Description
Bemotrizinol, or bis-ethylhexyloxyphenol methoxyphenyl triazine, is an organic UV filter found in over-the-counter sunscreen products. It primarily absorbs UV-A rays. Compared to older broad-spectrum chemical agents, bemotrizinol is more more fat soluble (oil soluble in cosmetic oils) to aid in efficacy and broad-spectrum activity. It is claimed to be photostable, which increases its onset of action and its efficiency in providing protection against UV-rays upon topical application. Bemotrizinol is commonly marketed as Tinosorb S and Escalol S.
Uses
Bemotrizinol is a broad-spectrum UV absorber, absorbing both UVA and UVB. Bemotrizinol is added to various sunscreens to absorb UV rays.
Definition
ChEBI: Bemotrizinol is a member of methoxybenzenes.
Brand name
Tinosorb S (Ciba
Specialty Chemicals).
Flammability and Explosibility
Nonflammable
Safety
Because bemotrizinol is relatively new to the sunscreen market there are few reports or studies available documenting its adverse effects and long term use. Studies to date have shown it to have a good safety profile. It is not significantly absorbed into the skin and rarely causes skin irritation. Unlike some other organic sunscreen agents, in vitro studies show that bemotrizinol does not appear to have hormonal effects. Further long-term human safety studies are required.
Synthesis
In a three-necked flask equipped with a stirrer, a thermometer and a condenser, 40.30 g (0.1 mol) of 2,4-bis(2,4-dihydroxyphenyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 29.02 g (0.21 mol) of potassium carbonate and 105 mL of N, N-dimethylformamide were added in sequence, and the temperature was raised to 100°C. Reflux and stir for 30 minutes; add 46.35g (0.24mol) of DMF solution containing isooctane bromide at a uniform rate within 1 hour, continue to reflux and stir at 100°C after the addition is complete, and monitor the reaction progress with a thin layer chromatography; after the reaction of the raw materials is completed, stop stirring, cool to room temperature, filter, add ethyl acetate to the filtrate for extraction, wash with saturated brine, dry the organic phase with anhydrous sodium sulfate, filter, and spin-dry the filtrate to obtain a colourless transparent oil, i.e. 50.4g of a crude product of bis-ethylhexyloxyphenol methoxyphenyl triazine (Bemotrizinol), with a yield of 80.2% and a purity of 89.90% detected by HPLC.
Advantages
The bis-ethylhexyloxyphenol methoxyphenyl triazine (Bemotrizinol) is a triazine ultraviolet absorbent, has efficient absorption in ultraviolet bands of UVA (320-400 nm) and UVB (280-320), has high molecular weight, is not easy to be absorbed by skin, has strong stability, and is widely applied to personal care and cosmetic products.
Regulations
Bemotrizinol is approved for use in Europe and Australasia. It is marketed under the brand names Tinosorb S and Escalol S. It is currently awaiting FDA approval so is not available in the USA.
