tartaric acid
American Heritage Dictionary:
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tartaric acid
n.
Any of four isomeric crystalline organic compounds, C4H6O6, used to make cream of tartar and baking powder, as a sequestrant, and in effervescent beverages and photographic chemicals.
McGraw-Hill Science & Technology Encyclopedia:
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Tartaric acid
Any of the stereoisomeric forms of 2,3-dihydroxybutanedioic acid: l(+), d(−), and meso [(1), (2), and (3), respectively]. l(+)-Tartaric acid is present in
Tartaric acid has played a central role in the discovery of several landmark stereochemical phenomena. In 1848, L. Pasteur isolated enantiomers (1) and (2) by mechanical separation of hemihedral crystals of the racemic mixture. He also used tartaric acid and its salts to demonstrate a distinction between the meso isomer (3) and the racemic mixture (1) + (2), and between enantiomers and diastereoisomers in general. The difference in properties between (1) [or (2)] and the meso form (3) was later a key in establishing the relative configuration of the pentose and hexose sugars.
Both l(+)- and d(−)-tartaric acid and the esters are inexpensive compounds and are used as chiral auxiliary reagents in the oxidation of alkenes to enantiomerically pure epoxides. This method employs a hydroperoxide oxidant, titanium alkoxide catalyst, and l(+)- or d(−)-tartrate, and involves chirality transfer from the tartrate to the product. See also Asymmetric synthesis; Epoxide.
Tartaric acid has some use as an acidulant in foods and also as a chelating agent. Potassium hydrogen tartrate (cream of tartar) is an ingredient of baking powder. The potassium sodium salt, commonly called Rochelle salt, was the first compound used as a piezoelectric crystal. See also Chelation; Piezoelectricity.
Oxford Food & Nutrition Dictionary:
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tartaric acid
A dibasic acid, chemically dihydroxysuccinic acid. Occurs in fruits, the chief source being grapes; used in preparing lemonade, added to jams when the fruit is not sufficiently acidic (citric acid also used) and in baking powder. Rochelle salt is potassium sodium tartrate. See also cream of tartar.
Barron's Food Lover's Companion:
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tartaric acid
[tahr-TAR-ihk; tahr-TAHR-ihk] A natural crystalline compound found in plants, especially those with tart characteristics such as tamarind and unripe grapes. The principal acid in wine, tartaric acid is the component that promotes graceful aging and crispness of flavor. One of the by-products of tartaric acid is cream of tartar, which is used in baking and candy-making.
Oxford A-Z of Medicinal Drugs:
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tartaric acid
A weak acid with laxative properties used in the preparation of effervescent powders, granules, and tablets. Tartaric acid or its salt sodium potassium tartrate are ingredients of antacid preparations used to relieve indigestion and heartburn and of mild laxatives, which are freely available over the counter.
Side effects:
strong solutions are irritant and when swallowed can cause vomiting, diarrhoea, abdominal pains, and thirst.
Proprietary preparation:
Jaap's Health Salts (combined with sodium bicarbonate).
| tar, tamsulosin hydrochloride, tamoxifen | |
| tasonermin, taxanes, tazarotene |
Columbia Encyclopedia:
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tartaric acid
tartaric acid, HO2CCHOHCHOHCO2H, white crystalline dicarboxylic acid. It occurs as three distinct isomers, the dextro-, levo-, and meso- forms. The dextro- and levo- forms are optically active; the meso- form is optically inactive, as is racemic acid, a mixture of equal parts of the dextro- and levo- forms. Tartaric acid is found in many plants, e.g., grapes; this natural acid is chiefly the dextrorotatory D-tartaric acid, called also D-2,3-dihydroxysuccinic acid or L-2,3-dihydroxybutanedioic acid. This form can be partially converted to the others by heating it with an aqueous alkali, e.g., potassium hydroxide. Tartaric acids can be synthesized from maleic acids or fumaric acids by reaction with aqueous potassium permanganate. The various isomeric forms differ in such physical properties as boiling point. Tartaric acid is used chiefly in the form of its salts, e.g., cream of tartar and Rochelle salt.
Oxford Dictionary of Biochemistry:
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tartaric acid
2,3-dihydroxybutanedioic acid; 2,3-dihydroxysuccinic acid; an aldaric acid formed by oxidation of a tetrose at C-1 and C-4. The lg(+) (see d/l convention), or 2R,3R, enantiomer occurs widely in plants, especially grape juice, and in fungi and bacteria; the dg( — ) (or 2S,3S) enantiomer and meso form have limited distribution in plants. The racemic mixture, dl-tartaric acid, sometimes occurs during wine manufacture; it was originally known as paratartaric acid. The first determination of an absolute configuration by anomalous dispersion of X-rays was made on sodium rubidium l(+)-tartrate in 1951. The property of optical activity of some substances was first described by Pasteur in experiments with crystals of sodium ammonium tartrate.
| targeting subunits, target validation, target theory | |
| tasiRNA, tat, tau |
Saunders Veterinary Dictionary:
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tartaric acid
A compound used in preparing effervescent powders.
Wikipedia on Answers.com:
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Tartaric acid
| Tartaric acid[1] | |
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2,3-dihydroxybutanedioic acid |
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Other names
2,3-dihydroxysuccinic acid |
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| Identifiers | |
| CAS number | 526-83-0  |
| PubChem | 875 |
| ChemSpider | 852 |
| DrugBank | DB01694 |
| KEGG | C00898 |
| MeSH | tartaric+acid |
| ChEBI | CHEBI:15674 |
| ChEMBL | CHEMBL333714 , CHEMBL1200861 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C4H6O6 (Basic formula) HO2CCH(OH)CH(OH)CO2H (Structural formula) |
| Molar mass | 150.087 g/mol |
| Appearance | white powder |
| Density | 1.79 g/mL (H2O) |
| Melting point |
171–174 °C (L or D-tartaric; pure) |
| Solubility in water | 133 g/100ml (20 °C) |
| Acidity (pKa) | L(+) 25 °C : pKa1= 2.95 pKa2= 4.25 meso 25 °C: pKa1= 3.22 pKa2= 4.85 |
| Hazards | |
| EU classification | Irritant(Xi) |
| R-phrases | R36 |
| Related compounds | |
| Other cations | Monosodium tartrate Disodium tartrate Monopotassium tartrate Dipotassium tartrate |
| Related carboxylic acids | Butyric acid Succinic acid Dimercaptosuccinic acid Malic acid Maleic acid Fumaric acid |
| Related compounds | 2,3-Butanediol Cichoric acid |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Tartaric acid is a white crystalline diprotic organic acid. It occurs naturally in many plants, particularly grapes, bananas, and tamarinds; is commonly combined with baking soda to function as a leavening agent in recipes, 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 dihydroxyl derivative of succinic acid.
Tartaric acid was first isolated from potassium tartrate, known to the ancients as tartar, c. 800 by the alchemist Jabir ibn Hayyan.[3] The modern process was developed in 1769 by the Swedish chemist Carl Wilhelm Scheele.
Tartaric acid played an important role in the discovery of chemical chirality. This property of tartaric acid was first observed 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 ammonium sodium tartrate crystals, which he found to be chiral. By manually sorting the differently shaped crystals under magnification, Pasteur was the first to produce a pure sample of levotartaric acid.[4][5][6][7]
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Contents
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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 rather indirectly[8] from their structural relation to D- or L-glyceraldehyde), but to the orientation of the optical rotation, (+) = dextrorotatory, (−) = levorotatory. Sometimes, instead of capital letters, small italic d and 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.[9][10]
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 copper(II) ions from reacting with the hydroxide ions present in the preparation of copper(I) oxide. Copper(I) oxide is a reddish brown solid, and is produced by the reduction of a Cu(II) salt with an aldehyde, in an alkaline solution.
| levotartaric acid (D-(−)-tartaric acid) |
dextrotartaric acid (L-(+)-tartaric acid) |
mesotartaric acid |
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DL-tartaric acid (racemic acid) |
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| Forms of tartaric acid | ||||||
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| 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 | ||||||
| CAS number | 526-83-0 | 147-71-7 | 87-69-4 | 147-73-9 | 133-37-9 | |
Derivatives
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)[11][12][13]. Diisopropyl tartrate is used as a catalyst in asymmetric synthesis.
Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death.[14] The median lethal dose (LD50) is about 7.5 grams/kg for a human, ~5.3 grams/kg for rabbits and ~4.4 grams/kg for mice.[15] Given this figure, it would take over 500 grams (18 oz) to kill a person weighing 70 kilograms (150 lb), 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, as the tartrate solution can dissolve the layer of copper(II) oxide present on the surface of the coin. The resulting copper(II)-tartrate complex is easily soluble in water.
Tartaric acid in wine
See also: Acids in wine
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 in the wine, although citric and malic acids also play a role.
References
- ^ Tartaric Acid – Compound Summary, PubChem.
- ^ Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. ISBN 0-8493-0486-5.
- ^ Lisa Solieri, Paolo Giudici (2009). Vinegars of the World. Springer. p. 29. ISBN 88-470-0865-4. http://books.google.com/?id=XuPWgEMx_eIC&pg=PA29.
- ^ L. Pasteur (1848) "Mémoire sur la relation qui peut exister entre la forme cristalline et la composition chimique, et sur la cause de la polarisation rotatoire" (Memoir on the relationship which can exist between crystalline form and chemical composition, and on the cause of rotary polarization)," Comptes rendus de l'Académie des sciences (Paris), vol. 26, pp. 535–538.
- ^ L. Pasteur (1848) "Sur les relations qui peuvent exister entre la forme cristalline, la composition chimique et le sens de la polarisation rotatoire" (On the relations that can exist between crystalline form, and chemical composition, and the sense of rotary polarization), Annales de Chimie et de Physique, 3rd series, vol. 24, no. 6, pages 442–459.
- ^ George B. Kauffman and Robin D. Myers (1998). "Pasteur's resolution of racemic acid: A sesquicentennial retrospect and a new translation". The Chemical Educator 3 (6): 1–4. doi:10.1007/s00897980257a. http://192.129.24.144/licensed_materials/00897/papers/0003006/36kau897.pdf.
- ^ H. D. Flack (2009). "Louis Pasteur's discovery of molecular chirality and spontaneous resolution in 1848, together with a complete review of his crystallographic and chemical work". Acta Crystallographica A 65 (5): 371–389. doi:10.1107/S0108767309024088. PMID 19687573. http://crystal.flack.ch/sh5092.pdf.
- ^ J. M. McBride's Yale lecture on history of stereochemistry of tartaric acid, the D/L and R/S systems
- ^ various (2007-07-23). Organic Chemistry. Global Media. p. 65. ISBN 978-81-89940-76-8. http://books.google.com/?id=lEHMm2yRqkoC&pg=PT65. Retrieved 2010-06-05.
- ^ "(WO/2008/022994) Use of azabicyclo hexane derivatives". http://www.wipo.int/pctdb/ja/wo.jsp?WO=2008022994&IA=EP2007058636&DISPLAY=DESC.
- ^ Zalkin, Allan; Templeton, David H.; Ueki, Tatzuo (1973). "Crystal structure of l-tris(1,10-phenathroline)iron(II) bis(antimony(III) d-tartrate) octahydrate". Inorganic Chemistry 12 (7): 1641. doi:10.1021/ic50125a033.
- ^ Haq, I; Khan, C (1982). "Hazards of a traditional eye-cosmetic--SURMA". JPMA. the Journal of the Pakistan Medical Association 32 (1): 7–8. PMID 6804665.
- ^ McCallum, RI (1977). "President's address. Observations upon antimony". Proceedings of the Royal Society of Medicine 70 (11): 756–63. PMC 1543508. PMID 341167. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1543508.
- ^ Alfred Swaine Taylor, Edward Hartshorne (1861). Medical jurisprudence. Blanchard and Lea. p. 61. http://books.google.com/?id=4qZSb7EHzekC&pg=PA61.
- ^ Joseph A. Maga, Anthony T. Tu (1995). Food additive toxicology. CRC Press. pp. 137–138. ISBN 0-8247-9245-9. http://books.google.com/?id=6mGmxYqqiREC&pg=PA137.
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American Heritage Dictionary
The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2009. Published by Houghton Mifflin Company. All rights reserved.
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McGraw-Hill Science & Technology Encyclopedia
McGraw-Hill Encyclopedia of Science and Technology. Copyright © 2005 by The McGraw-Hill Companies, Inc. All rights reserved.
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Oxford Food & Nutrition Dictionary
A Dictionary of Food and Nutrition. Copyright © 1995, 2003, 2005 by A. E. Bender and D. A. Bender. All rights reserved.
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Barron's Food Lover's Companion
Food Lover's Companion. Copyright © 2001 by Barron's Educational Series, Inc. All rights reserved.
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Oxford A-Z of Medicinal Drugs
Market University Press. © 2000, 2003, 2010 An A-Z of Medicinal Drugs. All rights reserved.
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Columbia Encyclopedia
The Columbia Electronic Encyclopedia, Sixth Edition Copyright © 2012, Columbia University Press. Licensed from Columbia University Press. All rights reserved. www.cc.columbia.edu/cu/cup/.
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Oxford Dictionary of Biochemistry
Oxford University Press. Oxford Dictionary of Biochemistry and Molecular Biology © 1997, 2000, 2006 All rights reserved.
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Saunders Veterinary Dictionary
Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved.
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