Biodegradation of diethyl phthalate in soil by a novel pathway

Cartwright, Colin D.; Owen, Sarah A.; Thompson, Ian P.; Burns, Richard G.

doi:10.1111/j.1574-6968.2000.tb09077.x

Cited by 114 publications

(39 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…MET production was only detected when MMT and ethanol were present, not methanol, suggesting that ethanol acted as the nucleophile in the trans-esterification of MMT to MET. A similar trans-esterification of ethyl group to methyl group was reported in biodegradation of diethyl phthalate in soil (Cartwright et al 2000). However, due to its weaker polarity, ethanol is a weaker nucleophile than H 2 O, hydrolysis of MMT is expected to proceed over trans-esterification, resulting in the formation of TA not MET.…”

Section: Discussionmentioning

confidence: 76%

Biodegradation of dimethyl terephthalate by Pasteurella multocida Sa follows an alternative biochemical pathway

2006

Ecotoxicology

View full text Add to dashboard Cite

Pasteurella multocida Sa, a bacterial strain isolated from mangrove sediment by enrichment technique, was capable of transforming dimethyl terephthalate (DMT). Biodegradation of DMT was shown to take place as a series of sequential steps involving the hydrolysis of two ester linkages between the carboxyl groups of the terephthalate and the methyl side-chain initially to produce mono-methyl terephthalate (MMT) and then terephthalic acid (TA), respectively. However, with ethanol as the carrying solvent, there was a formation of one metabolite previously not observed. The two metabolites were characterized by high performance-liquid chromatography-electron ionization mass spectrometry as MMT and mono-ethyl terephthalate (MET), suggesting the existence of an alternative biochemical pathway in the degradation of DMT by P. multocida Sa. Since the presence of MMT and ethanol in culture inoculated with P. multocida Sa was prerequisites for the formation of MET, biologically mediated trans-esterification was proposed as a mechanism for the novel biochemical process observed.

show abstract

Section: Discussionmentioning

confidence: 76%

Biodegradation of dimethyl terephthalate by Pasteurella multocida Sa follows an alternative biochemical pathway

2006

Ecotoxicology

View full text Add to dashboard Cite

show abstract

“…The plastic softener, di (2-ethylhexyl) phthalate (DEHP), has been used in industrial productions of various products such as polyvinyl chloride (PVC), glues, lubricants, and to a limited extent in food and medical products packaging (Cartwright et al 2000;de Jonge et al 2002;Marttinen et al 2003). DEHP can be released into the environment by means of volatilization and dissolution during the productions as well as during the usages and disposal of plastics because these chemicals do not form strong chemical bonds with structure of plastics (Fromme et al 2002;Psillakis et al 2004).…”

Section: Introductionmentioning

confidence: 99%

Distribution Coefficient and Adsorption–desorption Rates of di (2-ethylhexyl) Phthalate (DEHP) onto and from the Surface of Suspended Particles in Fresh Water

Sirivithayapakorn

Limtrakul

2007

Water Air Soil Pollut

View full text Add to dashboard Cite

The commonly used plastic softener, di (2-ethylhexyl) phthalate (DEHP), also a known Endocrine Disrupting Compound, was found contaminated in various aquatic environments, including river water in Thailand. The data of adsorption kinetics from this study indicated that DEHP can adsorb onto pure bentonite and natural suspended sediment with average adsorption rate constants of 0.0056 and 0.0039 min −1 respectively. The average distribution coefficients between suspended particles and water found in this study for pure bentonite and natural suspended sediment were 0.045 and 0.043 l g −1 respectively. Although the studies were carried out in pH 4.0, 7.0 and 10.0, there were no obvious influences of pH on adsorption rates and distribution coefficients of DEHP onto both pure bentonite and natural suspended particles. The desorption rate was very small and was estimated to be less than 0.03 μg min −1 . The results indicated that suspended sediment could become a long term release of DEHP and facilitate the transport of DEHP mainly due to fast adsorption rate and relatively high adsorption capacity.

show abstract

“…3), it is noticeable that the dicarboxylic ester substrate was hydrolyzed at the two ester-bonds initially. Many studies on microbial degradation of phthalate esters indicated that it is crucial that phthalate esters are hydrolyzed so that they can be assimilated efficiently by microorganisms (Jackson et al 1996;Cartwright et al 2000;Gryglewicz 2003). Monoesters of phthalate are more soluble in water than the diester and also more endocrine active.…”

Section: Mineralization and Enzyme Activitymentioning

confidence: 99%

Degradability of dimethyl terephthalate by Variovorax paradoxus T4 and Sphingomonas yanoikuyae DOS01 isolated from deep-ocean sediments

Wang

2006

Ecotoxicology

View full text Add to dashboard Cite

Two strains of bacteria were isolated from deep-ocean sediments of the South China Sea using enrichment culturing technique and they were identified as Sphingomonas yanoikuyae DOS01 (AY878409) and Variovorax paradoxus T4 (AY878410) based on 16S rRNA gene sequences. S. yanoikuyae DOS01 was only capable of transforming dimethyl terephthalate (DMTP) to monomethyl terephthalate (MMTP) without further degradation while V. paradoxus T4 exhibited ability in mineralizing DMTP as the sole source of carbon and energy. The biochemical pathway of DMTP degradation was through MMTP and terephthalic acid (TA) as major detectable degradation intermediates in the culture media by both microorganisms. V. paradoxus T4 utilized DMTP and MMTP via hydrolysis of diester and monoester in the initial steps in degradation as confirmed by total organic carbon analysis of the culture medium and esterase activity assay of the lysed cells and fraction. The specific hydrolysis activity of esterase induced by DMTP or MMTP showed that greater hydrolysis of p-nitrophenyl acetate by esterase induced by DMTP-grown cells than that induced by MMTP. Results of this research suggest that the cleavage of the two identical carboxylic ester groups of phthalate diester are carried out by highly specific esterases of the same bacteria in the environment.

show abstract

Biodegradation of diethyl phthalate in soil by a novel pathway

Cited by 114 publications

References 14 publications

Biodegradation of dimethyl terephthalate by Pasteurella multocida Sa follows an alternative biochemical pathway

Biodegradation of dimethyl terephthalate by Pasteurella multocida Sa follows an alternative biochemical pathway

Distribution Coefficient and Adsorption–desorption Rates of di (2-ethylhexyl) Phthalate (DEHP) onto and from the Surface of Suspended Particles in Fresh Water

Degradability of dimethyl terephthalate by Variovorax paradoxus T4 and Sphingomonas yanoikuyae DOS01 isolated from deep-ocean sediments

Contact Info

Product

Resources

About