Diethyl phthalate (DEP) is a phthalateester. It occurs as a colourless liquid without significant odour but has a bitter, disagreeable taste. It is more dense than water and insoluble in water; hence, it sinks in water.
It finds some use as a specialist plasticiser in PVC, it has also been used as a blender and fixative in perfume.[3]
Biodegradationedit
Biodegradation by microorganismsedit
Biodegradation of DEP in soil occurs by sequential hydrolysis of the two diethyl chains of the phthalate to produce monoethyl phthalate, followed by phthalic acid. This reaction occurs very slowly in an abiotic environment. Thus there exists an alternative pathway of biodegradation which includes transesterification or demethylation by microorganisms, if the soil is also contaminated with methanol, that would produce another three intermediate compounds, ethyl methyl phthalate, dimethyl phthalate and monomethyl phthalate. This biodegradation has been observed in several soil bacteria.[4] Some bacteria with these abilities have specific enzymes involved in the degradation of phthalic acid esters such as phthalate oxygenase, phthalate dioxygenase, phthalate dehydrogenase and phthalate decarboxylase.[5] The developed intermediates of the transesterification or demethylation, ethyl methyl phthalate and dimethyl phthalate, enhance the toxic effect and are able to disrupt the membrane of microorganisms.
Biodegradation by mammalsedit
Recent studies show that DEP, a phthalic acid ester (PAE), is enzymatically hydrolyzed to its monoesters by pancreatic cholesterol esterase (CEase) in pigs and cows. These mammalianpancreatic CEases have been found to be nonspecific for degradation in relation to the diversity of the alkyl side chains of PAEs.[5]
Toxicityedit
Little is known about the chronic toxicity of diethyl phthalate, but existing information suggests only a low toxic potential.[6] Studies suggest that some phthalates affect male reproductive development via inhibition of androgen biosynthesis. In rats, for instance, repeated administration of DEP results in loss of germ cell populations in the testis. However, diethyl phthalate does not alter sexual differentiation in male rats.[7][8][9][10] Dose response experiments in fiddler crabs have shown that seven-day exposure to diethyl phthalate at 50 mg/L significantly inhibited the activity of chitobiase in the epidermis and hepatopancreas.[11] Chitobiase plays an important role in degradation of the old chitinexoskeleton during the pre-moult phase.[12]
Teratogenicityedit
When pregnant rats were treated with diethyl phthalate, it became evident that certain doses caused skeletal malformations, whereas the untreated control group showed no resorptions. The amount of skeletal malformations was highest at highest dose.[13] In a following study it was found that both phthalate diesters and their metabolic products were present in each of these compartments, suggesting that the toxicity in embryos and fetuses could be the result of a direct effect.[14]
Future investigationedit
Some data suggest that exposure to multiple phthalates at low doses significantly increases the risk in a dose additive manner.[15][16][17] Therefore, the risk from a mixture of phthalates or phthalates and other anti-androgens, may not be accurately assessed studying one chemical at a time. The same may be said about risks from several exposure routes together. Humans are exposed to phthalates by multiple exposure routes (predominantly dermal), while toxicological testing is done via oral exposure.[18]
Referencesedit
^(PDF). Integrated Laboratory Systems, Inc. Archived from the original (PDF) on 1 February 2009. Retrieved 3 March 2009.
^Api, A.M. (February 2001). "Toxicological profile of diethyl phthalate: a vehicle for fragrance and cosmetic ingredients". Food and Chemical Toxicology. 39 (2): 97–108. doi:10.1016/s0278-6915(00)00124-1. PMID 11267702.
^Cartwright, C.D. (March 2000). "Biodegradation of diethyl phthalate in soil by a novel pathway". FEMS Microbiology Letters. 186 (1): 27–34. doi:10.1016/S0378-1097(00)00111-7. PMID 10779708.
^ abSaito, T.; Peng, H.; Tanabe, R.; Nagai, K.; Kato, K. (December 2010). "Enzymatic hydrolysis of structurally diverse phthalic acid esters by porcine and bovine pancreatic cholesterol esterases". Chemosphere. 81 (1): 1544–1548. Bibcode:2010Chmsp..81.1544S. doi:10.1016/j.chemosphere.2010.08.020. PMID 20822795. S2CID 6958344.
^J. Autian (1973). "Toxicity and health threats of phthalate esters: review of the literature". Environmental Health Perspectives. 4: 3–25. doi:10.2307/3428178. JSTOR 3428178. PMC1474854. PMID 4578674.
^Antonia M. Calafat; Richard H. McKee (2006). "Integrating Biomonitoring Exposure Data into the Risk Assessment Process: Phthalates [Diethyl Phthalate and Di(2-ethylhexyl) Phthalate] as a Case Study". Environmental Health Perspectives. 114 (11): 1783–1789. doi:10.1289/ehp.9059. PMC1665433. PMID 17107868.
^Paul M. D. Foster; et al. (1980). "Study of the testicular effects and changes in zinc excretion produced by some n-alkyl phthalates in the rat". Toxicology and Applied Pharmacology. 54 (3): 392–398. doi:10.1016/0041-008X(80)90165-9. PMID 7394794.
^P. M. D. Foster; et al. (1981). "Studies on the testicular effects and zinc excretion produced by various isomers of monobutyl-o-phthalate in the rat". Chemico-Biological Interactions. 34 (2): 233–238. doi:10.1016/0009-2797(81)90134-4. PMID 7460085.
^L. Earl Gray Jr; et al. (2000). "Perinatal Exposure to the Phthalates DEHP, BBP, and DINP, but Not DEP, DMP, or DOTP, Alters Sexual Differentiation of the Male Rat". Toxicological Sciences. 58 (2): 350–365. doi:10.1093/toxsci/58.2.350. PMID 11099647.
^Zou, Enmin; Fingerman, Milton (1999). "Effects of exposure to diethyl phthalate, 4-(tert)-octylphenol, and 2,4,5-trichlorobiphenyl on activity of chitobiase in the epidermis and hepatopancreas of the fiddler crab, Uca pugilator". Comparative Biochemistry and Physiology C. 122 (1): 115–120. doi:10.1016/S0742-8413(98)10093-2. PMID 10190035.
^M. A. Baars & S.S. Oosterhuis, "Free chitobiase, a marker enzyme for the growth of crustaceans", (PDF), Royal Netherlands Institute for Sea Research, Texel, pp. 62–64, archived from the original (PDF) on 2011-07-20
^A. R. Singh; W. H. Lawrence; J. Autian (1972). "Teratogenicity of Phthalate Esters in Rats". Journal of Pharmaceutical Sciences. 61 (1): 51–55. doi:10.1002/jps.2600610107. PMID 5058645.
^A. R. Singh; W. H. Lawrence; J. Autian (1975). "Maternal-Fetal transfer of 14C-Di-2-ethylhexyl phthalate and 14C-diethyl phthalate in rats". Journal of Pharmaceutical Sciences. 64 (8): 1347–1350. doi:10.1002/jps.2600640819. PMID 1151708.
^L. Earl Gray Jr; et al. (2006). "Adverse effects of environmental antiandrogens and androgens on reproductive development in mammals". International Journal of Andrology. 29 (1): 96–104. doi:10.1111/j.1365-2605.2005.00636.x. PMID 16466529.
^Kembra L. Howdeshell; et al. (2008). "A Mixture of Five Phthalate Esters Inhibits Fetal Testicular Testosterone Production in the Sprague-Dawley Rat in a Cumulative, Dose-Additive Manner". Toxicological Sciences. 105 (1): 153–165. doi:10.1093/toxsci/kfn077. PMID 18411233.
^Kembra L. Howdeshell; et al. (2008). "Mechanisms of action of phthalate esters, individually and in combination, to induce abnormal reproductive development in male laboratory rats". Environmental Research. 108 (2): 168–176. Bibcode:2008ER....108..168H. doi:10.1016/j.envres.2008.08.009. PMID 18949836.
^Shanna H. Swan (2008). "Environmental phthalate exposure in relation to reproductive outcomes and other health endpoints in humans". Environmental Research. 108 (2): 177–184. Bibcode:2008ER....108..177S. doi:10.1016/j.envres.2008.08.007. PMC2775531. PMID 18949837.
January 01, 1970
diethyl, phthalate, phthalate, ester, occurs, colourless, liquid, without, significant, odour, bitter, disagreeable, taste, more, dense, than, water, insoluble, water, hence, sinks, water, names, preferred, iupac, name, diethyl, benzene, dicarboxylate, other, . Diethyl phthalate DEP is a phthalate ester It occurs as a colourless liquid without significant odour but has a bitter disagreeable taste It is more dense than water and insoluble in water hence it sinks in water Diethyl phthalate 1 Names Preferred IUPAC name Diethyl benzene 1 2 dicarboxylate Other names Diethyl phthalate Identifiers CAS Number 84 66 2 Y 3D model JSmol Interactive image ChEBI CHEBI 34698 Y ChEMBL ChEMBL388558 Y ChemSpider 13837303 Y ECHA InfoCard 100 001 409 KEGG D03804 Y PubChem CID 6781 UNII UF064M00AF Y CompTox Dashboard EPA DTXSID7021780 InChI InChI 1S C12H14O4 c1 3 15 11 13 9 7 5 6 8 10 9 12 14 16 4 2 h5 8H 3 4H2 1 2H3 YKey FLKPEMZONWLCSK UHFFFAOYSA N YInChI 1 C12H14O4 c1 3 15 11 13 9 7 5 6 8 10 9 12 14 16 4 2 h5 8H 3 4H2 1 2H3Key FLKPEMZONWLCSK UHFFFAOYAV SMILES CCOC O c1ccccc1C O OCC Properties Chemical formula C12H14O4 Molar mass 222 24 g mol Appearance Colourless oily liquid Density 1 12 g cm3 at 20 C Melting point 4 C 25 F 269 K Boiling point 295 C 563 F 568 K Solubility in water 1080 mg L at 25 C log P 2 42 Vapor pressure 0 002 mmHg 25 C 2 Magnetic susceptibility x 127 5 10 6 cm3 mol Hazards NFPA 704 fire diamond 110 Flash point 161 1 C 322 0 F 434 2 K 2 Explosive limits 0 7 lower 2 Lethal dose or concentration LD LC LD50 median dose 8600 mg kg rat NIOSH US health exposure limits PEL Permissible None 2 REL Recommended TWA 5 mg m3 2 IDLH Immediate danger N D 2 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Synthesis and applications 2 Biodegradation 2 1 Biodegradation by microorganisms 2 2 Biodegradation by mammals 3 Toxicity 3 1 Teratogenicity 3 2 Future investigation 4 ReferencesSynthesis and applications editDiethyl phthalate is produced by the reaction of ethanol with phthalic anhydride in the presence of a strong acid catalyst nbsp It finds some use as a specialist plasticiser in PVC it has also been used as a blender and fixative in perfume 3 Biodegradation editBiodegradation by microorganisms edit Biodegradation of DEP in soil occurs by sequential hydrolysis of the two diethyl chains of the phthalate to produce monoethyl phthalate followed by phthalic acid This reaction occurs very slowly in an abiotic environment Thus there exists an alternative pathway of biodegradation which includes transesterification or demethylation by microorganisms if the soil is also contaminated with methanol that would produce another three intermediate compounds ethyl methyl phthalate dimethyl phthalate and monomethyl phthalate This biodegradation has been observed in several soil bacteria 4 Some bacteria with these abilities have specific enzymes involved in the degradation of phthalic acid esters such as phthalate oxygenase phthalate dioxygenase phthalate dehydrogenase and phthalate decarboxylase 5 The developed intermediates of the transesterification or demethylation ethyl methyl phthalate and dimethyl phthalate enhance the toxic effect and are able to disrupt the membrane of microorganisms Biodegradation by mammals edit Recent studies show that DEP a phthalic acid ester PAE is enzymatically hydrolyzed to its monoesters by pancreatic cholesterol esterase CEase in pigs and cows These mammalian pancreatic CEases have been found to be nonspecific for degradation in relation to the diversity of the alkyl side chains of PAEs 5 Toxicity editLittle is known about the chronic toxicity of diethyl phthalate but existing information suggests only a low toxic potential 6 Studies suggest that some phthalates affect male reproductive development via inhibition of androgen biosynthesis In rats for instance repeated administration of DEP results in loss of germ cell populations in the testis However diethyl phthalate does not alter sexual differentiation in male rats 7 8 9 10 Dose response experiments in fiddler crabs have shown that seven day exposure to diethyl phthalate at 50 mg L significantly inhibited the activity of chitobiase in the epidermis and hepatopancreas 11 Chitobiase plays an important role in degradation of the old chitin exoskeleton during the pre moult phase 12 Teratogenicity edit When pregnant rats were treated with diethyl phthalate it became evident that certain doses caused skeletal malformations whereas the untreated control group showed no resorptions The amount of skeletal malformations was highest at highest dose 13 In a following study it was found that both phthalate diesters and their metabolic products were present in each of these compartments suggesting that the toxicity in embryos and fetuses could be the result of a direct effect 14 Future investigation edit Some data suggest that exposure to multiple phthalates at low doses significantly increases the risk in a dose additive manner 15 16 17 Therefore the risk from a mixture of phthalates or phthalates and other anti androgens may not be accurately assessed studying one chemical at a time The same may be said about risks from several exposure routes together Humans are exposed to phthalates by multiple exposure routes predominantly dermal while toxicological testing is done via oral exposure 18 References edit Chemical Information Profile for Diethyl Phthalate PDF Integrated Laboratory Systems Inc Archived from the original PDF on 1 February 2009 Retrieved 3 March 2009 a b c d e f NIOSH Pocket Guide to Chemical Hazards 0213 National Institute for Occupational Safety and Health NIOSH Api A M February 2001 Toxicological profile of diethyl phthalate a vehicle for fragrance and cosmetic ingredients Food and Chemical Toxicology 39 2 97 108 doi 10 1016 s0278 6915 00 00124 1 PMID 11267702 Cartwright C D March 2000 Biodegradation of diethyl phthalate in soil by a novel pathway FEMS Microbiology Letters 186 1 27 34 doi 10 1016 S0378 1097 00 00111 7 PMID 10779708 a b Saito T Peng H Tanabe R Nagai K Kato K December 2010 Enzymatic hydrolysis of structurally diverse phthalic acid esters by porcine and bovine pancreatic cholesterol esterases Chemosphere 81 1 1544 1548 Bibcode 2010Chmsp 81 1544S doi 10 1016 j chemosphere 2010 08 020 PMID 20822795 S2CID 6958344 J Autian 1973 Toxicity and health threats of phthalate esters review of the literature Environmental Health Perspectives 4 3 25 doi 10 2307 3428178 JSTOR 3428178 PMC 1474854 PMID 4578674 Antonia M Calafat Richard H McKee 2006 Integrating Biomonitoring Exposure Data into the Risk Assessment Process Phthalates Diethyl Phthalate and Di 2 ethylhexyl Phthalate as a Case Study Environmental Health Perspectives 114 11 1783 1789 doi 10 1289 ehp 9059 PMC 1665433 PMID 17107868 Paul M D Foster et al 1980 Study of the testicular effects and changes in zinc excretion produced by some n alkyl phthalates in the rat Toxicology and Applied Pharmacology 54 3 392 398 doi 10 1016 0041 008X 80 90165 9 PMID 7394794 P M D Foster et al 1981 Studies on the testicular effects and zinc excretion produced by various isomers of monobutyl o phthalate in the rat Chemico Biological Interactions 34 2 233 238 doi 10 1016 0009 2797 81 90134 4 PMID 7460085 L Earl Gray Jr et al 2000 Perinatal Exposure to the Phthalates DEHP BBP and DINP but Not DEP DMP or DOTP Alters Sexual Differentiation of the Male Rat Toxicological Sciences 58 2 350 365 doi 10 1093 toxsci 58 2 350 PMID 11099647 Zou Enmin Fingerman Milton 1999 Effects of exposure to diethyl phthalate 4 tert octylphenol and 2 4 5 trichlorobiphenyl on activity of chitobiase in the epidermis and hepatopancreas of the fiddler crab Uca pugilator Comparative Biochemistry and Physiology C 122 1 115 120 doi 10 1016 S0742 8413 98 10093 2 PMID 10190035 M A Baars amp S S Oosterhuis Free chitobiase a marker enzyme for the growth of crustaceans NIOZ Annual Report 2006 PDF Royal Netherlands Institute for Sea Research Texel pp 62 64 archived from the original PDF on 2011 07 20 A R Singh W H Lawrence J Autian 1972 Teratogenicity of Phthalate Esters in Rats Journal of Pharmaceutical Sciences 61 1 51 55 doi 10 1002 jps 2600610107 PMID 5058645 A R Singh W H Lawrence J Autian 1975 Maternal Fetal transfer of 14C Di 2 ethylhexyl phthalate and 14C diethyl phthalate in rats Journal of Pharmaceutical Sciences 64 8 1347 1350 doi 10 1002 jps 2600640819 PMID 1151708 L Earl Gray Jr et al 2006 Adverse effects of environmental antiandrogens and androgens on reproductive development in mammals International Journal of Andrology 29 1 96 104 doi 10 1111 j 1365 2605 2005 00636 x PMID 16466529 Kembra L Howdeshell et al 2008 A Mixture of Five Phthalate Esters Inhibits Fetal Testicular Testosterone Production in the Sprague Dawley Rat in a Cumulative Dose Additive Manner Toxicological Sciences 105 1 153 165 doi 10 1093 toxsci kfn077 PMID 18411233 Kembra L Howdeshell et al 2008 Mechanisms of action of phthalate esters individually and in combination to induce abnormal reproductive development in male laboratory rats Environmental Research 108 2 168 176 Bibcode 2008ER 108 168H doi 10 1016 j envres 2008 08 009 PMID 18949836 Shanna H Swan 2008 Environmental phthalate exposure in relation to reproductive outcomes and other health endpoints in humans Environmental Research 108 2 177 184 Bibcode 2008ER 108 177S doi 10 1016 j envres 2008 08 007 PMC 2775531 PMID 18949837 Retrieved from https en wikipedia org w index php title Diethyl phthalate amp oldid 1187503434, wikipedia, wiki, book, books, library,
