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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:41:52 UTC

Update Date

2023-02-21 17:20:12 UTC

HMDB ID

HMDB0031249

Secondary Accession Numbers

HMDB31249

Metabolite Identification

Common Name

Methyl isobutyrate

Description

Methyl isobutyrate, also known as fema 2694, belongs to the class of organic compounds known as methyl esters. These are organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=H or organyl group and R'=methyl group. Methyl isobutyrate is an organic compound with the formula CH3O2CCH(CH3)2. Methyl isobutyrate is an apple, floral, and flower tasting compound. methyl isobutyrate has been detected, but not quantified, in several different foods, such as fruits, herbs and spices, pineapples, pomes, and potato. This could make methyl isobutyrate a potential biomarker for the consumption of these foods.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Methyl isobutyric acid	Generator
Methyl 2-methylpropanoate	MeSH
2-Methyl-propanoic acid, methyl ester	HMDB
FEMA 2694	HMDB
Isobutyric acid methyl ester	HMDB
Methyl 2-methylpropionate	HMDB
Methyl isobutanoate	HMDB
Propanoic acid, 2-methyl-, methyl ester	HMDB

Chemical Formula

C₅H₁₀O₂

Average Molecular Weight

102.1317

Monoisotopic Molecular Weight

102.068079564

IUPAC Name

methyl 2-methylpropanoate

Traditional Name

methyl isobutyrate

CAS Registry Number

547-63-7

SMILES

COC(=O)C(C)C

InChI Identifier

InChI=1S/C5H10O2/c1-4(2)5(6)7-3/h4H,1-3H3

InChI Key

BHIWKHZACMWKOJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methyl esters. These are organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=H or organyl group and R'=methyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Methyl esters

Alternative Parents

Substituents

Methyl 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

fatty acid methyl ester (CHEBI:73689 )

Ontology

Feces (PMID: 17314143)

Cellular substructure

Extracellular (HMDB: HMDB0031249)
Cytoplasm (HMDB: HMDB0031249)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031249)

Source

Endogenous

Endogenous (HMDB: HMDB0031249)

Plant

Plant (HMDB: HMDB0031249)

Exogenous

Food

Food (HMDB: HMDB0031249)

Fruit

Tropical fruit

Pineapple (FooDB: FOOD00012)

Berry

Pome

Pomes (FooDB: FOOD00856)

Fruits (FooDB: FOOD00871)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0031249)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031249)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-84.7 °C	Not Available
Boiling Point	91.00 to 93.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	9268 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.139 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	34.6 g/L	ALOGPS
logP	1.2	ALOGPS
logP	1.17	ChemAxon
logS	-0.47	ALOGPS
pKa (Strongest Basic)	-7.1	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	2	ChemAxon
Refractivity	26.61 m³·mol⁻¹	ChemAxon
Polarizability	11.19 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]+	121.208	31661259
DarkChem	[M-H]-	116.832	31661259
DeepCCS	[M+H]+	125.122	30932474
DeepCCS	[M-H]-	123.04	30932474
DeepCCS	[M-2H]-	158.763	30932474
DeepCCS	[M+Na]+	133.492	30932474
AllCCS	[M+H]+	126.3	32859911
AllCCS	[M+H-H2O]+	122.1	32859911
AllCCS	[M+NH4]+	130.3	32859911
AllCCS	[M+Na]+	131.4	32859911
AllCCS	[M-H]-	126.3	32859911
AllCCS	[M+Na-2H]-	130.3	32859911
AllCCS	[M+HCOO]-	134.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.18 minutes	32390414
Predicted by Siyang on May 30, 2022	12.9736 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.28 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	40.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1674.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	462.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	158.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	294.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	64.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	427.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	553.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	111.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	946.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	381.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1143.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	260.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	316.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	500.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	412.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	73.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl isobutyrate	COC(=O)C(C)C	914.8	Standard polar	33892256
Methyl isobutyrate	COC(=O)C(C)C	637.8	Standard non polar	33892256
Methyl isobutyrate	COC(=O)C(C)C	692.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Methyl isobutyrate EI-B (Non-derivatized)	splash10-0006-9000000000-cd801699f9c2a557b43f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl isobutyrate EI-B (Non-derivatized)	splash10-0006-9000000000-3e969deccf54a3de9a05	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl isobutyrate CI-B (Non-derivatized)	splash10-0fe0-9200000000-a852902f244e902cb44a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl isobutyrate EI-B (Non-derivatized)	splash10-0006-9000000000-036e1ab23d11bbe83602	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl isobutyrate EI-B (Non-derivatized)	splash10-0006-9000000000-cd801699f9c2a557b43f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl isobutyrate EI-B (Non-derivatized)	splash10-0006-9000000000-3e969deccf54a3de9a05	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl isobutyrate CI-B (Non-derivatized)	splash10-0fe0-9200000000-a852902f244e902cb44a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl isobutyrate EI-B (Non-derivatized)	splash10-0006-9000000000-036e1ab23d11bbe83602	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl isobutyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-a10cecf41a27b2809df8	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl isobutyrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-ee4a74a8e58214633453	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl isobutyrate 10V, Positive-QTOF	splash10-0udi-4900000000-4158b3942dd80630a16c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl isobutyrate 20V, Positive-QTOF	splash10-0fdo-9400000000-1fe485d0af82d169052b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl isobutyrate 40V, Positive-QTOF	splash10-0006-9000000000-4654b7b7e766fa0a4c2b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl isobutyrate 10V, Negative-QTOF	splash10-0udi-1900000000-301f5de58f5b6678317e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl isobutyrate 20V, Negative-QTOF	splash10-0udi-4900000000-9dcbeff47e662d7a1842	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl isobutyrate 40V, Negative-QTOF	splash10-0lki-9000000000-f7694af026d7ca6c20ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl isobutyrate 10V, Negative-QTOF	splash10-0udi-0900000000-4c159e60dacc58e6ba98	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl isobutyrate 20V, Negative-QTOF	splash10-0udj-7900000000-6a873d93371a96550a58	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl isobutyrate 40V, Negative-QTOF	splash10-0a4l-9000000000-d0e996d0a29f176d044d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl isobutyrate 10V, Positive-QTOF	splash10-0006-9000000000-0e91a487841f70ea0eac	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl isobutyrate 20V, Positive-QTOF	splash10-006x-9000000000-a5913aa9a7c22ca66228	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl isobutyrate 40V, Positive-QTOF	splash10-0006-9000000000-58c7a6fdbf983f1180bf	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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	17314143	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

FDB003279

KNApSAcK ID

Not Available

Chemspider ID

10571

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methyl isobutyrate

METLIN ID

Not Available

PubChem Compound

11039

PDB ID

Not Available

ChEBI ID

73689

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1008761

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 Methyl isobutyrate (HMDB0031249)

MOL for HMDB0031249 (Methyl isobutyrate)

3D MOL for HMDB0031249 (Methyl isobutyrate)

3D SDF for HMDB0031249 (Methyl isobutyrate)

3D-SDF for HMDB0031249 (Methyl isobutyrate)

PDB for HMDB0031249 (Methyl isobutyrate)

3D PDB for HMDB0031249 (Methyl isobutyrate)

SMILES for HMDB0031249 (Methyl isobutyrate)

INCHI for HMDB0031249 (Methyl isobutyrate)

Structure for HMDB0031249 (Methyl isobutyrate)

3D Structure for HMDB0031249 (Methyl isobutyrate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra