Tartaric acid
Systematic name	2,3-dihydroxybutanedioic acid
Other names	2,3-dihydroxysuccinic acid threaric acid racemic acid uvic acid paratartaric acid
Molecular formula	C4H6O6
SMILES	C(C(C(=O)O)O)(C(=O)O)O
Molar mass	150.087 g/mol
Appearance	white powder
CAS number	526-83-0
Properties
Solubility in water	133 g/100 ml (20 °C)
Melting point	168-170°C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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 dicarboxylic acid. Image File history File links Download high resolution version (889x501, 7 KB) Summary Created in Chem3D Ultra Licensing Permission is granted to copy, distribute and/or modify this document under the terms of the GNU Free Documentation License, Version 1. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article or section does not cite any references or sources. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Solubility refers to the ability for a given substance, the solute, to dissolve in a solvent. ... This article describes water from a scientific and technical perspective. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... An organic acid is an organic compound that is an acid. ... It has been suggested that Veraison be merged into this article or section. ... This article or section does not cite its references or sources. ... Binomial name Tamarindus indica L. This article refers to the tree – for other uses see Tamarindo (disambiguation). ... A glass of red wine This article is about the alcoholic beverage. ... Space-filling model of the antioxidant metabolite glutathione. ... A tartrate is a salt or ester of the organic compound tartaric acid, a dicarboxylic acid. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted...

Tartaric acid was first isolated from potassium tartrate, known to the ancients as tartar, c. 800 by the Persian alchemist Jabir ibn Hayyan, 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. Potassium tartrate structural formula Potassium tartrate or dipotassium tartrate has formula K2C4H4O6. ... Cream of tartar is the potassium salt of tartaric acid, KHC4H4O6. ... Events December 25, Rome, coronation of Charles the Great (Charlemagne) as emperor by Pope Leo III. Celtic monks begin work on the Book of Kells on the Island of Iona. ... For information about all peoples of Iran, see Demographics of Iran; for Central Asian Persians, see Tajiks. ... This article or section includes a list of works cited or a list of external links, but its sources remain unclear because it lacks in-text citations. ... 15th century European portrait of Geber, Codici Ashburnhamiani 1166, Biblioteca Medicea Laurenziana, Florence Abu Musa Jabir Ibn Hayyan, in Latin Geber, was one of the most notable Islamic alchemists. ... 1769 was a common year starting on Sunday (see link for calendar). ... Carl Wilhelm Scheele Scheeles house with his pharmacy in Köping. ... The term chiral (pronounced ) is used to describe an object which is non-superimposable on its mirror image. ... Jean-Baptiste Biot Jean-Baptiste Biot (April 21, 1774, Paris – February 3, 1862, Paris) was a French physicist and mathematician who in the early 1800s studied the relationship between electrical current and magnetism (see Biot-Savart Law), as well as the polarisation of light passing through chemical solutions. ... Louis Pasteur (December 27, 1822 – September 28, 1895) was a French chemist best known for his remarkable breakthroughs in microbiology. ... 1847 was a common year starting on Friday (see link for calendar). ...

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. The term chiral (pronounced ) is used to describe an object which is non-superimposable on its mirror image. ... Fischer projection of D-glyceraldehyde Glyceraldehyde is a triose monosaccharide with chemical formula C3H6O3. ... When polarized light is passed through a substance containing chiral molecules (or nonchiral molecules arranged asymmetrically), the direction of polarization can be changed. ... In chemistry, enantiomers (from the Greek ἐνάντιος, opposite, and μέρος, part or portion) are stereoisomers that are nonsuperimposable complete mirror images of each other, much as ones left and right hands are the same but opposite. ... Diastereomers (or diastereoisomers) are stereoisomers that are not enantiomers (mirror images of each other). ...

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. ­­ Latin is an ancient Indo-European language originally spoken in Latium, the region immediately surrounding Rome. ... In chemistry, a racemate is a mixture of equal amounts of left- and right-handed stereoisomers of a chiral molecules. ...

levotartaric acid (D-(−)-tartaric acid)	dextrotartaric acid (L-(+)-tartaric acid)	mesotartaric acid
Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ...
DL-tartaric acid (racemic acid) (when in 1:1 ratio) Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ...

Derivatives

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). In science, a common name is any name by which a species or other concept is known that is not the official scientific name. ... PubChem is a database of chemical molecules. ... The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each chemical substance commercially available in the European Union between 1 January 1971 and 18 September 1981. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... Image File history File links Metadata Size of this preview: 800 × 600 pixelsFull resolution (2816 × 2112 pixel, file size: 458 KB, MIME type: image/jpeg) Photo taken by me in September, 2006. ... Image File history File links Metadata Size of this preview: 800 × 600 pixelsFull resolution (2816 × 2112 pixel, file size: 458 KB, MIME type: image/jpeg) Photo taken by me in September, 2006. ... Potassium bitartrate also potassium hydrogen tartrate has formula KC4H5O6. ... Potassium sodium tartrate is a double salt first prepared (in about 1675) by an apothecary, Pierre Seignette, of La Rochelle, France. ... Laxatives are foods, compounds, or drugs taken to induce bowel movements, most often taken to treat constipation. ...

Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death. The minimum recorded fatal dose for a human is about 7,5 grams/kg. In spite of that, it is 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. A top-down view of skeletal muscle Muscle (from Latin musculus little mouse [1]) is contractile tissue of the body and is derived from the mesodermal layer of embryonic germ cells. ... This article or section does not cite any references or sources. ... Malic acid is a tart-tasting organic acid that plays a role in many sour or tart foods. ... Look up Sweet in Wiktionary, the free dictionary. ... Food additives are substances added to food to preserve flavor or improve its taste and appearance. ... Space-filling model of the antioxidant metabolite glutathione. ... For the mathematical constant see: E (mathematical constant). ... A tartrate is a salt or ester of the organic compound tartaric acid, a dicarboxylic acid. ... An emulsion is a mixture of two immiscible substances. ...

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 copper(II) oxide present on the surface of the coin. The resulting Copper(II)-tartrate complex that results is easily soluble in water. Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... General Name, Symbol, Number copper, Cu, 29 Chemical series transition metals Group, Period, Block 11, 4, d Appearance metallic pinkish red Standard atomic weight 63. ... This article does not cite its references or sources. ...

Tartaric acid in wine

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. Image File history File links Metadata Size of this preview: 800 × 600 pixelsFull resolution (2816 × 2112 pixel, file size: 586 KB, MIME type: image/jpeg) Photo taken by me in September, 2006. ... Image File history File links Metadata Size of this preview: 800 × 600 pixelsFull resolution (2816 × 2112 pixel, file size: 586 KB, MIME type: image/jpeg) Photo taken by me in September, 2006. ... Potassium bitartrate also potassium hydrogen tartrate has formula KC4H5O6. ... A cork stopper for a wine bottle Champagne corks Varnished cork tiles can be used for flooring, as a substitute for linoleum or tiles. ... Cold stabilization is a process used in winemaking to reduce tartrate in wine. ... Whiskey barrels at the Jack Daniels distillery Barrels for aging wine in Napa Valley An aging barrel is a barrel used to age wine or distilled spirits such as whiskey, brandy, or rum. ...

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. It has been suggested that this article or section be merged with Fermentation (biochemistry). ... Citric acid is a weak organic acid found in citrus fruits. ... Malic acid is a tart-tasting organic acid that plays a role in many sour or tart foods. ... Raisins Percentages are relative to US recommendations for adults. ...

External links

• "History of Tartaric Acid" from Linan Euro-China Co., Ltd.

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Tartaric acid