Trihydroxybenzenes
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Trihydroxybenzenes
The trihydroxybenzenes (or benzenetriols) are organic compounds with the formula C6H3(OH)3. Also classified as polyphenols, they feature three hydroxyl groups substituted onto a benzene ring. They are white solids with modest solubility in water. : The enzyme pyrogallol hydroxytransferase uses benzene-1,2,3,5-tetrol and benzene-1,2,3-triol (pyrogallol), whereas its two products are benzene-1,3,5-triol (phloroglucinol) and benzene-1,2,3,5-tetrol. This enzyme can be found in ''Pelobacter acidigallici.'' See also * Dihydroxybenzenes * Tetrahydroxybenzenes * Pentahydroxybenzene * Hexahydroxybenzene Benzenehexol, also called hexahydroxybenzene, is an organic compound with formula or . It is a six-fold Phenols, phenol of benzene. The product is also called hexaphenol, but this name has been used also for other substances. Benzenehexol is a c ... References {{aromatic-stub ...
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Dihydroxybenzenes
In organic chemistry, dihydroxybenzenes (benzenediols) are organic compounds in which two hydroxyl groups () are substituted onto a benzene ring (). These aromatic compounds are classed as phenols. There are three structural isomers: 1,2-dihydroxybenzene (the ''ortho'' isomer) is commonly known as catechol, 1,3-dihydroxybenzene (the ''meta'' isomer) is commonly known as resorcinol, and 1,4-dihydroxybenzene (the ''para'' isomer) is commonly known as hydroquinone. : All three of these compounds are colorless to white granular solids at room temperature and pressure, but upon exposure to oxygen they may darken. All three isomers have the chemical formula . Similar to other phenols, the hydroxyl groups on the aromatic ring of a benzenediol are weakly acidic. Each benzenediol can lose an from one of the hydroxyls to form a type of phenolate ion. The Dakin oxidation is an organic redox reaction in which an ''ortho''- or ''para''-hydroxylated phenyl aldehyde () or ketone () reacts ...
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1,2,3,5-tetrahydroxybenzene
1,2,3,5-Tetrahydroxybenzene is a benzenetetrol. It is a metabolite in the degradation of 3,4,5-trihydroxybenzoate (gallic acid) by ''Eubacterium oxidoreducens''. The enzyme pyrogallol hydroxytransferase uses 1,2,3,5-tetrahydroxybenzene and 1,2,3-trihydroxybenzene (pyrogallol), whereas its two products are 1,3,5-trihydroxybenzene (phloroglucinol) and 1,2,3,5-tetrahydroxybenzene.Pyrogallol hydroxytransferase
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See also

* Trihydroxybenzenes *
Pentahydroxybenzene Pentahydroxybenzene (C6H6O5) is a chemical compound whose structure consists of a benzene ...
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Tetrahydroxybenzenes
Tetrahydroxybenzenes or Benzenetetrols are a group of organic compounds which are tetrahydroxy derivatives of benzene. Tetrahydroxybenzene comes in three isomers: * 1,2,3,4-Tetrahydroxybenzene *1,2,3,5-Tetrahydroxybenzene * 1,2,4,5-Tetrahydroxybenzene All isomers share the molecular weight 142.11 g/mol and the chemical formula C6H6O4. See also * Dihydroxybenzenes * Trihydroxybenzenes * Pentahydroxybenzene * Hexahydroxybenzene Benzenehexol, also called hexahydroxybenzene, is an organic compound with formula or . It is a six-fold Phenols, phenol of benzene. The product is also called hexaphenol, but this name has been used also for other substances. Benzenehexol is a c ... {{Chemistry index Phenols ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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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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Benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon. Benzene is a natural constituent of petroleum and is one of the elementary petrochemicals. Due to the cyclic continuous pi bonds between the carbon atoms, benzene is classed as an aromatic hydrocarbon. Benzene is a colorless and highly flammable liquid with a sweet smell, and is partially responsible for the aroma of gasoline. It is used primarily as a precursor to the manufacture of chemicals with more complex structure, such as ethylbenzene and cumene, of which billions of kilograms are produced annually. Although benzene is a major industrial chemical, it finds limited use in consumer items because of its toxicity. History Discovery The word "''benzene''" derives from "''gum benzoin''" (benzoin res ...
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Pyrogallol
Pyrogallol is an organic compound with the formula C6H3(OH)3. It is a water-soluble, white solid although samples are typically brownish because of its sensitivity toward oxygen. It is one of three isomers of benzenetriols. Production and reactions It is produced in the manner first reported by Scheele in 1786: heating gallic acid to induce decarboxylation. Gallic acid is also obtained from tannin. Many alternative routes have been devised. One preparation involves treating ''para''-chlorophenoldisulfonic acid with potassium hydroxide, a variant on the time-honored route to phenols from sulfonic acids. When in alkaline solution, pyrogallol undergoes deprotonation of one or more phenolic groups. Such solutions absorb oxygen from the air, turning brown. This conversion can be used to determine the amount of oxygen in a gas sample, notably by the use of the Orsat apparatus. Polyhydroxybenzenes are relatively electron-rich. One manifestation is the easy C-acetylation of pyrog ...
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Hydroxyquinol
Hydroxyquinol is an organic compound with the formula C6H3(OH)3. It is one of three isomeric benzenetriols. The compound is a colorless solid that is soluble in water. It reacts with air to give a black insoluble solid. Production It is prepared industrially by acetylation of paraquinone with acetic anhydride followed by hydrolysis of the triacetate. Historically hydroxyquinol was produced by the action of potassium hydroxide on hydroquinone. It can also be prepared by dehydrating fructose. :C6H12O6 → 3 H2O + C6H6O3 Natural occurrence Hydroxyquinol is a common intermediate in the biodegradation of many aromatic compounds. These substrates include monochlorophenols, dichlorophenols, and more complex species such as the pesticide 2,4,5-T. Hydroxyquinol commonly occurs in nature as a biodegradation product of catechin, a natural phenol found in plants (e.g. by soil bacteria ''Bradyrhizobium japonicum''). Hydroxyquinol is also a metabolite in some organisms. For instance, ...
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Phloroglucinol
Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isomers are hydroxyquinol (1,2,4-benzenetriol) and pyrogallol (1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "phenols" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed "polyphenols" by the cosmetic and parapharmaceutical industries, which does not match the scientifically accepted definition. Synthesis and occurrence In 1855, phloroglucinol was first prepared from phloretin by the Austrian chemist Heinrich Hlasiwetz (1825–1875). A modern synthesis of involves hydrolysis of benzene-1,3,5-triamine and its derivatives. Representative is the following route from trinitrobenzene. : The synthesis is noteworthy because ordinary aniline derivatives are unre ...
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Pyrogallol2
Pyrogallol is an organic compound with the formula C6H3(OH)3. It is a water-soluble, white solid although samples are typically brownish because of its sensitivity toward oxygen. It is one of three isomers of benzenetriols. Production and reactions It is produced in the manner first reported by Scheele in 1786: heating gallic acid to induce decarboxylation. Gallic acid is also obtained from tannin. Many alternative routes have been devised. One preparation involves treating ''para''-chlorophenoldisulfonic acid with potassium hydroxide, a variant on the time-honored route to phenols from sulfonic acids. When in alkaline solution, pyrogallol undergoes deprotonation of one or more phenolic groups. Such solutions absorb oxygen from the air, turning brown. This conversion can be used to determine the amount of oxygen in a gas sample, notably by the use of the Orsat apparatus. Polyhydroxybenzenes are relatively electron-rich. One manifestation is the easy C-acetylation of pyroga ...
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Phloroglucinol Structure
Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isomers are hydroxyquinol (1,2,4-benzenetriol) and pyrogallol (1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "phenols" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed "polyphenols" by the cosmetic and parapharmaceutical industries, which does not match the scientifically accepted definition. Synthesis and occurrence In 1855, phloroglucinol was first prepared from phloretin by the Austrian chemist Heinrich Hlasiwetz (1825–1875). A modern synthesis of involves hydrolysis of benzene-1,3,5-triamine and its derivatives. Representative is the following route from trinitrobenzene. : The synthesis is noteworthy because ordinary aniline derivatives are un ...
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