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Tributyrin

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Tributyrin
Skeletal formula of butyrin
Ball-and-stick model of the butyrin molecule
Names
Systematic IUPAC name
Propane-1,2,3-triyl tributanoate
Other names
Tributyrin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.410 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C15H26O6/c1-4-7-13(16)19-10-12(21-15(18)9-6-3)11-20-14(17)8-5-2/h12H,4-11H2,1-3H3
    Key: UYXTWWCETRIEDR-UHFFFAOYSA-N
  • CCCC(=O)OCC(COC(=O)CCC)OC(=O)CCC
Properties
C15H26O6
Molar mass 302.367 g·mol−1
Appearance Oily liquid with bitter taste[1]
Density 1.032 g/cm3[1]
Melting point −75 °C (−103 °F; 198 K)[1]
Boiling point 305 to 310 °C (581 to 590 °F; 578 to 583 K)[1]
Insoluble[1]
Hazards
Safety data sheet (SDS) Tributyrin MSDS, Fischer Scientific
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tributyrin is a triglyceride naturally present in butter. It is an ester composed of butyric acid and glycerol.[1] Among other things, it is used as an ingredient in making margarine. It is present in butter and can be described as a liquid fat with an acrid taste.

Tributyrin is also used in microbiological laboratories to identify the bacterium Moraxella catarrhalis. [2]

Tributyrin is a stable and rapidly absorbed prodrug of butyric acid which enhances antiproliferative effects of dihydroxycholecalciferol in human colon cancer cells.[3]

References

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  1. ^ a b c d e f Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123
  2. ^ Pérez, José L.; Angeles Pulido; Florencia Pantozzi; Rogelio Martin (October 1990). "Butyrate esterase (4-methylumbelliferyl butyrate) spot test, a simple method for immediate identification of Moraxella (Branhamella) catarrhalis corrected" (PDF Reprint). Journal of Clinical Microbiology. 28 (10). Washington, DC: American Society for Microbiology: 2347–2348. doi:10.1128/jcm.28.10.2347-2348.1990. ISSN 1098-660X. PMC 268174. PMID 2121784.
  3. ^ Gaschott, Tanja; Dieter Steinhilber; Vladan Milovic; Jürgen Stein (June 2001). "Tributyrin, a Stable and Rapidly Absorbed Prodrug of Butyric Acid, Enhances Antiproliferative Effects of Dihydroxycholecalciferol in Human Colon Cancer Cells". The Journal of Nutrition. 131 (6). Bethesda, MD: The American Society for Nutritional Sciences: 1839–1843. doi:10.1093/jn/131.6.1839. ISSN 1541-6100. PMID 11385076. Retrieved 2009-08-17.