You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
| Record Information |
|---|
| Version | 3.6 |
|---|
| Creation Date | 2005-11-16 15:48:42 UTC |
|---|
| Update Date | 2017-03-02 21:25:35 UTC |
|---|
| HMDB ID | HMDB00039 |
|---|
| Secondary Accession Numbers | None |
|---|
| Metabolite Identification |
|---|
| 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. |
|---|
| Structure | |
|---|
| Synonyms | | Value | Source |
|---|
| 1-Butanoic acid | ChEBI | | 1-Butyric acid | ChEBI | | 1-Propanecarboxylic acid | ChEBI | | 4:0 | ChEBI | | Acide butanoique | ChEBI | | Acide butyrique | ChEBI | | Butanic acid | ChEBI | | Butanoate | ChEBI | | Butanoic acid | ChEBI | | Butoic acid | ChEBI | | Buttersaeure | ChEBI | | C4:0 | ChEBI | | CH3-[CH2]2-COOH | ChEBI | | Ethylacetic acid | ChEBI | | N-Butanoic acid | ChEBI | | N-Butyric acid | ChEBI | | Propanecarboxylic acid | ChEBI | | Propylformic acid | ChEBI | | 1-Butanoate | Generator | | Butyrate | Generator | | 1-Butyrate | Generator | | 1-Propanecarboxylate | Generator | | Butanate | Generator | | Butoate | Generator | | Ethylacetate | Generator | | N-Butanoate | Generator | | N-Butyrate | Generator | | Propanecarboxylate | Generator | | Propylformate | Generator | | Honey robber | HMDB | | Kyselina maselna | HMDB | | Butyrate, magnesium | MeSH | | Magnesium butyrate | MeSH | | Acid, butyric | MeSH | | Butyrate, sodium | MeSH | | Dibutyrate, magnesium | MeSH | | Magnesium dibutyrate | MeSH | | Sodium butyrate | MeSH | | Acid, butanoic | MeSH | | Butyric acid magnesium salt | MeSH | | Butyric acid, sodium salt | MeSH |
|
|---|
| Chemical Formula | C4H8O2 |
|---|
| Average Molecular Weight | 88.1051 |
|---|
| Monoisotopic Molecular Weight | 88.0524295 |
|---|
| IUPAC Name | butanoic acid |
|---|
| Traditional Name | butyric acid |
|---|
| CAS Registry Number | 107-92-6 |
|---|
| SMILES | CCCC(O)=O |
|---|
| InChI Identifier | InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6) |
|---|
| InChI Key | FERIUCNNQQJTOY-UHFFFAOYSA-N |
|---|
| Chemical Taxonomy |
|---|
| Description | This compound belongs to the class of chemical entities known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. |
|---|
| Kingdom | Chemical entities |
|---|
| Super Class | Organic compounds |
|---|
| Class | Lipids and lipid-like molecules |
|---|
| Sub Class | Fatty Acyls |
|---|
| Direct Parent | Straight 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 Framework | Aliphatic acyclic compounds |
|---|
| External Descriptors | |
|---|
| Ontology |
|---|
| Status | Detected and Quantified |
|---|
| Origin | |
|---|
| Biofunction | - Cell signaling
- DNA component
- Energy source
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
|
|---|
| Application | - Nutrients
- Stabilizers
- Surfactants and Emulsifiers
|
|---|
| Cellular locations | - Cytoplasm
- Extracellular
- Membrane
- Mitochondria
|
|---|
| Physical Properties |
|---|
| State | Liquid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | -5.7 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 60.0 mg/mL | Not Available | | LogP | 0.79 | HANSCH,C ET AL. (1995) |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | | Spectrum Type | Description | Splash Key | |
|---|
| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS | Not Available |
|---|
| GC-MS | GC-MS Spectrum - EI-B | splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1 | View in MoNA |
|---|
| GC-MS | GC-MS Spectrum - EI-B | splash10-03dl-9000000000-032fc35b394786b5896a | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-000i-9000000000-7f461db56bfd8568ec71 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-000i-9000000000-66f857fa612f773837bc | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-000i-9000000000-e6689b2e6bf21570b934 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-03dl-9000000000-b2ffa7d67b2466dea94f | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-03dl-9000000000-7467bf19c64fd3f51105 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-000i-9000000000-9ae015043b014b3c93d9 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-000i-9000000000-e30b3c6bd6218b9b49e1 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-000i-9000000000-efbb0e35a19a1713240b | View in MoNA |
|---|
| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-9000000000-acb5cf0017a9ee680dd8 | View in MoNA |
|---|
| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dl-9000000000-812e24462a71dccb0fec | View in MoNA |
|---|
| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-f9d30338ca1ee9409964 | View in MoNA |
|---|
| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9000000000-9d749b6b6cf2f93a8f85 | View in MoNA |
|---|
| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00ku-9000000000-ee742730266fb4997777 | View in MoNA |
|---|
| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-88fc445cddcb726e93d8 | View in MoNA |
|---|
| MS | Mass Spectrum (Electron Ionization) | splash10-03di-9000000000-5338ff8a9c4e59150aba | View in MoNA |
|---|
| 1D NMR | 1H NMR Spectrum | Not Available |
|---|
| 1D NMR | 13C NMR Spectrum | Not Available |
|---|
| 1D NMR | 1H NMR Spectrum | Not Available |
|---|
| 1D NMR | 13C NMR Spectrum | Not Available |
|---|
| 1D NMR | 1H NMR Spectrum | Not Available |
|---|
| 1D NMR | 13C NMR Spectrum | Not Available |
|---|
| 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available |
|---|
|
|---|
| Biological Properties |
|---|
| Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
- Mitochondria
|
|---|
| Biofluid Locations | - Blood
- Breast Milk
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
- Urine
|
|---|
| Tissue Location | - Fibroblasts
- Intestine
- Kidney
- Large Intestine
- Muscle
- Neuron
- Prostate
|
|---|
| Pathways | |
|---|
| Normal Concentrations |
|---|
| |
| Blood | Detected and Quantified | 1.0 (0.3- 1.5) uM | Adult (>18 years old) | Both | Normal | | details | | Breast Milk | Detected and Quantified | 192 +/- 149 uM | Adult (>18 years old) | Female | Normal | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 1.4 (0-2.8) uM | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Not Specified | Not Specified | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Infant (0-1 year old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected and Quantified | 6350 +/- 3130 nmol/g of feces | Adult (>18 years old) | Female | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Newborn (0-30 days old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected and Quantified | 0 - 15.01 ppm | Children (1-13 years old) | Not Specified | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Not Specified | Not Specified | Normal | | details | | Saliva | Detected and Quantified | 80 +/- 120 uM | Adult (>18 years old) | Both | Normal | | details | | Saliva | Detected and Quantified | 130 +/- 250 uM | Adult (>18 years old) | Both | Normal | | details | | Saliva | Detected and Quantified | 130 +/- 270 uM | Adult (>18 years old) | Both | Normal | | details | | Saliva | Detected and Quantified | 110 +/- 300 uM | Adult (>18 years old) | Both | Normal | | details | | Saliva | Detected and Quantified | 12.5 +/- 8.39 uM | Adult (>18 years old) | Both | Normal | | details | | Saliva | Detected and Quantified | 13.3 +/- 12.8 uM | Adult (>18 years old) | Not Specified | Normal | | details | | Saliva | Detected and Quantified | 110 +/- 310 uM | Adult (>18 years old) | Both | Normal | | details | | Saliva | Detected and Quantified | 170 +/- 600 uM | Adult (>18 years old) | Both | Normal | | details | | Saliva | Detected and Quantified | 18.3 +/- 13.0 uM | Adult (>18 years old) | Not Specified | Normal | | details | | Saliva | Detected and Quantified | 70 +/- 140 uM | Adult (>18 years old) | Both | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Not Specified | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Saliva | Detected and Quantified | 277.27 +/- 199.47 uM | Adult (>18 years old) | Both | Normal | | details | | Saliva | Detected and Quantified | 1470 (0.00-2940) uM | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 1.6 (0.5-4.0) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 0.131 +/- 0.013 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 3.2 (0.0-6.4) umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | | Urine | Detected and Quantified | 42.0 (21.0-81.0) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 4.002 +/- 2.176 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details |
|
|---|
| Abnormal Concentrations |
|---|
| |
| Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Campylobacter jejuni infection | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Clostridium difficile infection | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Ulcerative Colitis | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Irritable bowel syndrome | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Ulcerative colitis | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Crohn’s Disease | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Ulcerative Colitis | | details | | Feces | Detected and Quantified | 0 - 39.39 ppm | Children (1-13 years old) | Not Specified | Treated celiac disease | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Nonalcoholic fatty liver disease (NAFLD) | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | | Saliva | Detected and Quantified | 20.5 +/- 16.5 uM | Adult (>18 years old) | Both | Dental caries | | details | | Urine | Detected and Quantified | 0.18 +/- 0.044 umol/mmol creatinine | Adult (>18 years old) | Both | AIDS | | details | | Urine | Detected and Quantified | 4.256 +/- 3.945 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details |
|
|---|
| Associated Disorders and Diseases |
|---|
| Disease References | | AIDS |
|---|
- Stein TP, Koerner B, Schluter MD, Leskiw MJ, Gaprindachvilli T, Richards EW, Cope FO, Condolucci D: Weight loss, the gut and the inflammatory response in aids patients. Cytokine. 1997 Feb;9(2):143-7. [PubMed:9071566 ]
|
|
|---|
| Associated OMIM IDs | None |
|---|
| External Links |
|---|
| DrugBank ID | DB03568 |
|---|
| DrugBank Metabolite ID | Not Available |
|---|
| Phenol Explorer Compound ID | Not Available |
|---|
| Phenol Explorer Metabolite ID | Not Available |
|---|
| FoodDB ID | FDB012062 |
|---|
| KNApSAcK ID | C00001180 |
|---|
| Chemspider ID | 259 |
|---|
| KEGG Compound ID | C00246 |
|---|
| BioCyc ID | Not Available |
|---|
| BiGG ID | 34376 |
|---|
| Wikipedia Link | Butyric acid |
|---|
| NuGOwiki Link | HMDB00039 |
|---|
| Metagene Link | HMDB00039 |
|---|
| METLIN ID | 107 |
|---|
| PubChem Compound | 264 |
|---|
| PDB ID | BUA |
|---|
| ChEBI ID | 30772 |
|---|
| References |
|---|
| Synthesis Reference | Shan, Zhiping. Preparation of butyric acid by hydrogenation of maleic anhydride. U.S. Pat. Appl. Publ. (2008), 6pp. |
|---|
| Material Safety Data Sheet (MSDS) | Download (PDF) |
|---|
| General References | - McMillan L, Butcher SK, Pongracz J, Lord JM: Opposing effects of butyrate and bile acids on apoptosis of human colon adenoma cells: differential activation of PKC and MAP kinases. Br J Cancer. 2003 Mar 10;88(5):748-53. [PubMed:12618885 ]
- Bauer G: Induction of Epstein-Barr virus early antigens by corticosteroids: inhibition by TPA and retinoic acid. Int J Cancer. 1983 Mar 15;31(3):291-5. [PubMed:6826253 ]
- Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
- McIntosh GH, Noakes M, Royle PJ, Foster PR: Whole-grain rye and wheat foods and markers of bowel health in overweight middle-aged men. Am J Clin Nutr. 2003 Apr;77(4):967-74. [PubMed:12663299 ]
- Schwiertz A, Lehmann U, Jacobasch G, Blaut M: Influence of resistant starch on the SCFA production and cell counts of butyrate-producing Eubacterium spp. in the human intestine. J Appl Microbiol. 2002;93(1):157-62. [PubMed:12067385 ]
- Bauer G, Hofler P, Simon M: Epstein-Barr virus induction by a serum factor. Characterization of the purified factor and the mechanism of its activation. J Biol Chem. 1982 Oct 10;257(19):11411-5. [PubMed:6288683 ]
- Jin SE, Ban E, Kim YB, Kim CK: Development of HPLC method for the determination of levosulpiride in human plasma. J Pharm Biomed Anal. 2004 Jun 29;35(4):929-36. [PubMed:15193738 ]
- Welters CF, Heineman E, Thunnissen FB, van den Bogaard AE, Soeters PB, Baeten CG: Effect of dietary inulin supplementation on inflammation of pouch mucosa in patients with an ileal pouch-anal anastomosis. Dis Colon Rectum. 2002 May;45(5):621-7. [PubMed:12004211 ]
- Kurita-Ochiai T, Seto S, Ochiai K: Role of cell-cell communication in inhibiting butyric acid-induced T-cell apoptosis. Infect Immun. 2004 Oct;72(10):5947-54. [PubMed:15385498 ]
- Cruz HG, Ivanova T, Lunn ML, Stoffel M, Slesinger PA, Luscher C: Bi-directional effects of GABA(B) receptor agonists on the mesolimbic dopamine system. Nat Neurosci. 2004 Feb;7(2):153-9. Epub 2004 Jan 25. [PubMed:14745451 ]
- Yonemura K, Sairenji T, Hinuma Y: Inhibitory effect of 1-beta-D-arabinofuranosylthymine on synthesis of Epstein-Barr virus. Microbiol Immunol. 1981;25(6):557-63. [PubMed:6268944 ]
- Teichert J, Tuemmers T, Achenbach H, Preiss C, Hermann R, Ruus P, Preiss R: Pharmacokinetics of alpha-lipoic acid in subjects with severe kidney damage and end-stage renal disease. J Clin Pharmacol. 2005 Mar;45(3):313-28. [PubMed:15703366 ]
- Rephaeli A, Blank-Porat D, Tarasenko N, Entin-Meer M, Levovich I, Cutts SM, Phillips DR, Malik Z, Nudelman A: In vivo and in vitro antitumor activity of butyroyloxymethyl-diethyl phosphate (AN-7), a histone deacetylase inhibitor, in human prostate cancer. Int J Cancer. 2005 Aug 20;116(2):226-35. [PubMed:15800932 ]
- Kurita-Ochiai T, Ochiai K, Suzuki N, Otsuka K, Fukushima K: Human gingival fibroblasts rescue butyric acid-induced T-cell apoptosis. Infect Immun. 2002 May;70(5):2361-7. [PubMed:11953371 ]
- Jacobasch G, Jacobasch KH: [Molecular etiology of colorectal carcinogenesis, clinical manifestations and therapy]. Z Arztl Fortbild Qualitatssich. 1997 Mar;91(2):125-33. [PubMed:9244653 ]
- Velazquez OC, Lederer HM, Rombeau JL: Butyrate and the colonocyte. Production, absorption, metabolism, and therapeutic implications. Adv Exp Med Biol. 1997;427:123-34. [PubMed:9361838 ]
- Kawanishi M, Ito Y: Effect of short-chain fatty acids on Epstein-Barr virus early and viral capsid antigen induction in P3HR-1 cells. Cancer Lett. 1980 Dec;11(2):129-32. [PubMed:6257378 ]
- Stein TP, Koerner B, Schluter MD, Leskiw MJ, Gaprindachvilli T, Richards EW, Cope FO, Condolucci D: Weight loss, the gut and the inflammatory response in aids patients. Cytokine. 1997 Feb;9(2):143-7. [PubMed:9071566 ]
- Sengupta S, Muir JG, Gibson PR: Does butyrate protect from colorectal cancer? J Gastroenterol Hepatol. 2006 Jan;21(1 Pt 2):209-18. [PubMed:16460475 ]
|
|---|