MiMeDB: Showing metabocard for Diethyl malonate (MMDBc0033622)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:56:18 UTC

Update Date

2024-04-30 20:13:52 UTC

Metabolite ID

MMDBc0033622

Metabolite Identification

Common Name

Diethyl malonate

Description

Diethyl 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
Diethyl malonic acid	Generator
Carbethoxyacetic ester	HMDB
Dicarbethoxymethane	HMDB
Diethyl propanedioate	HMDB
Diethyl propanedioate, 9ci	HMDB
Ethyl malonate	HMDB
Ethyl methanedicarboxylate	HMDB
Ethyl propanedioate	HMDB
FEMA 2375	HMDB
Malonic acid diethyl ester	HMDB
Malonic acid, diethyl ester	HMDB
Malonic ester	HMDB
Methanedicarboxylic acid, diethyl ester	HMDB
Propanedioic acid, 1,3-diethyl ester	HMDB
Propanedioic acid, diethyl ester	HMDB
1,3-Diethyl propanedioic acid	Generator
Diethyl malonate	MeSH
Diethylmalonate	MeSH

Molecular Formula

C₇H₁₂O₄

Average Mass

160.1678

Monoisotopic Mass

160.073558872

IUPAC Name

1,3-diethyl propanedioate

Traditional Name

diethyl malonate

CAS Registry Number

105-53-3

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 Key

IYXGSMUGOJNHAZ-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic 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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Liquid

Predicted Properties

Property	Value	Source
Water Solubility	24.4 g/L	ALOGPS
logP	0.93	ALOGPS
logP	0.67	ChemAxon
logS	-0.82	ALOGPS
pKa (Strongest Acidic)	12.36	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	38.02 m³·mol⁻¹	ChemAxon
Polarizability	15.95 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-016u-9400000000-adc51f2543836992b5a7	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00pl-9100000000-686a923858ceb77f2ab3	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00ou-9300000000-baedf40984817543fb55	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00ou-9300000000-ca6a39f537696bdd1204	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-017i-9800000000-b9f129ca3341a0dc4057	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-016u-9400000000-adc51f2543836992b5a7	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00pl-9100000000-686a923858ceb77f2ab3	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00ou-9300000000-baedf40984817543fb55	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00ou-9300000000-ca6a39f537696bdd1204	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-017i-9800000000-b9f129ca3341a0dc4057	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9200000000-521aa9a304ed814bfb1d	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-f5ad3eda53f3b99fc2ed	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00kf-9700000000-ecca8ff833198def45b7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-016u-9300000000-2589b4ca78c97b95c191	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-2900000000-0dcf20fb7a7668f4991f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0292-9700000000-ebd4c59ff9ec0aa6674e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02g5-9000000000-c3d6ded5e3f0148b1eff	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-3900000000-cacc99a9a8f1cd451446	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06rj-9500000000-78842db871bcfa2f2842	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052g-9000000000-bcad04b3aebdaff62cfb	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-4900000000-7de68f92e6a8d0d22cab	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01w0-9200000000-2baec930662daf8d0390	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052e-9000000000-ce6ba549218977c8766c	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-015i-4900000000-1e726b2f9dc40b5f16fc	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0007-9100000000-26d1b01554b94a4c765d	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006w-9000000000-f0bf526552ec6cd9298b	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, experimental)		2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)		2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Juice	Rubus	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0029573

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000728

KNApSAcK ID

Not Available

Chemspider ID

13863636

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diethyl malonate

METLIN ID

Not Available

PubChem Compound

7761

PDB ID

Not Available

ChEBI ID

391281

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1139/m86-050. [PubMed:3011233 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for Diethyl malonate (MMDBc0033622)

MOL for #<Metabolite:0x0000564af3bb00a0>

3D MOL for #<Metabolite:0x0000564af3bb00a0>

3D SDF for #<Metabolite:0x0000564af3bb00a0>

3D-SDF for #<Metabolite:0x0000564af3bb00a0>

PDB for #<Metabolite:0x0000564af3bb00a0>

3D PDB for #<Metabolite:0x0000564af3bb00a0>

SMILES for #<Metabolite:0x0000564af3bb00a0>

INCHI for #<Metabolite:0x0000564af3bb00a0>

Structure for #<Metabolite:0x0000564af3bb00a0>

3D Structure for #<Metabolite:0x0000564af3bb00a0>