Cyclopentenone Prostaglandin
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Cyclopentenone Prostaglandin
Cyclopentenone prostaglandins are a subset of prostaglandins (PGs) or prostenoid, prostanoids (see eicosanoid#Classic eicosanoids and eicosanoid#Nonclassic eicosanoids) that has 15-deoxy-Δ12,14-prostaglandin J2 (15-d-Δ12,14-PGJ2), Δ12-PGJ2, and PGJ2 as its most prominent members but also including PGA2, PGA1, and, while not classified as such, other PGs. 15-d-Δ12,14-PGJ2, Δ12-PGJ2, and PGJ2 share a common mono-unsaturated cyclopentenone structure as well as a set of similar biological activities including the ability to suppress inflammation responses and the growth as well as survival of cells, particularly those of cancerous or neurological origin. Consequently, these three cyclopentenone-PGs and the two epoxyisoprostanes are suggested to be models for the development of novel anti-inflammatory and anti-cancer drugs. The cyclopenentone prostaglandins are structurally and functionally related to a subset of isoprostanes viz., two cyclopentenone isoprostanes, 5,6-epoxyisoprostan ...
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Prostaglandin
The prostaglandins (PG) are a group of physiologically active lipid compounds called eicosanoids having diverse hormone-like effects in animals. Prostaglandins have been found in almost every tissue in humans and other animals. They are derived enzymatically from the fatty acid arachidonic acid. Every prostaglandin contains 20 carbon atoms, including a 5-carbon ring. They are a subclass of eicosanoids and of the prostanoid class of fatty acid derivatives. The structural differences between prostaglandins account for their different biological activities. A given prostaglandin may have different and even opposite effects in different tissues in some cases. The ability of the same prostaglandin to stimulate a reaction in one tissue and inhibit the same reaction in another tissue is determined by the type of receptor to which the prostaglandin binds. They act as autocrine or paracrine factors with their target cells present in the immediate vicinity of the site of their secret ...
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Prostaglandin D2 Synthase
Prostaglandin-H2 D-isomerase (PTGDS) is an enzyme that in humans is encoded by the ''PTGDS'' gene. Function The protein encoded by this gene is a glutathione-independent prostaglandin D synthase that catalyzes the conversion of prostaglandin H2 (PGH2) to prostaglandin D2 (PGD2). PGD2 functions as a neuromodulator as well as a trophic factor in the central nervous system. PGD2 is also involved in smooth muscle contraction/relaxation and is a potent inhibitor of platelet aggregation. This gene is preferentially expressed in brain. Studies with transgenic mice over-expressing this gene suggest that this gene may be also involved in the regulation of non-rapid eye movement sleep. Furthermore, PTGDS and its product PGD2 are elevated in the bald-scalp areas of men with male pattern baldness (androgenetic alopecia). Clinical use Prostaglandin D2 synthase is used clinically as a diagnostic marker for liquorrhea, that is, to check whether fluid leaking from the nose or ear contai ...
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Chemical Reactivity
In chemistry, reactivity is the impulse for which a chemical substance undergoes a chemical reaction, either by itself or with other materials, with an overall release of energy. ''Reactivity'' refers to: * the chemical reactions of a single substance, * the chemical reactions of two or more substances that interact with each other, * the systematic study of sets of reactions of these two kinds, * methodology that applies to the study of reactivity of chemicals of all kinds, * experimental methods that are used to observe these processes * theories to predict and to account for these processes. The chemical reactivity of a single substance (reactant) covers its behavior in which it: * Decomposes * Forms new substances by addition of atoms from another reactant or reactants * Interacts with two or more other reactants to form two or more products The chemical reactivity of a substance can refer to the variety of circumstances (conditions that include temperature, pressure, prese ...
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Carbonyl Group
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containing a carbonyl group is often referred to as a carbonyl compound. The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e.g. nickel carbonyl). The remainder of this article concerns itself with the organic chemistry definition of carbonyl, where carbon and oxygen share a double bond. Carbonyl compounds In organic chemistry, a carbonyl group characterizes the following types of compounds: Other organic carbonyls are urea and the carbamates, the derivatives of acyl chlorides chloroformates and phosgene, carbonate esters, thioesters, lactones, lactams, hydroxamates, and isocyanates. Examples of inorganic carbonyl compounds are carbon dioxide and carbonyl sulfide. A ...
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Dihomo-γ-linolenic Acid
Dihomo-γ-linolenic acid (DGLA) is a 20-carbon ω−6 fatty acid. (also called, cis,cis,cis-8,11,14-Eicosatrienoic acid) In physiological literature, it is given the name 20:3 (ω−6). DGLA is a carboxylic acid with a 20-carbon chain and three ''cis'' double bonds; the first double bond is located at the sixth carbon from the omega end. DGLA is the elongation product of γ-linolenic acid (GLA; 18:3, ω−6). GLA, in turn, is a desaturation product (Delta 6 desaturase) of linoleic acid (18:2, ω−6). DGLA is made in the body by the elongation of GLA, by an efficient enzyme which does not appear to suffer any form of (dietary) inhibition. DGLA is an extremely uncommon fatty acid, found only in trace amounts in animal products. Biological effects The eicosanoid metabolites of DGLA are: * Series-1 thromboxanes (thromboxanes with 1 double-bond), via the COX-1 and COX-2 pathways. * Series-1 prostanoids, via the COX-1 and COX-2 pathways. * A 15-hydroxyl derivative that blocks t ...
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Isomerization
In chemistry, isomerization or isomerisation is the process in which a molecule, polyatomic ion or molecular fragment is transformed into an isomer with a different chemical structure. Enolization is an example of isomerization, as is tautomerization. When the isomerization occurs intramolecularly it may be called a rearrangement reaction. When the activation energy for the isomerization reaction is sufficiently small, both isomers will exist in a temperature-dependent equilibrium with each other. Many values of the standard free energy difference, \Delta G^\circ, have been calculated, with good agreement between observed and calculated data. Examples and applications Alkanes Skeletal isomerization occurs in the cracking process, used in the petrochemical industry. As well as reducing the average chain length, straight-chain hydrocarbons are converted to branched isomers in the process, as illustrated the following reaction of ''n''-butane to ''i''-butane. :\overset -> \o ...
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Electrophilic
In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons. Electrophiles mainly interact with nucleophiles through addition and substitution reactions. Frequently seen electrophiles in organic syntheses include cations such as H+ and NO+, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl2 and Br2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH3 and DIBAL. Organic chemistry Addition of halogens These occur between alkenes and electrophiles, often halogens as in halogen addition reactions. Common reaction ...
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Ketol
In organic chemistry a hydroxy ketone (often referred to simply as a ketol) is a functional group consisting of a ketone flanked by a hydroxyl group. In the two main classes, the hydroxyl group can be placed in the alpha position (an alpha-hydroxy ketone RCR′(OH)(CO)R) or in the beta position (a beta-hydroxy ketone, RCR′(OH)CR2(CO)R). * An α-hydroxy ketone can consist of either a primary alcohol (e.g. hydroxyacetone) or a secondary alcohol; the latter are often broadly referred to as acyloins * Prominent β-hydroxy ketones are aldol adducts. * Only terminal α-hydroxy ketones can give positive Fehling's test In organic chemistry, Fehling's solution is a chemical reagent used to differentiate between water-soluble carbohydrate and ketone () functional groups, and as a test for reducing sugars and non-reducing sugars, supplementary to the Tollens' r .... References {{chemistry-stub ...
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Hydroxyl
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy groups. Both the negatively charged anion , called hydroxide, and the neutral radical , known as the hydroxyl radical, consist of an unbonded hydroxy group. According to IUPAC definitions, the term ''hydroxyl'' refers to the hydroxyl radical () only, while the functional group is called a ''hydroxy group''. Properties Water, alcohols, carboxylic acids, and many other hydroxy-containing compounds can be readily deprotonated due to a large difference between the electronegativity of oxygen (3.5) and that of hydrogen (2.1). Hydroxy-containing compounds engage in intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds that lack this f ...
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Cyclopentanone
Cyclopentanone is the organic compound with the formula (CH2)4CO. This cyclic ketone is a colorless volatile liquid. Preparation Upon treatment with barium hydroxide at elevated temperatures, adipic acid undergoes ketonization to give cyclopentanone: :(CH2)4(CO2H)2 → (CH2)4CO + H2O + CO2 Uses Cyclopentanone is common precursor to fragrances, especially those related to jasmine and jasmone. Examples include 2-pentyl- and 2-heptylcyclopentanone.Johannes Panten and Horst Surburg "Flavors and Fragrances, 2. Aliphatic Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2015, Wiley-VCH, Weinheim. It is a versatile synthetic intermediate, being a precursor to cyclopentobarbital. Cyclopentanone is also used to make cyclopentamine, the pesticide pencycuron, and pentethylcyclanone Pentethylcyclanone is an antitussive medication A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to diagnose, c ...
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Double Bond
In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist between two different elements: for example, in a carbonyl group between a carbon atom and an oxygen atom. Other common double bonds are found in azo compounds (N=N), imines (C=N), and sulfoxides (S=O). In a skeletal formula, a double bond is drawn as two parallel lines (=) between the two connected atoms; typographically, the equals sign is used for this. Double bonds were first introduced in chemical notation by Russian chemist Alexander Butlerov. Double bonds involving carbon are stronger and shorter than single bonds. The bond order is two. Double bonds are also electron-rich, which makes them potentially more reactive in the presence of a strong electron acceptor (as in addition reactions of the halogens). File:Ethene structural.svg ...
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Dehydration Reaction
In chemistry, a dehydration reaction is a chemical reaction that involves the loss of water from the reacting molecule or ion. Dehydration reactions are common processes, the reverse of a hydration reaction. Dehydration reactions in organic chemistry Esterification The classic example of a dehydration reaction is the Fischer esterification, which involves treating a carboxylic acid with an alcohol to give an ester :RCO2H + R′OH RCO2R′ + H2O Often such reactions require the presence of a dehydrating agent, i.e. a substance that reacts with water. Etherification Two monosaccharides, such as glucose and fructose, can be joined together (to form saccharose) using dehydration synthesis. The new molecule, consisting of two monosaccharides, is called a disaccharide. Nitrile formation Nitriles are often prepared by dehydration of primary amides. :RC(O)NH2 → RCN + H2O Ketene formation Ketene is produced by heating acetic acid and trapping the product: :CH3CO2H → CH2=C= ...
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