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07-SEPTEMBER-2008 03:17:44 - Tartaric acid Tartaric acid1 IUPAC name 2,3-dihydroxybutanedioic acid Other names 2,3-dihydroxysuccinic acid threaric acid racemic acid uvic acid paratartaric acid Identifiers CAS number 526-83-0 PubChem 875 MeSH tartaric+acid SMILES CCC=OOOC=OOO Properties Molecular formula C4H6O6 Molar mass 150.087 g/mol Appearance white powder Melting point 171-174 °C L-tartaric 206 °C DL, racemic 146-148 °C meso 2 Solubility in water 133 g/100ml 20°C Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Tartaric acid is a white crystalline organic acid. It occurs naturally in many plants, particularly grapes, bananas, and tamarinds, and is one of the main acids found in wine. It is added to other foods to give a sour taste, and is used as an antioxidant. Salts of tartaric acid are known as tartrates. It is a dihydroxy derivative of succinic acid. Tartaric acid was first isolated from potassium tartrate, known to the ancients as tartar, c. 800 by the Persian alchemist Jabir ibn Hayyan,citation needed who was also responsible for numerous other basic chemical processes still in use today. The modern process was developed in 1769 by the Swedish chemist Carl Wilhelm Scheele. The chirality of tartaric acid was discovered in 1832 by Jean Baptiste Biot, who observed its ability to rotate polarized light. Louis Pasteur continued this research in 1847 by investigating the shapes of tartaric acid crystals, which he found to be asymmetric. Pasteur was the first to produce a pure sample of levotartaric acid. Contents 1 Stereochemistry 2 Derivatives 3 Tartaric acid in wine 4 References 5 External links Stereochemistry Naturally occurring tartaric acid is chiral, meaning that it has molecules that are non-superimposable on their mirror-images. It is a useful raw material in organic chemistry for the synthesis of other chiral molecules. The naturally occurring form of the acid is L-+-tartaric acid or dextrotartaric acid. The mirror-image enantiomeric form, levotartaric acid or D---tartaric acid, and the achiral form, mesotartaric acid, can be made artificially. Note, that the dextro and levo prefixes are not related to the D/L configuration which is derived from the reference D- or L-glyceraldehyde, but to the orientation of the optical rotation, + = dextrorotatory, - = levorotatory. Sometimes, instead of capital letters, small italic d, l are used. They are abbreviations of dextro- and levo-, and nowadays should not be used. Levotartaric and dextrotartaric acid are enantiomers, mesotartaric acid is a diastereomer of both of them. A rarely occurring optically inactive form of tartaric acid, DL-tartaric acid is a 1:1 mixture of the levo and dextro forms. It is distinct from mesotartaric acid and was called racemic acid from Latin racemus - a bunch of grapes. The word racemic later changed its meaning, becoming a general term for 1:1 enantiomeric mixtures - racemates. -- Tartaric acid is used to prevent CopperII ions from reacting with the hydroxide ions present in the preparation of copperI oxide. CopperI oxide is a reddish brown solid, and is produced by the reduction of a CuII salt with an aldehyde, in an alkaline solution. levotartaric acid D---tartaric acid dextrotartaric acid L-+-tartaric acid mesotartaric acid Image:D-tartaric acid.png Image:L-tartaric acid.png Image:DL-tartaric acid.png DL-tartaric acid racemic acid when in 1:1 ratio Forms of Tartaric Acid Common name tartaric acid levotartaric acid dextrotartaric acid mesotartaric acid racemic acid Synonyms D-S,S---tartaric acid unnatural isomer L-R,R-+-tartaric acid natural isomer 2R,3S-tartaric acid DL-S,S/R,R-±-tartaric acid PubChem CID 875 CID 439655 CID 444305 CID 78956 CID 5851 EINECS number 205-695-6 201-766-0 205-696-1 205-105-7 CAS number 526-83-0 147-71-7 87-69-4 147-73-9 133-37-9 Derivatives Commercially produced tartaric acid. Commercially produced tartaric acid. Important derivatives of tartaric acid include its salts, Cream of tartar potassium bitartrate, Rochelle salt potassium sodium tartrate, a mild laxative and tartar emetic antimony potassium tartrate. Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death.citation needed The minimum recorded fatal dose for a human is about 7.5 grams/kg.citation needed Given this figure, it would take over 500g to kill a person weighing 70kg, and so it may be safely included in many foods, especially sour-tasting sweets. As a food additive, tartaric acid is used as an antioxidant with E number E334, tartrates are other additives serving as antioxidants or emulsifiers. When cream of tartar is added to water, a suspension results which serves to clean copper coins very well. This is due to the fact that the tartrate solution can dissolve the layer of copperII oxide present on the surface of the coin. The resulting CopperII-tartrate complex that results is easily soluble in water. Tartaric acid in wine Unpurified tartaric acid, separated from grape juice, can take on the color of the latter. Unpurified tartaric acid, separated from grape juice, can take on the color of the latter. Tartaric acid may be most immediately recognizable to wine drinkers as the source of wine diamonds, the small potassium bitartrate crystals that sometimes form spontaneously on the cork. These tartrates are harmless, despite sometimes being mistaken for broken glass, and are prevented in many wines through cold stabilization. The tartrates that remain on the inside of aging barrels were at one time a major industrial source of potassium bitartrate. However, tartaric acid plays an important role chemically, lowering the pH of fermenting must to a level where many undesirable spoilage bacteria cannot live, and acting as a preservative after fermentation. In the mouth, tartaric acid provides some of the tartness that is currently out of fashion in the wine world, although citric and malic acids also play a role. The modern practice of extended hang time, where grapes are allowed to sit on the vine nearly until they become raisins, can dramatically reduce the taste of tartaric acid in a wine, leaving it smoother but also potentially less compatible with food. References ^ Tartaric Acid - Compound Summary, PubChem. ^ CRC Handbook External links PDB file for MSE History of Tartaric Acid from Linan Euro-China Co., Ltd. Wikimedia Commons has media related to: Tartaric acid Retrieved from http://en..org/wiki/Tartaric_acid Categories: Hydroxy acids | Dicarboxylic acids | Food antioxidants | Food acidity regulators | OenologyHidden categories: All articles with statements | Articles with statements since January 2008 | Articles with statements since May 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages БългарÑ?ки Català ÄŒesky Deutsch Ελληνικά Español Esperanto Français Galego 한국어 Italiano עברית LatvieÅ¡u Magyar Nederlands 日本語 Polski Português РуÑ?Ñ?кий SlovenÄ?ina Suomi Svenska Türkçe 中文 This page was last modified on 13 August 2008, at 12:32

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