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Record Information
Version1.0
Creation Date2016-09-30 22:18:50 UTC
Update Date2020-05-21 16:27:14 UTC
BMDB IDBMDB0000039
Secondary Accession Numbers
  • BMDB00039
Metabolite Identification
Common NameButyric acid
DescriptionButyric acid, also known as butyrate or butanoic acid, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. Butyric acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Butyric acid exists in all living species, ranging from bacteria to humans. Butyric acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
1-Butanoic acidChEBI
1-Butyric acidChEBI
1-Propanecarboxylic acidChEBI
4:0ChEBI
Acide butanoiqueChEBI
Acide butyriqueChEBI
Butanic acidChEBI
ButanoateChEBI
Butanoic acidChEBI
Butoic acidChEBI
ButtersaeureChEBI
C4:0ChEBI
CH3-[CH2]2-COOHChEBI
Ethylacetic acidChEBI
N-Butanoic acidChEBI
N-Butyric acidChEBI
Propanecarboxylic acidChEBI
Propylformic acidChEBI
ButyrateKegg
1-ButanoateGenerator
1-ButyrateGenerator
1-PropanecarboxylateGenerator
ButanateGenerator
ButoateGenerator
EthylacetateGenerator
N-ButanoateGenerator
N-ButyrateGenerator
PropanecarboxylateGenerator
PropylformateGenerator
Honey robberHMDB
Kyselina maselnaHMDB
Butyrate, magnesiumHMDB
Magnesium butyrateHMDB
Acid, butyricHMDB
Butyrate, sodiumHMDB
Dibutyrate, magnesiumHMDB
Magnesium dibutyrateHMDB
Sodium butyrateHMDB
Acid, butanoicHMDB
Butyric acid magnesium saltHMDB
Butyric acid, sodium saltHMDB
FA(4:0)HMDB
Butyric acidKEGG
Chemical FormulaC4H8O2
Average Molecular Weight88.1051
Monoisotopic Molecular Weight88.0524295
IUPAC Namebutanoic acid
Traditional Namebutyric acid
CAS Registry Number107-92-6
SMILES
CCCC(O)=O
InChI Identifier
InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
InChI KeyFERIUCNNQQJTOY-UHFFFAOYSA-N
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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-5.7 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility60.0 mg/mLNot Available
LogP0.79HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-032fc35b394786b5896aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-032fc35b394786b5896aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9000000000-a7792b54320e7c859731View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9100000000-d125b331c4a6d37648a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9000000000-7f461db56bfd8568ec71View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000i-9000000000-66f857fa612f773837bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000i-9000000000-e6689b2e6bf21570b934View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-03dl-9000000000-b2ffa7d67b2466dea94fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03dl-9000000000-7467bf19c64fd3f51105View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-9ae015043b014b3c93d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-e30b3c6bd6218b9b49e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-efbb0e35a19a1713240bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-9ae015043b014b3c93d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-e30b3c6bd6218b9b49e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-efbb0e35a19a1713240bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-acb5cf0017a9ee680dd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9000000000-812e24462a71dccb0fecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-f9d30338ca1ee9409964View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-9d749b6b6cf2f93a8f85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-9000000000-ee742730266fb4997777View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-88fc445cddcb726e93d8View in MoNA
MSMass Spectrum (Electron Ionization)splash10-03di-9000000000-5338ff8a9c4e59150abaView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Colostrum
  • Fibroblasts
  • Intestine
  • Kidney
  • Milk
  • Muscle
  • Neuron
  • Prostate Tissue
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FibroblastsExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
MilkDetected and Quantified37 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified34.9 +/- 0.2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified24 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified27 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified33 +/- 5 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified37 +/- 2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified41 +/- 3 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified52.55 +/- 6.31 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified42 +/- 4 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified56.75 +/- 5.46 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified21.84 +/- 3.36 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified20.16 +/- 5.04 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified46.08 +/- 0.72 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified31780.262 +/- 12485.103 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified44.606 +/- 0.76 uMNot SpecifiedNot Specified
Normal
    • Catrienus De Jong...
details
MilkDetected and Quantified43.93 +/- 16.09 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified6923.55 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified5675.04 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified35.91 +/- 16.47 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified1135.00808 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified2724.0194 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified17138.641 +/- 2724.0225 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MilkDetected and Quantified1135.00808 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified16798.139 +/- 2837.523 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MilkDetected and Quantified13393.0953 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified14641.6 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified12485.09 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
    • Lawrence K. Cream...
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
    • Lawrence K. Cream...
details
MilkDetected and Quantified0.9 (0.7 - 1.2) uMNot SpecifiedNot Specified
Normal
    • Harper, W. J., Go...
details
MilkDetected and Quantified0.8 (0.6 - 1.1) uMNot SpecifiedNot Specified
Normal
    • Harper, W. J., Go...
details
MilkDetected and Quantified29.22 +/- 5.72 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified1.2 (0.8 - 2.4) uMNot SpecifiedNot Specified
Normal
    • Harper, W. J., Go...
details
MilkDetected and Quantified5.6 (2.4 - 9.6) uMNot SpecifiedNot Specified
Normal
    • Harper, W. J., Go...
details
NeuronExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified7000-13000 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified10519-17242 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified689 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified642 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified19300 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified7970 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified25848+/-9273 uMNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
    • Hanne Christine B...
details
Ruminal FluidDetected and Quantified9386.24 +/- 1366.99 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified8100 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified8030 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified15130 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified9380 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified8100 +/- 1350 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified8103 +/- 1631 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified15131 +/- 2957 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified9386 +/- 1367 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
ColostrumDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Commercial Product/bacterial growth on ground beef
details
MuscleDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Commercial Product/bacterial growth on ground beef
details
Ruminal FluidDetected and Quantified15131.93 +/- 2863.24 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
details
HMDB IDHMDB0000039
DrugBank IDDB03568
Phenol Explorer Compound IDNot Available
FooDB IDFDB031031
KNApSAcK IDC00001180
Chemspider ID259
KEGG Compound IDC00246
BioCyc IDBUTYRIC_ACID
BiGG ID34376
Wikipedia LinkButyric_acid
METLIN ID107
PubChem Compound264
PDB IDNot Available
ChEBI ID30772
References
Synthesis ReferenceShan, Zhiping. Preparation of butyric acid by hydrogenation of maleic anhydride. U.S. Pat. Appl. Publ. (2008), 6pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. [PubMed:16899705 ]
  2. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
  3. Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
  4. Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22. [PubMed:23182357 ]
  5. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
  6. Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
  7. Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
  8. GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]
  9. Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
  10. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  11. Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]
  12. van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
  13. M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
  14. Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.
  15. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
  16. Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities as an acyl carrier protein.
Gene Name:
FASN
Uniprot ID:
Q71SP7
Molecular weight:
274554.0
Reactions
But-2-enoic acid → Butyric aciddetails
Butyric acid + Malonic acid → 3-Oxohexanoic aciddetails