2,2,2-trifluoroethyl methacrylate

Endpoint summary

Description of key information

TFMEA is likely to be readily absorbed by all routes. The ester is rapidly hydrolysed by carboxylesterases to methacrylic acid (MAA) and 2,2,2-Trifluoroethanol.  The primary metabolite, MAA, is subsequently cleared rapidly from blood by standard physiological pathways, with the majority of the administered dose being exhaled as CO2. 
2,2,2-Trifluoroethanol is oxidised to Trifluoroacetic acid and renally excreted. Based on physicochemical properties, no potential for bioaccumulation is to be expected.

Key value for chemical safety assessment

Bioaccumulation potential:

low bioaccumulation potential

Absorption rate - oral (%):

100

Absorption rate - dermal (%):

100

Absorption rate - inhalation (%):

100

Additional information

Absorption

Oral absorption

The physicochemical properties of TFMEA (log P = 2.3) and the molecular weight of168.12g/mol are in a range suggestive of absorption from the gastro-intestinal tract subsequent to oral ingestion.For chemical safety assessment an oral absorption rate of 100% is assumed as a worst case default value in the absence of other data.

Dermal absorption

Based on a QSAR Prediction of Dermal Absorption (extract from Heylings JR, 2013) TFMEA is predicted on the basis of their molecular weight and lipophilicity to have a relatively low ability to be absorbed through the skin. The predicted flux was 0.144 µg/cm²/h.

However, for chemical safety assessment, a dermal absorption rate of 100% was assumed as worst case default value.

 

Inhalative absorption

TFMEA has a vapour pressure of 2200 Pa at 20°C. Thus, inhalation is a likely route of exposure. For chemical safety assessment an inhalative absorption rate of 100% is assumed as a worst case default value in the absence of other data.

 

Distribution

As a small molecule a wide distribution can be expected. No information on potential target organs is available.

 

Metabolism and excretion

Ester hydrolysis has been established as the primary step in the metabolism of methacrylate esters. Carboxylesterases are a group of non-specific enzymes that are widely distributed throughout the body and are known to show high activity within many tissues and organs, including the liver, blood, GI tract, nasal epithelium and skin (Satoh & Hosokawa, 1998; Junge & Krish, 1975; Bogdanffy et al., 1987; Frederick et al., 1994). Those organs and tissues that play an important role and/or contribute substantially to the primary metabolism of the short-chain, volatile, methacrylate esters are the tissues at the primary point of exposure, namely the nasal epithelia and the skin, and systemically, the liver and blood. For TFMEA mostly the same would be the case except that because of the lower vapour pressure and hence lower likelihood of inhalation exposure the involvement of the nasal epithelium is less likely.

Ester hydrolysis of TFMEA would result in Methacrylic acid and2,2,2-Trifluoroethanol. 2,2,2-Trifluoroethanol is expected to be oxidised to 2,2,2-Trifluoroacetaldehyde and finally 2,2,2-Trifluoroacetic acid which can then be excreted via the urine.

Methacrylic acid is cleared rapidly from blood by standard physiological pathways, with the majority of the administered dose being exhaled as CO2.