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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 19:02:35 UTC

Update Date

2023-02-21 17:24:04 UTC

HMDB ID

HMDB0034239

Secondary Accession Numbers

HMDB34239

Metabolite Identification

Common Name

2-Methylpropyl propanoate

Description

2-Methylpropyl propanoate belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). 2-Methylpropyl propanoate is a sweet, banana, and bitter tasting compound. 2-Methylpropyl propanoate has been detected, but not quantified in, apples (Malus pumila). This could make 2-methylpropyl propanoate a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on 2-Methylpropyl propanoate.

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 propanoic acid	Generator
2-Methyl-1-propyl propanoate	HMDB
2-Methylpropyl propionate	HMDB
Cyclopropyl methyl ether	HMDB
FEMA 2212	HMDB
iso-Butyl N-propionate	HMDB
Isobutyl ester OF propanoic acid	HMDB
Isobutyl propanoate	HMDB
Isobutyl propionate	HMDB
Propanoic acid, 2-methylpropyl ester	HMDB
Propionic acid, isobutyl ester	HMDB
2-Methylpropyl propionic acid	Generator

Chemical Formula

C₇H₁₄O₂

Average Molecular Weight

130.1849

Monoisotopic Molecular Weight

130.099379692

IUPAC Name

2-methylpropyl propanoate

Traditional Name

2-methylpropyl propanoate

CAS Registry Number

540-42-1

SMILES

CCC(=O)OCC(C)C

InChI Identifier

InChI=1S/C7H14O2/c1-4-7(8)9-5-6(2)3/h6H,4-5H2,1-3H3

InChI Key

FZXRXKLUIMKDEL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic acid esters

Alternative Parents

Substituents

Carboxylic acid ester
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Wax monoesters (LMFA07010567 )

Ontology

Feces (PMID: 23454028)

Cellular substructure

Extracellular (HMDB: HMDB0034239)
Cytoplasm (HMDB: HMDB0034239)

Source

Exogenous

Exogenous (HMDB: HMDB0034239)

Food

Food (HMDB: HMDB0034239)

Fruit

Pome

Apple (FooDB: FOOD00105)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0034239)

Biological role

Nutrient (HMDB: HMDB0034239)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-71.4 °C	Not Available
Boiling Point	66.00 to 67.00 °C. @ 60.00 mm Hg	The Good Scents Company Information System
Water Solubility	1700 mg/L @ 25 °C (exp)	The Good Scents Company Information System
LogP	2.158 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.88 g/L	ALOGPS
logP	2.22	ALOGPS
logP	1.87	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	35.78 m³·mol⁻¹	ChemAxon
Polarizability	15.2 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	129.693	31661259
DarkChem	[M-H]-	126.298	31661259
DeepCCS	[M+H]+	131.094	30932474
DeepCCS	[M-H]-	128.51	30932474
DeepCCS	[M-2H]-	164.7	30932474
DeepCCS	[M+Na]+	139.879	30932474
AllCCS	[M+H]+	131.5	32859911
AllCCS	[M+H-H2O]+	127.4	32859911
AllCCS	[M+NH4]+	135.2	32859911
AllCCS	[M+Na]+	136.3	32859911
AllCCS	[M-H]-	132.0	32859911
AllCCS	[M+Na-2H]-	135.0	32859911
AllCCS	[M+HCOO]-	138.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methylpropyl propanoate	CCC(=O)OCC(C)C	1106.5	Standard polar	33892256
2-Methylpropyl propanoate	CCC(=O)OCC(C)C	805.4	Standard non polar	33892256
2-Methylpropyl propanoate	CCC(=O)OCC(C)C	883.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl propanoate EI-B (Non-derivatized)	splash10-0a4i-9000000000-696dd19162629b887c12	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl propanoate EI-B (Non-derivatized)	splash10-0a4i-9000000000-60240572ee92c5e157f9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl propanoate CI-B (Non-derivatized)	splash10-004i-9000000000-919e44e8bde570c9ba0e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl propanoate EI-B (Non-derivatized)	splash10-0a4i-9000000000-3034700b4ba8624cd760	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl propanoate EI-B (Non-derivatized)	splash10-0a4i-9000000000-696dd19162629b887c12	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl propanoate EI-B (Non-derivatized)	splash10-0a4i-9000000000-60240572ee92c5e157f9	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl propanoate CI-B (Non-derivatized)	splash10-004i-9000000000-919e44e8bde570c9ba0e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylpropyl propanoate EI-B (Non-derivatized)	splash10-0a4i-9000000000-3034700b4ba8624cd760	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylpropyl propanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6u-9000000000-ea8a99fa44312b7cc64c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylpropyl propanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylpropyl propanoate 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 propanoate 10V, Positive-QTOF	splash10-0a59-9600000000-3b25b4f09cf40eed9357	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl propanoate 20V, Positive-QTOF	splash10-0a4i-9000000000-1c165d9546552ff9f8a3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl propanoate 40V, Positive-QTOF	splash10-0a4i-9000000000-73b39a61cc8e3c594389	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl propanoate 10V, Negative-QTOF	splash10-056r-9800000000-0eec3454d95650ea6d32	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl propanoate 20V, Negative-QTOF	splash10-0ab9-9100000000-3ded77d4692fd483785b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl propanoate 40V, Negative-QTOF	splash10-0a4i-9000000000-632e1d45ae9563abe080	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl propanoate 10V, Negative-QTOF	splash10-00di-9100000000-5d89adf9344596842edf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl propanoate 20V, Negative-QTOF	splash10-0ab9-9000000000-98485b6ecce02be4dbd5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl propanoate 40V, Negative-QTOF	splash10-00di-9000000000-0c1580c18c32502e0476	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl propanoate 10V, Positive-QTOF	splash10-0a4i-9000000000-9197744c071f933b9ea9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl propanoate 20V, Positive-QTOF	splash10-0a6r-9000000000-5381516b53cf0128a96a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylpropyl propanoate 40V, Positive-QTOF	splash10-052f-9000000000-8f43a64df7c0feefad6b	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23454028	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Diarrhea-predominant IBS	23516449	details

Associated Disorders and Diseases

Disease References

Nonalcoholic fatty liver disease
Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Diarrhoea predominant irritable bowel syndrome
Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012551

KNApSAcK ID

Not Available

Chemspider ID

10433

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10895

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1020241

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 propanoate (HMDB0034239)

MOL for HMDB0034239 (2-Methylpropyl propanoate)

3D MOL for HMDB0034239 (2-Methylpropyl propanoate)

3D SDF for HMDB0034239 (2-Methylpropyl propanoate)

3D-SDF for HMDB0034239 (2-Methylpropyl propanoate)

PDB for HMDB0034239 (2-Methylpropyl propanoate)

3D PDB for HMDB0034239 (2-Methylpropyl propanoate)

SMILES for HMDB0034239 (2-Methylpropyl propanoate)

INCHI for HMDB0034239 (2-Methylpropyl propanoate)

Structure for HMDB0034239 (2-Methylpropyl propanoate)

3D Structure for HMDB0034239 (2-Methylpropyl propanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra