Glycerol tributyrate

Structural formula
General
Surname	Glycerol tributyrate
other names	1,2,3-propanetriyl tributanoate ( IUPAC ) ; Tributyrin; Glycerol tributyrate; Glycerol tributyrate; 1,2,3-tributyryl glycerol;
Molecular formula	C 15 H 26 O 6
Brief description	colorless, bitter-tasting liquid
External identifiers / databases
EC number	200-451-5
ECHA InfoCard	100,000,410
PubChem	6050
ChemSpider	13849665
DrugBank	DB12709
Wikidata	Q4116129
properties
Molar mass	302.36 g mol −1
Physical state	liquid
density	1.032 g cm −3 (20 ° C)
Melting point	−75 ° C
boiling point	305-310 ° C; 190 ° C (20 hPa)
solubility	Slightly soluble in water, readily soluble in ethanol , diethyl ether and acetone
Refractive index	1.435 (20 ° C)
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	3200 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Tributyrin (systematically Tributansäureglycerolester, common name tributyrin ) is formed by esterification of the trihydric alcohol glycerol (propane-1,2,3-triol) and butyric acid . It therefore belongs to the group of fats and fatty oils.

properties

Tributyrin is an oily, colorless liquid with a bitter taste. The ester is insoluble in water but dissolves in acetone , benzene , diethyl ether and ethanol .

Physiological properties

In the gastrointestinal tract, glycerol tributyrate is enzymatically split into glycerol and butyric acid; The carboxylic acid is necessary for nutrition and for the protection of intestinal epithelial cells and for the rebuilding of changed cells. Furthermore, butyric acid inhibits gastric and colon cancer cells in vitro .

Manufacturing

Tributyrin is made by esterifying butyric acid with glycerin.

use

The ester is used as a plasticizer , as an emulsifier and as a feed additive , in pharmaceutical and medical materials and as a starting material for partial transesterification with long-chain fatty acids to form fat substitutes ( salatrim ).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on glycerol tributyrate. In: Römpp Online . Georg Thieme Verlag, accessed on July 27, 2014.
↑ ^a ^b ^c ^d data sheet Glyceryl tributyrate, ≥99% from Sigma-Aldrich , accessed on February 1, 2013 ( PDF ).
↑ T. Gaschott, D. Steinhilber u. a .: Tributyrin, a stable and rapidly absorbed prodrug of butyric acid, enhances antiproliferative effects of dihydroxycholecalciferol in human colon cancer cells. In: The Journal of Nutrition. Volume 131, Number 6, June 2001, pp. 1839-1843, doi : 10.1093 / jn / 131.6.1839 , PMID 11385076 .
↑ T. Gaschott, CU Maassen, J. Stein: Tributyrin, a butyrate precursor, impairs growth and induces apoptosis and differentiation in pancreatic cancer cells. In: Anticancer Research . Volume 21, Number 4A, 2001 Jul-Aug, pp. 2815-2819, PMID 11724360 .
^ Justus Liebig (Baron von), Johann Christian Poggendorff, Friedrich Wöhler, Hermann Christian von Fehling, Pompejus Alexander Bolley: Concise dictionary of pure and applied chemistry . F. Vieweg and Son, 1859, p. 605 ( limited preview in Google Book search).

[roempp-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on glycerol tributyrate. In: Römpp Online . Georg Thieme Verlag, accessed on July 27, 2014.

[Sigma-2] ta sheet Glyceryl tributyrate, ≥99% from Sigma-Aldrich , accessed on February 1, 2013 ( PDF ).

[PMID11385076-3] T. Gaschott, D. Steinhilber u. a .: Tributyrin, a stable and rapidly absorbed prodrug of butyric acid, enhances antiproliferative effects of dihydroxycholecalciferol in human colon cancer cells. In: The Journal of Nutrition. Volume 131, Number 6, June 2001, pp. 1839-1843, doi : 10.1093 / jn / 131.6.1839 , PMID 11385076 .

[PMID11724360-4] T. Gaschott, CU Maassen, J. Stein: Tributyrin, a butyrate precursor, impairs growth and induces apoptosis and differentiation in pancreatic cancer cells. In: Anticancer Research . Volume 21, Number 4A, 2001 Jul-Aug, pp. 2815-2819, PMID 11724360 .

[Justus_Liebig_(Freiherr_von),_Johann_Christian_Poggendorff,_Friedrich_Wöhler,_Hermann_Christian_von_Fehling,_Pompejus_Alexander_Bolley-5] Justus Liebig (Baron von), Johann Christian Poggendorff, Friedrich Wöhler, Hermann Christian von Fehling, Pompejus Alexander Bolley: Concise dictionary of pure and applied chemistry . F. Vieweg and Son, 1859, p. 605 ( limited preview in Google Book search).