| Record Information |
|---|
| Version | 2.0 |
|---|
| Creation Date | 2009-12-03 20:32:43 UTC |
|---|
| Update Date | 2014-12-24 20:26:16 UTC |
|---|
| Accession Number | T3D3645 |
|---|
| Identification |
|---|
| Common Name | Diisodecyl phthalate |
|---|
| Class | Small Molecule |
|---|
| Description | Diisodecyl 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. (4) |
|---|
| Compound Type | - Aromatic Hydrocarbon
- Cosmetic Toxin
- Ester
- Ether
- Food Toxin
- Household Toxin
- Industrial/Workplace Toxin
- Organic Compound
- Phthalate
- Plasticizer
- Synthetic Compound
|
|---|
| Chemical Structure | |
|---|
| Synonyms | | Synonym | | 1,2-Benzenedicarboxylic acid 1,2-diisodecyl ester | | Bis(8-methylnonyl) phthalate | | Bis(isodecyl) phthalate | | Di(C9-C11) branched alkyl phthalate | | Di(I-decyl) phthalate | | Di-isodecyl phthalate | | Didp (plasticizer) | | DIIsodecyl phthalate | | Diisodecyl phthalic acid | | Isodecyl phthalate | | Phthalic acid bis(8-methylnonyl) ester | | Phthalic acid dIIsodecyl ester | | Plasticized DDP |
|
|---|
| Chemical Formula | C28H46O4 |
|---|
| Average Molecular Mass | 446.662 g/mol |
|---|
| Monoisotopic Mass | 446.340 g/mol |
|---|
| CAS Registry Number | 26761-40-0 |
|---|
| IUPAC Name | 1,2-bis(8-methylnonyl) benzene-1,2-dicarboxylate |
|---|
| Traditional Name | diisodecyl phthalate |
|---|
| SMILES | CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C |
|---|
| InChI Identifier | InChI=1S/C28H46O4/c1-23(2)17-11-7-5-9-15-21-31-27(29)25-19-13-14-20-26(25)28(30)32-22-16-10-6-8-12-18-24(3)4/h13-14,19-20,23-24H,5-12,15-18,21-22H2,1-4H3 |
|---|
| InChI Key | InChIKey=ZVFDTKUVRCTHQE-UHFFFAOYSA-N |
|---|
| Chemical Taxonomy |
|---|
| Description | belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Benzenoids |
|---|
| Class | Benzene and substituted derivatives |
|---|
| Sub Class | Benzoic acids and derivatives |
|---|
| Direct Parent | Benzoic acid esters |
|---|
| Alternative Parents | |
|---|
| Substituents | - Benzoate ester
- Benzoyl
- Dicarboxylic acid or derivatives
- Carboxylic acid ester
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homomonocyclic compound
|
|---|
| Molecular Framework | Aromatic homomonocyclic compounds |
|---|
| External Descriptors | |
|---|
| Biological Properties |
|---|
| Status | Detected and Not Quantified |
|---|
| Origin | Exogenous |
|---|
| Cellular Locations | |
|---|
| Biofluid Locations | Not Available |
|---|
| Tissue Locations | Not Available |
|---|
| Pathways | Not Available |
|---|
| Applications | Not Available |
|---|
| Biological Roles | Not Available |
|---|
| Chemical Roles | Not Available |
|---|
| Physical Properties |
|---|
| State | Liquid |
|---|
| Appearance | Colorless liquid. |
|---|
| Experimental Properties | | Property | Value |
|---|
| Melting Point | -50°C | | Boiling Point | Not Available | | Solubility | 0.00028 mg/mL at 25°C | | LogP | Not Available |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | | Spectrum Type | Description | Splash Key | Deposition Date | View |
|---|
| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-01ox-4951000000-1ddc66fe5d0366840457 | 2021-09-24 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-1330900000-b8abcda8338ac7332df8 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000f-6930100000-48bc223ff20a698d4ed2 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4l-9810000000-ad725a86b031403751b1 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0221900000-6f21bcdf32ce79d06faa | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4s-0957300000-d2433f24afa4cdf3e46b | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00y0-0910000000-bbd9a771f49a906bafc9 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000j-0490500000-fde844776abfda970bfa | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000b-9781800000-d589b1cbd801f2e45945 | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a5a-9400000000-5e9a344a67767fd89325 | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0000900000-8adcb3adc638457fd88c | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0933700000-0fa73e1c5de43efcc783 | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00xr-0931000000-f32b6576d3bf8dcda2b2 | 2021-10-12 | View Spectrum |
|
|---|
| Toxicity Profile |
|---|
| Route of Exposure | Oral (4) ; inhalation (4) ; dermal (4) |
|---|
| Mechanism of Toxicity | 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. (1) |
|---|
| 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. (2) |
|---|
| Toxicity Values | LD50: >3160 mg/kg (Dermal, Rabbit) (3)
LD50: 64 000 mg/kg (Oral, Rat) (3) |
|---|
| Lethal Dose | Not Available |
|---|
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
|---|
| 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. (4) |
|---|
| 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’. (1) |
|---|
| Symptoms | Phthalate esters are endocrine disruptors and can cause a number of developmental malformations termed 'phthalate syndrome'. (1) |
|---|
| Treatment | Not Available |
|---|
| Normal Concentrations |
|---|
| Not Available |
|---|
| Abnormal Concentrations |
|---|
| Not Available |
|---|
| External Links |
|---|
| DrugBank ID | Not Available |
|---|
| HMDB ID | Not Available |
|---|
| PubChem Compound ID | 33599 |
|---|
| ChEMBL ID | Not Available |
|---|
| ChemSpider ID | 30996 |
|---|
| KEGG ID | C14578 |
|---|
| UniProt ID | Not Available |
|---|
| OMIM ID | |
|---|
| 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 | Diisodecyl_phthalate |
|---|
| References |
|---|
| Synthesis Reference | Not Available |
|---|
| MSDS | T3D3645.pdf |
|---|
| General References | - Wilson VS, Blystone CR, Hotchkiss AK, Rider CV, Gray LE Jr: Diverse mechanisms of anti-androgen action: impact on male rat reproductive tract development. Int J Androl. 2008 Apr;31(2):178-87. doi: 10.1111/j.1365-2605.2007.00861.x. [18315717 ]
- Wittassek M, Angerer J: Phthalates: metabolism and exposure. Int J Androl. 2008 Apr;31(2):131-8. Epub 2007 Dec 7. [18070048 ]
- Lewis RJ Sr. (ed) (2004). Sax's Dangerous Properties of Industrial Materials. 11th Edition. Hoboken, NJ: Wiley-Interscience, Wiley & Sons, Inc.
- Wikipedia. Phthalate. Last Updated 22 November 2009. [Link]
|
|---|
| Gene Regulation |
|---|
| Up-Regulated Genes | | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
|---|
|
|---|
| Down-Regulated Genes | | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
|---|
|
|---|
