dibutyl phthalate (CHEBI:34687)

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ChEBI Name	dibutyl phthalate

ChEBI ID	CHEBI:34687

Definition	A phthalate ester that is the diester obtained by the formal condensation of the carboxy groups of phthalic acid with two molecules of butan-1-ol. Although used extensively as a plasticiser, it is a ubiquitous environmental contaminant that poses a risk to humans.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:535597

Supplier Information	ChemicalBook:CB2739302, ChemicalBook:CB2704227, eMolecules:476359, Selleckchem:Abitrexate, ZINC000001529323

Download	Molfile XML SDF

Wikipedia	License
Methotrexate, formerly known as amethopterin, is a chemotherapy agent and immune-system suppressant. It is used to treat cancer, autoimmune diseases, and ectopic pregnancies. Types of cancers it is used for include breast cancer, leukemia, lung cancer, lymphoma, gestational trophoblastic disease, and osteosarcoma. Types of autoimmune diseases it is used for include psoriasis, rheumatoid arthritis, and Crohn's disease. It can be given by mouth or by injection. Common side effects include nausea, feeling tired, fever, increased risk of infection, low white blood cell counts, and breakdown of the skin inside the mouth. Other side effects may include liver disease, lung disease, lymphoma, and severe skin rashes. People on long-term treatment should be regularly checked for side effects. It is not safe during breastfeeding. In those with kidney problems, lower doses may be needed. It acts by blocking the body's use of folic acid. Methotrexate was first made in 1947 and initially was used to treat cancer, as it was less toxic than the then-current treatments. In 1956 it provided the first cures of a metastatic cancer. It is on the World Health Organization's List of Essential Medicines. Methotrexate is available as a generic medication. In 2022, it was the 132nd most commonly prescribed medication in the United States, with more than 4 million prescriptions.
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Formula

C16H22O4

Net Charge

Average Mass

278.34350

Monoisotopic Mass

278.15181

InChI

InChI=1S/C16H22O4/c1-3-5-11-19-15(17)13-9-7-8-10-14(13)16(18)20-12-6-4-2/h7-10H,3-6,11-12H2,1-2H3

InChIKey

DOIRQSBPFJWKBE-UHFFFAOYSA-N

SMILES

CCCCOC(=O)c1ccccc1C(=O)OCCCC

Roles Classification
Chemical Role(s):	environmental contaminant Any minor or unwanted substance introduced into the environment that can have undesired effects.

Biological Role(s):	teratogenic agent A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. EC 3.2.1.20 (alpha-glucosidase) inhibitor An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-glucosidase (EC 3.2.1.20).

Application(s):	plasticiser Any compound that is used as an additive to increase the plasticity or fluidity of a substance, particularly but not exclusively to synthetic polymers. endocrine disruptor Any compound that can disrupt the functions of the endocrine (hormone) system (via phthalate ester )

ChEBI Ontology
Outgoing	dibutyl phthalate (CHEBI:34687) has functional parent butan-1-ol (CHEBI:28885) dibutyl phthalate (CHEBI:34687) has role EC 3.2.1.20 (α-glucosidase) inhibitor (CHEBI:67239) dibutyl phthalate (CHEBI:34687) has role environmental contaminant (CHEBI:78298) dibutyl phthalate (CHEBI:34687) has role metabolite (CHEBI:25212) dibutyl phthalate (CHEBI:34687) has role plasticiser (CHEBI:79056) dibutyl phthalate (CHEBI:34687) has role teratogenic agent (CHEBI:50905) dibutyl phthalate (CHEBI:34687) is a diester (CHEBI:51307) dibutyl phthalate (CHEBI:34687) is a phthalate ester (CHEBI:35484)

IUPAC Name

dibutyl benzene-1,2-dicarboxylate

Synonyms	Sources
1,2-Benzenedicarboxylic acid dibutyl ester	ChemIDplus
Benzene-o-dicarboxylic acid di-n-butyl ester	NIST Chemistry WebBook
Benzene-o-dicarboxylic acid di-n-butyl ester	ChemIDplus
Benzenedicarboxylic acid dibutyl ester	NIST Chemistry WebBook
Butyl phthalate	ChemIDplus
DBP	ChEBI
Di-n-butyl phthalate	KEGG COMPOUND
Dibutyl 1,2-benzenedicarboxylate	KEGG COMPOUND
Dibutyl o-phthalate	NIST Chemistry WebBook
Dibutyl phthalate	KEGG COMPOUND
Dibutyl-o-phthalate	ChemIDplus
n-Butyl phthalate	ChemIDplus
o-Benzenedicarboxylic acid dibutyl ester	NIST Chemistry WebBook
o-Benzenedicarboxylic acid dibutyl ester	ChemIDplus
Phthalic acid di-n-butyl ester	NIST Chemistry WebBook
Phthalic acid dibutyl ester	NIST Chemistry WebBook

Last Modified

24 August 2017