Record Information |
---|
Version | 2.0 |
---|
Creation Date | 2014-09-05 17:11:48 UTC |
---|
Update Date | 2014-12-24 20:26:53 UTC |
---|
Accession Number | T3D4592 |
---|
Identification |
---|
Common Name | Butyric acid |
---|
Class | Small Molecule |
---|
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. (19) 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. |
---|
Compound Type | - Animal Toxin
- Food Toxin
- Metabolite
- Natural Compound
- Organic Compound
|
---|
Chemical Structure | |
---|
Synonyms | Synonym | 1-Butanoate | 1-Butanoic acid | 1-Butyrate | 1-Butyric acid | 1-Propanecarboxylate | 1-Propanecarboxylic acid | Butanate | Butanic acid | Butanoate | Butanoic acid | Buttersaeure | Butyrate | Ethylacetate | Ethylacetic acid | Honey robber | Kyselina maselna | N-Butanoate | N-Butanoic acid | N-Butyrate | N-Butyric acid | Propanecarboxylate | Propanecarboxylic acid | Propylformate | Propylformic acid |
|
---|
Chemical Formula | C4H8O2 |
---|
Average Molecular Mass | 88.105 g/mol |
---|
Monoisotopic Mass | 88.052 g/mol |
---|
CAS Registry Number | 107-92-6 |
---|
IUPAC Name | butanoic acid |
---|
Traditional Name | butyric acid |
---|
SMILES | CCCC(O)=O |
---|
InChI Identifier | InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6) |
---|
InChI Key | InChIKey=FERIUCNNQQJTOY-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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Fatty Acyls |
---|
Sub Class | Fatty acids and conjugates |
---|
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 | |
---|
Biological Properties |
---|
Status | Detected and Not Quantified |
---|
Origin | Endogenous |
---|
Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
- Mitochondria
|
---|
Biofluid Locations | Not Available |
---|
Tissue Locations | - Fibroblasts
- Intestine
- Kidney
- Large Intestine
- Muscle
- Neuron
- Prostate
|
---|
Pathways | Not Available |
---|
Applications | Not Available |
---|
Biological Roles | Not Available |
---|
Chemical Roles | Not Available |
---|
Physical Properties |
---|
State | Liquid |
---|
Appearance | Not Available |
---|
Experimental Properties | Property | Value |
---|
Melting Point | -5.7°C | Boiling Point | 163.7°C | Solubility | 6E+004 mg/L (at 25°C) | LogP | 0.79 |
|
---|
Predicted Properties | |
---|
Spectra |
---|
Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
---|
GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1 | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-03dl-9000000000-032fc35b394786b5896a | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1 | 2018-05-18 | View Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-03dl-9000000000-032fc35b394786b5896a | 2018-05-18 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-002f-9000000000-a7792b54320e7c859731 | 2016-09-22 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00fr-9100000000-d125b331c4a6d37648a1 | 2017-10-06 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-000i-9000000000-7f461db56bfd8568ec71 | 2012-07-24 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-000i-9000000000-66f857fa612f773837bc | 2012-07-24 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-000i-9000000000-e6689b2e6bf21570b934 | 2012-07-24 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-03dl-9000000000-b2ffa7d67b2466dea94f | 2012-08-31 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-03dl-9000000000-7467bf19c64fd3f51105 | 2012-08-31 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-000i-9000000000-9ae015043b014b3c93d9 | 2012-08-31 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-000i-9000000000-e30b3c6bd6218b9b49e1 | 2012-08-31 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-000i-9000000000-efbb0e35a19a1713240b | 2012-08-31 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9000000000-9ae015043b014b3c93d9 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9000000000-e30b3c6bd6218b9b49e1 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9000000000-efbb0e35a19a1713240b | 2017-09-14 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-9000000000-acb5cf0017a9ee680dd8 | 2015-05-26 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dl-9000000000-812e24462a71dccb0fec | 2015-05-26 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-f9d30338ca1ee9409964 | 2015-05-26 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9000000000-9d749b6b6cf2f93a8f85 | 2015-05-27 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00ku-9000000000-ee742730266fb4997777 | 2015-05-27 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-88fc445cddcb726e93d8 | 2015-05-27 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9000000000-4b3590a18d40d4d58a01 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014r-9000000000-140190568a3f2b3c6f01 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kf-9000000000-1f7dab1fbd0179ef6d17 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00dl-9000000000-020fcfb652dc5a6f3036 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9000000000-3e4b1bc1291a3fbf86c9 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-1f57e9adb6de1499caf5 | 2021-09-22 | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-03di-9000000000-5338ff8a9c4e59150aba | 2014-09-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Not Available | 2012-12-04 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | Not Available | 2012-12-04 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | Not Available | 2014-09-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental) | Not Available | 2014-09-23 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | Not Available | 2016-10-22 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | Not Available | 2016-10-22 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Not Available | 2012-12-04 | View Spectrum |
|
---|
Toxicity Profile |
---|
Route of Exposure | Not Available |
---|
Mechanism of Toxicity | Butyric acid is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen. |
---|
Metabolism | Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of OP exposure. |
---|
Toxicity Values | Not Available |
---|
Lethal Dose | Not Available |
---|
Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
---|
Uses/Sources | This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation. |
---|
Minimum Risk Level | Not Available |
---|
Health Effects | Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides. |
---|
Symptoms | Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result. |
---|
Treatment | If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally. |
---|
Normal Concentrations |
---|
| Not Available |
---|
Abnormal Concentrations |
---|
| Not Available |
---|
External Links |
---|
DrugBank ID | DB03568 |
---|
HMDB ID | HMDB00039 |
---|
PubChem Compound ID | 264 |
---|
ChEMBL ID | CHEMBL14227 |
---|
ChemSpider ID | 259 |
---|
KEGG ID | C00246 |
---|
UniProt ID | Not Available |
---|
OMIM ID | |
---|
ChEBI ID | 30772 |
---|
BioCyc ID | Not Available |
---|
CTD ID | Not Available |
---|
Stitch ID | Not Available |
---|
PDB ID | BUA |
---|
ACToR ID | Not Available |
---|
Wikipedia Link | Butyric acid |
---|
References |
---|
Synthesis Reference | Haruhiko Kikuchi, “Process for preparing 4-(4-biphenylyl)-4-oxo-butanoic acid.” U.S. Patent US4621154, issued November, 1977. |
---|
MSDS | Link |
---|
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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [11953371 ]
- Jacobasch G, Jacobasch KH: [Molecular etiology of colorectal carcinogenesis, clinical manifestations and therapy]. Z Arztl Fortbild Qualitatssich. 1997 Mar;91(2):125-33. [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. [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. [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. [9071566 ]
- Sengupta S, Muir JG, Gibson PR: Does butyrate protect from colorectal cancer? J Gastroenterol Hepatol. 2006 Jan;21(1 Pt 2):209-18. [16460475 ]
|
---|
Gene Regulation |
---|
Up-Regulated Genes | Not Available |
---|
Down-Regulated Genes | Not Available |
---|