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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:13 UTC
Update Date2020-02-26 21:43:57 UTC
HMDB IDHMDB0029573
Secondary Accession Numbers
  • HMDB29573
Metabolite Identification
Common NameDiethyl malonate
DescriptionDiethyl malonate, also known as dicarbethoxymethane or ethyl propanedioate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Diethyl malonate is an extremely weak basic (essentially neutral) compound (based on its pKa). Diethyl malonate is a sweet, apple, and fruity tasting compound. Outside of the human body, Diethyl malonate has been detected, but not quantified in, a few different foods, such as alcoholic beverages, evergreen blackberries, and fruits. This could make diethyl malonate a potential biomarker for the consumption of these foods. Like other esters, this compound undergoes bromination at the alpha position. Fischer esterification gives diethyl malonate:One of the principal uses of this compound is in the malonic ester synthesis. It occurs naturally in grapes and strawberries as a colourless liquid with an apple-like odour, and is used in perfumes. Malonic acid is a rather simple dicarboxylic acid, with two the carboxyl groups close together. The hydrogen atoms on a carbon adjacent to two carbonyl groups are even more acidic because the carbonyl groups help stabilize the carbanion resulting from the removal of a proton from the methylene group between them. Like many other esters, this compound undergoes the Claisen ester condensations. This alkylated 1,3-dicarbonyl compound (3) readily undergoes decarboxylation with loss of carbon dioxide, to give a substituted acetic acid (4):Sodium ethoxide is preferred as the base. The use of aqueous sodium hydroxide may give the base hydrolysis products: sodium malonate and ethanol.
Structure
Data?1582753437
Synonyms
ValueSource
Diethyl malonic acidGenerator
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
1,3-Diethyl propanedioic acidGenerator
Diethyl malonateMeSH
DiethylmalonateMeSH
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
Description 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
  • Organic oxygen compound
  • Organic oxide
  • 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
Polarizability15.95 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-016u-9400000000-adc51f2543836992b5a7Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00pl-9100000000-686a923858ceb77f2ab3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00ou-9300000000-baedf40984817543fb55Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00ou-9300000000-ca6a39f537696bdd1204Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-017i-9800000000-b9f129ca3341a0dc4057Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-016u-9400000000-adc51f2543836992b5a7Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00pl-9100000000-686a923858ceb77f2ab3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00ou-9300000000-baedf40984817543fb55Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00ou-9300000000-ca6a39f537696bdd1204Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-017i-9800000000-b9f129ca3341a0dc4057Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9200000000-521aa9a304ed814bfb1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2900000000-0dcf20fb7a7668f4991fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0292-9700000000-ebd4c59ff9ec0aa6674eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02g5-9000000000-c3d6ded5e3f0148b1effSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-3900000000-cacc99a9a8f1cd451446Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06rj-9500000000-78842db871bcfa2f2842Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-9000000000-bcad04b3aebdaff62cfbSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
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.. .