An assessment of biodegradability of quaternary carbon-containing fragrance compounds: comparison of experimental OECD screening test results and in silico prediction data.
An assessment of biodegradability was carried out for fragrance substances containing quaternary carbons by using data obtained from Organisation for Economic Co-operation and Development (OECD) 301F screening tests for ready biodegradation and from Biowin and Catalogic prediction models. Despite an expected challenging profile, a relatively high percentage of common-use fragrance substances showed significant biodegradation under the stringent conditions applied in the OECD 301F test. Among 27 test compounds, 37% met the pass level criteria after 28 d, while another 26% indicated partial breakdown (≥20% biodegradation). For several compounds for which structural analogs were available, the authors found that structures that were rendered less water soluble by either the presence of an acetate ester or the absence of oxygen tended to degrade to a lesser extent compared to the primary alcohols or oxygenated counterparts under the test conditions applied. Difficulties were encountered when attempting to correlate experimental with in silico data. Whereas the Biowin model combinations currently recommended by regulatory agencies did not allow for a reliable discrimination between readily and nonbiodegradable compounds, only a comparably small proportion of the chemicals studied (30% and 63% depending on the model) fell within the applicability domain of Catalogic, a factor that critically reduced its predictive power. According to these results, currently neither Biowin nor Catalogic accurately reflects the potential for biodegradation of fragrance compounds containing quaternary carbons.
Firmenich SA, Geneva, Switzerland.
Markus
M
Seyfried
Alain
A
Boschung
D001673:Biodegradation, Environmental; D002244:Carbon / Q000378:metabolism; D003198:Computer Simulation; D008956:Models, Chemical; D039821:Monoterpenes / Q000737:chemistry / Q000378:metabolism; D009930:Organic Chemicals / Q000378:metabolism*; D010476:Perfume / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism
D039821:Monoterpenes; D009930:Organic Chemicals; D010476:Perfume; D012717:Sesquiterpenes; D002244:Carbon
Biodegradation; Fragrances; Prediction model; Quantitative structure-activity relationships; Quaternary carbon