isobutanoic acid (YMDB01320)

Identification

YMDB ID

YMDB01320

Name

isobutanoic acid

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Isobutyric acid, also known as isobutyrate or iso-C3H7COOH, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Isobutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Isobutyric acid exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

2-METHYL-PROPIONIC ACID
2-Methylpropanoate
2-Methylpropanoic acid
2-Methylpropionate
2-Methylpropionic acid
2-Methylpropionsaeure
2,2-dimethylacetic acid
a-Methylpropanoate
a-Methylpropanoic acid
a-Methylpropionate
a-Methylpropionic acid
Acetic acid, dimethyl-
alpha-isobutyric acid
alpha-Methylpropanoate
alpha-Methylpropanoic acid
alpha-Methylpropionate
alpha-Methylpropionic acid
Dimethylacetate
Dimethylacetic acid
dimethylethanoic acid
i-Butyrate
i-Butyric acid
iso-Butyrate
iso-Butyric acid
iso-C3H7COOH
Isobutanoate
isobutanoic acid
Isobuttersaeure
Isobutyrate
isobutyric acid
Isopropylformate
Isopropylformic acid
Kyselina isomaselna
Methyl propanoic acid
Methylpropionic acid
perisobutyric acid
Propanoic acid, 2-methyl-
Propionic acid, 2-methyl-
valerianic acid
2,2-Dimethylacetate
2-METHYL-propionate
a-Isobutyrate
a-Isobutyric acid
alpha-Isobutyrate
Α-isobutyrate
Α-isobutyric acid
Α-methylpropanoate
Α-methylpropanoic acid
Α-methylpropionate
Α-methylpropionic acid
Ammonium isobutyrate
Isobutyric acid, ammonium salt
Isobutyric acid, sodium salt
2-Methpropanoic acid
Isobutyric acid, hemiammoniate
Sodium isobutyrate
Isobutyric acid, calcium salt
Isobutyric acid, nickel salt
Isobutyric acid, potassium salt
Isobutyric acid, sodium salt, 11C-labeled
Isobutyric acid, sodium salt, 14C-labeled

CAS number

79-31-2

Weight

Average: 88.1051
Monoisotopic: 88.0524295

InChI Key

KQNPFQTWMSNSAP-UHFFFAOYSA-N

InChI

InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)

IUPAC Name

2-methylpropanoic acid

Traditional IUPAC Name

isobutyric acid

Chemical Formula

C₄H₈O₂

SMILES

[H]OC(=O)C([H])(C([H])([H])[H])C([H])([H])[H]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acids

Direct Parent

Carboxylic acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

branched-chain saturated fatty acid (CHEBI:16135 )
methyl-branched fatty acid (CHEBI:16135 )
short-chain fatty acid (CHEBI:16135 )
Branched fatty acids (LMFA01020071 )

Physical Properties

State

Liquid

Charge

Melting point

-46 °C

Experimental Properties

Property	Value	Reference
Water Solubility	167 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	0.94 [SANGSTER (1993)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	197 g/L	ALOGPS
logP	0.78	ALOGPS
logP	1.02	ChemAxon
logS	0.35	ALOGPS
pKa (Strongest Acidic)	4.87	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	1	ChemAxon
Refractivity	21.85 m³·mol⁻¹	ChemAxon
Polarizability	9.12 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
Butter	FDB003277
Cheese	FDB003277
Rancid	FDB003277
Strawberry	FDB003277

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)	splash10-0006-9000000000-4c977a2f823cde05363a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-e8e4dc7f7f3f492ec19c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-4c977a2f823cde05363a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-e8e4dc7f7f3f492ec19c	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-d3c10d617448ce79a5a1	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0076-9100000000-80d574b59e1edc9d7535	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00dr-9000000000-67f1d07ca106199c76d3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-d5e7b5664f34e843b614	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0f79-9200000000-b18c55d6aa937214dca2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0006-9000000000-688272ebde48c146c6d7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9000000000-f1d1211c63775f704d72	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-d5f9008f8738e9ee1206	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-3b1bc720943b7b4b9b7b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-af791f98a192fc352a65	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-d5f9008f8738e9ee1206	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-3b1bc720943b7b4b9b7b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-af791f98a192fc352a65	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9000000000-b9f811f5e57b3eeeb842	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-eabd518990089acf84ca	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-9ec563a3b4f50dc2aaaf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-eee01af90e21c20eb584	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-4952a01442de6ea6ecfe	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-23cf7c0a08ac346b6bfe	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00rl-9000000000-7ca1184fbf16cfe0b735	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-4b3590a18d40d4d58a01	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-4b3590a18d40d4d58a01	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-9000000000-97afb40e14188e82aee9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-82e9a26713840d90625e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-f007a4a376085ff3e56a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-17c0b668153fbfe212cb	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-ce74765d5e4785841363	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	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Patching, J. W., Rose, A. H. (1971). "Cold osmotic shock in Saccharomyces cerevisiae." J Bacteriol 108:451-458.5001201
Antonelli, A., Castellari, L., Zambonelli, C., Carnacini, A. (1999). "Yeast influence on volatile composition of wines." J Agric Food Chem 47:1139-1144.10552428
Dickinson, J. R., Harrison, S. J., Hewlins, M. J. (1998). "An investigation of the metabolism of valine to isobutyl alcohol in Saccharomyces cerevisiae." J Biol Chem 273:25751-25756.9748245
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:

Wang, Hengxiu; Chen, Weibin; Zhao, Dehua; Zhang, Jianbin. Preparation of isobutyric acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 5 pp.

External Links:

Resource	Link
CHEBI ID	16135
HMDB ID	HMDB01873
Pubchem Compound ID	6590
Kegg ID	C02632
ChemSpider ID	6341
FOODB ID	FDB003277
Wikipedia	Isobutyric acid
BioCyc ID	ISOBUTANOATE

Structure for #<Compound:0xaf2dd55c>