due to the adverse effects of ultraviolet (UV) radiation on human health. The safety of their active ingredients as well as that of any modified versions generated during use is thus of concern.

Benzophenone-4 (Sulisobenzone) is a chemical compound, sodium salt of benzenesulfonic acid.

The name describes the structure of the molecule:

• Benzene is a simple aromatic ring (a hexagonal ring of carbon atoms) with single and double alternating bonds. It is one of the fundamental structures in organic chemistry. Benzene is used in the production of a wide variety of chemicals and is also a natural component of crude oil.
• Phenone refers to a compound that contains a carbonyl group (C=O) attached to two carbon atoms, one of which is part of an aromatic ring. The carbonyl group is a functional group characterized by a double carbon-oxygen bond. Phenons are often used in organic chemistry as building blocks for more complex molecules.
• Sulfonyl group (SO₂) is a functional group consisting of a sulfur atom bound to two oxygen atoms (double bonds) and a carbon atom of the benzene ring. Sulfonyl groups are often found in organic sulfur compounds, including some medications and dyes.
• Hydroxyl group (-OH) consists of an oxygen atom bound to a hydrogen atom. It is a common functional group in organic chemistry and is characteristic of alcohols. Hydroxyl groups can increase the polarity of organic molecules and improve their solubility in water.
• Second benzene ring is attached to the sulfonyl group. As mentioned above, benzene is a fundamental structure in organic chemistry and is used in the production of a wide variety of chemicals.

The synthesis process takes place in different steps:

• Preparation of benzophenone. Benzophenone can be synthesized from benzene Friedel-Crafts acylation with benzoyl chloride in the presence of Lewis acid typically aluminum chloride (AlCl₃).
• Sulfonation of benzophenone. Benzophenone is sulfonated using sulfuric acid (H₂SO₄₎ to form benzophenone-4-sulfonic acid.
• Neutralization. Benzophenone-4-sulfonic acid is then neutralized with a base such as sodium hydroxide (NaOH) to form the sodium salt, which is benzophenone-4.

It appears in the form of a white powder

What it is used for and where

Cosmetics

It is widely used as a UV filter in sunscreens but is a restricted ingredient as VI/22 a Relevant Item in the Annexes of the European Cosmetics Regulation 1223/2009.

It has the following INCI functions:

Light stabilizer. It prevents light from degrading light-sensitive components and slows down degradation reactions that have already begun. The mechanism is, in a way, similar to antioxidants and the effectiveness depends on the.complexity of the formulation and the density of the product.

UV absorber. It acts by intercepting ultraviolet light before it can cause damage by reducing its energy through dissipation and returning it to a lower energy state.

UV filter. It is the defining ingredient in sun creams that can mitigate the sun's ultraviolet (UV) radiation, which is a high risk factor for the development of skin cancer, erythema and photo-ageing.

Other Uses

Moreover this substance is used in the following products:

• cosmetics and personal care products
• washing & cleaning products
• leather treatment products
• pharmaceuticals
• polishes and waxes
• coating products
• adhesives and sealants
• air care products
• plant protection products
• machine wash liquids/detergents
• automotive care products
• paints and coating or adhesives
• fragrances and air fresheners

Sulisobenzone studies

Appearance	White powder
Melting Point	170°C
Density	1.4±0.1 g/cm3
PSA	109.28000
Refraction Index	1.617
LogP	0.89
Storage
Safety

• Formula molecolare: C₁₄H₁₂O₆S
• Peso molecolare: 308.304 g/mol
• Massa esatta   308.035461
• UNII: 1W6L629B4K
• CAS: 4065-45-6  6628-37-1  62121-63-5
• EC Number: 223-772-2    613-918-7
• PubChem Substance ID 329757575
• MDL number MFCD00024962
• Beilstein Registry Number 2889165
• DSSTox Substance ID  
• IUPAC  5-benzoyl-4-hydroxy-2-methoxybenzenesulfonic acid
• InChI=1S/C14H12O6S/c1-20-12-8-11(15)10(7-13(12)21(17,18)19)14(16)9-5-3-2-4-6-9/h2-8,15H,1H3,(H,17,18,19)
• InChl Key      CXVGEDCSTKKODG-UHFFFAOYSA-N
• SMILES   COC1=C(C=C(C(=C1)O)C(=O)C2=CC=CC=C2)S(=O)(=O)O   
• ChEBI  135312
• RTECS   DB5044300

Synonyms:

• Sulisobenzone
• 5-benzoyl-4-hydroxy-2-methoxy-benzenesulfonic acid
• 4-hydroxy-2-methoxy-5-(phenylcarbonyl)benzenesulfonic acid
• Benzophenone-4
• 5-Benzoyl-4-hydroxy-2-methoxybenzolsulfonsaeure
• 5-Benzoyl-4-hydroxy-2-methoxybenzene sulfonic acid
• 1-Phenol-4-sulfonic acid, 2-benzoyl-5-methoxy-
• 5-Benzoyl-4-hydroxy-2-methoxybenzenesulfonic acid ammoniate
• 5-Benzoyl-4-hydroxy-2-methoxybenzenesulfonic acid
• 2-Hydroxy-4-methoxybenzophenone-5-sulfonic acid
• 1-Phenol-4-sulfonic acid, 2-benzoyl-5-methoxy-, sodium salt
• 4-hydroxy-2-methoxy-5-(oxo-phenylmethyl)benzenesulfonic acid
• Benzenesulfonic acid, 5-benzoyl-4-hydroxy-2-methoxy-, sodium salt
• SCHEMBL16330
• 2-Hydroxy-4-Methoxy-5-sulfonylbenzophenone(BP-4)
• 1-Phenol-4-sulfonic acid, 2-benzoyl-5-methoxy- (6CI)
• Spectra-Sorb U.V. 284
• 3-Benzoyl-4-hydroxy-6-methoxybenzenesulfonic acid
• Sungard
• Benzophenone 4
• Uval
• Sulisobenzona
• Sulisobenzonum
• Uvinul
• Seesorb 101S
• Syntase 230
• Uvinul MS 40
• Benzenesulfonic acid, 5-benzoyl-4-hydroxy-2-methoxy-
• Spectra-Sorb UV 284
• Uvinuc ms 40