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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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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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Taurochenodeoxycholic Acid
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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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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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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Triple Quadrupole Mass Spectrometer
A triple quadrupole mass spectrometer (TQMS), is a tandem mass spectrometer consisting of two quadrupole mass analyzers in series, with a (non-mass-resolving) radio frequency (RF)–only quadrupole between them to act as a cell for collision-induced dissociation. This configuration is often abbreviated QqQ, here Q1q2Q3. History The arrangement of three quadrupoles was first developed by J.D. Morrison of La Trobe University, Australia for the purpose of studying the photodissociation of gas-phase ions. After coming into contact with Prof. Christie G. Enke and his then graduate student Richard Yost, Morrison's linear arrangement of the three quadrupoles probed the construction of the first triple-quadrupole mass spectrometer. In the years following, the first commercial triple-quadrupole mass spectrometer was developed at Michigan State University by Enke and Yost in the late 1970s. It was later found that the triple-quadrupole mass spectrometer could be utilized to study organic ...
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Sulfonate
In organosulfur chemistry, a sulfonate is a salt or ester of a sulfonic acid. It contains the functional group , where R is an organic group. Sulfonates are the conjugate bases of sulfonic acids. Sulfonates are generally stable in water, non-oxidizing, and colorless. Many useful compounds and even some biochemicals feature sulfonates. Sulfonate salts Anions with the general formula are called sulfonates. They are the conjugate bases of sulfonic acids with formula . As sulfonic acids tend to be strong acids, the corresponding sulfonates are weak bases. Due to the stability of sulfonate anions, the cations of sulfonate salts such as scandium triflate have application as Lewis acids. A classic preparation of sulfonates is the Strecker sulfite alkylation, in which an alkali sulfite salt displaces a halide, typically in the presence of an iodine catalyst: :RX + M2SO3 -> RSO3M + MX An alternative is the condensation of a sulfonyl halide with an alcohol in pyridine: :ROH + R' ...
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Time-of-flight Mass Spectrometry
Time-of-flight mass spectrometry (TOFMS) is a method of mass spectrometry in which an ion's mass-to-charge ratio is determined by a time of flight measurement. Ions are accelerated by an electric field of known strength. This acceleration results in an ion having the same kinetic energy as any other ion that has the same charge. The velocity of the ion depends on the mass-to-charge ratio (heavier ions of the same charge reach lower speeds, although ions with higher charge will also increase in velocity). The time that it subsequently takes for the ion to reach a detector at a known distance is measured. This time will depend on the velocity of the ion, and therefore is a measure of its mass-to-charge ratio. From this ratio and known experimental parameters, one can identify the ion. Theory The potential energy of a charged particle in an electric field is related to the charge of the particle and to the strength of the electric field: where ''E''p is potential energy, ''q'' ...
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Solid-phase Extraction
Solid-phase extraction (SPE) is an extractive technique by which compounds that are dissolved or suspended in a liquid mixture are separated from other compounds in the mixture according to their physical and chemical properties. Analytical laboratories use solid phase extraction to concentrate and purify samples for analysis. Solid phase extraction can be used to isolate analytes of interest from a wide variety of matrices, including urine, blood, water, beverages, soil, and animal tissue. SPE uses the affinity of solutes dissolved or suspended in a liquid (known as the mobile phase) for a solid through which the sample is passed (known as the stationary phase) to separate a mixture into desired and undesired components. The result is that either the desired analytes of interest or undesired impurities in the sample are retained on the stationary phase. The portion that passes through the stationary phase is collected or discarded, depending on whether it contains the desired ...
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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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Sulfonic Acids
In organic chemistry, sulfonic acid (or sulphonic acid) refers to a member of the class of organosulfur compounds with the general formula , where R is an organic alkyl or aryl group and the group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound (with the organic substituent replaced by hydrogen) is the parent sulfonic acid, , a tautomer of sulfurous acid, . Salts or esters of sulfonic acids are called sulfonates. Preparation Aryl sulfonic acids are produced by the process of sulfonation. Usually the sulfonating agent is sulfur trioxide. A large scale application of this method is the production of alkylbenzenesulfonic acids: :RC6H5 + SO3 -> RC6H4SO3H In this reaction, sulfur trioxide is an electrophile and the arene is the nucleophile. The reaction is an example of electrophilic aromatic substitution. Alkylsulfonic acids ...
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