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butanoic acid (YMDB01392)

Identification
YMDB IDYMDB01392
Namebutanoic acid
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionButyric acid, also known as butanoic acid or butyrate, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. Butyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Butyric acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-butanoate
  • 1-butanoic acid
  • 1-Butyrate
  • 1-Butyric acid
  • 1-Propanecarboxylate
  • 1-Propanecarboxylic acid
  • acide butanoique
  • acide butyrique
  • BUA
  • Butanate
  • Butanic acid
  • butanoate
  • Butanoic acid
  • butoic acid
  • Buttersaeure
  • Butyrate
  • butyric acid
  • C4:0
  • Ethylacetate
  • Ethylacetic acid
  • Honey robber
  • Kyselina maselna
  • n-Butanoate
  • n-Butanoic acid
  • n-Butyrate
  • n-Butyric acid
  • n-C3H7COOH
  • Propanecarboxylate
  • Propanecarboxylic acid
  • Propylformate
  • Propylformic acid
  • 4:0
  • CH3-[CH2]2-COOH
  • Butoate
  • Butyrate, magnesium
  • Magnesium butyrate
  • Acid, butyric
  • Butyrate, sodium
  • Dibutyrate, magnesium
  • Magnesium dibutyrate
  • Sodium butyrate
  • Acid, butanoic
  • Butyric acid magnesium salt
  • Butyric acid, sodium salt
  • FA(4:0)
CAS number107-92-6
WeightAverage: 88.1051
Monoisotopic: 88.0524295
InChI KeyFERIUCNNQQJTOY-UHFFFAOYSA-N
InChIInChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
IUPAC Namebutanoic acid
Traditional IUPAC Namebutyric acid
Chemical FormulaC4H8O2
SMILES[H]OC(=O)C([H])([H])C([H])([H])C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentStraight chain fatty acids
Alternative Parents
Substituents
  • Straight chain 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point-5.7 °C
Experimental Properties
PropertyValueReference
Water Solubility60 mg/mL at 25 oC [HEMPHILL,L & SWANSON,WS (1964)]PhysProp
LogP0.79 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility239 g/LALOGPS
logP0.78ALOGPS
logP0.92ChemAxon
logS0.43ALOGPS
pKa (Strongest Acidic)4.91ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity21.87 m³·mol⁻¹ChemAxon
Polarizability9.22 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
AceticFDB031031
ButterFDB031031
CheeseFDB031031
FruitFDB031031
RancidFDB031031
SharpFDB031031
SweatFDB031031
SMPDB Pathways
Fatty acid biosynthesisPW002458 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Butanoate metabolismec00650 Map00650
Fatty acid biosynthesisec00061 Map00061
SMPDB Reactions
butanoic acid + Malonate → 3-Oxohexanoic acid
But-2-enoic acid → butanoic acid
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-032fc35b394786b5896aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-032fc35b394786b5896aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9000000000-a7792b54320e7c859731JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9100000000-d125b331c4a6d37648a1JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9000000000-7f461db56bfd8568ec71JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000i-9000000000-66f857fa612f773837bcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000i-9000000000-e6689b2e6bf21570b934JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-03dl-9000000000-b2ffa7d67b2466dea94fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03dl-9000000000-7467bf19c64fd3f51105JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-9ae015043b014b3c93d9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-e30b3c6bd6218b9b49e1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-efbb0e35a19a1713240bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-9ae015043b014b3c93d9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-e30b3c6bd6218b9b49e1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-efbb0e35a19a1713240bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-acb5cf0017a9ee680dd8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9000000000-812e24462a71dccb0fecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-f9d30338ca1ee9409964JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-9d749b6b6cf2f93a8f85JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-9000000000-ee742730266fb4997777JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-88fc445cddcb726e93d8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-4b3590a18d40d4d58a01JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-9000000000-140190568a3f2b3c6f01JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-1f7dab1fbd0179ef6d17JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-9000000000-020fcfb652dc5a6f3036JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-3e4b1bc1291a3fbf86c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-1f57e9adb6de1499caf5JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-03di-9000000000-5338ff8a9c4e59150abaJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C 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:
  • 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
  • Kogan, G. L., Filipp, D., Arman, I. P., Leibovich, B. A., Beliaeva, E. S. (1991). "[Cloning of segments of the Drosophila melanogaster genome using artificial chromosomes of the yeast Saccharomyces cerevisiae]." Genetika 27:1316-1323.1761208
Synthesis Reference:Shan, Zhiping. Preparation of butyric acid by hydrogenation of maleic anhydride. U.S. Pat. Appl. Publ. (2008), 6pp.
External Links:
ResourceLink
CHEBI ID30772
HMDB IDHMDB00039
Pubchem Compound ID264
Kegg IDC00246
ChemSpider ID259
FOODB IDFDB031031
WikipediaButyric_acid
BioCyc IDBUTYRIC_ACID