Please note that T3DB is currently undergoing changes to improve data quality and
website features. You can access the original version of T3DB
here.
T3D3642 - Diallyl phthalate
| Record Information | |
|---|---|
| Version | 1.0 |
| Creation Date | 2009-12-03 20:09:49 UTC |
| Update Date | 2013-04-25 08:48:22 UTC |
| Accession Number | T3D3642 |
| Identification | |
| Common Name | Diallyl phthalate |
| Description | Diallyl phthalate is a phthalate ester. Phthalate esters are esters of phthalic acid and are mainly used as plasticizers, primarily used to soften polyvinyl chloride. They are found in a number of products, including glues, building materials, personal care products, detergents and surfactants, packaging, children's toys, paints, pharmaceuticals, food products, and textiles. Phthalates are hazardous due to their ability to act as endocrine disruptors. They are being phased out of many products in the United States and European Union due to these health concerns. (W647) |
| Compound Type |
|
| Chemical Structure |
|
| Synonyms |
|
| Chemical Formula | C14H14O4 |
| Average Molecular Weight | 246.2586 |
| Monoisotopic Molecular Weight | 246.089208936 |
| Chemical IUPAC Name | diallylphthalate |
| CAS Registry Number | 131-17-9 |
| SMILES | C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C |
| InChI Identifier | InChI=1S/C14H14O4/c1-3-9-17-13(15)11-7-5-6-8-12(11)14(16)18-10-4-2/h3-8H,1-2,9-10H2 |
| InChI Key | InChIKey=QUDWYFHPNIMBFC-UHFFFAOYSA-N |
| Chemical Taxonomy | |
| Kingdom | Organic Compounds |
| Super Class | Benzenoids |
| Class | Benzene and Substituted Derivatives |
| Sub Class | Benzoic Acid and Derivatives |
| Direct Parent | o-Phthalic Acid and Derivatives |
| Alternative Parents |
|
| Molecular Framework | Aromatic Homomonocyclic Compounds |
| Substituents |
|
| External Descriptors | Not Available |
| External Links | |
| DrugBank ID | Not Available |
| PubChem Compound ID | 8560  |
| KEGG ID | C02391 |
| UniProt ID | Not Available |
| OMIM ID | Not Available |
| ChEBI ID | 33308 |
| BioCyc ID | O-ACETYLCARNITINE |
| CTD ID | Not Available |
| Stitch ID | Not Available |
| PDB ID | Not Available |
| ACToR ID | Not Available |
| Wikipedia Link | Not Available |
| Physical Properties | |
| Appearance | Colorless liquid. |
| Melting Point | -70 C |
| Solubility | 0.182 mg/mL at 20 oC |
| Predicted LogP | 3.4426993906666663 |
| Toxicity Profile | |
| Route of Exposure | Oral (W647) ; inhalation (W647) ; dermal (W647) |
| Mechanism of Action | Phthalate esters are endocrine disruptors. They decrease foetal testis testosterone production and reduce the expression of steroidogenic genes by decreasing mRNA expression. Some phthalates have also been shown to reduce the expression of insulin-like peptide 3 (insl3), an important hormone secreted by the Leydig cell necessary for development of the gubernacular ligament. Animal studies have shown that these effects disrupt reproductive development and can cause a number of malformations in affected young. (W642) |
| Metabolism | Phthalate esters are first hydrolyzed to their monoester derivative. Once formed, the monoester derivative can be further hydrolyzed in vivo to phthalic acid or conjugated to glucuronide, both of which can then be excreted. The terminal or next-to-last carbon atom in the monoester can also be oxidized to an alcohol, which can be excreted as is or first oxidized to an aldehyde, ketone, or carboxylic acid. The monoester and oxidative metabolites are excreted in the urine and faeces. (W643) |
| Toxicity Values | LD50: 656 mg/kg (Oral, Rat) (R261) LD50: 3.8-3.9 g/kg (Dermal, Rabbit) (R327) LD50: 700 mg/kg (Intraperitoneal, Mouse) (W657) |
| Lethal Dose | Not Available |
| Carcinogenicity (IARC Classification) | Not Available |
| Uses/Sources | Phthalate esters are mainly used as plasticizers, primarily used to soften polyvinyl chloride. They are found in a number of products, including glues, building materials, personal care products, detergents and surfactants, packaging, children's toys, paints, pharmaceuticals, food products, and textiles. Phthalates are used in a variety of household applications such as shower curtains, vinyl upholstery, adhesives, floor tiles, food containers and wrappers, and cleaning materials. Personal care items containing phthalates include perfume, eye shadow, moisturizer, nail polish, liquid soap, and hair spray. (W647) |
| Minimum Risk Level | Not Available |
| Health Effects | Phthalate esters are endocrine disruptors. Animal studies have shown that they disrupt reproductive development and can cause a number of malformations in affected young, such as reduced anogenital distance (AGD), cryptorchidism, hypospadias, and reduced fertility. The combination of effects associated with phthalates is called 'phthalate syndrome’. (W642) |
| Symptoms | Phthalate esters are endocrine disruptors and can cause a number of developmental malformations termed 'phthalate syndrome'. (W642) |
| Treatment | Not Available |
| References | |
| General References |
|