Tartaric acid

**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.https://en.wikipedia.org/wiki/Tartaric_acid