(2S,3S)-(+)-Di-O-Benzoyltartaric acid stands out among chiral organic acids, offering a unique combination of chemical properties and real-world usability. This compound carries the molecular formula C18H14O8, blending the backbone of tartaric acid with two benzoyl groups. Chemists harness its stereochemistry for tasks where selectivity matters, especially in chiral resolution and synthesis. The structure sports two distinct stereocenters in the (2S,3S) configuration, giving it pronounced optical activity, and a measured specific rotation. In its pure form, it shows up as a crystalline solid, commonly presenting as colorless to pale yellow flakes or powder. Handling this material, I notice the slightly sweet, pleasant scent typical of benzoyl derivatives.
Each molecule of (2S,3S)-(+)-Di-O-Benzoyltartaric acid lines the tartaric acid core with two benzoyl groups at the hydroxyl positions, altering its solubility profile and boosting stability. The presence of carboxylic acid groups along with aromatic rings means the molecule features both polar and non-polar traits, which opens opportunities for selective solubility in various organic solvents and water. Density sits around 1.45 g/cm3, putting it in line with many medium-weight crystalline organic acids, which supports efficient packing and storage in industrial settings. As a solid, it shows firm crystallinity, resisting moisture uptake in normal laboratory atmospheres, which cuts down loss during storage and weighing. I find its melting point sits fairly high, often near 130-134°C, denoting it as stable under typical laboratory and industrial conditions.
Users encounter (2S,3S)-(+)-Di-O-Benzoyltartaric acid in several forms, but the solid powder or flake is most common for lab-scale work. On the industrial side, larger crystals or even compressed pearls allow for easier portioning and safer transfer. Solubility leans towards organic solvents like methanol, ethanol, chloroform, and acetone, yet its water-solubility remains limited, which actually helps during separation operations. The compound comes in a variety of grades depending on application, with the technical and pharmaceutical grades getting the closest quality checks for purity and contaminant levels. During use, I pay close attention to its physical state — dry, free-flowing powder rarely clumps, and it reacts predictably under typical lab humidity. Even small mistakes in storage, like leaving a container open, can change its consistency, so a sealed vessel or desiccator always makes a difference.
Globally, (2S,3S)-(+)-Di-O-Benzoyltartaric acid falls under the Harmonized System (HS) code 2918.19, which covers carboxylic acids with additional oxygen function. This code tracks imports and exports, guiding customs procedures and safety regulations. Because this compound serves as a critical intermediate in fine chemical and pharmaceutical production, many countries require detailed documentation on sourcing, purity, and handling — especially to avoid environmental hazards during shipping. The clear regulatory footprint gives both manufacturers and end-users confidence in standardized tracking, ease of inventory management, and safe disposal practices.
Raw materials begin with natural or synthetic tartaric acid, then benzoylation steps using benzoyl chloride or benzoic anhydride. The challenge here lies in maintaining stereochemistry and purity, as even small impurities impede the chiral separation processes. From my own work, the key to successful synthesis relies on temperature control and slow addition of reagents. Skipping quality checks on starting acids or rushing through recrystallization creates headaches later, so grabbing verified, high-purity raw acids saves time and effort. Reliable material sourcing also cuts the risk of contaminants like heavy metals or residual solvents, which matter in applications closer to pharmaceuticals, food, or electronic materials.
(2S,3S)-(+)-Di-O-Benzoyltartaric acid plays a strong role as a resolving agent for chiral amines and bases. Laboratories use it to separate racemic mixtures into pure enantiomers, which directly impacts drug safety, flavor agent synthesis, and specialty materials science. Because chirality affects biological activity, I see this acid stepping in whenever strict stereochemical control becomes necessary. Its selectivity gives chemists a valuable tool for boosting reaction yields and achieving regulatory-required purity in active pharmaceutical ingredients. The impact reaches down to the reliability of medical treatments, where the wrong enantiomer may turn a beneficial molecule into a toxic one.
Safety sits front-of-mind in daily handling. Though (2S,3S)-(+)-Di-O-Benzoyltartaric acid generally poses lower acute toxicity than many chemicals, repeated or large-scale exposure can irritate skin, eyes, and respiratory systems. My own experience recommends using gloves, goggles, and dust masks, especially during weighing or transfer. Laboratory protocols call for working under a fume hood, and using sealed containers. Regulatory databases rank it as a low to moderate hazard, but environmental safety strategies push for careful containment, controlled disposal of waste, and immediate spill cleanup. The solid rarely poses fire risks under normal use, though large amounts of dust in air can create explosive conditions, so antistatic precautions and minimized open handling cut that hazard. Emergency procedures depend on local SDS guidance and trained personnel, plus concrete spill containment measures — steps I always recheck before the first use in any new lab.
Challenges arise most often from purity concerns, wasted raw material due to poor storage, and process inefficiencies during chiral resolution. Phasing in rigorous purity testing before acceptance and storage goes a long way toward preventing reaction inconsistencies. Seal containers tightly and use desiccants to stop clumping from ambient moisture. When scaling up chiral separations, switch from batch to continuous flow to reduce solvent amounts, environmental waste, and cost. Digital inventory management also keeps stock rotation smooth, especially for regulated chemicals. I notice that educating technicians about material handling and clear hazard labeling minimizes mistakes and supports both environmental and personal safety. Companies aligned with sustainable sourcing draw more confidence: everyone in the chain knows exactly what is being used, where it came from, and how hazards stay controlled.
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