Names | |
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Systematic IUPAC name Propane-1,2,3-triyl tributanoate | |
Other names Tributyrin | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.000.410 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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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). |
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]
The large intestine, also known as the large bowel, is the last part of the gastrointestinal tract and of the digestive system in tetrapods. Water is absorbed here and the remaining waste material is stored in the rectum as feces before being removed by defecation. The colon is the longest portion of the large intestine, and the terms are often used interchangeably but most sources define the large intestine as the combination of the cecum, colon, rectum, and anal canal. Some other sources exclude the anal canal.
Dietary fiber or roughage is the portion of plant-derived food that cannot be completely broken down by human digestive enzymes. Dietary fibers are diverse in chemical composition, and can be grouped generally by their solubility, viscosity, and fermentability, which affect how fibers are processed in the body. Dietary fiber has two main components: soluble fiber and insoluble fiber, which are components of plant-based foods, such as legumes, whole grains and cereals, vegetables, fruits, and nuts or seeds. A diet high in regular fiber consumption is generally associated with supporting health and lowering the risk of several diseases. Dietary fiber consists of non-starch polysaccharides and other plant components such as cellulose, resistant starch, resistant dextrins, inulin, lignins, chitins, pectins, beta-glucans, and oligosaccharides.
A nutrient is a substance used by an organism to survive, grow, and reproduce. The requirement for dietary nutrient intake applies to animals, plants, fungi, and protists. Nutrients can be incorporated into cells for metabolic purposes or excreted by cells to create non-cellular structures, such as hair, scales, feathers, or exoskeletons. Some nutrients can be metabolically converted to smaller molecules in the process of releasing energy, such as for carbohydrates, lipids, proteins, and fermentation products, leading to end-products of water and carbon dioxide. All organisms require water. Essential nutrients for animals are the energy sources, some of the amino acids that are combined to create proteins, a subset of fatty acids, vitamins and certain minerals. Plants require more diverse minerals absorbed through roots, plus carbon dioxide and oxygen absorbed through leaves. Fungi live on dead or living organic matter and meet nutrient needs from their host.
Drug resistance is the reduction in effectiveness of a medication such as an antimicrobial or an antineoplastic in treating a disease or condition. The term is used in the context of resistance that pathogens or cancers have "acquired", that is, resistance has evolved. Antimicrobial resistance and antineoplastic resistance challenge clinical care and drive research. When an organism is resistant to more than one drug, it is said to be multidrug-resistant.
Butyric acid, also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula CH3CH2CH2CO2H. It is an oily, colorless liquid with an unpleasant odor. Isobutyric acid is an isomer. Salts and esters of butyric acid are known as butyrates or butanoates. The acid does not occur widely in nature, but its esters are widespread. It is a common industrial chemical and an important component in the mammalian gut.
The enzyme alkaline phosphatase has the physiological role of dephosphorylating compounds. The enzyme is found across a multitude of organisms, prokaryotes and eukaryotes alike, with the same general function but in different structural forms suitable to the environment they function in. Alkaline phosphatase is found in the periplasmic space of E. coli bacteria. This enzyme is heat stable and has its maximum activity at high pH. In humans, it is found in many forms depending on its origin within the body – it plays an integral role in metabolism within the liver and development within the skeleton. Due to its widespread prevalence in these areas, its concentration in the bloodstream is used by diagnosticians as a biomarker in helping determine diagnoses such as hepatitis or osteomalacia.
Indole-3-acetic acid is the most common naturally occurring plant hormone of the auxin class. It is the best known of the auxins, and has been the subject of extensive studies by plant physiologists. IAA is a derivative of indole, containing a carboxymethyl substituent. It is a colorless solid that is soluble in polar organic solvents.
Moraxella catarrhalis is a fastidious, nonmotile, Gram-negative, aerobic, oxidase-positive diplococcus that can cause infections of the respiratory system, middle ear, eye, central nervous system, and joints of humans. It causes the infection of the host cell by sticking to the host cell using trimeric autotransporter adhesins.
A diplococcus is a round bacterium that typically occurs in the form of two joined cells.
The rumen, also known as a paunch, is the largest stomach compartment in ruminants and the larger part of the reticulorumen, which is the first chamber in the alimentary canal of ruminant animals. The rumen's microbial favoring environment allows it to serve as the primary site for microbial fermentation of ingested feed. The smaller part of the reticulorumen is the reticulum, which is fully continuous with the rumen, but differs from it with regard to the texture of its lining.
Gut microbiota, gut microbiome, or gut flora, are the microorganisms, including bacteria, archaea, fungi, and viruses, that live in the digestive tracts of animals. The gastrointestinal metagenome is the aggregate of all the genomes of the gut microbiota. The gut is the main location of the human microbiome. The gut microbiota has broad impacts, including effects on colonization, resistance to pathogens, maintaining the intestinal epithelium, metabolizing dietary and pharmaceutical compounds, controlling immune function, and even behavior through the gut–brain axis.
Resistant starch (RS) is starch, including its degradation products, that escapes from digestion in the small intestine of healthy individuals. Resistant starch occurs naturally in foods, but it can also be added as part of dried raw foods, or used as an additive in manufactured foods.
Betulinic acid is a naturally occurring pentacyclic triterpenoid which has antiretroviral, antimalarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch from which it gets its name, but also the ber tree, selfheal, the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas, a member of the persimmon family, Tetracera boiviniana, the jambul, flowering quince, rosemary, and Pulsatilla chinensis.
Short-chain fatty acids (SCFAs) are fatty acids of two to six carbon atoms. The SCFAs lower limit is interpreted differently, either with 1, 2, 3 or 4 carbon atoms. Derived from intestinal microbial fermentation of indigestible foods, SCFAs in human gut are acetic, propionic, and butyric acid. They are the main energy source of colonocytes, making them crucial to gastrointestinal health. SCFAs all possess varying degrees of water solubility, which distinguishes them from longer chain fatty acids that are immiscible.
Maslinic acid is a compound derived from dry olive-pomace oil which is a byproduct of olive oil extraction. It is a member of the group of triterpenes known as oleananes.
Hydroxycarboxylic acid receptor 2 (HCA2), also known as niacin receptor 1 (NIACR1) and GPR109A, is a protein which in humans is encoded by the HCAR2 gene. HCA2, like the other hydroxycarboxylic acid receptors HCA1 and HCA3, is a Gi/o-coupled G protein-coupled receptor (GPCR). The primary endogenous agonists of HCA2 are D-β-hydroxybutyric acid and butyric acid (and their conjugate bases, β-hydroxybutyrate and butyrate). HCA2 is also a high-affinity biomolecular target for niacin (aka nicotinic acid).
In enzymology, a butyrate kinase is an enzyme that catalyzes the chemical reaction
Sodium butyrate is a compound with formula Na(C3H7COO). It is the sodium salt of butyric acid. It has various effects on cultured mammalian cells including inhibition of proliferation, induction of differentiation and induction or repression of gene expression. As such, it can be used in lab to bring about any of these effects. Specifically, butyrate treatment of cells results in histone hyperacetylation, and butyrate itself inhibits class I histone deacetylase (HDAC) activity, specifically HDAC1, HDAC2, HDAC3, and butyrate can be used in determining histone deacetylene in chromatin structure and function. Inhibition of HDAC activity is estimated to affect the expression of only 2% of mammalian genes.
Anaerostipes is a Gram positive and anaerobic bacterial genus from the family of Lachnospiraceae. Anaerostipes occurs in the human gut. Anaerostipes may protect against colon cancer in humans by producing butyric acid.