2-Methylbutyric acid (YMDB01587)

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Identification

YMDB ID

YMDB01587

Name

2-Methylbutyric acid

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Ethylmethylacetic acid, also known as alpha-methyl butyric acid or a-methyl butyrate, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Based on a literature review a small amount of articles have been published on Ethylmethylacetic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(+/-)-2-methylbutyrate
(+/-)-2-methylbutyric acid
2-Ethylpropionate
2-Ethylpropionic acid
2-Methybutyrate
2-Methybutyric acid
2-Methyl butyrate
2-Methyl butyric acid
2-Methylbutanoate
2-Methylbutanoic acid
2-Methylbutyrate
2-Methylbutyrate, (+-)-isomer
2-Methylbutyrate, sodium salt
2-Methylbutyric acid
a-Methyl butyrate
a-Methyl butyric acid
a-Methylbutyrate
a-Methylbutyric acid
alpha-Methyl butyrate
alpha-Methylbutyrate
alpha-Methylbutyric acid
Butane-2-carboxylate
Butane-2-carboxylic acid
D-2-Methyl butyrate
D-2-Methyl butyric acid
DL-2-Methy butyrate
DL-2-Methy butyric acid
DL-2-Methylbutyrate
DL-2-Methylbutyric acid
Ethylmethylacetate
Ethylmethylacetic acid
Methylethylacetate
Methylethylacetic acid
RS-2-Methylbutyrate
α-methyl butyrate
α-methyl butyric acid
α-methylbutyrate
α-methylbutyric acid
alpha-Methyl butyric acid

CAS number

116-53-0

Weight

Average: 102.1317
Monoisotopic: 102.068079564

InChI Key

WLAMNBDJUVNPJU-UHFFFAOYSA-N

InChI

InChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)

IUPAC Name

2-methylbutanoic acid

Traditional IUPAC Name

(+-)-2-methylbutyrate

Chemical Formula

C₅H₁₀O₂

SMILES

CCC(C)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-branched fatty acids

Alternative Parents

Substituents

Methyl-branched fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

methylbutyric acid (CHEBI:37070 )
Branched fatty acids (LMFA01020072 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	45 mg/mL at 20 oC [RIEMENSCHNEIDER,W (1986)]	PhysProp
LogP	1.18 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	57.2 g/L	ALOGPS
logP	1.47	ALOGPS
logP	1.46	ChemAxon
logS	-0.25	ALOGPS
pKa (Strongest Acidic)	4.97	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	26.45 m³·mol⁻¹	ChemAxon
Polarizability	10.98 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

Not Available

Organoleptic Properties

Flavour/Odour	Source
Acid	FDB008135
Cheese	FDB008135
Pungent	FDB008135
Roquefort cheese	FDB008135
Sour	FDB008135
Strawberry	FDB008135
Sweat	FDB008135

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)	splash10-05i3-9000000000-0aaa78177c0a6f4e0f30	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05i3-9000000000-0aaa78177c0a6f4e0f30	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-9000000000-2909ffab0f5a63851edf	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05dr-9200000000-d03c368f82e8aafbbf2e	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-05i3-9000000000-1b5a036458bffab2edb2	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-9500000000-015593bb5625d47062e0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9100000000-9cefc93a02ed409afaa7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-4c09f00d4b395429c15f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-9500000000-015593bb5625d47062e0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9100000000-9cefc93a02ed409afaa7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-4c09f00d4b395429c15f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-2900000000-91099c4563c2a38048c7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-9500000000-614d914711126947b2cc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-0c48b735fe7cb3bd438f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-2900000000-91099c4563c2a38048c7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-9500000000-614d914711126947b2cc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-0c48b735fe7cb3bd438f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-4c159e60dacc58e6ba98	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2900000000-3de63f631f358f44d663	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-49980d35bd5bcf94041b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zg0-9500000000-ebceed22ebf0c3f30cbf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-ee8b144eb008ebfb745c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-b0c600bc4b289c4f5f6d	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-05i0-9000000000-5202133990304f535e3e	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
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:

Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	37070
HMDB ID	HMDB02176
Pubchem Compound ID	8314
Kegg ID	C18319
ChemSpider ID	8012
FOODB ID	FDB008135
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xadd2ff70>