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. mesoTartaric Acid: Formed by heating dextrotartaric 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.