1.0 2010-04-08 22:09:33 UTC 2020-09-17 15:35:02 UTC FDB011261 Dibutyl phthalate Dibutyl phthalate, also known as DBP or butyl phthalic acid, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Dibutyl phthalate (DBP) is a commonly used plasticizer. It is a paint tasting, colorless oil, although commercial samples are often yellow. Metabolism of dibutyl phthalate proceeds mainly by nonspecific esterases in the gastrointestinal tract, which hydrolyze one of the butyl ester bonds to yield mono-n-butyl phthalate, the primary toxic metabolite. Dibutyl phthalate is absorbed via oral, inhalation, and dermal routes. It is rapidly distributed and cleared from the body. Mono-butyl phthalate is conjugated with glucuronic acid via glucuronosyltransferase and excreted in the urine. Dibutyl phthalate is a potentially toxic compound. The most characteristic effect of dibutyl phthalate on mammals is testicular atrophy. Animal studies have shown that dibutyl phthalate can affect the reproductive ability by decreasing sperm count and causing birth defects. DBT has also exhibited toxic effects in liver mitochondria by uncoupling energy-linked processes and inhibiting the succinate dehydrogenase. Adverse effects from dibutyl phthalate exposure have not yet been reported in humans. Dibutyl phthalate is a commonly used plasticizer. It is also used as an additive to adhesives or printing inks. DBP is also used as an ectoparasiticide. Dibutyl phthalate, and other phthalates, are often reported as components of natural products extracts. However, due to their high solubility in organic solvents (e.g. ethanol, ethers, dichloromethane, and benzene) they are most likely a contaminant analyte, introduced into the sample through the use of plastics during sample preparation or from contaminated solvents, especially in gas chromatography analyses. 1,2-Benzenedicarboxylate dibutyl ester 1,2-Benzenedicarboxylic acid dibutyl ester 1,2-Benzenedicarboxylic acid, 1,2-dibutyl ester 1,2-Benzenedicarboxylic acid, dibutyl ester Araldite 502 Benzene-O-dicarboxylate di-N-butyl ester Benzene-o-dicarboxylic acid di-n-butyl ester Benzene-o-dicarboxylic acid, di-n-butyl ester Benzenedicarboxylate dibutyl ester Benzenedicarboxylic acid dibutyl ester Benzenedicarboxylic acid, dibutyl ester BUFA Butyl phthalate Butyl phthalic acid Celluflex DPB DBP DBP (ester) Di n butyl phthalate Di-n-butyl phthalate Di-n-butyl phthalate (dbup) Di-N-butyl phthalic acid Di-n-butylester kyseliny ftalove Di-n-butylorthophthalate Dibutyl 1, 2-benzenedicarboxylate Dibutyl 1,2-benzenedicarboxylate Dibutyl 1,2-benzenedicarboxylic acid Dibutyl ester of 1,2-benzenedicarboxylic acid Dibutyl o-phthalate Dibutyl O-phthalic acid Dibutyl phthalate Dibutyl phthalated Dibutyl phthalic acid Dibutyl-1,2-benzenedicarboxylate Dibutyl-o-phthalate Dibutyl-O-phthalic acid Dibutyl-phthalate Dibutyll phthalate Dibutylphthatlate Elaol Ergoplast FDB Ersoplast fda Genoplast b Hatcol DBP Hexaplas m/b Kodaflex DBP Morflex 240 N-butyl phthalate N-Butyl phthalic acid N-butylphthalate O-Benzenedicarboxylate dibutyl ester O-Benzenedicarboxylic acid dibutyl ester O-benzenedicarboxylic acid, dibutyl ester Ortho-dibutyl phthalate Palatinol c Palatinol DBP Phthalate di-N-butyl ester Phthalate dibutyl ester Phthalate, butyl Phthalate, di-n-butyl Phthalate, dibutyl Phthalate, dibutyl- 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 C16H22O4 278.3435 278.151809192 1,2-dibutyl benzene-1,2-dicarboxylate dibutyl-phthalate 84-74-2 CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC 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 DOIRQSBPFJWKBE-UHFFFAOYSA-N belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Benzoic acid esters Organic compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Aromatic homomonocyclic compounds Benzoyl derivatives Carboxylic acid esters Dicarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Organooxygen compounds Aromatic homomonocyclic compound Benzoate ester Benzoyl Carboxylic acid derivative Carboxylic acid ester Dicarboxylic acid or derivatives Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Insect repellents Phthalates diester phthalate ester logp 4.53 ALOGPS logs -4.67 ALOGPS solubility 5.96e-03 g/l ALOGPS melting_point Mp ?35° logp 4.63 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac 1,2-dibutyl benzene-1,2-dicarboxylate ChemAxon average_mass 278.3435 ChemAxon mono_mass 278.151809192 ChemAxon smiles CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC ChemAxon formula C16H22O4 ChemAxon 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 ChemAxon inchikey DOIRQSBPFJWKBE-UHFFFAOYSA-N ChemAxon polar_surface_area 52.6 ChemAxon refractivity 77.86 ChemAxon polarizability 32.15 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 2672 Specdb::NmrOneD 3359 Specdb::EiMs 913 Specdb::CMs 10221 Specdb::CMs 27120 Specdb::CMs 27478 Specdb::CMs 28050 Specdb::CMs 28187 Specdb::CMs 29144 Specdb::CMs 101317 Specdb::CMs 101318 Specdb::CMs 101319 Specdb::CMs 101320 Specdb::CMs 101321 Specdb::CMs 148961 Specdb::MsMs 51882 Specdb::MsMs 51883 Specdb::MsMs 51884 Specdb::MsMs 119532 Specdb::MsMs 119533 Specdb::MsMs 119534 Specdb::MsMs 436806 Specdb::MsMs 436807 Specdb::MsMs 436808 Specdb::MsMs 436809 Specdb::MsMs 436810 Specdb::MsMs 436811 Specdb::MsMs 436812 Specdb::MsMs 436813 Specdb::MsMs 436814 Specdb::MsMs 444662 Specdb::MsMs 444663 Specdb::MsMs 444664 Specdb::MsMs 444665 Specdb::MsMs 444666 Specdb::MsMs 444667 Specdb::MsMs 444668 Specdb::MsMs 444669 Specdb::MsMs 444670 Specdb::MsMs 449139 HMDB33244 535597 #<Reference:0x000055ce31bc4b98> #<Reference:0x000055ce31bc49e0> #<Reference:0x000055ce31bc4828> #<Reference:0x000055ce31bc4670> #<Reference:0x000055ce31bc44b8> #<Reference:0x000055ce31bc4300> #<Reference:0x000055ce31bc4148> #<Reference:0x000055ce31bc3f40> #<Reference:0x000055ce31bc3d88> #<Reference:0x000055ce31bc3bd0> #<Reference:0x000055ce31bc3a18> #<Reference:0x000055ce31bc3860> #<Reference:0x000055ce31bc36a8> #<Reference:0x000055ce31bc34f0> #<Reference:0x000055ce31bc3338> Cloves Type 1 specific Syzygium aromaticum 219868 Kohlrabi Type 1 specific Brassica oleracea var. gongylodes 109379 0.152 0.152 0.152 mg/100 g faint