Bemotrizinol Chemical Properties

Melting point:

83-85°; mp 80° (Mongiat)

Boiling point:

782.0±70.0 °C(Predicted)

Density 

1.109±0.06 g/cm3(Predicted)

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

pka

8.08±0.40(Predicted)

form 

Solid

color 

Light Yellow to Yellow

Odor

Odorless

BRN 

11322254

InChI

InChI=1S/C38H49N3O5/c1-6-10-12-26(8-3)24-45-30-18-20-32(34(42)22-30)37-39-36(28-14-16-29(44-5)17-15-28)40-38(41-37)33-21-19-31(23-35(33)43)46-25-27(9-4)13-11-7-2/h14-23,26-27,42-43H,6-13,24-25H2,1-5H3

InChIKey

SUKLKCPPDPQLNJ-UHFFFAOYSA-N

SMILES

N1=C(C2=CC=C(OC)C=C2)N=C(C2=CC=C(OCC(CC)CCCC)C=C2O)N=C1C1=CC=C(OCC(CC)CCCC)C=C1O

LogP

7.647 (est)

Safety Information

WGK Germany 

3

HS Code 

2933690000

Bemotrizinol Usage And Synthesis

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.
The INCI name of Bemotrizinol is bis-ethylhexyloxyphenol methoxyphenyl triazine

Application

Bemotrizinol is an active sunscreen agent used in Europe and Australia and will often be paired with less photostable UV blockers such as avobenzone, as the combination creates a much more stable sunscreen that will not degrade and lose its efficacy when exposed to sunlight. In Australia, we need to wear sunscreen every day due to our high rates of skin cancer, and the fact that bemotrizinol can absorb both UVA and UVB rays, providing protection from skin diseases while also not losing effectiveness is an important consideration to make when purchasing sunscreen. Software's Daily Sun Defence SPF50+ protects against both UVA and UVB rays, helping to prevent photoageing, sun spots, and some skin cancers. The lightweight formulation blends seamlessly into the skin, sitting nicely under makeup without leaving a white cast.

brand name

Tinosorb S (Ciba Specialty Chemicals).

Flammability and Explosibility

Non flammable

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.

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