Ethyl butanoate (YMDB01385)

Identification

YMDB ID

YMDB01385

Name

Ethyl butanoate

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Ethyl butanoate (ethyl butyrate) is a volatile ethyl ester found in alcoholic beverages and produced during fermentation by yeast. Ethyl esters are formed by the reaction of ethanol with a fatty acid. Ethyl butanoate is responsible for apple-like aromas, pineapple aromas and blue cheese aromas. The concentrations of ethyl ester decrease over time as an alcoholic beverage ages due to spontaneous hydrolysis.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Butanoic acid, ethyl ester
Butyric acid, ethyl ester
Butyric ester
Butyric ether
ethyl 1-butyrate
ethyl butanoate (ethyl butyrate)
Ethyl butyrate
Ethyl ester of butanoic acid
Ethyl n-butanoate
Ethyl n-butyrate
n-Butyric acid ethyl ester
Butanoic acid ethyl ester
Butyric acid ethyl ester
Ethyl butanoate
Butanoate ethyl ester
Butyrate ethyl ester
Ethyl 1-butyric acid
Ethyl butanoic acid
Ethyl ester OF butanoate
Ethyl N-butanoic acid
Ethyl N-butyric acid
N-Butyrate ethyl ester
Ethyl butyric acid
FEMA 2427

CAS number

105-54-4

Weight

Average: 116.1583
Monoisotopic: 116.083729628

InChI Key

OBNCKNCVKJNDBV-UHFFFAOYSA-N

InChI

InChI=1S/C6H12O2/c1-3-5-6(7)8-4-2/h3-5H2,1-2H3

IUPAC Name

ethyl butanoate

Traditional IUPAC Name

ethyl butyrate

Chemical Formula

C₆H₁₂O₂

SMILES

CCCC(=O)OCC

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

Not Available

Physical Properties

State

Liquid

Charge

Melting point

-98 °C

Experimental Properties

Property	Value	Reference
Water Solubility	4.9 mg/mL at 20 oC [RIDDICK,JA et al. (1986)]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	11.8 g/L	ALOGPS
logP	1.8	ALOGPS
logP	1.42	ChemAxon
logS	-0.99	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	31.39 m³·mol⁻¹	ChemAxon
Polarizability	13.24 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular

Organoleptic Properties

Flavour/Odour	Source
Apple	FDB012082
Banana	FDB012082
Cognac	FDB012082
Fruit	FDB012082
Fruity	FDB012082
Juicy	FDB012082
Pineapple	FDB012082

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00g3-9000000000-78bbe008aa184177c5ca	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00du-9000000000-5cfbe6fd33a8e1accffd	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00du-9000000000-c6cfb5c94d0be8f6153a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0096-9000000000-8f2e75f476f548f5d68d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00g3-9000000000-78bbe008aa184177c5ca	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00du-9000000000-5cfbe6fd33a8e1accffd	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00du-9000000000-c6cfb5c94d0be8f6153a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0096-9000000000-8f2e75f476f548f5d68d	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9000000000-681e8d0e7e97ea57bfbb	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-9200000000-3568e345aee8469c2994	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03di-0900000000-32a00a5f041be990cde0	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-7900000000-ea02ea57673f2490b51a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xs-9100000000-df0b54ac1fa8525b1134	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-9000000000-7cbb94a53431764f494f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-9800000000-8c3309a6f50be5bc0172	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9200000000-66220671a69653c03e79	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kg-9000000000-4d7029f372de06bbfb66	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00kk-9100000000-04d594827ffb1ee4fcf6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9000000000-79ee53f899ebd32622e2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-caf247292d3074b4c7f6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-9000000000-d9c4257770ffe04a8c1f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-943b0d60015b8b4d4e42	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-6c6087ea2f0351280d9e	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0096-9000000000-92f15d6d1e57255a3478	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Vianna, E., Ebeler, S. E. (2001). "Monitoring ester formation in grape juice fermentations using solid phase microextraction coupled with gas chromatography-mass spectrometry." J Agric Food Chem 49:589-595.11261997
Tsakiris, A., Koutinas, A. A., Psarianos, C., Kourkoutas, Y., Bekatorou, A. (2010). "A new process for wine production by penetration of yeast in uncrushed frozen grapes." Appl Biochem Biotechnol 162:1109-1121.20151225
Patel, S., Shibamoto, T. (2002). "Effect of different strains of Saccharomyces cerevisiae on production of volatiles in Napa Gamay wine and Petite Sirah wine." J Agric Food Chem 50:5649-5653.12236692

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	17968
HMDB ID	HMDB0033889
Pubchem Compound ID	7762
Kegg ID	Not Available
ChemSpider ID	7475
FOODB ID	FDB012082
Wikipedia	Ethyl_butyrate
BioCyc ID	BUTYRIC_ACID

Structure for #<Compound:0x98095ba8>