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Record Information
Version1.0
Creation Date2016-07-13 19:40:27 UTC
Update Date2016-09-23 18:44:28 UTC
LmdbLMDB00013
Secondary Accession NumbersNone
Metabolite Identification
Common NameButyric acid
DescriptionButyric acid, a four-carbon fatty acid, is formed in the animal colon by bacterial fermentation of carbohydrates (including dietary fiber), and putatively suppresses colorectal cancer (CRC). Butyrate has diverse and apparently paradoxical effects on cellular proliferation, apoptosis and differentiation that may be either pro-neoplastic or anti-neoplastic, depending upon factors such as the level of exposure, availability of other metabolic substrate and the intracellular milieu. In animals, the relationship between luminal butyrate exposure and CRC has been examined only indirectly in case-control studies, by measuring fecal butyrate concentrations, although this may not accurately reflect effective butyrate exposure during carcinogenesis. Perhaps not surprisingly, results of these investigations have been mutually contradictory. The direct effect of butyrate on tumorigenesis has been assessed in a no. of in vivo animal models, which have also yielded conflicting results. In part, this may be explained by methodology: differences in the amount and route of butyrate administration, which are likely to significantly influence delivery of butyrate to the distal colon. (PMID: 16460475 ) Butyric acid is a carboxylic acid found in rancid butter, parmesan cheese, and vomit, and has an unpleasant odor and acrid taste, with a sweetish aftertaste (similar to ether). Butyric acid is a fatty acid occurring in the form of esters in animal fats and plant oils. Interestingly, low-molecular-weight esters of butyric acid, such as methyl butyrate, have mostly pleasant aromas or tastes. As a consequence, they find use as food and perfume additives. Butyrate is produced as end-product of a fermentation process solely performed by obligate anaerobic bacteria.
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
1-ButanoateGenerator
ButyrateGenerator
1-ButyrateGenerator
1-PropanecarboxylateGenerator
ButanateGenerator
ButoateGenerator
EthylacetateGenerator
N-ButanoateGenerator
N-ButyrateGenerator
PropanecarboxylateGenerator
PropylformateGenerator
Honey robberHMDB
Kyselina maselnaHMDB
Butyrate, magnesiumMeSH
Magnesium butyrateMeSH
Acid, butyricMeSH
Butyrate, sodiumMeSH
Dibutyrate, magnesiumMeSH
Magnesium dibutyrateMeSH
Sodium butyrateMeSH
Acid, butanoicMeSH
Butyric acid magnesium saltMeSH
Butyric acid, sodium saltMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity21.87 m3·mol-1ChemAxon
Polarizability9.22 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - EI-Bsplash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-03dl-9000000000-032fc35b394786b5896aView 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
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 Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Colostrum
  • Feces
  • Meat
  • Milk
  • Plasma
  • Rumen
  • Ruminal Fluid
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
FecesDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
MeatDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableOvine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableEquine details
MilkDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableOvine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Lawrence K. Cream...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableOvine
    • Park, Y. W; Juáre...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • Park, Y. W; Juáre...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Lawrence K. Cream...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • H. Steinshamn, R....
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • H. Steinshamn, R....
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • H. Steinshamn, R....
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • H. Steinshamn, R....
details
MilkDetected and Quantified11.8 mol/100 molNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
RumenDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Hanne Christine B...
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine details
Ruminal FluidDetected and Quantified10800 +/- 1100 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified8040 +/- 600 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified9780 +/- 500 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified5350 uMNot AvailableCaprine details
Ruminal FluidDetected and Quantified8790 uMNot AvailableCaprine details
Ruminal FluidDetected and Quantified10710 uMNot AvailableCaprine details
Ruminal FluidDetected and Quantified11600 +/- 1500 uMNot AvailableCaprine details
Ruminal FluidDetected and Quantified15,131 +/- 2,957 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified7,400 +/- 800 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified8,100 +/- 1,350 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified8,103 +/- 1,631 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified9,386 +/- 1,367 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified9,386 +/- 1,367 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified8030 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified8100 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified9380 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified15130 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified6420 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified6890 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified7970 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified19300 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified70000 uMNot AvailableOvine
    • M.L.K. Bonsi, P.O...
details
Ruminal FluidDetected and Quantified70000-81000 uMNot AvailableOvine
    • M.L.K. Bonsi, P.O...
details
Ruminal FluidDetected and Quantified72000-82000 uMNot AvailableOvine
    • M.L.K. Bonsi, P.O...
details
DrugBank IDDB03568
HMDB IDHMDB00039
FooDB IDFDB012062
Phenol Explorer IDNot Available
KNApSAcK IDC00001180
BiGG ID34376
BioCyc IDBUTYRIC_ACID
METLIN ID107
PDB IDBUA
Wikipedia LinkButyric_acid
Chemspider ID259
ChEBI ID30772
PubChem Compound ID264
Kegg Compound IDC00246
YMDB IDNot Available
ECMDB IDECMDB00039
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sengupta S, Muir JG, Gibson PR: Does butyrate protect from colorectal cancer? J Gastroenterol Hepatol. 2006 Jan;21(1 Pt 2):209-18. [16460475 ]