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Name Description
id 48
T3DB ID T3D0052
Name Dibutyl phthalate
Class SmallMolecule
Description Dibutyl phthalate is found in cloves. DBP was added to the California Proposition 65 (1986) list of suspected teratogens in November 2006. It is a suspected endocrine disruptor. It was used in some nail polishes; all major producers began eliminating this chemical from nail polishes in the Fall of 2006. Dibutyl phthalate (DBP) is a commonly used plasticizer. It is also used as an additive to adhesives or printing inks. It is soluble in various organic solvents, e.g. in alcohol, ether and benzene. DBP is also used as an ectoparasiticide.
Categories "Household Toxin", "Industrial/Workplace Toxin", "Pollutant", "Airborne Pollutant", "Food Toxin", "Natural Toxin"
Types "Organic Compound", "Plasticizer", "Aromatic Hydrocarbon", "Phthalate", "Ether", "Ester", "Pollutant", "Food Toxin", "Metabolite", "Cosmetic Toxin", "Household Toxin", "Industrial/Workplace Toxin", "Natural Compound"
Synonyms "1,2-Benzenedicarboxylic acid, 1,2-dibutyl ester", "1,2-Benzenedicarboxylic acid, dibutyl ester", "Araldite 502", "Benzene-O-dicarboxylic acid di-N-butyl ester", "Benzene-O-dicarboxylic acid, di-N-butyl ester", "Benzenedicarboxylic acid, dibutyl ester", "BUFA", "Butyl phthalate", "Butylphthalate", "Celluflex DPB", "DBP (ester)", "Di N butyl phthalate", "Di-N-butyl phthalate", "Di-N-butyl phthalate (dbup)", "Di-N-butylester kyseliny ftalove", "Di-N-butylorthophthalate", "di-N-butyphthalatel", "Dibutyl 1, 2-benzenedicarboxylate", "Dibutyl 1,2-benzenedicarboxylate", "Dibutyl ester of 1,2-benzenedicarboxylic acid", "Dibutyl O-phthalate", "Dibutyl phthalated", "Dibutyl phthalic acid", "Dibutyl-1,2-benzenedicarboxylate", "Dibutyl-O-phthalate", "Dibutyl-Phthalate", "Dibutyll phthalate", "Dibutylphthalate", "Dibutylphthatlate", "Elaol", "Ergoplast FDB", "Ersoplast fda", "Genoplast B", "Hatcol DBP", "Hexaplas m/b", "Kodaflex DBP", "Morflex 240", "N-Butyl phthalate", "N-Butylphthalate", "O-Benzenedicarboxylic acid, dibutyl ester", "Ortho-dibutyl phthalate", "Phthalic acid di-N-butyl ester", "Phthalic acid dibutyl ester", "Phthalic acid, dibutyl ester", "Polycizer DBP", "Rapidcelltrade markP", "RC plasticizer DBP", "Staflex DBP", "Uniflex DBP", "Unimoll DB", "Uniplex 150", "Witcizer 300"
CAS Number 84-74-2
Chemical Formula C16H22O4
Average Molecular Mass 278.34
Monoisotopic Mass 278.15
IUPAC Name 1,2-dibutyl benzene-1,2-dicarboxylate
Traditional Name dibutyl-phthalate
SMILES CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC
InChI Identifier 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
InChI Key InChIKey=DOIRQSBPFJWKBE-UHFFFAOYSA-N
Kingdom Organic Compounds
Super Class Benzenoids
Class Benzene and Substituted Derivatives
Sub Class Benzoic Acids and Derivatives
Direct Parent o-Phthalic Acid and Derivatives
Alternate Parents "Benzylethers", "Benzoyl Derivatives", "Dicarboxylic Acids and Derivatives", "Carboxylic Acid Esters", "Ethers", "Carbonyl Compounds"
Geometric Description Aromatic Homomonocyclic Compounds
Substituents "benzoate ester", "benzylether", "benzoyl", "carboxylic acid ester", "Ether", "Organooxygen Compound", "Carbonyl Group", "Aromatic Homomonocyclic Compound", "Carboxylic Acid Derivative", "Dicarboxylic acid or derivatives"
Descriptors "diester (ChEBI)", "phthalate ester (ChEBI)", "Phthalates (KEGG)", "Insect repellents (KEGG)"
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Membrane"
Biofluids
Tissues
Pathways
State Solid
Appearance Colorless oily liquid.
Melting Point 35°C
Boiling Point 340 °C
Solubility 0.0112 mg/mL at 25°C
LogP 4.5
Route of Exposure Oral (L133) ; inhalation (L133) ; dermal (L133)
Mechanism of Toxicity The most characteristic effect of di-n-butyl phthalate is testicular atrophy. Di-n-butyl phthalate exposure causes both the release of iron from hemoglobin and/or transferrin in the liver and spleen, and the subsequent depletion of iron in the blood and testes. The decreased amount of available iron results in a decrease in succinate dehydrogenase activity in the Sertoli cells. This results in disturbances in the energy transfer system between Sertoli cells and germ cells, which is required for the differentiation of male germ cells and their progression through the seminiferous epithelium and release as mature spermatozoa. Di-n-butyl phthalate may also exhibit weak estrogenic activity. It has been shown to exhibit toxic effects in liver mitochondria by uncoupling energy-linked processes and inhibiting succinate dehydrogenase. (L133, A105)
Metabolism Di-n-butyl phthalate is absorbed via oral, inhalation, and dermal routes. It is rapidly distributed and cleared from the body. Metabolism of di-n-butyl phthalate proceeds mainly by nonspecific esterases in the gastrointestinal tract, which hydrolyze of one butyl ester bond to yield mono-n-butyl phthalate, the primary toxic metabolite. Mono-n-butyl phthalate is conjugated with glucuronic acid via glucuronosyltransferase and excreted in the urine. (L133)
Toxicity LD50: 3050 mg/kg (Intraperitoneal, Rat) (T13) LD50: 720 mg/kg (Intravenous, Mouse) (T13) LD50: 5289 mg/kg (Oral, Mouse) (T13) LC50: 25 g/m3 over 2 hours (Inhalation, Mouse) (T13)
Lethal Dose
Carcinogenicity No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sources Di-n-butyl phthalate is used to make plastics more flexible and is also in carpet backings, paints, glue, insect repellents, hair spray, nail polish, and rocket fuel. (L133)
Minimum Risk Level
Health Effects Adverse effects from di-n-butyl phthalate exposure have not yet been reported in humans. However, animals studies have shown that di-n-butyl phthalate can affect reproductive ability by decreasing sperm count and causing birth defects. (L133)
Symptoms Skin contact with di-n-butyl phthalate may cause mild irritation. (L133)
Treatment
DrugBank ID
HMDB ID HMDB33244
PubChem Compound ID 3026
ChEMBL ID
ChemSpider ID 13837319
KEGG Compound ID C14214
UniProt ID 0
OMIM ID 0
ChEBI ID 535597
BioCyc ID
CTD ID D003993
Stitch ID Di-n-butyl phthalate
PDB ID
ACToR ID 1740
Wikipedia Link http://en.wikipedia.org/wiki/Dibutyl_phthalate
Creation Date 2009-03-06 18:57:59
Update Date 2014-12-24 20:20:59