1-Butyl 2-methyl 1,2-benzenedicarboxylate
Basic information
- CAS
34006-76-3- Standard SMILES
CCCCOC(=O)c1ccccc1C(=O)OC- InChIKey
XXFSYINDUHLBIL-UHFFFAOYSA-N- Molecular formula
- C13H16O4
- Average molar mass
- 236.26 g/mol
- Monoisotopic mass
- 236.10485899
Overview
Bis(2-methoxyethyl) phthalate (DMEP) is a specialty plasticiser, used in cellulose ester plastics, and can also be used as a solvent. This compound can form peroxides. (L1210)
Names & identifiers
- Preferred name
- 1-Butyl 2-methyl 1,2-benzenedicarboxylate
- IUPAC
- 2-O-butyl 1-O-methyl benzene-1,2-dicarboxylate
- English name
- DMEP
- Molecular formula
- C13H16O4
- Molecular weight
- 236.26
Names & synonyms
BUTYL METHYL PHTHALATE34006-76-3DTXSID7074325RefChem:1055158DTXCID30387771-Butyl 2-methyl 1,2-benzenedicarboxylateMethyl butyl phthalate2-O-butyl 1-O-methyl benzene-1,2-dicarboxylatePhthalic acid, butyl methyl ester1,2-Benzenedicarboxylic acid, butyl methyl esterAI3-033421-butyl 2-methyl benzene-1,2-dicarboxylate
Show more names
DmepPhthalic acid 1-butyl 2-methyl ester1,2-Benzenedicarboxylic acid, 1-butyl 2-methyl ester
1-Butyl 2-methyl phthalate #SCHEMBL6057141XXFSYINDUHLBIL-UHFFFAOYSA-NAKOS007848104Butyl methyl benzene-1,2-dicarboxylateEBC-618318NS000963721,2-BENZENEDICARBOXYLIC ACID BUTYL METHYLESTER
Database identifiers
- CAS
34006-76-3- PubChem CID
- 36655
- DTXSID
DTXSID7074325- Nikkaji
- J46.700F
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 52.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 7
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 262
Experimental & physicochemical properties
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Boiling point
- 384.9 °C · 384.9°C (rough estimate)
- Density
- 1.264 · 1.2640 (rough estimate)
- refractive index
- 1.4795 · 1.4795 (estimate)
- Water Solubility
- 8.43 g/L · 8.43g/L(20 ºC)
- EPA Substance Registry System
- Butyl methyl phthalate (34006-76-3)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
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’. (A2883)
Exposure RoutesOral (L1903) ; inhalation (L1903) ; dermal (L1903)
Toxicity Summary
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. (A2883)
Signs and SymptomsPhthalate esters are endocrine disruptors and can cause a number of developmental malformations termed 'phthalate syndrome'. (A2883)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Chemistry & industry
Pharmacology
Metabolism/Metabolites
In pregnant rat, DMEP rapidly undergoes hydrolysis to 2-methoxyethanol (2-ME) and mono-2-methoxyethyl phthalate (MMEP). 2-ME is then oxidised to methoxyacetic acid (MAA). The rat foetus has little or no ability to hydrolyse DMEP to the monoester and intact DMEP is rapidly transferred across the placenta into the foetus. (L1210)
Uses & manufacturing
UsesBis(2-methoxyethyl) phthalate (DMEP) is a specialty plasticizer, used in cellulose ester plastics, and can also be used as a solvent. (L1210)
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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