You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:45:27 UTC
Update Date2021-09-14 15:47:15 UTC
HMDB IDHMDB0040220
Secondary Accession Numbers
  • HMDB40220
Metabolite Identification
Common NameDiethyl L-malate
DescriptionDiethyl L-malate belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Diethyl L-malate is an extremely weak basic (essentially neutral) compound (based on its pKa). A malate ester obtained by the formal condensation of the two carboxy groups of malic acid with two molecules of ethanol respectively.
Structure
Data?1563863508
Synonyms
ValueSource
Diethyl L-malic acidGenerator
Butanedioic acid, 2-hydroxy-, 1,4-diethyl esterHMDB
Butanedioic acid, hydroxy-, diethyl esterHMDB
Diethyl (1)-malateHMDB
Diethyl hydroxybutanedioateHMDB
Diethyl hydroxybutanoateHMDB
Diethyl malateHMDB
Ethyl DL-malateHMDB
Ethyl malateHMDB
Ethyl-DL-malateHMDB
Hydroxy-diethyl ester(.+/-.)-butanedioic acidHMDB
L-(-)-Malic acid diethyl esterHMDB
Malic acid, diethyl esterHMDB
Diethyl malate, (R)-isomerHMDB
Diethyl malate, (+-)-isomerHMDB
Diethyl malate, (S)-isomerHMDB
Diethyl malic acidGenerator
Chemical FormulaC8H14O5
Average Molecular Weight190.1938
Monoisotopic Molecular Weight190.084123558
IUPAC Name1,4-diethyl 2-hydroxybutanedioate
Traditional Name1,4-diethyl 2-hydroxybutanedioate
CAS Registry Number7554-28-1
SMILES
CCOC(=O)CC(O)C(=O)OCC
InChI Identifier
InChI=1S/C8H14O5/c1-3-12-7(10)5-6(9)8(11)13-4-2/h6,9H,3-5H2,1-2H3
InChI KeyVKNUORWMCINMRB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility96.5 g/LALOGPS
logP0.34ALOGPS
logP-0.11ChemAxon
logS-0.29ALOGPS
pKa (Strongest Acidic)12.44ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity43.91 m³·mol⁻¹ChemAxon
Polarizability18.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00vl-9200000000-0e2b63fa1358ecc4727d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00vl-9200000000-0e2b63fa1358ecc4727d2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-9800000000-c3cb88ecf650c67efe5e2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-8920000000-732bc15836f011a383a32017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0101-9600000000-9430bba755197c69b92e2021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-1900000000-815e69499173edb4db802016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-9800000000-b787dba980fd1db16e612016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9200000000-4e46a07b9fd73378c9ca2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-3900000000-f255ae39fead1d6d56dd2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0075-9800000000-916e9fe90e1aecbe634d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dv-9100000000-c36e5fae8fc58b06cf202016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-3900000000-349bf26b0d73cd973a8c2021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fv-9400000000-2464ee9878c2e2c698a02021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0076-9000000000-888ebde00273a66ebeb02021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-3900000000-8c2cbe244fa84072171c2021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fxt-8900000000-7b232d5d7b06aaf439bb2021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006w-9100000000-a25e4bfa8d5a0b9203da2021-09-09View Spectrum
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 IDFDB019933
KNApSAcK IDNot Available
Chemspider ID22619
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24197
PDB IDNot Available
ChEBI ID87368
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .