Bemotrizinol
[CAS# 187393-00-6]

Identification

• Classification: Analytical chemistry >> Standard >> Volatile organic compounds (VOCs)
• Name: Bemotrizinol
• Synonyms: 2,4-Bis[4-(2-ethylhexyloxy)-2-hydroxyphenyl]-6-(4-methoxyphenyl)-1,3,5-triazine; BEMT; CGF 1607; FAT 70'884; Tinosorb S; Tinosorb S Aqua
• Molecular Formula: C₃₈H₄₉N₃O₅
• Molecular Weight: 627.81
• CAS Registry Number: 187393-00-6
• EC Number: 425-950-7
• SMILES: CCCCC(CC)COC1=CC(=C(C=C1)C2=NC(=NC(=N2)C3=CC=C(C=C3)OC)C4=C(C=C(C=C4)OCC(CC)CCCC)O)O

Properties

• Solubility: Insoluble (1.8E^-7 g/L) (25 °C), Calc.^*
• Density: 1.109±0.06 g/cm³ (20 °C 760 Torr), Calc.^*)
• Boiling point: 782.0±70.0 °C 760 mmHg (Calc.)^*
• Flash point: 426.7±35.7 °C (Calc.)^*
• Index of refraction: 1.56 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovery and Applications

Bemotrizinol, also known by its chemical name bis-ethylhexyloxyphenol methoxyphenyl triazine, is an organic compound used as a broad-spectrum ultraviolet (UV) light absorber in sunscreens and personal care products. It was developed in the 1990s and has been widely adopted in various regions for its strong photostability and effective UV filtering properties.

Bemotrizinol is classified as a chemical sunscreen agent that protects the skin by absorbing, rather than reflecting or scattering, ultraviolet radiation. Its molecular structure includes a triazine core substituted with aromatic groups that absorb both ultraviolet A (UVA) and ultraviolet B (UVB) radiation. This dual absorption capability provides comprehensive protection against the harmful effects of sun exposure, including erythema, photoaging, and DNA damage.

One of the key advantages of bemotrizinol is its exceptional photostability. Unlike some older sunscreen agents that degrade quickly upon UV exposure, bemotrizinol remains stable and maintains its effectiveness even after extended sunlight exposure. It does not break down into reactive or harmful byproducts, which contributes to its safety and long-lasting protective performance.

Bemotrizinol is typically incorporated into oil-based or water-resistant sunscreen formulations. It is highly lipophilic, which allows it to remain on the skin surface and resist being washed off by water or perspiration. It is often used in combination with other UV filters to enhance the overall sun protection factor (SPF) and to stabilize less photostable ingredients such as avobenzone.

Regulatory approvals for bemotrizinol vary by country. It is widely approved for use in the European Union, Australia, and several Asian countries. However, it has not been approved for use in over-the-counter sunscreen products in the United States as of the current regulatory status.

Toxicological evaluations have demonstrated that bemotrizinol is well tolerated by the skin and does not exhibit significant systemic absorption. It is considered non-sensitizing and non-irritating in topical formulations and has not shown evidence of endocrine disruption or mutagenic effects in standard safety testing.

In practical applications, bemotrizinol contributes to the efficacy and stability of high-performance sunscreens designed for daily use or for outdoor and sports activities. It plays a critical role in broad-spectrum UV protection, helping to prevent sunburn, premature skin aging, and the development of skin cancers associated with UV exposure.

In summary, bemotrizinol is a modern, photostable, and broad-spectrum UV absorber used in sunscreens to protect against UVA and UVB radiation. Its chemical properties and safety profile have established its role in effective sun protection formulations in many parts of the world.

References

2021. Sunscreens and Photoaging: A Review of Current Literature. American Journal of Clinical Dermatology, 22(6).
DOI: 10.1007/s40257-021-00632-5

2020. Bemotrizinol-Loaded Carnauba Wax-Based Nanostructured Lipid Carriers for Sunscreen: Optimization, Characterization, and In vitro Evaluation. AAPS PharmSciTech, 21(7).
DOI: 10.1208/s12249-020-01821-x

2019. Molecular modeling as a design tool for sunscreen candidates: a case study of bemotrizinol. Journal of Molecular Modeling, 25(12).
DOI: 10.1007/s00894-019-4237-7