ContaminantDB: Dimethyl phthalate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (8)XML

Record Information

Version

1.0

Creation Date

2009-12-04 03:13:09 UTC

Update Date

2026-05-14 19:32:22 UTC

Accession Number

CHEM002621

Identification

Common Name

Dimethyl phthalate

Class

Small Molecule

Description

Dimethyl 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)

Contaminant Sources

Clean Air Act Chemicals
Cosmetic Chemicals
EPA Endocrine Screening
HPV EPA Chemicals
My Exposome Chemicals
STOFF IDENT Compounds
Sludge Chemicals
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Cosmetic Toxin
Ester
Ether
Food Toxin
Household Toxin
Industrial/Workplace Toxin
Organic Compound
Phthalate
Plasticizer
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Dimethylphthalic acid	Generator
Methyl phthalate	ChEMBL
Methyl phthalic acid	Generator
Dimethyl phthalic acid	Generator
Dimethyl phthalate, conjugate diacid	MeSH
Dimethylphthalate	MeSH

Chemical Formula

C₁₀H₁₀O₄

Average Molecular Mass

194.184 g/mol

Monoisotopic Mass

194.058 g/mol

CAS Registry Number

131-11-3

IUPAC Name

1,2-dimethyl benzene-1,2-dicarboxylate

Traditional Name

dimethyl phthalate

SMILES

COC(=O)C1=CC=CC=C1C(=O)OC

InChI Identifier

InChI=1S/C10H10O4/c1-13-9(11)7-5-3-4-6-8(7)10(12)14-2/h3-6H,1-2H3

InChI Key

NIQCNGHVCWTJSM-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
Methyl ester
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

2-hydroxyisophthalic acid (CHEBI:4609 )
Insect repellents (C11233 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

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	5.5°C
Boiling Point	283 - 284 °C
Solubility	4 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	1.09 g/L	ALOGPS
logP	1.96	ALOGPS
logP	1.98	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	50.11 m³·mol⁻¹	ChemAxon
Polarizability	19.39 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-4900000000-8f6b7990a7ff0c457426	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-4900000000-4b5a7315902788fc4921	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-4900000000-bf5f1bff942c9a67e0dc	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-1900000000-b47c903ab98e49f0056a	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-03dj-0900000000-a563da8e92c894b54d40	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-3900000000-e194a5ec6782fe9c8422	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-3900000000-cbc240470004eaf36e39	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dr-2900000000-d1447ddccee80ba373fa	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-0900000000-e28cad3fb0aa046c7359	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-0900000000-6d3539313a4f94a36894	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-0900000000-b83c6a1b33adc5b2b008	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-0900000000-7a5db9a65e7ae849df28	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-08j0-4900000000-a2f666b3eb48d44433f2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0a74-9700000000-ca3df3c80bc8fb799ec7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-002g-9100000000-c25dca7bd8a39ec5ab15	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0iml-9000000000-fa059e88f109c84e6767	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0ik9-9000000000-dffbad3fff43b73a5a74	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-03ej-6900000000-bfc3b30f8614ed3c90a8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0002-9400000000-5c3355010245fd970ff8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-03di-0900000000-7f03cc51fd528e887850	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004l-9100000000-56b3970fd191f6d47e49	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 150V, Positive	splash10-0iml-9000000000-1edfc13e94008e4992fe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-03di-0900000000-0306dc7e20b91e4629d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-03di-0900000000-193e199af796475d7d2d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-8b9794b4dee783302c55	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-4f3c2a4fce097edf9861	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 120V, Positive	splash10-002g-9100000000-48f6752b2e12915c0d97	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-83e4d9ddfd72538b7afe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ot-0900000000-6a6b41107955a633d088	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01q9-2900000000-ef9df520589a1781542a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-c7e72bd53097e76f06f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-edff401c34fcbdc585fd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03e9-2900000000-8af8fb20c500572b7539	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-5900000000-c9e53f21e2d71bd53b8f	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	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: 6800 mg/kg (Oral, Rat) (6) LD50: 3375 mg/kg (Intraperitoneal, Rat) (6) LD50: 38000 mg/kg (Dermal, Rat) (3) LD50: 324 mg/kg (Intravenous, Rat) (3)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Dimethyl phthalate is an ectoparasiticide and has many other uses, including in solid rocket propellants, plastics, and insect repellants. (5)

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

Concentrations

Not Available

External Links

DrugBank ID

DB13336

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Dimethyl phthalate

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

8554

Kegg Compound ID

C11233

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Dimethyl phthalate (CHEM002621)

Structure for CHEM002621: Dimethyl phthalate