2,5-Pyridinedicarboxylic acid, dipropyl ester (CHEM002747)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (8)XML
Record Information
Version1.0
Creation Date2013-04-25 07:28:09 UTC
Update Date2026-03-27 00:29:33 UTC
Accession NumberCHEM002747
Identification
Common Name2,5-Pyridinedicarboxylic acid, dipropyl ester
ClassSmall Molecule
Description2,5-Pyridinedicarboxylic acid, dipropyl ester is also known as Repellent MGK 326. It was initially registered by the USDA in 1957 as an insect repellent for livestock. MGK Repellent 326 works to broaden the spectrum of repellency of insect repellents, such as DEET (N,N-diethyl-m-toluamide) or pyrethrins, to repel flies, gnats, and other flying and biting insects. It functions as an insect attractant, an insect repellent and chemosterilant. It is still widely used as an insect repellent.
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Ether
  • Household Toxin
  • Lachrymator
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,5-Pyridinedicarboxylate, dipropyl esterGenerator
Chemical FormulaC13H17NO4
Average Molecular Mass251.278 g/mol
Monoisotopic Mass251.116 g/mol
CAS Registry Number136-45-8
IUPAC Name2,5-dipropyl pyridine-2,5-dicarboxylate
Traditional Name2,5-dipropyl pyridine-2,5-dicarboxylate
SMILESCCCOC(=O)C1=CC=C(N=C1)C(=O)OCCC
InChI IdentifierInChI=1S/C13H17NO4/c1-3-7-17-12(15)10-5-6-11(14-9-10)13(16)18-8-4-2/h5-6,9H,3-4,7-8H2,1-2H3
InChI KeyIITCWRFYJWUUPC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic acids
Alternative Parents
Substituents
  • Pyridine carboxylic acid
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling Point278 °C
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.85 g/LALOGPS
logP2.61ALOGPS
logP2.71ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)0.31ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area65.49 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity66.12 m³·mol⁻¹ChemAxon
Polarizability27.17 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udl-3590000000-335283d5c3f5b46e5b58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-8920000000-9f595dfb716e05fd030aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9400000000-3c3114ef191182e79d27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-1890000000-a12c2b09a85d2b9d46c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-1950000000-5fc268f83e9ea6969bebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xr-3900000000-af8fe618b77fd3075e61Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureDermal
Mechanism of ToxicityNot known.
MetabolismRapidly hydrolyzed to 2,5-pyridinedicarboxylic acid.
Toxicity ValuesLD50: 5230 mg/kg (Oral, Rat) LD50 9500 mg/kg (Dermal, Rat)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC. The EPA classifies it as a Tentative Class B Carcinogen.
Uses/SourcesInsect repellent, found in many commercial insect repellents and mosquito sprays.
Minimum Risk LevelNot Available
Health EffectsMay cause respiratory tract irritation and skin irritation. May also cause eye irritation. Harmful if swallowed. Rats tolerated MGK-326 in the diet for two years up to 100 mg/kg/day. MGK-326 increased the incidence of liver tumors (males and females) in the 100 mg/kg/day group. The tumor rates in both sexes in the 65 and 250 mg/kg/day groups were comparable to those of the control group. The insect repellent produced increases in the incidence of benign interstitial cell tumors in the testis and benign uterine tumors. Group mean body weights were significantly decreased for males and females at the 1000 mg/kg/day dosage level when compared to the controls. There was no observed teratogenicity.
SymptomsNot Available
TreatmentEYES: Hold eye open and rinse slowly and gently with water for 15-20 minutes. Remove contact lenses, if present, after the first 5 minutes, then continue rinsing eye. Call a poison control center or doctor for treatment advice. SKIN: Take off contaminated clothing. Rinse skin immediately with plenty of water for 15-20 minutes. Call a poison control center or doctor for treatment advice. INHALATION: Move person to fresh air. If person is not breathing, call 911 or an ambulance, then give artificial respiration, preferably by mouth-to-mouth if possible. Call a poison control center or doctor for further treatment advice. INGESTION: Call a poison control center or doctor immediately for treatment advice. Have person sip a glass of water if able to swallow. Do not induce vomiting unless told to do so by a physicican or poison control centre.
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID8693
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available