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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:41:51 UTC

Update Date

2023-02-21 17:20:11 UTC

HMDB ID

HMDB0031248

Secondary Accession Numbers

HMDB31248

Metabolite Identification

Common Name

Ethyl 2-methylpropanoate

Description

Ethyl 2-methylpropanoate, also known as ethyl 2,2-dimethylacetate or isobutyric acid ethyl ester, 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). Ethyl 2-methylpropanoate is a sweet, alcoholic, and ethereal tasting compound. Ethyl 2-methylpropanoate is found, on average, in the highest concentration within red wine. Ethyl 2-methylpropanoate has also been detected, but not quantified in, several different foods, such as apples (Malus pumila), pineapples (Ananas comosus), evergreen blackberries (Rubus laciniatus), fruits, and spearmints (Mentha spicata). This could make ethyl 2-methylpropanoate a potential biomarker for the consumption of these foods. Ethyl 2-methylpropanoate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Ethyl 2-methylpropanoate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ethyl 2,2-dimethylacetate	ChEBI
Isobutyric acid ethyl ester	ChEBI
Ethyl 2,2-dimethylacetic acid	Generator
Isobutyrate ethyl ester	Generator
Ethyl 2-methylpropanoic acid	Generator
Ethyl 2-methylpropanoate, 9ci	HMDB
Ethyl 2-methylpropionate	HMDB
Ethyl ester OF 2-methyl-propanoic acid	HMDB
Ethyl isobutanoate	HMDB
Ethyl isobutyrate	HMDB
Ethyl-2-methylproanoate	HMDB
Ethylisobutyrate	HMDB
Ethylmethylpropanoate	HMDB
FEMA 2428	HMDB
Isobutyric acid, ethyl ester	HMDB
Propanoic acid, 2-methyl-, ethyl ester	HMDB
Propionic acid, 2-methyl-, ethyl ester	HMDB
Ethyl 2-methylpropanoate	MeSH

Chemical Formula

C₆H₁₂O₂

Average Molecular Weight

116.1583

Monoisotopic Molecular Weight

116.083729628

IUPAC Name

ethyl 2-methylpropanoate

Traditional Name

ethyl isobutyrate

CAS Registry Number

97-62-1

SMILES

CCOC(=O)C(C)C

InChI Identifier

InChI=1S/C6H12O2/c1-4-8-6(7)5(2)3/h5H,4H2,1-3H3

InChI Key

WDAXFOBOLVPGLV-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

fatty acid methyl ester (CHEBI:87303 )
Wax monoesters (LMFA07010503 )

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Feces (PMID: 24130822)

Cellular substructure

Extracellular (HMDB: HMDB0031248)
Cytoplasm (HMDB: HMDB0031248)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031248)

Source

Endogenous

Endogenous (HMDB: HMDB0031248)

Plant

Plant (HMDB: HMDB0031248)

Exogenous

Food

Food (HMDB: HMDB0031248)

Beverage

Fermented beverage

White wine (FooDB: FOOD00917)
Red wine (FooDB: FOOD00911)

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Fruit

Pome

Apple (FooDB: FOOD00105)
Asian pear (FooDB: FOOD00291)
Pomes (FooDB: FOOD00856)

Other fruit

Fig (FooDB: FOOD00081)

Tropical fruit

Pineapple (FooDB: FOOD00012)

Berry

Citrus

Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)
Spearmint (FooDB: FOOD00112)

Exogenous (HMDB: HMDB0031248)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031248)
Flavor (HMDB: HMDB0031248)

Biological role

Irritant (HMDB: HMDB0031248)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-88.2 °C	Not Available
Boiling Point	112.00 to 113.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	3172 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.648 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	13.6 g/L	ALOGPS
logP	1.72	ALOGPS
logP	1.52	ChemAxon
logS	-0.93	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	3	ChemAxon
Refractivity	31.36 m³·mol⁻¹	ChemAxon
Polarizability	13.23 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]+	125.543	31661259
DarkChem	[M-H]-	120.045	31661259
DeepCCS	[M+H]+	128.887	30932474
DeepCCS	[M-H]-	126.71	30932474
DeepCCS	[M-2H]-	162.927	30932474
DeepCCS	[M+Na]+	137.635	30932474
AllCCS	[M+H]+	128.1	32859911
AllCCS	[M+H-H2O]+	123.9	32859911
AllCCS	[M+NH4]+	131.9	32859911
AllCCS	[M+Na]+	133.1	32859911
AllCCS	[M-H]-	128.3	32859911
AllCCS	[M+Na-2H]-	131.7	32859911
AllCCS	[M+HCOO]-	135.5	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.	3.54 minutes	32390414
Predicted by Siyang on May 30, 2022	14.2689 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.42 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	32.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1878.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	522.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	170.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	315.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	99.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	519.2 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	626.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	187.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1034.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	420.3 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	1316.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	350.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	337.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	523.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	475.9 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	66.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 2-methylpropanoate	CCOC(=O)C(C)C	973.4	Standard polar	33892256
Ethyl 2-methylpropanoate	CCOC(=O)C(C)C	698.8	Standard non polar	33892256
Ethyl 2-methylpropanoate	CCOC(=O)C(C)C	767.7	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-methylpropanoate EI-B (Non-derivatized)	splash10-0006-9000000000-f3988eecc5f86a2f81e5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl 2-methylpropanoate EI-B (Non-derivatized)	splash10-0006-9000000000-cda38c45f8e8f3e49d4f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl 2-methylpropanoate CI-B (Non-derivatized)	splash10-00dr-9100000000-16a5b597c42a23d7f22b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl 2-methylpropanoate EI-B (Non-derivatized)	splash10-002f-9000000000-a2cde32043924be5f69d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl 2-methylpropanoate EI-B (Non-derivatized)	splash10-0006-9000000000-f3988eecc5f86a2f81e5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl 2-methylpropanoate EI-B (Non-derivatized)	splash10-0006-9000000000-cda38c45f8e8f3e49d4f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl 2-methylpropanoate CI-B (Non-derivatized)	splash10-00dr-9100000000-16a5b597c42a23d7f22b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl 2-methylpropanoate EI-B (Non-derivatized)	splash10-002f-9000000000-a2cde32043924be5f69d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 2-methylpropanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-78006c6c9d7cc2f64b40	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 2-methylpropanoate 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-methylpropanoate 10V, Positive-QTOF	splash10-014i-5900000000-b497e527a00dd10ccf60	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 20V, Positive-QTOF	splash10-00xu-9200000000-15b9cf1d24ca63e9478b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 40V, Positive-QTOF	splash10-006x-9000000000-487b56262921939df240	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 10V, Negative-QTOF	splash10-014i-3900000000-fa1705aa5e16f6891659	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 20V, Negative-QTOF	splash10-014i-9600000000-ccf9216bb7c78dde21d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 40V, Negative-QTOF	splash10-00kr-9000000000-5f89823d58cd88cdbaf6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 10V, Negative-QTOF	splash10-000i-9100000000-9adcf5fbf8874986b60c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 20V, Negative-QTOF	splash10-00ku-9200000000-24df36816c44949c3b3b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 40V, Negative-QTOF	splash10-000i-9000000000-0a440708e26c224768c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 10V, Positive-QTOF	splash10-0006-9000000000-e18148c70c476d448538	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 20V, Positive-QTOF	splash10-006x-9000000000-dee9505deb846ba46f5b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 40V, Positive-QTOF	splash10-0006-9000000000-a56976d42756d59af747	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

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	Children (1-13 years old)	Both	Normal	24130822	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Autism	24130822	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Pervasive Developmental Disorder Not Otherwise Specified	24130822	details

Associated Disorders and Diseases

Disease References

Autism
De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]

Associated OMIM IDs

209850 (Autism)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003278

KNApSAcK ID

C00053169

Chemspider ID

7065

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7342

PDB ID

Not Available

ChEBI ID

87303

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1000751

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 Ethyl 2-methylpropanoate (HMDB0031248)

MOL for HMDB0031248 (Ethyl 2-methylpropanoate)

3D MOL for HMDB0031248 (Ethyl 2-methylpropanoate)

3D SDF for HMDB0031248 (Ethyl 2-methylpropanoate)

3D-SDF for HMDB0031248 (Ethyl 2-methylpropanoate)

PDB for HMDB0031248 (Ethyl 2-methylpropanoate)

3D PDB for HMDB0031248 (Ethyl 2-methylpropanoate)

SMILES for HMDB0031248 (Ethyl 2-methylpropanoate)

INCHI for HMDB0031248 (Ethyl 2-methylpropanoate)

Structure for HMDB0031248 (Ethyl 2-methylpropanoate)

3D Structure for HMDB0031248 (Ethyl 2-methylpropanoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra