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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 18:30:19 UTC

Update Date

2023-02-21 17:23:34 UTC

HMDB ID

HMDB0033745

Secondary Accession Numbers

HMDB33745

Metabolite Identification

Common Name

Ethyl 2-methylbutyrate

Description

Ethyl 2-methylbutyrate, also known as ethyl α-methylbutyric acid, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Based on a literature review a significant number of articles have been published on Ethyl 2-methylbutyrate.

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-Methylbutanoic acid ethyl ester	ChEBI
Butanoic acid, 2-methyl-, ethyl ester	ChEBI
Butyric acid, 2-methyl-, ethyl ester	ChEBI
Ethyl 2-methylbutanoate	ChEBI
Ethyl alpha-methylbutyrate	ChEBI
2-Methylbutanoate ethyl ester	Generator
Butanoate, 2-methyl-, ethyl ester	Generator
Butyrate, 2-methyl-, ethyl ester	Generator
Ethyl 2-methylbutanoic acid	Generator
Ethyl a-methylbutyrate	Generator
Ethyl a-methylbutyric acid	Generator
Ethyl alpha-methylbutyric acid	Generator
Ethyl α-methylbutyrate	Generator
Ethyl α-methylbutyric acid	Generator
Ethyl 2-methylbutyric acid	Generator
2-Methyl-ethyl ester(.+-.)-butanoic acid	HMDB
2-Methyl-ethyl ester(.+/-.)-butanoic acid	HMDB
Butyric acid, 2-methyl-, ethyl ester (8ci)	HMDB
Ethyl 2-methyl butyrate	HMDB
Ethyl alpha -methylbutyrate	HMDB
FEMA 2443	HMDB
Ethyl 2-methyl-butanoic acid	Generator

Chemical Formula

C₇H₁₄O₂

Average Molecular Weight

130.1849

Monoisotopic Molecular Weight

130.099379692

IUPAC Name

ethyl 2-methylbutanoate

Traditional Name

ethyl 2-methylbutanoate

CAS Registry Number

7452-79-1

SMILES

CCOC(=O)C(C)CC

InChI Identifier

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

InChI Key

HCRBXQFHJMCTLF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
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

Wax monoesters (LMFA07010506 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	132.00 to 133.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1070 mg/L @ 25 °C (est)	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	4.16 g/L	ALOGPS
logP	2.38	ALOGPS
logP	1.97	ChemAxon
logS	-1.5	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	4	ChemAxon
Refractivity	35.96 m³·mol⁻¹	ChemAxon
Polarizability	15.09 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]+	129.246	31661259
DarkChem	[M-H]-	125.251	31661259
DeepCCS	[M+H]+	133.895	30932474
DeepCCS	[M-H]-	131.542	30932474
DeepCCS	[M-2H]-	167.836	30932474
DeepCCS	[M+Na]+	142.868	30932474
AllCCS	[M+H]+	131.9	32859911
AllCCS	[M+H-H2O]+	127.8	32859911
AllCCS	[M+NH4]+	135.7	32859911
AllCCS	[M+Na]+	136.8	32859911
AllCCS	[M-H]-	132.7	32859911
AllCCS	[M+Na-2H]-	135.6	32859911
AllCCS	[M+HCOO]-	138.8	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.	4.61 minutes	32390414
Predicted by Siyang on May 30, 2022	15.5197 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.06 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	30.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2051.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	561.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	191.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	348.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	166.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	606.0 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	677.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	172.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1170.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	454.1 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	1433.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	389.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	363.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	503.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	515.8 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	57.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 2-methylbutyrate	CCOC(=O)C(C)CC	1051.1	Standard polar	33892256
Ethyl 2-methylbutyrate	CCOC(=O)C(C)CC	837.2	Standard non polar	33892256
Ethyl 2-methylbutyrate	CCOC(=O)C(C)CC	869.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Ethyl 2-methylbutyrate EI-B (Non-derivatized)	splash10-0pdi-9200000000-bdeaf3cfa63daefe3b19	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl 2-methylbutyrate EI-B (Non-derivatized)	splash10-0pdi-9200000000-bdeaf3cfa63daefe3b19	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 2-methylbutyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9100000000-c67ce7d1e083ae180d47	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 2-methylbutyrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 2-methylbutyrate 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 - Ethyl 2-methylbutyrate 10V, Positive-QTOF	splash10-001i-3900000000-1f771d5f122d8509ac26	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylbutyrate 20V, Positive-QTOF	splash10-053i-9300000000-9d896e54b70902ce1a56	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylbutyrate 40V, Positive-QTOF	splash10-0a4i-9000000000-929834da4bfe99de3b57	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylbutyrate 10V, Negative-QTOF	splash10-004i-2900000000-71f2b191506baa048335	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylbutyrate 20V, Negative-QTOF	splash10-004i-9800000000-ea2d1545369149cc6c65	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylbutyrate 40V, Negative-QTOF	splash10-0a4i-9100000000-ea16ca910e6ea9fbf53f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylbutyrate 10V, Negative-QTOF	splash10-0udi-1900000000-c83f92da456b78baea0e	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylbutyrate 20V, Negative-QTOF	splash10-0fba-9800000000-cc057d042e5f608aaa5a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylbutyrate 40V, Negative-QTOF	splash10-0pb9-9100000000-93094248cf7d4c3b50b8	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylbutyrate 10V, Positive-QTOF	splash10-052r-9100000000-88ec4256d75360c1f963	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylbutyrate 20V, Positive-QTOF	splash10-0a4r-9000000000-cd986aae045be0820fb7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylbutyrate 40V, Positive-QTOF	splash10-0a4i-9000000000-88b9f9e582718680dd72	2021-09-25	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
Membrane

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	Newborn (0-30 days old)	Both	Normal	21386183	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	Clostridium difficile infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	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 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011877

KNApSAcK ID

C00030220

Chemspider ID

22453

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24020

PDB ID

Not Available

ChEBI ID

88452

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1004871

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Ethyl 2-methylbutyrate (HMDB0033745)

MOL for HMDB0033745 (Ethyl 2-methylbutyrate)

3D MOL for HMDB0033745 (Ethyl 2-methylbutyrate)

3D SDF for HMDB0033745 (Ethyl 2-methylbutyrate)

3D-SDF for HMDB0033745 (Ethyl 2-methylbutyrate)

PDB for HMDB0033745 (Ethyl 2-methylbutyrate)

3D PDB for HMDB0033745 (Ethyl 2-methylbutyrate)

SMILES for HMDB0033745 (Ethyl 2-methylbutyrate)

INCHI for HMDB0033745 (Ethyl 2-methylbutyrate)

Structure for HMDB0033745 (Ethyl 2-methylbutyrate)

3D Structure for HMDB0033745 (Ethyl 2-methylbutyrate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra