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Showing Compound Diethyl malonate (FDB000728)

Record Information
Version1.0
Creation date2010-04-08 22:04:41 UTC
Update date2020-02-24 19:10:13 UTC
Primary IDFDB000728
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDiethyl malonate
DescriptionDiethyl malonate is a flavouring ingredient. It 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)-). Diethyl malonate is found in alcoholic beverages such as wines, and in fruits such as guava, melon, concord grape, pineapple, blackberry.
CAS Number105-53-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
Diethyl propanedioate, 9CIdb_source
Ethyl malonate (van)biospider
Malonate diethyl esterGenerator
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
Chemical FormulaC7H12O4
IUPAC name1,3-diethyl propanedioate
InChI IdentifierInChI=1S/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3
InChI KeyIYXGSMUGOJNHAZ-UHFFFAOYSA-N
Isomeric SMILESCCOC(=O)CC(=O)OCC
Average Molecular Weight160.1678
Monoisotopic Molecular Weight160.073558872
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 52.49%; H 7.55%; O 39.96%DFC
Melting PointMp -50°DFC
Boiling PointBp20 85°DFC
Experimental Water Solubility23.2 mg/mL at 37 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP0.96POMONA (1987)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 1.06DFC
Refractive Indexn20D 1.4143DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSDiethyl malonate, non-derivatized, GC-MS Spectrumsplash10-016u-9400000000-adc51f2543836992b5a7Spectrum
GC-MSDiethyl malonate, non-derivatized, GC-MS Spectrumsplash10-00pl-9100000000-686a923858ceb77f2ab3Spectrum
GC-MSDiethyl malonate, non-derivatized, GC-MS Spectrumsplash10-00ou-9300000000-baedf40984817543fb55Spectrum
GC-MSDiethyl malonate, non-derivatized, GC-MS Spectrumsplash10-00ou-9300000000-ca6a39f537696bdd1204Spectrum
GC-MSDiethyl malonate, non-derivatized, GC-MS Spectrumsplash10-017i-9800000000-b9f129ca3341a0dc4057Spectrum
GC-MSDiethyl malonate, non-derivatized, GC-MS Spectrumsplash10-016u-9400000000-adc51f2543836992b5a7Spectrum
GC-MSDiethyl malonate, non-derivatized, GC-MS Spectrumsplash10-00pl-9100000000-686a923858ceb77f2ab3Spectrum
GC-MSDiethyl malonate, non-derivatized, GC-MS Spectrumsplash10-00ou-9300000000-baedf40984817543fb55Spectrum
GC-MSDiethyl malonate, non-derivatized, GC-MS Spectrumsplash10-00ou-9300000000-ca6a39f537696bdd1204Spectrum
GC-MSDiethyl malonate, non-derivatized, GC-MS Spectrumsplash10-017i-9800000000-b9f129ca3341a0dc4057Spectrum
Predicted GC-MSDiethyl malonate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-9200000000-521aa9a304ed814bfb1dSpectrum
Predicted GC-MSDiethyl malonate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiethyl malonate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-f5ad3eda53f3b99fc2ed2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00kf-9700000000-ecca8ff833198def45b72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-016u-9300000000-2589b4ca78c97b95c1912021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2900000000-0dcf20fb7a7668f4991f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0292-9700000000-ebd4c59ff9ec0aa6674e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02g5-9000000000-c3d6ded5e3f0148b1eff2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-3900000000-cacc99a9a8f1cd4514462016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06rj-9500000000-78842db871bcfa2f28422016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-9000000000-bcad04b3aebdaff62cfb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-4900000000-7de68f92e6a8d0d22cab2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01w0-9200000000-2baec930662daf8d03902021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052e-9000000000-ce6ba549218977c8766c2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015i-4900000000-1e726b2f9dc40b5f16fc2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-9100000000-26d1b01554b94a4c765d2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006w-9000000000-f0bf526552ec6cd9298b2021-09-25View Spectrum
NMRNot Available
ChemSpider ID13863636
ChEMBL IDCHEMBL177114
KEGG Compound IDNot Available
Pubchem Compound ID7761
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29573
CRC / DFC (Dictionary of Food Compounds) IDBGJ46-J:BGJ46-J
EAFUS ID892
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID105-53-3
GoodScent IDrw1004331
SuperScent IDNot Available
Wikipedia IDDiethyl_malonate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
apple
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference