Tartaric acid

  • tartaric acid[1]
    tartaric acid.svg
    tartaric-acid-3d-balls.png
    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
    • 526-83-0 ☑y
    3d model (jsmol)
    • interactive image
    chebi
    • chebi:15674 ☑y
    chembl
    • chembl333714 ☑y
    • chembl1200861 ☑y
    chemspider
    • 852 ☑y
    drugbank
    • db01694 ☑y
    echa infocard 100.121.903
    kegg
    • c00898 ☑y
    mesh tartaric+acid
    pubchem cid
    • 875
    comptox dashboard (epa)
    • dtxsid5046986 edit this at wikidata
    properties
    chemical 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 to 174 °c (340 to 345 °f; 444 to 447 k) (l or d-tartaric; pure)
    206 °c (dl, racemic)
    165–166 °c (meso-anhydrous)
    146–148 °c (meso-hydrous)[3]
    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
    eu classification (dsd) (outdated)
    irritant(xi)
    r-phrases (outdated) r36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
    except where otherwise noted, data are given for materials in their standard state (at 25 °c [77 °f], 100 kpa).
    ☑y verify (what is ☑y☒n ?)
    infobox references

    tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes, but also in bananas, tamarinds, and citrus.[4] its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of winemaking. it 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.

    tartaric acid is an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics, and is a dihydroxyl derivative of succinic acid.

  • history
  • stereochemistry
  • production
  • reactivity
  • derivatives
  • tartaric acid in wine
  • tartaric acid in fruits
  • superconductivity
  • applications
  • references
  • external links

Tartaric acid[1]
Tartaric acid.svg
Tartaric-acid-3D-balls.png
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.121.903
KEGG
MeSH tartaric+acid
Properties
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 to 174 °C (340 to 345 °F; 444 to 447 K) (L or D-tartaric; pure)
206 °C (DL, racemic)
165–166 °C (meso-anhydrous)
146–148 °C (meso-hydrous)[3]
  • 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
−67.5·10−6 cm3/mol
Hazards
Irritant(Xi)
R-phrases (outdated) R36
Related compounds
Other cations
Monosodium tartrate
Disodium tartrate
Monopotassium tartrate
Dipotassium tartrate
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).
☑Y verify (what is ☑Y☒N ?)
Infobox references

Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes, but also in bananas, tamarinds, and citrus.[4] Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of winemaking. It 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.

Tartaric acid is an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics, and is a dihydroxyl derivative of succinic acid.