Phthalic Acid Esters

Giam, C. S.; Atlas, E.; Powers, Madison; Leonard, Jack E.

doi:10.1007/978-3-540-38819-7_3

Cited by 91 publications

(45 citation statements)

References 200 publications

(245 reference statements)

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“…Dimethylsulfoxide and ethyleneglycolmonomethyl ether at 5 94 (v/v) inhibited by about 70%. In order to avoid artifacts by the well-known adsorption tendency of DEHP [7] 0.03 yi (w/v) Triton X-100 was included in the standard assay mixture. This addition resulted in less than 10 ?/, inhibition.…”

Section: Properties Qf D E H P Esterase Jiom Wheat Cellsmentioning

confidence: 99%

“…The 1979 production figure of DEHP was about 300 million pounds for the US alone [7]. DEHP is found world-wide as a contaminant of sediments and air.…”

mentioning

confidence: 99%

“…[8]), but many of these reports may have been due to contamination of the solvents used for extraction. The occurrence and toxicology of phthalate diesters have been thoroughly reviewed [7,9,101.…”

mentioning

confidence: 99%

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Plant biochemistry of xenobiotics. Purification and properties of a wheat esterase hydrolyzing the plasticizer chemical, bis(2-ethylhexyl)phthalate

Krell

Sandermann

1984

Eur J Biochem

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A soluble wheat esterase, catalyzing a cleavage of the mass-produced plasticizer chemical, bis(2-ethylhexy1)phthalate (DEHP), has been discovered. Although wheat plants and seeds as well as cultured wheat cells contained more than 12 non-specific esterase activities, only a single protein with a marked preference for a substrate chain-length of 6-8 carbon atoms was active with DEHP. This enzyme is shown to differ from all previously characterized plant lipases and esterases.The enzyme was purified 10-fold from wheat plants and 280-fold, to electrophoretic homogeneity, from cultured wheat cells. An apparent functional molecular mass of 38000Da and an apparent subunit molecular mass of 22000 D a were determined. Inhibitor experiments pointed to the catalytic involvement of a serine residue. Cleavage of DEHP by the purified enzyme was about lo4 times slower than cleavage of 4-nitrophenyl octanoate. This was consistent with previous evidence for a rate-limiting role of the esterase reaction in DEHP metabolism by intact wheat cellsThe fate of environmental chemicals in plants is of great practical concern in view of the huge global plant biomass and of the widespread use of pesticides in agriculture. It is clear that plants play an important role in the transformation of environmental chemicals [I, 21. However, the state of biochemical knowledge on the plant metabolism of xenobiotics is poor when compared to the detailed knowledge on the mammalian metabolism of xenobiotics [3]. Only few plant enzymes acting on xenobiotics have so far been purified and characterizedThe present report deals with a plant enzyme acting on the mass-produced plasticizer chemical, bis(2-ethy1hexyl)phthalate (DEHP, Fig.l). The 1979 production figure of DEHP was about 300 million pounds for the US alone [7]. DEHP is found world-wide as a contaminant of sediments and air. Phthalates, including DEHP, have also repeatedly been isolated from plant material (e.g. [8]), but many of these reports may have been due to contamination of the solvents used for extraction. The occurrence and toxicology of phthalate diesters have been thoroughly reviewed [7, 9, 101. The plant metabolism of phthalate diester plasticizers has only very recently been studied. A small amount (1.2%) of metabolites was present in the plant component (Elocku canademis) of a model ecosystem [l I]. Much higher amounts of DEHP conversion products were isolated from the plant components (Chara chara, Mentha aguatica) of another model ecosystem [12]. However, it remained unclear whether these products had been formed by the plant, by other components of the model ecosystems or through abiotic mechanisms. DEHP [4-61.Abbreviations. DEHP, bis(2-ethylhexy1)phthalate; MEHP, mono-(2-ethylhexy1)phthalate.

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Section: Properties Qf D E H P Esterase Jiom Wheat Cellsmentioning

confidence: 99%

“…The 1979 production figure of DEHP was about 300 million pounds for the US alone [7]. DEHP is found world-wide as a contaminant of sediments and air.…”

mentioning

confidence: 99%

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Plant biochemistry of xenobiotics. Purification and properties of a wheat esterase hydrolyzing the plasticizer chemical, bis(2-ethylhexyl)phthalate

Krell

Sandermann

1984

Eur J Biochem

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“…Phthalate acid esters (PAEs) are a class of chemical compounds that are widely used 29 in various industrial production as plasticizers for the production of polyvinyl chloride 30 resins, adhesives, and cellulose film coating (about 85% of the whole production) in 31 order to improve the mechanical properties of the plastic resin, particularly its 32 flexibility and softness (Giam et al, 1984;Nilsson, 1994;Vitali et al, 1997). 33 However, to provide the required flexibility, the phthalate plasticizer is not covalently 34 bound to the resin and is therefore capable of migrating into the environment (Nilsson,35 1994).…”

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confidence: 99%

Aqueous oxidation of dimethyl phthalate in a Fe(VI)-TiO2-UV reaction system

Yuan

Graham

2008

Water Research

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“…Phthalates are industrial chemicals that are widely used as additives to improve flexibility in polyvinyl chloride (PVC) [3]. In the world, Xie et al [4] reported that approximately 6,000,000 tons per year are produced which has been at a constant level for 20 years.…”

Section: Introductionmentioning

confidence: 99%

Phthalate and alkylphenol removal within wastewater treatment plants using physicochemical lamellar clarification and biofiltration

Bergé

Gaspéri

Rocher³

et al. 2012

Water Pollution XI

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Endocrine disrupting compounds (EDCs) have been found in surface waters worldwide. They are known for exerting adverse effects on animals of many species, including humans. EDCs comprise compounds of anthropogenic origin. They can enter waterways via either discharges from wastewater treatment plant (WWTPs), combined sewer overflows (CSO) or atmospheric deposition. In this work, the fate and removal of four phthalates and two alkylphenols: Diethyl phthalate (DEP), Di-n-Butyl phthalate (DnBP), Butyl Benzyl phthalate (BBP), Di-(2-ethylhexyl) phthalate (DEHP), nonylphenol (NP) and octylphenol (OP) were investigated within a wastewater treatment plant (WWTP) using lamellar clarification and biofiltration. This plant receives about 240,000 m 3 d −1 of wastewater. The whole treatment process comprises: screening, grit removal, primary sedimentation using coagulant and flocculant, followed by biofiltration units. Phthalates and alkylphenols were monitored at three locations, including raw sewage, before primary treatment, decanted effluents, before biological treatment, and final effluents, just before discharge to receiving waters. Nine campaigns were performed in 2011 during different seasons.In 2.95 µg.l -1 ), followed by DEHP (0.95 to 6.43, median 2.30 µg.l -1 ) and NP (0.31 to 1.36, median 0.63 µg.l -1 ). Contaminant removal depends on the physicochemical characteristics of the compounds. For example, for lamellar clarification, removal efficiency was found to be strongly dependent to log Kow and, hence, to be highly correlated with their sorption coefficient (Kd). As a consequence, compounds with high log Kow (>3) were removed to a significant extent. DEHP was highly removed by lamellar clarification (68.8%), followed by BBP (61.5%) and NP (51.0%). Besides, DEP (log Kow < 3) was slightly removed (13.8%). During biofiltration, both hydrophilic and hydrophobic compounds were equally eliminated. Therefore, DEP (87.3%), OP (88.0%) and DEHP (81.9%) were mostly removed during biological treatment.

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Phthalic Acid Esters

Cited by 91 publications

References 200 publications

Plant biochemistry of xenobiotics. Purification and properties of a wheat esterase hydrolyzing the plasticizer chemical, bis(2-ethylhexyl)phthalate

Plant biochemistry of xenobiotics. Purification and properties of a wheat esterase hydrolyzing the plasticizer chemical, bis(2-ethylhexyl)phthalate

Aqueous oxidation of dimethyl phthalate in a Fe(VI)-TiO2-UV reaction system

Phthalate and alkylphenol removal within wastewater treatment plants using physicochemical lamellar clarification and biofiltration

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