Term: Tartaric acid

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**1. History and Stereochemistry:**
– Known to winemakers for centuries
– Chemical extraction process developed in 1769 by Carl Wilhelm Scheele
– Important role in discovery of chemical chirality
– Property observed by Jean Baptiste Biot in 1832
– Louis Pasteur produced pure levotartaric acid in 1847
– Naturally occurring form is dextro tartaric acid
– Cheaper than enantiomer and meso isomer
– Modern textbooks refer to natural form as (2)-tartaric acid
– Dextro and levo form different crystal structures
– Anhydrous meso tartaric acid forms two polymorphs

**2. meso-Tartaric Acid:**
– Formed by heating dextro-tartaric acid in water
– Prepared from dibromosuccinic acid using silver hydroxide
– Separated from racemic acid by crystallization
– Used in Fehlings solution to bind to copper(II) ions
– Prepared in multistep reaction from maleic acid

**3. Reactivity and Derivatives:**
– L-(+)-tartaric acid reacts to produce dihydroxymaleic acid
– Dihydroxymaleic acid can be oxidized to tartronic acid
– Participates in several reactions
– Important derivatives include sodium ammonium tartrate and cream of tartar
– Tartar emetic is a resolving agent
– Diisopropyl tartrate used in asymmetric synthesis
– Median lethal dose is about 7.5 grams/kg for humans
– Used as antioxidant with E number E334 in foods

**4. Applications and Toxicity:**
– Used in pharmaceuticals for effervescent salts
– Combined with citric acid to improve taste of oral medications
– Diverse applications in pharmaceutical industry
– Tartaric acid toxicity in dogs can lead to fatal outcomes
– Studies suggest a connection between tartaric acid and toxic effects in canines
– April 2021 research highlights the potential dangers of tartaric acid for canines

**5. Tartaric Acid in Wine, Fruits, and Compound Summary:**
– Source of wine diamonds (potassium bitartrate crystals)
– Harmless but sometimes mistaken for broken glass
– Lowers pH of fermenting must and acts as preservative
– Provides tartness in wine
– Highest levels in grapes and tamarinds
– Also found in bananas, avocados, apples, cherries, citrus fruits, etc.
– Toxicity in Canines
– Compound Summary: Extensively studied in biochemical research, available on PubChem.

Tartaric acid (Wikipedia)

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. Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of fermentation. 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. 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.

Tartaric acid

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.121.903 Edit this at Wikidata
E number E334 (antioxidants, ...)
KEGG
MeSH tartaric+acid
  • 875 unspecified isomer
UNII
  • 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
  • O=C(O)C(O)C(O)C(=O)O
Properties
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)
  • 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

Conjugate base Bitartrate
−67.5·10−6 cm3/mol
Hazards
GHS labelling:
GHS05: Corrosive
Danger
H318
P280, P305+P351+P338+P310
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).
checkY verify (what is checkY☒N ?)

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