Current limitations of biodegradation screening tests and prediction of biodegradability: A focus on fragrance substances

Published on Apr 1, 2016in Environmental Technology and Innovation3.356
· DOI :10.1016/J.ETI.2016.03.002
Christophe Dick1
Estimated H-index: 1
Sylvain Rey2
Estimated H-index: 2
+ 2 AuthorsMarkus Seyfried3
Estimated H-index: 3
Abstract Key parameters of OECD biodegradation screening tests were analyzed for impact on the assessment of biodegradation potential of selected fragrance compounds. Comparison of official Japanese OECD 301C test results for 48 predominantly readily biodegradable chemicals with recent OECD 301F screening data demonstrated a significantly higher occurrence of false negatives potentially attributable to inoculum limitations for the former, while for the latter, restriction to 28 days was frequently limiting. Influence of test concentration was studied for two groups of quaternary carbon-containing compounds under high (OECD 301F) and low (OECD 301D) concentrations and extended incubations. Ionones were generally ultimately biodegradable within 28 days or readily biodegradable, whereas damascones reached ultimate biodegradation in OECD 301D tests only and required extended incubations. Predictions from Biowin and Catalogic models were analyzed for ionones, damascones and other selected structural groups of fragrance compounds. Comparison with previously published experimental data revealed significant differences in results between OECD screening tests, thus illustrating the shortcomings of currently available data collections and the potential risk of training prediction models with false negative results, particularly if used for models that are primarily based on data from one specific test. In addition, the analysis revealed specific limitations for prediction models that cannot take into account positioning of fragments within a structure. As a result, it appears that the presence of more than one unfavorable fragment usually does not allow reaching currently accepted threshold scores that would identify a given compound as biodegradable. The outcome of the analyses of this study underlines the need to take into account results from OECD screening tests that are best adapted to physico-chemical properties of fragrances (hydrophobicity, volatility and inhibition potential at high test concentration) and conducted at reduced stringency compared to OECD guidelines (extended incubation owing to reduced bioavailability). Negative MITI database results should be critically reviewed, particularly for quaternary carbon-containing compounds. For future efforts aimed at designing more environmentally benign chemicals, the apparent underestimations will have to be overcome by providing more realistic experimental data that should subsequently be used to improve current biodegradation prediction models for better guidance.
📖 Papers frequently viewed together
38 Citations
21 Citations
45 Citations
#1Markus SeyfriedH-Index: 4
#2C.G. van Ginkel (AkzoNobel)H-Index: 21
Last. Alain ChaintreauH-Index: 25
view all 9 authors...
Abstract The persistence of synthetic cyclohexyl- and norbornyl-derived ketones was assessed by using OECD 301F and 301D biodegradation tests. While cyclohexyl-derived ketones either reached or came close to the pass level (60%) after 60 d, the corresponding norbornyl derivatives yielded significantly less biodegradation ( We conclude that despite the potential for ultimate biodegradation of norbornyl-derived ketones, current screening tests yield an incomplete picture of their biodegradability,...
5 CitationsSource
#1Lidia Ceriani (University of Insubria)H-Index: 3
#2Ester PapaH-Index: 31
Last. Paola Gramatica (University of Insubria)H-Index: 61
view all 5 authors...
In the present study, quantitative structure activity relationships were developed for predicting ready biodegradability of approximately 200 heterogeneous fragrance materials. Two classification methods, classification and regression tree (CART) and k-nearest neighbors (kNN), were applied to perform the modeling. The models were validated with multiple external prediction sets, and the structural applicability domain was verified by the leverage approach. The best models had good sensitivity (i...
13 CitationsSource
#1Agnieszka Kowalczyk (Warw.: University of Warwick)H-Index: 3
#2Timothy J. Martin (Newcastle University)H-Index: 5
Last. Gary D. Bending (Warw.: University of Warwick)H-Index: 54
view all 9 authors...
Society׳s reliance upon chemicals over the last few decades has led to their increased production, application and release into the environment. Determination of chemical persistence is crucial for risk assessment and management of chemicals. Current established OECD biodegradation guidelines enable testing of chemicals under laboratory conditions but with an incomplete consideration of factors that can impact on chemical persistence in the environment. The suite of OECD biodegradation tests do ...
53 CitationsSource
#1Robert S. Boethling (EPA: United States Environmental Protection Agency)H-Index: 28
Abstract Biodegradability is fundamental to the assessment of environmental exposure and risk from organic chemicals. Predictive models can be used to pursue both regulatory and chemical design (green chemistry) objectives, which are most effectively met when models are easy to use and available free of charge. The objective of this work was to evaluate no-cost estimation programs with respect to prediction of ready biodegradability. Fragrance materials, which are structurally diverse and have s...
11 CitationsSource
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 ...
5 CitationsSource
The Organisation for Economic Co-operatoin and development (OECD) Guidelines for the Testing of Chemicals list 7 types of tests for determining the ready biodegradability of chemical compounds (301A–F and 310). The present study compares the biodegradation performance of test guideline 301C, which is applied in Japan's Chemical Substances Control Law, with the performance of the other 6 ready biodegradability tests (RBTs) listed in the guidelines. Test guideline 301C specifies use of activated s...
8 CitationsSource
The degradation of Romandolide® ([1-(3′,3′-dimethyl-1′-cyclohexyl)ethoxycarbonyl] methyl propanoate), a synthetic alicyclic musk, by activated sludge inocula was investigated using both the manometric respirometry test OECD 301F and the CO2 evolution test. In addition to measuring its biodegradability, key steps of the upper part of the metabolic pathway responsible for Romandolide® degradation were identified using extracts at different time points of incubation. Early metabolism of Romandolide...
11 CitationsSource
In the context of sustainable and green chemistry, the ‘benign by design’ concept requires information on a compound's biodegradability to be available at an early stage, even before synthesis. Computer models for predicting biodegradation therefore are increasingly important. In this work various approaches to predict aquatic aerobic biodegradation are critically reviewed from a user's point of view. Some fundamental problems in modeling biodegradation are discussed, as well as more general iss...
69 CitationsSource
#1Robert S. Boethling (EPA: United States Environmental Protection Agency)H-Index: 28
The design of the molecule itself is the earliest phase in the process of developing useful products. Two of the 12 green chemistry principles, which state that chemicals should be designed to have minimal toxicity and degrade environmentally to innocuous products, are central to chemical design. Previously we used a series of case studies to show that generalizations about the effects of molecular structure can be used to design small molecules for biodegradability. Here, we extend one of the c...
14 CitationsSource
The unprecedented pollution of the environment by xenobiotic compounds has provoked the need to understand the biodegradation potential of chemicals. Mechanistic understanding of microbial degradation is a premise for adequate modelling of the environmental fate of chemicals. The aim of the present paper is to describe abiotic and biotic models implemented in CATALOGIC software. A brief overview of the specificities of abiotic and microbial degradation is provided followed by detailed descriptio...
43 CitationsSource
Cited By12
#1Qiaorong Guo (CAS: Chinese Academy of Sciences)H-Index: 1
#2Dongbin Wei (CAS: Chinese Academy of Sciences)H-Index: 25
Last. Yuguo Du (CAS: Chinese Academy of Sciences)H-Index: 32
view all 5 authors...
Wastewater reclamation and reuse is a sustainable solution for alleviating the scarcity of water resources. However, the potential risks resulting from the residual pollutants in reclaimed water are of concern. Identifying of priority pollutants would be a practical approach for the management and scientific evaluation of risks associated with reclaimed water reuse. In this study, a novel risk score-based method is proposed for prioritizing residual pollutants in reclaimed water. First, target t...
#1Ankita Srivastava (MNNIT: Motilal Nehru National Institute of Technology Allahabad)H-Index: 5
#2Lalit Kumar Dangi (MNNIT: Motilal Nehru National Institute of Technology Allahabad)
Last. Radha Rani (MNNIT: Motilal Nehru National Institute of Technology Allahabad)H-Index: 10
view all 4 authors...
Reactive Black 5 is one of the most widely used dye in textile and other industries. It is one of the significantly toxic azo dye which poses a serious threat to the environment when discharged into water bodies. A bacterial isolate showed 98% dye removal from aqueous medium within 38hours under optimum parameters pH 7, temperature 400C, in the presence of 1% yeast extract as a co-substrate, and 25% inoculum size at an initial concentration of 50mg/l. Kinetic and thermodynamic study revealed the...
#1B. D. Özel Duygan (UNIL: University of Lausanne)
#2Sylvain ReyH-Index: 2
Last. J.R. van der Meer (UNIL: University of Lausanne)H-Index: 7
view all 6 authors...
ABSTRACT Compound biodegradability tests with natural microbial communities form an important keystone in the ecological assessment of chemicals. However, biodegradability tests are frequently limited by a singular focus either on the chemical and potential transformation products or on the individual microbial species degrading the compound. Here, we investigated a methodology to simultaneously analyze community compositional changes and biomass growth on dosed test compound from flow cytometry...
1 CitationsSource
#1Joost A. Dalmijn (UvA: University of Amsterdam)
#2Baptiste A. J. Poursat (UvA: University of Amsterdam)H-Index: 3
Last. John R. Parsons (UvA: University of Amsterdam)H-Index: 32
view all 6 authors...
Ready biodegradability tests (RBTs) are extensively used to screen the potential of chemicals to be biodegraded. The use of RBT protocols often results in large variations of test results that may lead to wrong interpretations. The present study aims to obtain a fundamental understanding of this variability. For this, we subjected the compounds 4-chloroaniline (4CA), carbamazepine (CBZ), metformin (MET), and N-methylpiperazine (NMP) to a variety of different test conditions. Inocula from five lo...
#1Tom M. Nolte (ETH Zurich)H-Index: 6
#2Willie J.G.M. Peijnenburg (LEI: Leiden University)H-Index: 61
Last. A.J. Hendriks (Radboud University Nijmegen)H-Index: 3
view all 4 authors...
Biodegradation is a predominant removal mechanism for organic pollutants in the aquatic and terrestrial environment and needs to be determined to design ‘green chemicals’ amongst an increasingly large set of industrial chemicals. Decades of research have been dedicated to produce biodegradation models, though, improving those models has become problematic due to ‘black box’ models driven by incongeneric or conflicting experimental results. In this study, we tested the plausibility and applicabil...
1 CitationsSource
#1Baptiste A. J. Poursat (UvA: University of Amsterdam)H-Index: 3
Last. John R. Parsons (UvA: University of Amsterdam)H-Index: 32
view all 6 authors...
Abstract Exposure history and adaptation of the inoculum to chemicals have been shown to influence the outcome of ready biodegradability tests. However, there is a lack of information about the mechanisms involved in microbial adaptation and the implication thereof for the tests. In the present study, we investigated the impact of a long-term exposure to N-methylpiperazine (NMP) and 4-chloroaniline (4CA) of an activated sludge microbial community using chemostat systems. The objective was to cha...
7 CitationsSource
Perfume encapsulates are widely used in commercial products to control the kinetic release of odorant molecules, increase storage stability and/or improve deposition on different substrates. In most of the cases, they consist of core-shell polymeric microcapsules that contain fragrance molecules. A current challenge is to design and produce polymeric materials for encapsulation that are both resistant and non-persistent. The selection of such eco-friendly formulations is linked to a deep underst...
2 CitationsSource
#1Yolanda Martín-Biosca (University of Valencia)H-Index: 18
#2Laura Escuder-Gilabert (University of Valencia)H-Index: 19
Last. María José Medina-Hernández (University of Valencia)H-Index: 15
view all 5 authors...
Environmental context Obtaining biodegradation data over time can be difficult, especially when dealing with environmental compartments of increasing complexity. We evaluated the possibility of obtaining a full biodegradation depletion curve from a single biodegradation-time experimental measurement, and found that environmental information related to potential chemical persistence can be derived. The applicability of this ‘single-data’ strategy is illustrated using simulated and experimental da...
#1Madan Mohan Reddy Nune (BITS: Birla Institute of Technology and Science)H-Index: 2
#2Phaneendra Kiran Chaganti (BITS: Birla Institute of Technology and Science)H-Index: 5
Abstract In this work, a new metalworking fluid (MWF) is developed. The developed MWF is eco-friendly, safe for worker’s health while satisfying the minimum criterion of lubrication and cooling. In the first step, a new MWF with additives like silicon dioxide nanoparticles, menthol, surfactant, and Xanthan were added in appropriate proportion to obtain the MWF with required properties. The preliminary experiments were conducted to analyze and compare the properties of developed MWF with conventi...
14 CitationsSource
#1Baptiste A. J. Poursat (UvA: University of Amsterdam)H-Index: 3
Last. John R. Parsons (UvA: University of Amsterdam)H-Index: 32
view all 4 authors...
AbstractPersistency of organic chemicals is a key property in their environmental risk assessment. Information on persistency is often derived from the results of biodegradability screening tests s...
35 CitationsSource