ContaminantDB: Dicyclohexyl phthalate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2009-12-03 20:13:26 UTC

Update Date

2026-04-17 19:22:41 UTC

Accession Number

CHEM002612

Identification

Common Name

Dicyclohexyl phthalate

Class

Small Molecule

Description

Dicyclohexyl 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

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
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Dicyclohexyl phthalic acid	Generator

Chemical Formula

C₂₀H₂₆O₄

Average Molecular Mass

330.418 g/mol

Monoisotopic Mass

330.183 g/mol

CAS Registry Number

84-61-7

IUPAC Name

1,2-dicyclohexyl benzene-1,2-dicarboxylate

Traditional Name

dicyclohexyl phthalate

SMILES

O=C(OC1CCCCC1)C1=CC=CC=C1C(=O)OC1CCCCC1

InChI Identifier

InChI=1S/C20H26O4/c21-19(23-15-9-3-1-4-10-15)17-13-7-8-14-18(17)20(22)24-16-11-5-2-6-12-16/h7-8,13-16H,1-6,9-12H2

InChI Key

VOWAEIGWURALJQ-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

2-hydroxyisophthalic acid (CHEBI:34693 )
Phthalates (C14529 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

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

Solid

Appearance

Colorless liquid.

Experimental Properties

Property	Value
Melting Point	66°C
Boiling Point	Not Available
Solubility	0.004 mg/mL at 24°C

Predicted Properties

Property	Value	Source
Water Solubility	0.0011 g/L	ALOGPS
logP	5.01	ALOGPS
logP	5.58	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	-6.7	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	6	ChemAxon
Refractivity	92.14 m³·mol⁻¹	ChemAxon
Polarizability	36.74 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9130000000-bf0948298eaf003c4b85	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0002-0900000000-6292662bbf9b60a81a1f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-0900000000-2cfad1f4af158b70d42b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0002-0900000000-b282160570c579fdfe29	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-014j-0900000000-485433678a4139d43b45	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-0900000000-1571f7fd0d316e936cd1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-0961000000-c88d62b294acffd6dcb1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-0900000000-2efae9c6305335252bfa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0900000000-1a9c5667074c58fd3aea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-000i-0900000000-dc2329b6e9627b0ab41e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-000i-0900000000-0e9e05d84dece9c4fcf4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0592-1900000000-5dde58db5f1d07da7958	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-004i-0009000000-d6f710e95c96144c9293	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004r-0908000000-2feeaa694888a4f85bc6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-059b-1900000000-1bcdee72e6811fa5577a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-006t-2900000000-7fd656f0fb35208fe09e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-0900000000-65d03365935b622d1c5a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0002-0900000000-7d99b84ee48e55ce76c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0002-0900000000-5b09efcb9bfbcd703743	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-4049000000-19a242cdddec79ba89d4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9252000000-827bb993f2bceb843e28	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0536-9200000000-85eeb6af0b4b3ace20c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2019000000-b1267d2f456e3940f8d8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-6289000000-9268ea958926bcb137a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9210000000-911ce1d58439498b5221	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1295000000-0cb0458e63126d3c03d4	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-4900000000-a0f78df766b297c29260	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. (2)

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. (3)

Toxicity Values

LD50: >3200 mg/kg (Oral, Mouse) (1) LD50: 1600 mg/kg (Intraperitoneal, Mouse) (1)

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’. (2)

Symptoms

Phthalate esters are endocrine disruptors and can cause a number of developmental malformations termed 'phthalate syndrome'. (2)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0251213

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

Not Available

Chemspider ID

6519

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

C14529

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Dicyclohexyl phthalate (CHEM002612)

Structure for CHEM002612: Dicyclohexyl phthalate