Benzyl butyl phthalate (CHEM000174)

Record Information
Version1.0
Creation Date2009-03-06 18:58:15 UTC
Update Date2026-08-20 02:58:32 UTC
Accession NumberCHEM000174
Identification
Common NameBenzyl butyl phthalate
ClassSmall Molecule
Description
Benzyl butyl phthalate (BBzP) is a phthalate ester mostly used as a plasticizer for PVC. Phthalate esters can cause reproductive and developmental toxicity. (1, 5)
Contaminant Sources
  • Clean Air Act Chemicals
  • EPA Endocrine Screening
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • My Exposome Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • Sludge Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Cosmetic Toxin
  • Ester
  • Ether
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Phthalate
  • Plasticizer
  • Pollutant
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Butyl phenylmethyl 1,2-benzenedicarboxylateKegg
Butyl phenylmethyl 1,2-benzenedicarboxylic acidGenerator
Benzyl butyl phthalic acidGenerator
BBPHTMeSH
Butyl benzyl phthalateMeSH
Butylbenzyl phthalateMeSH
Chemical FormulaC19H20O4
Average Molecular Mass312.360 g/mol
Monoisotopic Mass312.136 g/mol
CAS Registry Number85-68-7
IUPAC Name1-benzyl 2-butyl benzene-1,2-dicarboxylate
Traditional Namebenzyl butyl phthalate
SMILESCCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1
InChI IdentifierInChI=1S/C19H20O4/c1-2-3-13-22-18(20)16-11-7-8-12-17(16)19(21)23-14-15-9-5-4-6-10-15/h4-12H,2-3,13-14H2,1H3
InChI KeyIRIAEXORFWYRCZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzyloxycarbonyl
  • 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColourless oily liquid. (4)
Experimental Properties
PropertyValue
Melting Point< -35°C
Boiling Point370 °C
Solubility0.00269 mg/mL at 25 °C [HOWARD,PH et al. (1985)]
Predicted Properties
PropertyValueSource
Water Solubility0.003 g/LALOGPS
logP4.54ALOGPS
logP5.03ChemAxon
logS-5ALOGPS
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity88.59 m³·mol⁻¹ChemAxon
Polarizability33.87 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
Mechanism of ToxicityPhthalate 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)
MetabolismPhthalate 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 ValuesLD50: 3160 mg/kg (Intraperitoneal, Mouse) (4) LD50: 2330 mg/kg (Oral, Rat) (4) LD50: 4170 mg/kg (Oral, Mouse) (4)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (3)
Uses/SourcesBenzyl butyl phthalate (BBzP) is mostly used as a plasticizer for PVC. (5)
Minimum Risk LevelNot Available
Health EffectsPhthalate 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)
SymptomsPhthalate esters are endocrine disruptors and can cause a number of developmental malformations termed 'phthalate syndrome'. (1)
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0249068
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00040340
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBenzyl butyl phthalate
Chemspider ID2257
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDC14211
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References