Dimethyl itaconate

Endpoint summary

Additional information

The submission item Dimethyl itaconate (DMI) was experimentally found readily biodegradable. In agreement with this, DMI seems based on its chemical structure likely to mineralize under environmental conditions and to integrate into natural cycles of materials. According to literature data DMI is significantly hydrolysed to mono- and diacid by a stereoselective carboxyesterase from a mirco-organism occurring in soils and waters (Bacillus subtilus) as evidenced by Smeets & Kieboom (1992, see section on Toxicokinetics). A precursor and/or possible transformation product of DMI, Itaconic acid (CAS 97-65-4, EINECS 202-599-6) is known to be synthesized by naturally occurring fungi (Aspergillus terreus, A. itanicus) as evidenced by Calam et al. (1939) and Kinoshita (1931) respectively. According to Karanov et al. (1975 referring to Tschesnokow & Schabotinski 1958) some authors published data indicating Itaconic acid is a constituent of plant leaves (e.g. beans, soy bean, lupine and makhorka) contributing to up to 4 % of the dry matter. As hydrolytic cleaving of an ester bridge is a likely transformation reaction it seems probable the DMI gets transformed to this naturally occurring compound. In conclusion ready biodegradability is evidenced and further degradation / stability tests are not required.

Based on its low n-octanol/water partition coefficient, bioaccumulation testing with DMI is not required and the related risks are low.

The Koc was experimentally found to be ca. 2.5 L/kg. DMI is expected to be very mobile in soils due to the insignificant adsorption, but considering the rapid and ready biodegradation it seems nonetheless unlikely that DMI can reach ground waters. In surface waters, shifting to suspended matter and sediments can be assumed irrelevantly low and no shifting to sediments and soils can be expected.

The fugacity properties indicate furthermore insignificant vaporisation of DMI from water and wet or dry surfaces to air. The phototransformation of DMI was assessed on the basis of QSPR estimation, indicating rapid depletion from the troposphere, i.e. with a half-life of ca. half a day. Therefore no DMI is expected in environmental air compartments.

DMI was detected in landfill leachate secondary effluent from industrially contaminated sites Sang et al. (2008). It was found 100 % removable using poly-aluminium(III)-magnesium(II)-sulphate, a common flocculation agent. These data deal on remediation of contaminated sites they point out an effective method for removal of DMI from any effluent including industrial waste water treatment plants.

In conclusion it is assessed that DMI will not pose concerns with regard to its environmental fate and behaviour.

• Calam CT, Oxford AE, Raistrick H (1939). Studies in the biochemistry of microorganisms Itaconic acid, a metabolic product of a strain of Aspergillus terreus. PMID 16747058 Thom Biochem J 33(9):1488-95. URL http://www.biochemj.org/bj/033/1488/0331488.pdf
• Karanov EN, Vasilev GN, Hristova LN (1975). Growth-retarding activity and chemical structure of certain derivatives of itaconic acid. Doklady Bolgarskoi Akademii Nauk 28(8):1085-8.
• Kinoshita Y (1931). Itaconic acid, a metabolic product of Aspergillus itanicus. Acta Phyrochim (Tokyo) 5:271
• Sang YM, Gu QB, Sun TC, Li FS (2008). Color and organic compounds removal from secondary effluent of landfill leachate with a novel inorganic polymer coagulant. PMID 18957755 DOI 10.2166/wst.2008.446 ISSN 0273-1223 Water Sci Technol 58(7):1423-32.
• Tschesnokow WA, Schabotinski G (1958) ISSN 0321-186X Vestn Leningr Univ Biol 3(1):148 Чесноков ВА, Жаботинскнй ГХ (1958). В-к Ленингр. гос. у-та 3, сер. биол. 1:148.