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Bovine Rumen Metabolome Database



Showing metabocard for Butyric acid (RMDB00039)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:39
Accession Number RMDB00039
Common Name Butyric acid
Description Butyric acid, a four-carbon fatty acid, is formed in the human 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 humans, 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.
Synonyms
  1. 1-Butyrate
  2. 1-Butyric acid
  3. 1-Propanecarboxylate
  4. 1-Propanecarboxylic acid
  5. 1-butanoate
  6. 1-butanoic acid
  7. Butanate
  8. Butanic acid
  9. Butanoate
  10. Butanoic acid
  11. Buttersaeure
  12. Butyrate
  13. Ethylacetate
  14. Ethylacetic acid
  15. Honey robber
  16. Kyselina maselna
  17. Propanecarboxylate
  18. Propanecarboxylic acid
  19. Propylformate
  20. Propylformic acid
  21. butyric acid
  22. n-Butanoate
  23. n-Butanoic acid
  24. n-Butyrate
  25. n-Butyric acid
Chemical IUPAC Name Butanoic acid
Chemical Formula C4H8O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Fatty Acids
Sub Class
  • Short chain fatty acids
Family
  • Microbial_Metabolite
Species
  • carboxylic acid
Biofunction
  • Energy source; DNA component
Application
Source
  • Endogenous
Average Molecular Weight 88.105
Monoisotopic Molecular Weight 88.052429
Isomeric SMILES CCCC(O)=O
Canonical SMILES CCCC(O)=O
KEGG Compound ID C00246 Link Image
BioCyc ID Not Available
BiGG ID 34376 Link Image
Wikipedia Link Butyric acid Link Image
METLIN ID 107 Link Image
PubChem Compound 264 Link Image
PubChem Substance 3545 Link Image
ChEBI ID 30772 Link Image
CAS Registry Number 107-92-6
InChI Identifier InChI=1/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
Synthesis Reference Shan, Zhiping. Preparation of butyric acid by hydrogenation of maleic anhydride. U.S. Pat. Appl. Publ. (2008), 6pp.
Melting Point (Experimental) -5.7 oC
Experimental Water Solubility 60.0 mg/mL [HEMPHILL,L & SWANSON,WS (1964)] Source: PhysProp
Predicted Water Solubility 239.00002 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Liquid
Experimental LogP/Hydrophobicity 0.79 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity 0.78 [Predicted by ALOGPS]; 0.7 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
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High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • Extracellular
  • mitochondria
Biofluid Location
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 9386.24 +/- 1366.99 uM
Age 4-5 years old
Sex Female (lactating)
Condition Normal (0% barley grain in dry matter (DM) basis)
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 64.7 +/- 12.0 uM
Age N/A
Sex Female
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Burim N. Ametaj, Qendrim Zebeli, Fozia Saleem, Nikolaos Psychogios, Michael J. Lewis, Suzanna M. Dunn, Jianguo Xia and David S. Wishart Metabolomics 2010;6(4):583-594
Concentrations (Abnormal)
Biofluid Rumen
Value 8100 +/- 1350 uM
Age 4-5 years old
Sex Female (lactating)
Condition 15% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 8103+/- 1631 uM
Age 4-5 years old
Sex Female (lactating)
Condition 30% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 15131 +/- 2957 uM
Age 4-5 years old
Sex Female (lactating)
Condition 45% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image