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EC number: 222-340-0 | CAS number: 3437-84-1
Biodegradation in water: screening tests
Administrative data
Link to relevant study record(s)
- Endpoint:
- biodegradation in water: ready biodegradability
- Type of information:
- other: Literature
- Adequacy of study:
- weight of evidence
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- data from handbook or collection of data
- Qualifier:
- no guideline followed
- Principles of method if other than guideline:
- See Results field.
- GLP compliance:
- no
- Inoculum or test system:
- other: see summary on results
- Parameter:
- other: see results field
- Remarks:
- see results field
- Remarks on result:
- other: see results field
- Remarks on result:
- other: see results field
- Interpretation of results:
- readily biodegradable
- Conclusions:
- The wide distribution of isobutyric acid degrading microorganisms, the very high growth rate of a few competent microorganisms, and the complete degradation of isobutyuric acid lead to the conclusion that isobutyric acid and diisobutyryl peroxide (Trigonox 187) are readily biodegradable.
- Executive summary:
The wide distribution of isobutyric acid degrading microorganisms, the very high growth rate of a few competent microorganisms, and the complete degradation of isobutyuric acid lead to the conclusion that isobutyric acid and diisobutyryl peroxide (Trigonox 187) are readily biodegradable.
Reference
ASSESSMENT OF READY BIODEGRADABILITY OF DIISOBUTYRYL PEROXIDE (TRIGONOX 187) USING WEIGHT OF EVIDENCE APPROACH
Diisobutyryl peroxide is an instable substance. It is therefore assumed that in soils and surface waters rapid conversion of this peroxide into isobutyric acid takes place. The biodegradability of diisobutyryl peroxide and isobutyric acid are therefore equal. The branched fatty acid, isobutyric acid (2-methyl-propionic acid) is an intermediate in the microbial degradation of valine (dePaul Marshal and Sokatch, 1972). Isobutyric acid is also excreted by microorganisms during fermentation of valine (Sanceda et al. 2003). Valine is initially deaminated and subsequently decarboxylated. As a result isobutyric acid is present in many fermented food products (Allison and Bryant 1963; Beck 2005). It is also present in certain plants, fruits (Panagou and Tassou 2006; Cantalejo 1997) and insects (Seigler and Lampman 2000). Isobutyric acid consequently occurs naturally in soils and fresh water systems. Natural occurrence already points to the ready biodegradability of this fatty acid. A ready biodegradability test result provides the following information about different aspects of biodegradation 1) ultimate (complete) biodegradation by micro-organism capable of utilizing the test substance as sole carbon and energy source, 2) high rate of biodegradation by micro-organisms growing on isobutyric acid and finally 3) the wide-spread occurrence of competent micro-organisms present in ecosystems and biological treatment plants. Below all three aspects are dealt with to enable classification of isobutyric acid. Ultimate (complete) biodegradation; The enzymes involved in microbial isobutyrate degradation have been identified. Isobutyrate is activated to its CoA derivative and subsequently oxidized to methylmalonate semialdehyde. Decarboxylation of methylmalonate semialdehyde yields propionyl CoA. Propionyl- CoA is channeled into the citric acid cycle. Microorganisms therefore have the ability to degrade isobutyric acid completely. Rate of biodegradation; Growth rates on isobutyric acid were only determined for bacteria isolated from a soda lake and soda soil (very alkaline environments). The growth rates of these bacteria were 0.045, 0.25, 0.16 and 0.33 h-1 (Sorokin et al. 2007). Rates in alkaline environments are usually low compared to environments with a pH of 6 to 8. Painter and King (1983) used a model based on the Monod equation to interpret the biodegradation curves in ready biodegradability tests. According to this model growth rates of competent micro-organisms of 0.025 h-1 or higher will result in a ready biodegradation of the test substance (degradation within 28 days in an OECD 301 test).
Ubiquitousness of competent micro-organisms; Isobutyric acid utilizing bacteria (also anaerobic) were present in industrial waste water treatment plants (Cibis et al. 2002; Tholozan et al. 1988), a thermophilic sludge pretreatment plant (Haner et al. 1994), bacteria isolated from wastewater treatment plants capable of utilizing isobutyric acid were Denitratisoma oestradiolicum (Fahrbach et al. 2006), Delftia tsuruhatensis (Shigematsu et al. 2003), Comamonas nitrativorans (Kim et al. 2008) and Clostridium thiosulfatireducens (Hernández-Eugenio et al. 2002). Actinobacteria and in the Marinospirillia were isolated from the soda lake sediment (Sorokin et al. 2007). Desulfococcus multivorans was found in a marine sediment was (Stieb and Schink 1989). Isobutyric acid utilizing bacteria are therefore expected to be widely distributed in the environment. The wide distribution of isobutyric acid degrading microorganisms, the very high growth rate of a few competent microorganisms, and the complete degradation of isobutyuric acid lead to the conclusion that isobutyric acid and diisobutyryl peroxide (Trigonox 187) are readily biodegradable.
Description of key information
The instable nature of Diisobutyryl peroxide leads to rapid thermal and hydrolytic breakdown of the substance to Isobutyric acid (main degradation
product). Isobutyric acid is naturally occurring and is itself readily biodegradable. Literature references supporting this are listed in the expert
statement (below) in the discussion.
Key value for chemical safety assessment
- Biodegradation in water:
- readily biodegradable
Additional information
ASSESSMENT OF READY BIODEGRADABILITY OF DIISOBUTYRYL PEROXIDE (TRIGONOX 187) USING WEIGHT OF EVIDENCE APPROACH
Diisobutyryl peroxide is an instable substance. It is therefore assumed that in soils and surface waters rapid conversion of this peroxide into isobutyric acid takes place. The biodegradability of diisobutyryl peroxide and isobutyric acid are therefore equal. The branched fatty acid, isobutyric acid (2-methyl-propionic acid) is an intermediate in the microbial degradation of valine (dePaul Marshal and Sokatch, 1972). Isobutyric acid is also excreted by microorganisms during fermentation of valine (Sanceda et al. 2003). Valine is initially deaminated and subsequently decarboxylated. As a result isobutyric acid is present in many fermented food products (Allison and Bryant 1963; Beck 2005). It is also present in certain plants, fruits (Panagou and Tassou 2006; Cantalejo 1997) and insects (Seigler and Lampman 2000). Isobutyric acid consequently occurs naturally in soils and fresh water systems. Natural occurrence already points to the ready biodegradability of this fatty acid. A ready biodegradability test result provides the following information about different aspects of biodegradation 1) ultimate (complete) biodegradation by micro-organism capable of utilizing the test substance as sole carbon and energy source, 2) high rate of biodegradation by micro-organisms growing on isobutyric acid and finally 3) the wide-spread occurrence of competent micro-organisms present in ecosystems and biological treatment plants. Below all three aspects are dealt with to enable classification of isobutyric acid. Ultimate (complete) biodegradation; The enzymes involved in microbial isobutyrate degradation have been identified. Isobutyrate is activated to its CoA derivative and subsequently oxidized to methylmalonate semialdehyde. Decarboxylation of methylmalonate semialdehyde yields propionyl CoA. Propionyl- CoA is channeled into the citric acid cycle. Microorganisms therefore have the ability to degrade isobutyric acid completely. Rate of biodegradation; Growth rates on isobutyric acid were only determined for bacteria isolated from a soda lake and soda soil (very alkaline environments). The growth rates of these bacteria were 0.045, 0.25, 0.16 and 0.33 h-1 (Sorokin et al. 2007). Rates in alkaline environments are usually low compared to environments with a pH of 6 to 8. Painter and King (1983) used a model based on the Monod equation to interpret the biodegradation curves in ready biodegradability tests. According to this model growth rates of competent micro-organisms of 0.025 h-1 or higher will result in a ready biodegradation of the test substance (degradation within 28 days in an OECD 301 test).
Ubiquitousness of competent micro-organisms; Isobutyric acid utilizing bacteria (also anaerobic) were present in industrial waste water treatment plants (Cibis et al. 2002; Tholozan et al. 1988), a thermophilic sludge pretreatment plant (Haner et al. 1994), bacteria isolated from wastewater treatment plants capable of utilizing isobutyric acid were Denitratisoma oestradiolicum (Fahrbach et al. 2006), Delftia tsuruhatensis (Shigematsu et al. 2003), Comamonas nitrativorans (Kim et al. 2008) and Clostridium thiosulfatireducens (Hernández-Eugenio et al. 2002). Actinobacteria and in the Marinospirillia were isolated from the soda lake sediment (Sorokin et al. 2007). Desulfococcus multivorans was found in a marine sediment was (Stieb and Schink 1989). Isobutyric acid utilizing bacteria are therefore expected to be widely distributed in the environment. The wide distribution of isobutyric acid degrading microorganisms, the very high growth rate of a few competent microorganisms, and the complete degradation of isobutyuric acid lead to the conclusion that isobutyric acid and diisobutyryl peroxide (Trigonox 187) are readily biodegradable.
References
Allison MJ, Bryant MP (1963) Biosynthesis of branched-chain amino acids from branched-chain fatty acids by rumen bacteria. Archives of Biochemistry and Biophysics 101 (2):269-277 Beck HC (2005) Branched-chain fatty acid biosynthesis in a branched-chain amino acid aminotransferase mutant of Staphylococcus carnosus. FEMS Microbiology Letters 243 (1):37-44 Cantalejo MJ (1997) Analysis of Volatile Components Derived from Raw and Roasted Earth-Almond (Cyperus esculentus L.). Journal of Agricultural and Food Chemistry 45 (5):1853-1860 Cibis E, Kent CA, Krzywonos M, Garncarek Z, Garncarek B, Mikiewicz T (2002) Biodegradation of potato slops from a rural distillery by thermophilic aerobic bacteria. Bioresource Technology 85 (1):57-61 Fahrbach M, Kuever J, Meinke R, Kämpfer P, Hollender J (2006) Denitratisoma oestradiolicum gen. nov., sp. nov., a 17 -oestradiol-degrading, denitrifying betaproteobacterium. International Journal of Systematic and Evolutionary Microbiology 56 (7):1547-1552 Haner A, Mason CA, Hamer G (1994) Aerobic thermophilic waste sludge biotreatment: Carboxylic acid production and utilization during biodegradation of bacterial cells under oxygen limitation. Applied Microbiology and Biotechnology 40 (6):904-909 Hernández-Eugenio G, Fardeau ML, Cayol JL, Patel BKC, Thomas P, Macarie H, Garcia JL, Ollivier B (2002) Clostridium thiosulfatireducens sp. nov., a proteolytic, thiosulfate- and sulfur-reducing bacterium isolated from an upflow anaerobic sludge blanket (UASB) reactor. International Journal of Systematic and Evolutionary Microbiology 52 (5):1461-1468 Kim KH, Ten LN, Liu QM, Im WT, Lee ST (2008) Comamonas granuli sp. nov., isolated from granules used in a wastewater treatment plant. Journal of Microbiology 46 (4):390-395 dePaul Marshall V, Sokatch JR (1972) Regulation of valine catabolism in Pseudomonas putida J Bac 110 (3) 1073-1081Painter HA, King EF (1983) A mathematical model of biodegradability screening tests as an aid to interpretation of observed results. Regulatory Toxicology and Pharmacology 3 (2):144-151 Panagou EZ, Tassou CC (2006) Changes in volatile compounds and related biochemical profile during controlled fermentation of cv. Conservolea green olives. Food Microbiology 23 (8):738-746 Sanceda NG, Suzuki E, Kurata T (2003) Branched chain amino acids as source of specific branched chain volatile fatty acids during the fermentation process of fish sauce. Amino Acids 24 (1-2):81-87 Seigler DS, Lampman RL (2000) Isobutyric Acid from the Brindley's Glands of Triatoma Lecticularia. Journal of the American Mosquito Control Association 16 (1):36-37 Shigematsu T, Yumihara K, Ueda Y, Numaguchi M, Morimura S, Kida K (2003) Delftia tsuruhatensis sp. nov., a terephthalate-assimilating bacterium isolated from activated sludge. International Journal of Systematic and Evolutionary Microbiology 53 (5):1479-1483 Sorokin DY, Van Pelt S, Tourova TP, Muyzer G (2007) Microbial isobutyronitrile utilization under haloalkaline conditions. Applied and Environmental Microbiology 73 (17):5574-5579 Stieb M, Schink B (1989) Anaerobic degradation of isobutyrate by methanogenic enrichment cultures and by a Desulfococcus multivorans strain. Archives of Microbiology 151 (2):126-132 Tholozan J-L, Samain E, Grivet J-P (1988) Isomerization between n-butyrate and isobutyrate in enrichment cultures. FEMS Microbiology Letters 53 (3- 4):187-19
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