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Showing NP-Card for Diethyl malonate (NP0001248)

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Record Information
Version2.0
Created at2012-09-11 17:31:13 UTC
Updated at2024-09-03 04:22:06 UTC
NP-MRD IDNP0001248
Natural Product DOIhttps://doi.org/10.57994/2742
Secondary Accession NumbersNone
Natural Product 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 a sweet, apple, and fruity tasting compound. Diethyl malonate has been detected, but not quantified, in a few different foods, such as alcoholic beverages, evergreen blackberries, and fruits. Like other esters, this compound can undergo 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 the two 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 that proton. Like many other esters, this compound can undergo the Claisen ester condensation. This alkylated 1,3-dicarbonyl compound (3) readily undergoes decarboxylation with loss of carbon dioxide, to give a substituted acetic acid, using Sodium ethoxide as the preferred base. The use of aqueous sodium hydroxide may give the base hydrolysis products: Sodium malonate and ethanol.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0001248 (Diethyl malonate)


  Mrv1652305271900092D          

 11 10  0  0  0  0            999 V2000
   -2.1771    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0949    0.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4376    1.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6981    0.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4376   -0.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1771    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0415    1.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6981    0.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6981    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407   -0.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407   -1.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
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3D MOL for NP0001248 (Diethyl malonate)

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3D SDF for NP0001248 (Diethyl malonate)

  Mrv1652305271900092D          

 11 10  0  0  0  0            999 V2000
   -2.1771    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0949    0.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4376    1.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6981    0.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4376   -0.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1771    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0415    1.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6981    0.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6981    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407   -0.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407   -1.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001248

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
IYXGSMUGOJNHAZ-UHFFFAOYSA-N

> <FORMULA>
C7H12O4

> <MOLECULAR_WEIGHT>
160.1678

> <EXACT_MASS>
160.073558872

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
15.951087561820216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-diethyl propanedioate

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
0.6742867529999996

> <ALOGPS_LOGS>
-0.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.359424246273893

> <JCHEM_PKA_STRONGEST_BASIC>
-6.846154885175358

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
38.02320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.44e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diethyl malonate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0001248 (Diethyl malonate)
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PDB for NP0001248 (Diethyl malonate)
HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -4.064   0.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.910   1.533   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.684   2.300   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.303   0.001   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.684  -0.766   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.064   0.001   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.077   2.300   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.303   1.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.303   0.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.076  -0.766   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.076  -2.300   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    8                                                       
CONECT    4    5   10                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    8                                                            
CONECT    8    3    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    4    9   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0001248 (Diethyl malonate)
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SMILES for NP0001248 (Diethyl malonate)
CCOC(=O)CC(=O)OCC
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INCHI for NP0001248 (Diethyl malonate)
InChI=1S/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3
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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 Mass160.1678 Da
Monoisotopic Mass160.07356 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
Species
Species of Origin
  • Animalia
  •  Plantae
    • 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
    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
    HMDB IDHMDB0029573  
    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  
    Good Scents IDNot Available
    References
    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.. .