Record Information
Version1.0
Creation date2011-09-26 22:55:59 UTC
Update date2015-07-21 07:00:55 UTC
Primary IDFDB029757
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namehydroxy-butanedioic acid
DescriptionFlavouring compound [Flavornet]
CAS Number7554-12-3
Structure
Thumb
Synonyms
SynonymSource
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
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC8H14O5
IUPAC name1,4-diethyl 2-hydroxybutanedioate
InChI IdentifierInChI=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
Isomeric SMILESCCOC(=O)CC(O)C(=O)OCC
Average Molecular Weight190.1938
Monoisotopic Molecular Weight190.084123558
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00vl-9200000000-0e2b63fa1358ecc4727dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00vl-9200000000-0e2b63fa1358ecc4727dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-9800000000-c3cb88ecf650c67efe5eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-8920000000-732bc15836f011a383a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-1900000000-815e69499173edb4db80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-9800000000-b787dba980fd1db16e61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9200000000-4e46a07b9fd73378c9caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-3900000000-f255ae39fead1d6d56ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0075-9800000000-916e9fe90e1aecbe634dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dv-9100000000-c36e5fae8fc58b06cf20View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet ID7554-12-3
GoodScent IDrw1421041
SuperScent IDNot Available
Wikipedia IDNot Available
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
brown sugar
  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
sweet
  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.
brown
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
wine
  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.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sugar
  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