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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:41:51 UTC
Update Date2023-02-21 17:20:11 UTC
HMDB IDHMDB0031248
Secondary Accession Numbers
  • HMDB31248
Metabolite Identification
Common NameEthyl 2-methylpropanoate
DescriptionEthyl 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
Data?1677000011
Synonyms
ValueSource
Ethyl 2,2-dimethylacetateChEBI
Isobutyric acid ethyl esterChEBI
Ethyl 2,2-dimethylacetic acidGenerator
Isobutyrate ethyl esterGenerator
Ethyl 2-methylpropanoic acidGenerator
Ethyl 2-methylpropanoate, 9ciHMDB
Ethyl 2-methylpropionateHMDB
Ethyl ester OF 2-methyl-propanoic acidHMDB
Ethyl isobutanoateHMDB
Ethyl isobutyrateHMDB
Ethyl-2-methylproanoateHMDB
EthylisobutyrateHMDB
EthylmethylpropanoateHMDB
FEMA 2428HMDB
Isobutyric acid, ethyl esterHMDB
Propanoic acid, 2-methyl-, ethyl esterHMDB
Propionic acid, 2-methyl-, ethyl esterHMDB
Ethyl 2-methylpropanoateMeSH
Chemical FormulaC6H12O2
Average Molecular Weight116.1583
Monoisotopic Molecular Weight116.083729628
IUPAC Nameethyl 2-methylpropanoate
Traditional Nameethyl isobutyrate
CAS Registry Number97-62-1
SMILES
CCOC(=O)C(C)C
InChI Identifier
InChI=1S/C6H12O2/c1-4-8-6(7)5(2)3/h5H,4H2,1-3H3
InChI KeyWDAXFOBOLVPGLV-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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentCarboxylic 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-88.2 °CNot Available
Boiling Point112.00 to 113.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility3172 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.648 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility13.6 g/LALOGPS
logP1.72ALOGPS
logP1.52ChemAxon
logS-0.93ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.36 m³·mol⁻¹ChemAxon
Polarizability13.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+125.54331661259
DarkChem[M-H]-120.04531661259
DeepCCS[M+H]+128.88730932474
DeepCCS[M-H]-126.7130932474
DeepCCS[M-2H]-162.92730932474
DeepCCS[M+Na]+137.63530932474
AllCCS[M+H]+128.132859911
AllCCS[M+H-H2O]+123.932859911
AllCCS[M+NH4]+131.932859911
AllCCS[M+Na]+133.132859911
AllCCS[M-H]-128.332859911
AllCCS[M+Na-2H]-131.732859911
AllCCS[M+HCOO]-135.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethyl 2-methylpropanoateCCOC(=O)C(C)C973.4Standard polar33892256
Ethyl 2-methylpropanoateCCOC(=O)C(C)C698.8Standard non polar33892256
Ethyl 2-methylpropanoateCCOC(=O)C(C)C767.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ethyl 2-methylpropanoate EI-B (Non-derivatized)splash10-0006-9000000000-f3988eecc5f86a2f81e52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl 2-methylpropanoate EI-B (Non-derivatized)splash10-0006-9000000000-cda38c45f8e8f3e49d4f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl 2-methylpropanoate CI-B (Non-derivatized)splash10-00dr-9100000000-16a5b597c42a23d7f22b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl 2-methylpropanoate EI-B (Non-derivatized)splash10-002f-9000000000-a2cde32043924be5f69d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl 2-methylpropanoate EI-B (Non-derivatized)splash10-0006-9000000000-f3988eecc5f86a2f81e52018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl 2-methylpropanoate EI-B (Non-derivatized)splash10-0006-9000000000-cda38c45f8e8f3e49d4f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl 2-methylpropanoate CI-B (Non-derivatized)splash10-00dr-9100000000-16a5b597c42a23d7f22b2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl 2-methylpropanoate EI-B (Non-derivatized)splash10-002f-9000000000-a2cde32043924be5f69d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl 2-methylpropanoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-78006c6c9d7cc2f64b402017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl 2-methylpropanoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 10V, Positive-QTOFsplash10-014i-5900000000-b497e527a00dd10ccf602016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 20V, Positive-QTOFsplash10-00xu-9200000000-15b9cf1d24ca63e9478b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 40V, Positive-QTOFsplash10-006x-9000000000-487b56262921939df2402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 10V, Negative-QTOFsplash10-014i-3900000000-fa1705aa5e16f68916592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 20V, Negative-QTOFsplash10-014i-9600000000-ccf9216bb7c78dde21d12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 40V, Negative-QTOFsplash10-00kr-9000000000-5f89823d58cd88cdbaf62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 10V, Negative-QTOFsplash10-000i-9100000000-9adcf5fbf8874986b60c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 20V, Negative-QTOFsplash10-00ku-9200000000-24df36816c44949c3b3b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 40V, Negative-QTOFsplash10-000i-9000000000-0a440708e26c224768c12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 10V, Positive-QTOFsplash10-0006-9000000000-e18148c70c476d4485382021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 20V, Positive-QTOFsplash10-006x-9000000000-dee9505deb846ba46f5b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl 2-methylpropanoate 40V, Positive-QTOFsplash10-0006-9000000000-a56976d42756d59af7472021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAutism details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
Associated Disorders and Diseases
Disease References
Autism
  1. 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
  1. 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
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003278
KNApSAcK IDC00053169
Chemspider ID7065
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7342
PDB IDNot Available
ChEBI ID87303
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1000751
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .