2R3Rtartaric

2R,3R-tartaric acid, commonly referred to as 2R3RTartaric or simply meso-tartaric acid when in its racemic form, is a stereoisomer of tartaric acid, an organic compound with the chemical formula C₄H₆O₆. Tartaric acid is naturally occurring in many fruits, particularly grapes, and has been historically used in winemaking and food preservation. The 2R,3R configuration refers to the spatial arrangement of its chiral centers, where both hydroxyl-bearing carbon atoms have the same absolute configuration (R).

Tartaric acid exists in several stereoisomeric forms due to its two chiral centers, leading to three distinct stereoisomers: the (2R,3R)-enantiomer, the (2S,3S)-enantiomer (its mirror image), and the meso form (2R,3S or 2S,3R), which is achiral despite having two chiral centers. The 2R,3R-tartaric acid is one of the two optically active enantiomers, meaning it rotates plane-polarized light in a specific direction (dextrorotatory).

This isomer is significant in organic synthesis and biochemical research due to its ability to form crystalline salts with bases, known as tartrates. The 2R,3R configuration is often used in asymmetric synthesis to induce specific stereochemical outcomes in reactions. Tartaric acid and its derivatives are also employed in pharmaceuticals, as buffering agents, and in analytical chemistry for chiral resolution techniques.

In nature, tartaric acid is found in grapes and other fruits, where it contributes to the tartness of flavors. Industrially, it is produced through fermentation or chemical synthesis, often derived from the hydrolysis of starch or other carbohydrates. The 2R,3R-tartaric acid is particularly relevant in studies of enantioselectivity, where the precise stereochemistry of reactants can influence reaction pathways and product formation.