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isobutanoic acid (YMDB01320)

Identification
YMDB IDYMDB01320
Nameisobutanoic acid
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionIsobutyric 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
Thumb
MOLSDFPDBSMILESInChI
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 number79-31-2
WeightAverage: 88.1051
Monoisotopic: 88.0524295
InChI KeyKQNPFQTWMSNSAP-UHFFFAOYSA-N
InChIInChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)
IUPAC Name2-methylpropanoic acid
Traditional IUPAC Nameisobutyric acid
Chemical FormulaC4H8O2
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point-46 °C
Experimental Properties
PropertyValueReference
Water Solubility167 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP0.94 [SANGSTER (1993)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility197 g/LALOGPS
logP0.78ALOGPS
logP1.02ChemAxon
logS0.35ALOGPS
pKa (Strongest Acidic)4.87ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity21.85 m³·mol⁻¹ChemAxon
Polarizability9.12 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
Organoleptic Properties
Flavour/OdourSource
ButterFDB003277
CheeseFDB003277
RancidFDB003277
StrawberryFDB003277
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4c977a2f823cde05363aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e8e4dc7f7f3f492ec19cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4c977a2f823cde05363aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e8e4dc7f7f3f492ec19cJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-d3c10d617448ce79a5a1JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0076-9100000000-80d574b59e1edc9d7535JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00dr-9000000000-67f1d07ca106199c76d3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-d5e7b5664f34e843b614JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0f79-9200000000-b18c55d6aa937214dca2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-688272ebde48c146c6d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-f1d1211c63775f704d72JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-d5f9008f8738e9ee1206JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-3b1bc720943b7b4b9b7bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-af791f98a192fc352a65JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-d5f9008f8738e9ee1206JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-3b1bc720943b7b4b9b7bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-af791f98a192fc352a65JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9000000000-b9f811f5e57b3eeeb842JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-eabd518990089acf84caJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-9ec563a3b4f50dc2aaafJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-eee01af90e21c20eb584JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-4952a01442de6ea6ecfeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-23cf7c0a08ac346b6bfeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00rl-9000000000-7ca1184fbf16cfe0b735JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-4b3590a18d40d4d58a01JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-4b3590a18d40d4d58a01JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9000000000-97afb40e14188e82aee9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-82e9a26713840d90625eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-f007a4a376085ff3e56aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-17c0b668153fbfe212cbJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-ce74765d5e4785841363JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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:
ResourceLink
CHEBI ID16135
HMDB IDHMDB01873
Pubchem Compound ID6590
Kegg IDC02632
ChemSpider ID6341
FOODB IDFDB003277
WikipediaIsobutyric acid
BioCyc IDISOBUTANOATE