[{"@context":"http:\/\/schema.org\/","@type":"BlogPosting","@id":"https:\/\/wiki.edu.vn\/all2en\/wiki2\/gentisic-acid-wikipedia\/#BlogPosting","mainEntityOfPage":"https:\/\/wiki.edu.vn\/all2en\/wiki2\/gentisic-acid-wikipedia\/","headline":"Gentisic acid – Wikipedia","name":"Gentisic acid – Wikipedia","description":"Structural formula General Name Gentismic acid other names 2.5 dihydroxybenzoic acid 5-hydroxysalicylic acid Hydrochinon carboxylic acid DHB 2,5-DIHYDROXYBENZOIC ACID (PEARL)","datePublished":"2017-10-23","dateModified":"2017-10-23","author":{"@type":"Person","@id":"https:\/\/wiki.edu.vn\/all2en\/wiki2\/author\/lordneo\/#Person","name":"lordneo","url":"https:\/\/wiki.edu.vn\/all2en\/wiki2\/author\/lordneo\/","image":{"@type":"ImageObject","@id":"https:\/\/secure.gravatar.com\/avatar\/44a4cee54c4c053e967fe3e7d054edd4?s=96&d=mm&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/44a4cee54c4c053e967fe3e7d054edd4?s=96&d=mm&r=g","height":96,"width":96}},"publisher":{"@type":"Organization","name":"Enzyklop\u00e4die","logo":{"@type":"ImageObject","@id":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","url":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","width":600,"height":60}},"image":{"@type":"ImageObject","@id":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/c\/cb\/Gentisins%C3%A4ure.svg\/150px-Gentisins%C3%A4ure.svg.png","url":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/c\/cb\/Gentisins%C3%A4ure.svg\/150px-Gentisins%C3%A4ure.svg.png","height":"127","width":"150"},"url":"https:\/\/wiki.edu.vn\/all2en\/wiki2\/gentisic-acid-wikipedia\/","wordCount":2994,"articleBody":"Structural formula  General Name Gentismic acid other names 2.5 dihydroxybenzoic acid 5-hydroxysalicylic acid Hydrochinon carboxylic acid DHB 2,5-DIHYDROXYBENZOIC ACID (PEARL) [first] Mash formula C 7 H 6 O 4 Brief description light yellow, odorless solid [2] External identifiers\/databases  Characteristics Molar masses 154,12 g \u00b7 mol \u22121 Aggregate state fest Melting point 199\u2013200 \u00b0C (Decomposition) [3] p K S -Value 2.95 (COOH) [3] solubility badly soluble in water: 5 g \u00b7 l \u22121 (5\u00a0\u00b0C) [3] soluble in ethanol and ether [4] safety instructions  Toxicological data  As far as possible and common, SI units are used. Unless otherwise noted, the data provided applies to standard conditions. Gentismic acid (2,5-dihydroxybenzoic acid) is an aromatic connection that formally derives both the benzoic acid and hydrochinone (1.4-dihydroxybenzene). The structure consists of a benzene ring with a carboxy group (\u2013cooh) and two hydroxy groups (\u2013oh) as substituents. It belongs to the group of dihydroxybenzoic acids and comes in some plants such as caraway and lavender as well as gentian (scientific name Gentian ) before. [6] Gentismic acid is a by -product (1%) in metabolism of acetylsalicylic acid, which is excreted by the kidneys. [7] Historically, gantic acid was made from 5-bromsalicylic acid by melting with sodium hydroxide. [8] Furthermore, in 1881 Ferdinand Tiemann was able to represent the melting of potassium hydroxide with Gentisinaldehyde, which was made from hydrochinone and chloroform in the presence of sodium hydroxide solution. [9] Gentismic acid is produced by carboxylation of hydrochinone using Kolbe-Schmitt reaction. [ten]  Synthesis also succeeds in the case of atmospheric pressure by cooking hydrochinone with tetrachlorben fabric and copper powder. Tetrachlormethane is redoxequent to carbon dioxide. [11] Also in the oxidation of salicylic acid with potassium per sulfate [twelfth] Create in the presence of iron (II) sulfate gentian acid. [13]  Direct bromization of gantic acid delivers 3-bromgentisic acid. [14] [15] Bromine’s elimination leads to the elimination of the carboxy group, and Bromanil (2,3,5,6-tetrabrom-1,4-benzochinone) is created. [16] When heating the bromgentic acid to 160 \u00b0 C in the presence of water, brom hydrochinone is created. [16]  Acetylation with acetic acid anhydride delivers the diacetylgentic acid, which melts at 118\u2013119 \u00b0 C. [16] The methylester can be produced with diazomethane. [17] The direct nitration of gantic acid is only possible with low yields with heavily diluted nitric acid, mainly an oxidation with the formation of oxalic acid. [16] The direct nitration of the diacetyl derivative also fails. [16] However, the synthesis of 3-nitrogenic acid can be carried out via the methylester of the diacetylgentic acid. [17] By reducing tin (II) chloride and hydrochloric acid, 3-aminogenic acid is created from 3-nitrogenic acid. [18]  Like most hydrochinoners, genttisic acid can be easily oxidized. Gentic acid is used as an intermediate in the production of pharmaceuticals (especially analgesics and anti -rheumatics) and other organic compounds. It is used in maldia-tof analysis as a matrix for ionization of peptides, proteins and carbohydrates. [19] It can be used as a reagent for the detection of boric acid in peptides. [20] It is also used in medicine as glucosamide (Amid of Glucosamin) for parenterals.Gentismic acid, like salicylic acid, inhibits prostaglandin synthesis and was therefore used earlier as an anti -rheumatics. [6] Sodium genitatism is used as a medication for rheumatic fever. [21] [22] Zinc and Mangangentisat can be used as catalysts for polyester formation. [23] 2-aminogenic acid has antibiotic properties compared to gram-positive and gram-negative bacteria. [24] 2.5 dihydroxybenzoic acid Beilstein (Syst.No. 1105), volume. 10: \u2191  Entry to 2,5-DIHYDROXYBENZOIC ACID in the Cosing database of the EU Commission, accessed on May 13, 2020.  \u2191  data sheet Gentismic acid at Merck, accessed on January 18, 2011.  \u2191 a b c d It is  Entry to Gentisic acid In the United States National Library of Medicine (NLM) (Page no longer available , Content now available via Pubchem ID 3469 )  \u2191  Mary Eagleson: Concise Encyclopedia Chemistry . Walter The Gruryter, 1994, ISBN 3-11-011451-8, S.  449 ( limited preview in the Google book search).   \u2191 a b  data sheet 2,5-Dihydroxybenzoic acid at Sigma-Aldrich, accessed on May 14, 2017 ( PDF ).  \u2191 a b  Entry to Gentismic acid . In: R\u00f6mpp Online. Georg Thieme Verlag, accessed June 13, 2014.  \u2191  G. Levy, T. Tsuchiya: Salicylate Accumulation Kinetics in Man . In: New England Journal of Medicine . 287, no. 9, 1972, pp. 430\u2013432, doi:10.1056\/NEJM197208312870903 .  \u2191  P. v. Rakowski, W. Leppert: About hydrochinon carboxylic acid . In: Reports of the German Chemical Society , 8, no. 1, 1875, pp. 788\u2013790; Two: 10.1002\/CBER.187500801256 , Gallica.bnf.fr .  \u2191  F. Tiemann, M. M\u00fcller: About descendants of the hydrochinon . In: Reports of the German Chemical Society , 1881, 14, S.\u00a01985\u20131999 Gallica.bnf.fr .  \u2191  P. M. Hudnall: Hydroquinone . In Ullmann\u2019s Encyclopedia of Industrial Chemistry . Wiley-VCH, Weinheim 2002, Doi: 10.1002\/14356007.A13_499 .  \u2191  J. Zeltner, Max Landau “Procedure for the representation of phenol carboxylic acids”, Of 258887 , registered January 10, 1912.  \u2191  M. B. Fawzi: Gentisic acid salts as radiographic scanning agent stabilizers . US Patent 4497744 , registered November 3, 1980.  \u2191  S. G. Morris: Preparation of Gentisic Acid and its Fatty Alcohol Esters in J. Am. Chem. Soc. 71, no. 6, 1949, pp. 2056\u20132057, Two: 10.1021\/Ja01174A046 .  \u2191  R. L. Crawford, S. W. Hutton, P. J. Chapman: Purification and Properties of Gentisate 1,2-Dioxygenase from Moraxella osloensis . In: Journal of Bacteriology . 121, no. 3, 1975, pp. 794\u2013799; PMC\u00a0246005 (Free full text).  \u2191  M. C. Kloetzel, B. Y. Abadir: Synthetic Analogs of Cortical Hormones. II. 3-Substituted a-2,5-Trihydroxyacetophenone Derivatives . In: J. Am. Chem. Soc. 77, no. 14, 1955, pp. 3823\u20133826, Two: 10.1021\/Ja01619a043 .  \u2191 a b c d It is  F. v. Hemmelmayr: To the knowledge of the gantisic acid (2, 5-dioxybenzencarboxylic acid (1)) and some of their derivatives . In: Monthly booklets for chemistry . 30, no. 3, 1909, pp. 255\u2013269, doi:10.1007\/BF01519683 .  \u2191 a b  A. Klemenc: About nitrogenic acids . In: Monthly booklets for chemistry . 1912, 33 , S.\u00a01243\u20131254, doi:10.1007\/BF01518823 .  \u2191  F. v. Hemmelmayr: About some new derivatives of di and trioxybenzoic acids . In: Monthly booklets for chemistry . 1914, 35 , S.\u00a01\u20138, doi:10.1007\/BF01519727 .  \u2191  K. Poison, M. Karas, F. Hillenkamp: 2,5-Dihydroxybenzoic acid: a new matrix for laser desorption\u2014ionization mass spectrometry . In: International Journal of Mass Spectrometry and Ion Processes . 1991, 111 , S.\u00a089\u2013102, two: 10.1016\/0168-1176 (91) 85050-v .  \u2191  J. B. Crumpton, W. Zhang, W. L. Santos: Facile Analysis and Sequencing of Linear and Branched Peptide Boronic Acids by MALDI Mass Spectrometry . In: Analytical Chemistry . 83, no. 9, 2011, pp. 3548\u20133554, doi:10.1021\/ac2002565 .  \u2191  B. W. Meade, M. J. H. Smith: The estimation of Sodium Gentisate in Plasma and Urine . In: Journal of Clinical Pathology , 1951, 4, S.\u00a0226; PMC\u00a01023403 (Free full text).  \u2191  L. E. Schaefer, I. A. Rashkoff, R. S. Megibow: Sodium Gentisate in the Treatment of Acute Rheumatic Fever (PDF; 1,2\u00a0MB). In: Circulation , 1950, 2, S.\u00a0265\u2013270.  \u2191  J. A. Price: Zinc and manganese gentisate as polyester catalysts and molecular weight enhancer . US Patent Nr. 3673157 n registered July 31, 1970.  \u2191  A. Zeeck, S. Breiding-Mack, S. Grabley, H. Voelskow, G. Seibert (Hoechst AG): Gentisic acid derivatives having antibiotic activity . US Patent 4861796 , registered December 19, 1988.   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