| Record Information |
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| Version | 2.0 |
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| Created at | 2005-11-16 15:48:42 UTC |
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| Updated at | 2023-09-28 21:29:20 UTC |
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| NP-MRD ID | NP0000892 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Butyric acid |
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| Description | Butyric acid is a short-chain fatty acid (SCFA) formed in the mammalian colon by bacterial fermentation of carbohydrates (including dietary fibre). It is a straight-chain alkyl carboxylic acid that appears as an oily, colorless liquid with an unpleasant (rancid butter) odor. The name butyric acid comes from the Greek word for "butter", the substance in which it was first found. Triglycerides of butyric acid constitute 3–4% of butter. When butter goes rancid, butyric acid is liberated from the short-chain triglycerides via hydrolysis. Butyric acid is a widely distributed SCFA and is found in all organisms ranging from bacteria to plants to animals. It is present in animal fat and plant oils, bovine milk, breast milk, butter, parmesan cheese, body odor and vomit. While butyric acid has an unpleasant odor, it does have a pleasant buttery taste. As a result, butyric acid is used as a flavoring agent in food manufacturing. Low-molecular-weight esters of butyric acid, such as methyl butyrate, also have very pleasant aromas or tastes. As a result, several butyrate esters are used as food and perfume additives. Butyrate is naturally produced by fermentation processes performed by obligate anaerobic bacteria found in the mammalian gut. It is a metabolite of several bacterial genera including Anaerostipes, Coprococcus, Eubacterium, Faecalibacterium and Roseburia (PMID: 12324374 ; PMID: 27446020 ). Highly-fermentable fiber residues, such as those from resistant starch, oat bran, pectin, and guar can be transformed by colonic bacteria into butyrate. One study found that resistant starch consistently produces more butyrate than other types of dietary fibre (PMID: 14747692 ). The production of butyrate from fibres in ruminant animals such as cattle is responsible for the butyrate content of milk and butter. Butyrate has a number of important biological functions and binds to several specific receptors. In humans, butyric acid is one of two primary endogenous agonists of human hydroxycarboxylic acid receptor 2 (HCA2), a G protein-coupled receptor. Like other SCFAs, butyrate is also an agonist at the free fatty acid receptors FFAR2 and FFAR3, which function as nutrient sensors that facilitate the homeostatic control of energy balance. Butyrate is essential to host immune homeostasis (PMID: 25875123 ). Butyrate's effects on the immune system are mediated through the inhibition of class I histone deacetylases (specifically, HDAC1, HDAC2, HDAC3, and HDAC8) and activation of its G-protein coupled receptor targets including HCA2, FFAR2 and FFAR3. Among the short-chain fatty acids, butyrate is the most potent promoter of intestinal regulatory T cells in vitro and the only SCFA that is an HCA2 ligand (PMID: 25741338 ). Butyrate has been shown to be a critical mediator of the colonic inflammatory response. It possesses both preventive and therapeutic potential to counteract inflammation-mediated ulcerative colitis and colorectal cancer. As a short-chain fatty acid, butyrate is metabolized by mitochondria as an energy source through fatty acid metabolism. In particular, it is an important energy source for cells lining the mammalian colon (colonocytes). Without butyrate, colon cells undergo autophagy (i.E., Self-digestion) and die. |
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| Structure | InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6) |
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| Synonyms | | Value | Source |
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| 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 | | Butyrate | Kegg | | 1-Butanoate | 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 | HMDB | | Magnesium butyrate | HMDB | | Acid, butyric | HMDB | | Butyrate, sodium | HMDB | | Dibutyrate, magnesium | HMDB | | Magnesium dibutyrate | HMDB | | Sodium butyrate | HMDB | | Acid, butanoic | HMDB | | Butyric acid magnesium salt | HMDB | | Butyric acid, sodium salt | HMDB | | FA(4:0) | HMDB | | Butyric acid | KEGG |
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| Chemical Formula | C4H8O2 |
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| Average Mass | 88.1051 Da |
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| Monoisotopic Mass | 88.05243 Da |
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| IUPAC Name | butanoic acid |
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| Traditional Name | butyric acid |
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| CAS Registry Number | 107-92-6 |
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| SMILES | CCCC(O)=O |
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| InChI Identifier | InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6) |
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| InChI Key | FERIUCNNQQJTOY-UHFFFAOYSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-05-31 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Fatty Acyls |
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| Sub Class | Fatty acids and conjugates |
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| Direct Parent | Straight chain fatty acids |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Liquid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| 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 ]
- 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 ]
- Duncan SH, Barcenilla A, Stewart CS, Pryde SE, Flint HJ: Acetate utilization and butyryl coenzyme A (CoA):acetate-CoA transferase in butyrate-producing bacteria from the human large intestine. Appl Environ Microbiol. 2002 Oct;68(10):5186-90. doi: 10.1128/AEM.68.10.5186-5190.2002. [PubMed:12324374 ]
- Riviere A, Selak M, Lantin D, Leroy F, De Vuyst L: Bifidobacteria and Butyrate-Producing Colon Bacteria: Importance and Strategies for Their Stimulation in the Human Gut. Front Microbiol. 2016 Jun 28;7:979. doi: 10.3389/fmicb.2016.00979. eCollection 2016. [PubMed:27446020 ]
- Lupton JR: Microbial degradation products influence colon cancer risk: the butyrate controversy. J Nutr. 2004 Feb;134(2):479-82. doi: 10.1093/jn/134.2.479. [PubMed:14747692 ]
- Kasubuchi M, Hasegawa S, Hiramatsu T, Ichimura A, Kimura I: Dietary gut microbial metabolites, short-chain fatty acids, and host metabolic regulation. Nutrients. 2015 Apr 14;7(4):2839-49. doi: 10.3390/nu7042839. [PubMed:25875123 ]
- Onyszkiewicz M, Gawrys-Kopczynska M, Konopelski P, Aleksandrowicz M, Sawicka A, Kozniewska E, Samborowska E, Ufnal M: Butyric acid, a gut bacteria metabolite, lowers arterial blood pressure via colon-vagus nerve signaling and GPR41/43 receptors. Pflugers Arch. 2019 Dec;471(11-12):1441-1453. doi: 10.1007/s00424-019-02322-y. Epub 2019 Nov 15. [PubMed:31728701 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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