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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:13 UTC
Update Date2019-01-11 19:38:22 UTC
HMDB IDHMDB0029573
Secondary Accession Numbers
  • HMDB29573
Metabolite Identification
Common NameDiethyl malonate
DescriptionDiethyl malonate is found in alcoholic beverages. Diethyl malonate is a flavour ingredient. Diethyl malonate is present in guava fruit, melon, concord grape, pineapple, blackberry and many wines and spirits Malonic acid is a rather simple dicarboxylic acid, with two carboxyl groups close together in its molecule. In forming diethyl malonate from malonic acid, the hydroxyl group (-OH) on both of the carboxyl groups is replaced by an ethoxy group (-OEt; -OCH2CH3). The methylene group (-CH2-) in the middle of the malonic part of the diethyl malonate molecule is neighboured by two carbonyl groups (-C(=O)-)
Structure
Data?1547235502
Synonyms
ValueSource
Carbethoxyacetic esterHMDB
DicarbethoxymethaneHMDB
Diethyl propanedioateHMDB
Diethyl propanedioate, 9ciHMDB
Ethyl malonateHMDB
Ethyl methanedicarboxylateHMDB
Ethyl propanedioateHMDB
FEMA 2375HMDB
Malonic acid diethyl esterHMDB
Malonic acid, diethyl esterHMDB
Malonic esterHMDB
Methanedicarboxylic acid, diethyl esterHMDB
Propanedioic acid, 1,3-diethyl esterHMDB
Propanedioic acid, diethyl esterHMDB
Chemical FormulaC7H12O4
Average Molecular Weight160.1678
Monoisotopic Molecular Weight160.073558872
IUPAC Name1,3-diethyl propanedioate
Traditional Namediethyl malonate
CAS Registry Number105-53-3
SMILES
CCOC(=O)CC(=O)OCC
InChI Identifier
InChI=1S/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3
InChI KeyIYXGSMUGOJNHAZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • 1,3-dicarbonyl compound
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-50 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility23.2 mg/mL at 37 °CNot Available
LogP0.96Not Available
Predicted Properties
PropertyValueSource
Water Solubility24.4 g/LALOGPS
logP0.93ALOGPS
logP0.67ChemAxon
logS-0.82ALOGPS
pKa (Strongest Acidic)12.36ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity38.02 m³·mol⁻¹ChemAxon
Polarizability15.94 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-016u-9400000000-adc51f2543836992b5a7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00pl-9100000000-686a923858ceb77f2ab3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00ou-9300000000-baedf40984817543fb55JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00ou-9300000000-ca6a39f537696bdd1204JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-017i-9800000000-b9f129ca3341a0dc4057JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-016u-9400000000-adc51f2543836992b5a7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00pl-9100000000-686a923858ceb77f2ab3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00ou-9300000000-baedf40984817543fb55JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00ou-9300000000-ca6a39f537696bdd1204JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-017i-9800000000-b9f129ca3341a0dc4057JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9200000000-521aa9a304ed814bfb1dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2900000000-0dcf20fb7a7668f4991fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0292-9700000000-ebd4c59ff9ec0aa6674eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02g5-9000000000-c3d6ded5e3f0148b1effJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-3900000000-cacc99a9a8f1cd451446JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06rj-9500000000-78842db871bcfa2f2842JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-9000000000-bcad04b3aebdaff62cfbJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000728
KNApSAcK IDNot Available
Chemspider ID13863636
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiethyl malonate
METLIN IDNot Available
PubChem Compound7761
PDB IDNot Available
ChEBI ID391281
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chevanet C, Besson F, Michel G: Effect of various growth conditions on spore formation and bacillomycin L production in Bacillus subtilis. Can J Microbiol. 1986 Mar;32(3):254-8. [PubMed:3011233 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .