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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:31:52 UTC

Update Date

2023-02-21 17:25:21 UTC

HMDB ID

HMDB0036395

Secondary Accession Numbers

HMDB36395

Metabolite Identification

Common Name

2-Methylpropyl 3-oxobutanoate

Description

2-Methylpropyl 3-oxobutanoate belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom. 2-Methylpropyl 3-oxobutanoate is a sweet, brandy, and fruity tasting compound. Based on a literature review very few articles have been published on 2-Methylpropyl 3-oxobutanoate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Methylpropyl 3-oxobutanoic acid	Generator
Acetoacetic acid, isobutyl ester	HMDB
ACIB	HMDB
Butanoic acid, 3-oxo-, 2-methylpropyl ester	HMDB
FEMA 2177	HMDB
Isobutyl 3-oxobutanoate	HMDB
Isobutyl acetoacetate	HMDB

Chemical Formula

C₈H₁₄O₃

Average Molecular Weight

158.195

Monoisotopic Molecular Weight

158.094294314

IUPAC Name

2-methylpropyl 3-oxobutanoate

Traditional Name

2-methylpropyl 3-oxobutanoate

CAS Registry Number

7779-75-1

SMILES

CC(C)COC(=O)CC(C)=O

InChI Identifier

InChI=1S/C8H14O3/c1-6(2)5-11-8(10)4-7(3)9/h6H,4-5H2,1-3H3

InChI Key

ZYXNLVMBIHVDRH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Beta-keto acids and derivatives

Direct Parent

Beta-keto acids and derivatives

Alternative Parents

Substituents

Fatty acid ester
Beta-keto acid
Fatty acyl
1,3-dicarbonyl compound
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Exogenous (HMDB: HMDB0036395)

Food

Food (HMDB: HMDB0036395)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036395)

Biological role

Nutrient (HMDB: HMDB0036395)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	196.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	17420 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.230 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.22 g/L	ALOGPS
logP	0.99	ALOGPS
logP	1.39	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	9.93	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	41.05 m³·mol⁻¹	ChemAxon
Polarizability	17.05 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.159	31661259
DarkChem	[M-H]-	133.118	31661259
DeepCCS	[M+H]+	139.798	30932474
DeepCCS	[M-H]-	136.762	30932474
DeepCCS	[M-2H]-	173.748	30932474
DeepCCS	[M+Na]+	148.765	30932474
AllCCS	[M+H]+	136.4	32859911
AllCCS	[M+H-H2O]+	132.6	32859911
AllCCS	[M+NH4]+	140.0	32859911
AllCCS	[M+Na]+	141.0	32859911
AllCCS	[M-H]-	136.8	32859911
AllCCS	[M+Na-2H]-	138.9	32859911
AllCCS	[M+HCOO]-	141.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methylpropyl 3-oxobutanoate	CC(C)COC(=O)CC(C)=O	1567.2	Standard polar	33892256
2-Methylpropyl 3-oxobutanoate	CC(C)COC(=O)CC(C)=O	1041.2	Standard non polar	33892256
2-Methylpropyl 3-oxobutanoate	CC(C)COC(=O)CC(C)=O	1106.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Methylpropyl 3-oxobutanoate,1TMS,isomer #1	CC(=CC(=O)OCC(C)C)O[Si](C)(C)C	1300.0	Semi standard non polar	33892256
2-Methylpropyl 3-oxobutanoate,1TMS,isomer #1	CC(=CC(=O)OCC(C)C)O[Si](C)(C)C	1277.7	Standard non polar	33892256
2-Methylpropyl 3-oxobutanoate,1TMS,isomer #2	C=C(CC(=O)OCC(C)C)O[Si](C)(C)C	1253.9	Semi standard non polar	33892256
2-Methylpropyl 3-oxobutanoate,1TMS,isomer #2	C=C(CC(=O)OCC(C)C)O[Si](C)(C)C	1264.6	Standard non polar	33892256
2-Methylpropyl 3-oxobutanoate,1TBDMS,isomer #1	CC(=CC(=O)OCC(C)C)O[Si](C)(C)C(C)(C)C	1505.5	Semi standard non polar	33892256
2-Methylpropyl 3-oxobutanoate,1TBDMS,isomer #1	CC(=CC(=O)OCC(C)C)O[Si](C)(C)C(C)(C)C	1482.0	Standard non polar	33892256
2-Methylpropyl 3-oxobutanoate,1TBDMS,isomer #2	C=C(CC(=O)OCC(C)C)O[Si](C)(C)C(C)(C)C	1450.7	Semi standard non polar	33892256
2-Methylpropyl 3-oxobutanoate,1TBDMS,isomer #2	C=C(CC(=O)OCC(C)C)O[Si](C)(C)C(C)(C)C	1466.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylpropyl 3-oxobutanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-1651f073cbf032c123e0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylpropyl 3-oxobutanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 10V, Positive-QTOF	splash10-0a4i-8900000000-8d22b72300ba62429628	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 20V, Positive-QTOF	splash10-0a4i-9100000000-b13aadf248760f14a6e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 40V, Positive-QTOF	splash10-0a4i-9000000000-7d24f841eadc50502513	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 10V, Negative-QTOF	splash10-0a59-8900000000-9554d900bd23e9773f18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 20V, Negative-QTOF	splash10-0a59-9400000000-650e600e3fa08377b358	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 40V, Negative-QTOF	splash10-0a59-9000000000-1074f050fca1907fe572	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 10V, Negative-QTOF	splash10-00di-9000000000-81b42c092cc1bf1cb6b4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 20V, Negative-QTOF	splash10-0019-9700000000-ac055b724e00ec103cdb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 40V, Negative-QTOF	splash10-0ab9-9000000000-bb05d98696f3549681e6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 10V, Positive-QTOF	splash10-0a4l-9000000000-6bbd0e2dce65753bcf73	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 20V, Positive-QTOF	splash10-052f-9000000000-04e5c133e269bb729595	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 40V, Positive-QTOF	splash10-052f-9000000000-d3bf30a1e3e6f9aadf5c	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015274

KNApSAcK ID

Not Available

Chemspider ID

21105926

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

522677

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1013091

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-Methylpropyl 3-oxobutanoate (HMDB0036395)

MOL for HMDB0036395 (2-Methylpropyl 3-oxobutanoate)

3D MOL for HMDB0036395 (2-Methylpropyl 3-oxobutanoate)

3D SDF for HMDB0036395 (2-Methylpropyl 3-oxobutanoate)

3D-SDF for HMDB0036395 (2-Methylpropyl 3-oxobutanoate)

PDB for HMDB0036395 (2-Methylpropyl 3-oxobutanoate)

3D PDB for HMDB0036395 (2-Methylpropyl 3-oxobutanoate)

SMILES for HMDB0036395 (2-Methylpropyl 3-oxobutanoate)

INCHI for HMDB0036395 (2-Methylpropyl 3-oxobutanoate)

Structure for HMDB0036395 (2-Methylpropyl 3-oxobutanoate)

3D Structure for HMDB0036395 (2-Methylpropyl 3-oxobutanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra