<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">77</id>
  <title>T3D0076</title>
  <common-name>Di(2-ethylhexyl)phthalate</common-name>
  <description>Di(2-ethylhexyl) phthlate (DEHP) is a manufactured chemical that is commonly added to plastics to make them flexible. DEHP exposure is generally low and not harmful, but increased exposures resulting from intravenous fluids delivered through plastic tubing or ingesting contaminated foods or water may have toxic effects. This is of particular concern since DEHP is known to leach into liquid that come in contact with DEHP containing plastic. (L181, L182)</description>
  <cas>117-81-7</cas>
  <pubchem-id>8343</pubchem-id>
  <chemical-formula>C24H38O4</chemical-formula>
  <weight>390.277010</weight>
  <appearance>Coloress liquid.</appearance>
  <melting-point>-55°C</melting-point>
  <boiling-point>385°C</boiling-point>
  <density nil="true"/>
  <solubility>0.00027 mg/mL at 25 °C [DEFOE,DL et al. (1990)]</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral (L1903) ; inhalation (L1903) ; dermal (L1903)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Monoethylhexylphthalate (MEHP), one of the major metabolites of DEHP, induces peroxisome proliferation by activating peroxisome proliferator activated receptors. This is believed to increase production of hydrogen peroxide by peroxisomes and enhance cell proliferation, leading to hepatotoxic and carcinogenic effects. MEHP is also believed to exhibit testicular toxicity by targeting and damaging the Sertoli cells. DEHP may act as an antiandrogen during a critical stage of reproductive tract differentiation by reducing testosterone in fetal males, hindering development. (L181, A106)</mechanism-of-toxicity>
  <metabolism>DEHP is mainly absorbed via ingestion. It is hydrolyzed in the small intestine and absorbed as monoethylhexylphthalate (MEHP) and 2-ethylhexanol, then likely distributed to the adipose tissues and kidneys. MEHP is further metabolized via numerous oxidative reactions, resulting in the formation of 30 or more metabolites, some of which can be conjugated with glucuronic acid for excretion. Oxidation of 2-ethylhexanol primarily yields 2-ethylhexanoic acid and several keto acid derivatives. Most DEHP metabolites are excreted in the urine as glucuronide conjugates, while unmetabolized DEHP is excreted in the faeces. (L181)</metabolism>
  <toxicity>LD50: 33.9 g/kg (Oral, Rabbit) (T33)
LD50: 10 g/kg (Dermal, Guinea pig) (T33)
LD50: 30.7 g/kg (Intraperitoneal, Rat) (T33)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>2B, possibly carcinogenic to humans. (L135)</carcinogenicity>
  <use-source>DEHP is present in plastic products such as wall coverings, tablecloths, floor tiles, furniture upholstery, shower curtains, garden hoses, swimming pool liners, rainwear, baby pants, dolls, some toys, shoes, automobile upholstery and tops, packaging film and sheets, sheathing for wire and cable, medical tubing, and blood storage bags. (L181)</use-source>
  <min-risk-level>Intermediate Oral: 0.1 mg/kg/day (L134)
Chronic Oral: 0.06 mg/kg/day (L134)</min-risk-level>
  <health-effects>Chronic and/or high levels of DEHP exposure may cause reproductive and developmental damage. This includes damaged sperm, delayed sexual maturity, and deficiencies in the development of male babies. DEHP may also cause liver and kidney damage, and is potentially carcinogenic. (L181, L182)</health-effects>
  <symptoms>Phthalate esters are endocrine disruptors and can cause a number of developmental malformations termed 'phthalate syndrome'. (A2883)</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-03-06T18:58:02Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:21:03Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>http://en.wikipedia.org/wiki/Bis(2-ethylhexyl)phthalate</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C03690</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>17747</chebi-id>
  <biocyc-id>BIS2-ETHYLHEXYLPHTHALATE</biocyc-id>
  <ctd-id>D004051</ctd-id>
  <stitch-id>Di(2-ethylhexyl)phthalate</stitch-id>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id>617</actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC</moldb-smiles>
  <moldb-formula>C24H38O4</moldb-formula>
  <moldb-inchi>InChI=1S/C24H38O4/c1-5-9-13-19(7-3)17-27-23(25)21-15-11-12-16-22(21)24(26)28-18-20(8-4)14-10-6-2/h11-12,15-16,19-20H,5-10,13-14,17-18H2,1-4H3</moldb-inchi>
  <moldb-inchikey>InChIKey=BJQHLKABXJIVAM-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">390.5561</moldb-average-mass>
  <moldb-mono-mass type="decimal">390.277009704</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Liquid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id>CHEMBL1242017</chembl-id>
  <chemspider-id>21106505</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
