Taurochenodeoxycholate
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Taurochenodeoxycholate
Taurochenodeoxycholic acid is a bile acid formed in the liver of most species, including humans, by conjugation of chenodeoxycholic acid with taurine. It is secreted into bile and then into intestine. It is usually ionized at physiologic pH, although it can be crystallized as the sodium salt. It acts as detergent to solubilize fats in the small intestine and is itself absorbed by active transport in the terminal ileum. It is used as a cholagogue and choleretic. See also * Tauroursodeoxycholic acid, an epimer * See article about Taurodeoxycholic acid as an interferent in Perfluorooctanesulfonic acid Perfluorooctanesulfonic acid (PFOS) (conjugate base perfluorooctanesulfonate) is a chemical compound having an eight-carbon fluorocarbon chain and a sulfonic acid functional group and thus a perfluorosulfonic acid. It is an anthropogenic (man-ma ... (PFOS) mass spectrometry analysis. References Bile acids Sulfonic acids Carboxamides Diols Cholanes {{steroid-stub ...
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Chenodeoxycholic Acid
Chenodeoxycholic acid (CDCA; also known as chenodesoxycholic acid, chenocholic acid and 3α,7α-dihydroxy-5β-cholan-24-oic acid) is a bile acid. Salts of this carboxylic acid are called chenodeoxycholates. Chenodeoxycholic acid is one of the main bile acids. It was first isolated from the bile of the domestic goose, which gives it the "cheno" portion of its name (Greek: χήν = goose). Structure Chenodeoxycholic acid and cholic acid are the two primary bile acids in humans. Chenodeoxycholic acid has two hydroxyl groups and is modified with the addition of another hydroxyl group to produce cholic acid. Some other mammals have muricholic acid or deoxycholic acid rather than chenodeoxycholic acid. It occurs as a white crystalline substance insoluble in water but soluble in alcohol and acetic acid, with melting point at 165–167 °C. Biosynthesis and function Chenodeoxycholic acid is synthesized in the liver from cholesterol via several enzymatic steps. Like other bile a ...
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Taurine
Taurine (), or 2-aminoethanesulfonic acid, is an organic compound that is widely distributed in animal tissues. It is a major constituent of bile and can be found in the large intestine, and accounts for up to 0.1% of total human body weight. It is named after Latin (cognate to Ancient Greek ταῦρος, ''taûros'') meaning bull or ox, as it was first isolated from ox bile in 1827 by German scientists Friedrich Tiedemann and Leopold Gmelin. It was discovered in human bile in 1846 by Edmund Ronalds. It has many biological roles, such as conjugation of bile acids, antioxidation, osmoregulation, membrane stabilization, and modulation of calcium signaling. It is essential for cardiovascular function, and development and function of skeletal muscle, the retina, and the central nervous system. It is an unusual example of a naturally occurring sulfonic acid. Chemical and biochemical features Taurine exists as a zwitterion , as verified by X-ray crystallography. The sulfonic aci ...
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Bile Acid
Bile acids are steroid acids found predominantly in the bile of mammals and other vertebrates. Diverse bile acids are synthesized in the liver. Bile acids are conjugated with taurine or glycine residues to give anions called bile salts. Primary bile acids are those synthesized by the liver. Secondary bile acids result from bacterial actions in the colon (anatomy), colon. In humans, taurocholic acid and glycocholic acid (derivatives of cholic acid) and taurochenodeoxycholic acid and glycochenodeoxycholic acid (derivatives of chenodeoxycholic acid) are the major bile salts. They are roughly equal in concentration. The salts of their 7-alpha-dehydroxylated derivatives, deoxycholic acid and lithocholic acid, are also found, with derivatives of cholic, chenodeoxycholic and deoxycholic acids accounting for over 90% of human biliary bile acids. Bile acids comprise about 80% of the organic compounds in bile (others are phospholipids and cholesterol). An increased secretion of bile acids ...
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Bile
Bile (from Latin ''bilis''), or gall, is a dark-green-to-yellowish-brown fluid produced by the liver of most vertebrates that aids the digestion of lipids in the small intestine. In humans, bile is produced continuously by the liver (liver bile) and stored and concentrated in the gallbladder. After eating, this stored bile is discharged into the duodenum. The composition of hepatic bile is (97–98)% water, 0.7% bile salts, 0.2% bilirubin, 0.51% fats (cholesterol, fatty acids, and lecithin), and 200 meq/L inorganic salts. The two main pigments of bile are bilirubin, which is yellow, and its oxidised form biliverdin, which is green. When mixed, they are responsible for the brown color of feces. About 400 to 800 millilitres of bile is produced per day in adult human beings. Function Bile or gall acts to some extent as a surfactant, helping to emulsify the lipids in food. Bile salt anions are hydrophilic on one side and hydrophobic on the other side; consequently, they tend ...
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Ileum
The ileum () is the final section of the small intestine in most higher vertebrates, including mammals, reptiles, and birds. In fish, the divisions of the small intestine are not as clear and the terms posterior intestine or distal intestine may be used instead of ileum. Its main function is to absorb vitamin B12, bile salts, and whatever products of digestion that were not absorbed by the jejunum. The ileum follows the duodenum and jejunum and is separated from the cecum by the ileocecal valve (ICV). In humans, the ileum is about 2–4 m long, and the pH is usually between 7 and 8 (neutral or slightly basic). ''Ileum ''is derived from the Greek word ''eilein'', meaning "to twist up tightly". Structure The ileum is the third and final part of the small intestine. It follows the jejunum and ends at the ileocecal junction, where the terminal ileum communicates with the cecum of the large intestine through the ileocecal valve. The ileum, along with the jejunum, is suspended ...
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Cholagogue
A cholagogue is a substance that is purported by humoral practitioners to encourage the discharge of bile from the system, purging it downward. Deployment is no longer recommended because the biliary purge, like the traditional kidney purge, can cause pancreatic problems. In Patrick O'Brian's ''Post Captain'' (Ch. 10), which is set in the Napoleonic era, Stephen Maturin, one of the book's main characters (who is also a physician, naturalist and spy) sits in the snug of the Rose and Crown in Deal, Kent Deal is a coastal town in Kent, England, which lies where the North Sea and the English Channel meet, north-east of Dover and south of Ramsgate. It is a former fishing, mining and garrison town whose history is closely linked to the anchora ..., and drinks a "good" tea described as an "unrivalled cholagogue". Cyclovalone is a choleretic and cholagogic agent. References * Chambers, Ephraim, ed. (1728). '' Cyclopaedia, or an Universal Dictionary of Arts and Sciences'' (firs ...
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Choleretic
Choleretics are substances that increase the volume of secretion of bile from the liver as well as the amount of solids secreted. See also * Cholekinetic * Hydrocholeretic Hydrocholeretics are substances that increase the volume of secretion of bile from the liver without increasing the amount of solids secreted. Some substances can result in decreased solid production, possibly due to circulatory effects. Cyclobuty ... References {{gastrointestinal-drug-stub Bile acids ...
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Tauroursodeoxycholic Acid
Ursodoxicoltaurine is the international nonproprietary name (INN) for the pharmaceutical form of tauroursodeoxycholic acid (TUDCA). It is also known as taurursodiol. Tauroursodeoxycholic acid is a naturally occurring hydrophilic bile acid which is the taurine conjugated form of ursodeoxycholic acid (UDCA). Humans have only trace amounts of tauroursodeoxycholic acid but bears have large amounts of tauroursodeoxycholic acid and ursodeoxycholic acid in their bile. Synthesis Bile acids are naturally synthesized from cholesterol in the liver and are conjugated with specific amino-acids, specifically taurine. Bear bile contains several bile acids including taurochenodeoxycholic acid, ursodeoxycholic acid, and chenodeoxycholic acid. UDCA and its taurine conjugates comprise about 47% of the bile in American black bears and up to 76% in Asiatic bears. Ursodeoxycholic acid and tauroursodeoxycholic acid were first chemically synthesized in 1954 in Japan. Ursodeoxycholic acid is produc ...
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Epimer
In stereochemistry, an epimer is one of a pair of diastereomers. The two epimers have opposite configuration at only one stereogenic center out of at least two. All other stereogenic centers in the molecules are the same in each. Epimerization is the interconversion of one epimer to the other epimer. Doxorubicin and epirubicin are two epimers that are used as drugs. Examples The stereoisomers β-D- glucopyranose and β-D- mannopyranose are epimers because they differ only in the stereochemistry at the C-2 position. The hydroxy group in β-D-glucopyranose is equatorial (in the "plane" of the ring), while in β-D-mannopyranose the C-2 hydroxy group is axial (up from the "plane" of the ring). These two molecules are epimers but, because they are not mirror images of each other, are not enantiomers. (Enantiomers have the same name, but differ in D and L classification.) They are also not sugar anomers, since it is not the anomeric carbon involved in the stereochemistry. Simila ...
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Taurodeoxycholic Acid
Taurodeoxycholic acid is a bile acid. This compound is a closely related isomer of Taurochenodeoxycholic acid and Tauroursodeoxycholic acid sharing the exact molecular formula and molecular weight. Mass Spectrometry Interference with PFOS Benskin and colleagues (https://pubs.acs.org/doi/pdf/10.1021/ac070802d) published in 2007 an article identifying Taurodeoxycholic acid and isomers as mass spectrometry interferents with PFOS (Perfluorooctanesulfonic acid) as the two compounds share the m/z transition of 498-80. The molecular weight of PFOS and taurodeoxycholic acid and isomers are similar enough in molecular weight that most low resolution Triple quadrupole mass spectrometer are unable to distinguish these two chemicals from each other. Additionally both compounds share a Sulfonate group (leading to the ''m/z'' 80 loss) in the common mass spectrometry transition. Reiner and colleagues https://pubs.acs.org/doi/pdf/10.1021/es800770f found these bile acid compounds in chicken e ...
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Perfluorooctanesulfonic Acid
Perfluorooctanesulfonic acid (PFOS) (conjugate base perfluorooctanesulfonate) is a chemical compound having an eight-carbon fluorocarbon chain and a sulfonic acid functional group and thus a perfluorosulfonic acid. It is an anthropogenic (man-made) fluorosurfactant, now regarded as a global pollutant. PFOS was the key ingredient in Scotchgard, a fabric protector made by 3M, and related stain repellents. The acronym "PFOS" refers to the parent sulfonic acid and to various salts of perfluorooctanesulfonate. These are all colorless or white, water soluble solids. Although of low acute toxicity, PFOS has attracted much attention for its pervasiveness and environmental impact. It was added to Annex B of the Stockholm Convention on Persistent Organic Pollutants in May 2009. History In 1949, 3M began producing PFOS-based compounds by electrochemical fluorination resulting in the synthetic precursor perfluorooctanesulfonyl fluoride. In 1968, organofluorine content was detected in the ...
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Bile Acids
Bile acids are steroid acids found predominantly in the bile of mammals and other vertebrates. Diverse bile acids are synthesized in the liver. Bile acids are conjugated with taurine or glycine residues to give anions called bile salts. Primary bile acids are those synthesized by the liver. Secondary bile acids result from bacterial actions in the colon. In humans, taurocholic acid and glycocholic acid (derivatives of cholic acid) and taurochenodeoxycholic acid and glycochenodeoxycholic acid (derivatives of chenodeoxycholic acid) are the major bile salts. They are roughly equal in concentration. The salts of their 7-alpha-dehydroxylated derivatives, deoxycholic acid and lithocholic acid, are also found, with derivatives of cholic, chenodeoxycholic and deoxycholic acids accounting for over 90% of human biliary bile acids. Bile acids comprise about 80% of the organic compounds in bile (others are phospholipids and cholesterol). An increased secretion of bile acids produces an inc ...
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