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Tartaric acid information


Tartaric acid[1]

Ball-and-stick model of L-(+)-tartaric acid
Names
Preferred IUPAC name
2,3-Dihydroxybutanedioic acid
Other names
Tartaric acid
2,3-Dihydroxysuccinic acid
Threaric acid
Racemic acid
Uvic acid
Paratartaric acid
Winestone
Identifiers
CAS Number
  • R,R-isomer: 87-69-4
  • S,S-isomer: 147-71-7
  • racemic: 133-37-9
  • meso-isomer: 147-73-9
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:15674 checkY
ChEMBL
  • ChEMBL333714 checkY
  • ChEMBL1200861 checkY
ChemSpider
  • 852 checkY
DrugBank
  • DB01694 checkY
ECHA InfoCard 100.121.903 Edit this at Wikidata
E number E334 (antioxidants, ...)
KEGG
  • C00898 checkY
MeSH tartaric+acid
PubChem CID
  • 875 unspecified isomer
UNII
  • W4888I119H checkY
CompTox Dashboard (EPA)
  • DTXSID5046986 Edit this at Wikidata
InChI
  • InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10) checkY
    Key: FEWJPZIEWOKRBE-UHFFFAOYSA-N checkY
  • InChI=1/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)
    Key: FEWJPZIEWOKRBE-UHFFFAOYAZ
SMILES
  • O=C(O)C(O)C(O)C(=O)O
Properties
Chemical formula
C4H6O6 (basic formula)
HO2CCH(OH)CH(OH)CO2H (structural formula)
Molar mass 150.087 g/mol
Appearance White powder
Density 1.737 g/cm3 (R,R- and S,S-)
1.79 g/cm3 (racemate)
1.886 g/cm3 (meso)
Melting point 169, 172 °C (R,R- and S,S-)
206 °C (racemate)
165-6 °C (meso)
Solubility in water
  • 1.33 kg/L (L or D-tartaric)
  • 0.21 kg/L (DL, racemic)
  • 1.25 kg/L ("meso")
Acidity (pKa) L(+) 25 °C :
pKa1= 2.89, pKa2= 4.40
meso 25 °C:
pKa1= 3.22, pKa2= 4.85

[2]

Conjugate base Bitartrate
Magnetic susceptibility (χ)
−67.5·10−6 cm3/mol
Hazards
GHS labelling:[3]
Pictograms
GHS05: Corrosive
Signal word
Danger
Hazard statements
H318
Precautionary statements
P280, P305+P351+P338+P310
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes but also in tamarinds, bananas, avocados, and citrus.[1] Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of fermentation. Potassium bitartrate is commonly mixed with sodium bicarbonate and is sold as baking powder used as a leavening agent in food preparation. The acid itself is added to foods as an antioxidant E334 and to impart its distinctive sour taste. Naturally occurring tartaric acid is a useful raw material in organic chemical synthesis. Tartaric acid, an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics and is a dihydroxyl derivative of succinic acid.

  1. ^ a b Tartaric Acid – Compound Summary, PubChem.
  2. ^ Dawson, R.M.C. et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
  3. ^ GHS: Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

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Tartaric acid

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Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes but also in tamarinds, bananas, avocados...

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Potassium bitartrate

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of uses. It is the potassium acid salt of tartaric acid (a carboxylic acid). In cooking, it is known as cream of tartar. It is used as a as a component...

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Acids in wine

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of the wine such as tannins. Three primary acids are found in wine grapes: tartaric, malic, and citric acids. During the course of winemaking and in the...

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Baking powder

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cream of tartar (KC4H5O6), a derivative of tartaric acid. The use of two acidic components is the basis of the term "double acting". The acid in a baking...

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Tartar

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Ukraine Tatar language Potassium bitartrate, also called cream of tartar Tartaric acid, commonly mixed with sodium bicarbonate and sold as baking powder...

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Organic acid

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organic acids. A few common examples include: Lactic acid Acetic acid Formic acid Citric acid Oxalic acid Uric acid Malic acid Tartaric acid Butyric acid Folic...

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DATEM

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DATEM (diacetyl tartaric acid ester of mono- and diglycerides, also E472e) is an emulsifier primarily used in baking to strengthen the gluten network...

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Pyruvic acid

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Pelouze distilled tartaric acid and isolated glutaric acid and another unknown organic acid. Jöns Jacob Berzelius characterized this other acid the following...

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Stereoisomerism

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example shown below, the meso form of tartaric acid forms a diastereomeric pair with both levo- and dextro-tartaric acids, which form an enantiomeric pair...

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Caftaric acid

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esterified phenolic acid, composed of caffeic acid, a hydroxycinnamate produced by plants, and tartaric acid, the principal organic acid found in grape berries...

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Racemic acid

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Racemic acid is an old name for an optically inactive or racemic form of tartaric acid. It is an equal mixture of two mirror-image isomers (enantiomers)...

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Racemic mixture

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racemic mixture was racemic acid, which Louis Pasteur found to be a mixture of the two enantiomeric isomers of tartaric acid. He manually separated the...

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Sour Patch Kids

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sugar and sour sugar (a combination of citric acid, tartaric acid, and sugar). The tartaric and citric acids provide the candy with a sharp burst of tartness...

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Tamarind

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injury in dogs following ingestion of cream of tartar and tamarinds and the connection to tartaric acid as the proposed toxic principle in grapes and raisins"...

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Choline bitartrate

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powder with an acid taste. It is hygroscopic when exposed to air. Modern texts refer to the choline salt of the natural form of tartaric acid, that is, the...

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Sugar acid

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Tartrate

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commercially are pure crystalline tartaric acid used as an acidulant in non-alcoholic drinks and foods, cream of tartar used in baking, and Rochelle salt...

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Meso compound

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optically active pair of levotartaric acid (L-(R,R)-(+)-tartaric acid) and dextrotartaric acid (D-(S,S)-(-)-tartaric acid). The meso compound is bisected by...

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Bitartrate

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anion which is the conjugate base of tartaric acid. It may also refer to any salt or monoester of tartaric acid. Some examples of bitartrate salts include:...

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Soured milk

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glucono-delta-lactone, hydrochloric acid, lactic acid, malic acid, phosphoric acid, succinic acid, and tartaric acid. Soured milk is commonly made at home or...

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White wine

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on the tartaric stability of wines and the validity of the tartaric stabilisation test, L. Blateyron, R&D de l'ICV à Lattes. (in French) Tartaric Stabilisation...

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Enantiomer

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mirror-symmetric pairs, and are known as meso compounds. For instance, meso tartaric acid (shown on the right) has two asymmetric carbon atoms, but it does not...

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Potassium sodium tartrate

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tartrate tetrahydrate, also known as Rochelle salt, is a double salt of tartaric acid first prepared (in about 1675) by an apothecary, Pierre Seignette, of...

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Digestive biscuit

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oil, wholemeal, raising agents (usually sodium bicarbonate, tartaric acid and malic acid), and salt. Some varieties also contain dried whey, oatmeal,...

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Stinging plant

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the long-lasting pain caused by stings was attributed to oxalic and tartaric acid, although a synergistic effect of the other components of the stinging...

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Isocitric acid

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Wine preservatives

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Germany, Austria, Oregon and New Zealand. In contrast to tartaric acid, if the grapes are too acidic, calcium carbonate is used to bring them down to the...

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Potassium tartrate

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It is the potassium salt of tartaric acid. It is often confused with potassium bitartrate, also known as cream of tartar. As a food additive, it shares...

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Optical rotation

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In 1849, Louis Pasteur resolved a problem concerning the nature of tartaric acid. A solution of this compound derived from living things (to be specific...

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Carbonated water

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probably made using "soda powders" containing bicarbonate of soda and tartaric acid. The name soda water arose from the fact that soda (sodium carbonate...

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