Chemists exploring tartrates got their hands on tartaric acid long before the luxury of automation and high-throughput screening. Pasteur’s dissection of tartrate crystals in the 19th century cracked open the door to chirality—a concept as central to chemistry as gravity is to physics. Out of these discoveries, derivatives like (2S,3S)-(+)-Di-O-benzoyltartaric acid emerged, not by accident, but through trials fueled by curiosity and necessity. Scientists kept modifying tartaric acid, searching for reagents that could steer reactions with a surgeon’s hand, setting the groundwork in chiral resolution and analytical chemistry. The acid's story can't be told apart from the progression of stereochemistry itself—a field shaping industries from pharmaceuticals to flavors for well over a century.
This compound stands out for delivering chiral separation in a world demanding purity at the molecular level. It appears as a solid, color shifting between white and faint yellow depending on how it’s made and stored. It brings structure and reliability, often finding its way to the benchtop of labs reining in the quirks of natural product synthesis or purifying active drug ingredients. Commercial samples typically arrive with clear labeling, batch data, and confident claims about enantiomeric excess—details expected by any seasoned chemist who understands the frustration of inconsistent reagents. Despite competition from newer compounds, (2S,3S)-(+)-Di-O-benzoyltartaric acid still earns trust by delivering results in tried-and-true protocols.
It melts around 150-152°C, floats easily in organic solvents, and boasts a chemical stability that proves its worth through cycles of use. This compound displays low hygroscopicity—a trait saving many from the despair of spoiled stock. Its optical rotation gives chemists quick feedback on purity and stereochemistry, saving long nights of doubt in front of an NMR machine. Its benzoyl groups lend rigidity, impacting both solubility and reactivity compared to unmodified tartaric acid. Experience in the lab confirms: small deviations in storage or handling rarely cripple its performance, a relief for those tasked with delicate preparative work.
Labels typically show the molecular formula C18H14O8, a CAS number, origin, batch number, purity (often above 98%), and sometimes recommended storage conditions. Suppliers put an emphasis on chiral purity data—anyone frustrated by unknown isomeric blends will know the value of this transparency. I’ve come to expect accompanying safety data, with instructions clear enough for undergrads and time-strapped postdocs alike. Consistent documentation builds the trust necessary in pharmaceutical, food, and fine chemicals sectors.
The route generally starts with tartaric acid reacting with benzoyl chloride or benzoyl anhydride in the presence of a base like pyridine. Optimizing this reaction for yield and enantiomeric purity requires a careful control of temperature and stoichiometry—mistakes here mean hours cleaning up oily byproducts. After reaction completion, chemists typically filter or extract the product, relying on recrystallization to achieve the right chirality and remove persistent impurities. Personal experience tells me that patience pays dividends; rushing crystal growth often trades purity for speed, shortchanging downstream applications.
Chiral separation stands as the flagship use, but its chemical backbone allows subtle tweaks. Derivatization swaps out benzoyl groups for other protecting groups, tuning polarity or reactivity to fit new separation challenges. Sometimes the acid forms salts with bases, expanding its reach into less explored analytical territory. In asymmetric catalysis, chemists adapt it into ligands or auxiliaries, extending its reach far beyond simple resolution agents. Reactive centers sometimes fall prey to nucleophilic attack or hydrolysis, but careful handling keeps these side reactions at bay.
Depending on supplier or literature origin, it shows up as (+)-Di-O-Benzoyltartaric acid, Dibenzoyl-L-tartaric acid, or even by the shorthand DBTA. Search for it in catalogs and you may find reference to L-(+)-Di-O-Benzoyltartaric acid, reflecting its S,S configuration. Avoiding mix-ups between isomers remains crucial—a lesson learned by double-checking not just the bottle, but the supplier’s certificates and supporting chromatograms.
Careful handling goes a long way. Benzoyl derivatives rarely trigger violent reactions, but they cause irritation if mishandled. Anyone who’s accidentally inhaled or spilled fine organic acids will remember the sharp sting. The MSDS points out respiratory irritation, advise gloves, goggles, and lab coats. Disposal often involves neutralization before adding wastes to organic solvent incineration streams—an expense justified by stricter environmental rules. Training and clear standard operating procedures mean less risk, fewer accidents, and uninterrupted workflow.
Chiral resolution consumes the most product, with the compound acting as a tool for splitting racemic mixtures into their mirror-image components—a demand felt keenly in pharmaceuticals, where wrong-handed isomers can heal or harm. Analytical chemists use it for derivatization before running chiral chromatography, improving the detection and separation of enantiomers. Synthesis routes for agrochemicals and flavors often depend on access to pure stereoisomers, funneling more applications back toward this compound. Whether tackling a stubborn intermediate or refining an API, experienced chemists reach for this acid when the stakes include regulatory approval and patient safety.
Synthetic and analytical chemists haven’t stopped seeking improvements. Recent research moves toward greener syntheses, trying to replace aromatic reagents or cut down on waste acid. Academia and industry press on, using DBTA as a launching pad to design new chiral imaging agents, or tweaking its skeleton for greater selectivity in chromatographic phases. Collaborative projects, often between chemical companies and university labs, keep pushing its applications and derivatives into previously inaccessible reaction spaces.
Literature surveys show low acute toxicity in cell and animal models, but the presence of benzoyl groups and acid functions demands caution. Chronic studies lag behind acute reports, leaving an opening for new work on metabolites and breakdown products. Earlier safety documents sometimes relied on analogies and sparse animal data; contemporary research rightly asks for more, combining cell culture, high-throughput analysis, and careful documentation. General lab experience teaches that exposure remains low with good practice, yet as regulations tighten and expectations of safety rise, legacy data needs supplementing with current, comprehensive assessment.
Chiral chemistry keeps expanding, and as synthetic targets grow more complex, the demand for robust chiral reagents stays high. Green chemistry pressures drive development of more biodegradable tartaric derivatives using renewable feedstocks, aligning both efficiency and environmental responsibility. Digital tools and machine learning promise to accelerate the discovery of new analogues, while deeper collaboration between suppliers and regulatory agencies ensures continuity and compliance. (2S,3S)-(+)-Di-O-benzoyltartaric acid may eventually share the stage with new molecules, but its historical reliability and adaptability suggest that any replacement will have formidable standards to meet. With this level of momentum, expect the acid’s derivatives to anchor the next wave of breakthroughs in synthesis, separation, and analysis.
In the world of chemistry, especially labs working on pharmaceuticals and fine chemicals, separating mirror-image molecules often leads to big headaches. Many drugs work in one “handed” form but not the other. A molecule like (2S,3S)-(+)-di-O-benzoyltartaric acid gives chemists a powerful way to make that cut. It’s what we call a chiral resolving agent. Through my own background in organic synthesis, I’ve seen researchers reach for this tartaric acid derivative when they’re out of other options to separate racemic mixtures. If you make a molecule and half of it is the “wrong” version, you can’t ship a medicine that’s only 50% effective (or possibly toxic).
Chirality splits the chemical universe in two. Limonene in oranges smells sweet, but the mirror form goes in cleaning products for a sharp, pine scent. The same split causes massive consequences in medicine—thalidomide’s racemic mix gave healing with one hand and harm with the other. With (2S,3S)-(+)-di-O-benzoyltartaric acid, chemists create diastereomeric salts that separate easily. By crystallizing the pieces apart, labs sift out the form they need for further reactions.
It’s not only about pharmaceuticals. This resolving agent shows up in pilot plants and specialty production units, making precise separations in fields as diverse as agrochemicals and flavor chemistry. Every year brings dozens of newly patented drugs and chemical entities, many relying on chiral purity. The demand for reliable, reproducible methods isn't going away.
Years spent running column chromatography drive home how much faster clean salt formation can be. The real-world benefit: it cuts time, labor, and cost. Even larger companies, with access to chiral chromatography, keep stockpiles of proven agents like this one on the shelf. The trusted status comes from years of documented success. Highly cited journals, reference books, and chemical catalogs list (2S,3S)-(+)-di-O-benzoyltartaric acid as essential for resolving bases or amines that don’t cooperate with other approaches.
This isn’t obscure stuff. Peer-reviewed work in Journal of the American Chemical Society explores these very separations. Major pharmaceutical manufacturers name hydrophobic tartaric acid derivatives in patent documents for active ingredient preparation. The evidence base covers experiments, clinical supply demands, and industrial safety assessments.
Research quality suffers if starting materials contain impurities or the wrong enantiomer. That’s why experienced chemists confirm the absolute configuration, double-check certificates of analysis, and work with trusted suppliers. Without careful sourcing, failed resolutions waste money and days of work. Lab managers build relationships with vendors known for quality and service. In tight regulatory environments, supply chain trust matters as much as molecular structure.
New chiral technologies like enzymatic catalysis and asymmetric synthesis have cut into the market for classical resolution. Still, (2S,3S)-(+)-di-O-benzoyltartaric acid remains an irreplaceable benchmark. It’s one thing to make theoretical improvements, quite another to keep pace with the daily reality of delivering pure molecules. Labs rely on proven agents, building on a deep body of experience and published results.
Chemistry has a way of rolling tongue-twisting names off the lab bench and into industries ranging from pharmaceuticals to chemical research. (2S,3S)-(+)-di-O-benzoyltartaric acid stands out not just for its name, but also for its role as a dependable resolving agent in chiral chemistry. With the increasing focus on enantiopure substances, synthetic chemists turn to this compound regularly. Its formula? That’s C18H14O8—not the sort of lineup you’d want to forget when sorting out reagents on a crowded shelf.
Most folks working out of an organic lab have run into tartaric acid derivatives. This particular tartaric acid swaps out a couple of hydroxyl hydrogens for benzoyl groups. The result—C18H14O8—adds mass and makes the molecule heavier. We’re looking at a molecular weight that clocks in at 358.3 g/mol. That number carries more than academic value. Accuracy with molecular weight ensures your scale tips just right during synthesis. Mess up the math or look up the wrong isomer, and the results spiral—not just in your yield, but in your downstream resolution experiments.
Why care about the formula and weight? In my own bench days, I poured over molecular formulas because tiny errors chipped away at time, money, and trust in the lab. Pharma R&D demands reproducibility and razor-thin margins for error. Using (2S,3S)-(+)-di-O-benzoyltartaric acid, researchers can separate racemic mixtures into pure enantiomers—hugely important for drugs whose left-handed version works, and right-handed version does nothing, or worse, harms the patient. This chiral resolving agent’s identity is more than trivia; it’s foundational for safety and legal compliance in the supply chain. The wrong compound brings audit disasters or even regulatory penalties.
The formula and weight of (2S,3S)-(+)-di-O-benzoyltartaric acid didn’t spring up overnight. Chemists untangled the structure through NMR, crystallography, and years of literature. Reproducible chemical data acts as a collective promise: your batch matches the standard. Industry giants won’t touch a product they can’t independently verify. Only with the accepted numbers—C18H14O8, 358.3 grams per mole—do deals close and processes scale up from grams to kilograms without surprises.
Mislabeling or confusing similar-sounding tartaric acid esters leads to costly errors. It helps to set up clear storage labels and digital tracking in the inventory. Cross-checking supplier specs against reputable chemical databases lowers the chance of mismatches. I’ve seen labs implement barcode systems tied to up-to-date databases so every chemist double-checks identity and weight before starting a reaction. Training new staff to respect the chain from supplier certificate to shelf pays off in safety and reliability down the line.
Relying on accurate molecular formulas and weights is not paperwork—it’s good science. Adopting digital inventory, regular audits, and open communication in the team makes slippery errors rare and promotes confidence in every experiment. At the end of the day, the small details—C18H14O8 and 358.3—mean big outcomes in both the lab notebook and the larger world of medicine and manufacturing.
(2S,3S)-(+)-di-O-benzoyltartaric acid isn’t just a tongue-twister of a name, it’s a key chiral resolving agent for chemists. In the lab, I’ve seen plenty of folks learn a tough lesson: how you store chemicals like this sets you up for success or risk. Choosing a spot on a shelf won’t cut it, and throwing it in with the rest of the acids invites trouble.
Humidity messes with benzoate esters, and from personal experience, I’ve learned that a humid lab bench gets you clumpy, useless material far too quickly. Moisture creeping in can prompt hydrolysis, and that’s just wasteful. Keep this chemical in a tightly sealed amber glass bottle—preferably one with a fresh desiccant pack in the storage cabinet.
Light degrades many organic compounds over time. I remember a colleague who ignored this and left a similar acid in a clear bottle. After a week, the sample turned slightly off-color and didn’t perform the same way in resolution experiments. Sunlight, even from a window, brings enough energy to start unwanted reactions. Sticking with amber or opaque containers avoids this problem.
Lab freezers or refrigerators aren’t always the answer for organic acids. With (2S,3S)-(+)-di-O-benzoyltartaric acid, long-term temperature swings or extremes may not outright destroy it, but you’ll shorten its usable life. Standard practice keeps it at 2–8°C—refrigerator temps, not on the back shelf or next to equipment that throws off heat. Our lab fridge had a section just for sensitive reagents, clearly labeled and away from the regular grind of opened and closed doors.
Handling safety matters too. Some acids tempt people to skip gloves because they don’t fume or splash like strong mineral acids. This compound can still irritate skin, and nobody enjoys tracking down a mystery rash. I always set up a labeled work area, reinforced with gloves and eye protection near the storage site.
Mislabeling is another hazard. Once, our storage got mixed up with similar glass bottles, and an undergrad grabbed the wrong acid for a chiral separation. That cost the lab a day’s work and almost ruined an expensive batch. Clear, durable labels that highlight both the full name and hazard class prevent those headaches.
Routine checks matter more than fancy monitoring systems. I make a habit of inspecting seals and label readability at least once a month. Any sign of caking or color change gets logged so we can investigate right away. Sharing tips during group meetings keeps everyone in the loop.
Chemical suppliers recommend storage in a cool, dry place, protected from light and moisture. As obvious as this sounds, reminders and practical routines keep everyone disciplined. In my experience, a well-organized chemical inventory cuts down on error and waste more than any policy ever could.
Proper storage isn’t an afterthought—it saves time, protects experiments, and keeps the lab safe. That’s worth every extra minute spent getting it right.
In the chemical world, the concept of “enantiomeric purity” often grabs the spotlight for the right reasons. I’ve seen firsthand in laboratory settings how one enantiomer can make all the difference — especially in pharmaceuticals, food additives, and specialty chemicals. With tartaric acid and its derivatives such as (2S,3S)-(+)-di-O-benzoyltartaric acid, this purity translates directly to effectiveness and, in some cases, safety. Regulators and quality control teams keep a close eye on optical isomers because a molecule's “handedness” influences everything from reactivity to biological effect.
This specific tartaric acid derivative pops up everywhere experimental chemists want to separate racemic mixtures. Organic synthesis often relies on resolving agents, and this compound stands out because its two stereocenters (the 2S,3S configuration) create a highly predictable chiral environment. Based on firsthand experience managing resolution protocols, it’s clear that the purity and “direction” of this molecule affect the yield and quality of downstream products.
Enantiomeric purity, or enantiomeric excess (ee), essentially measures how much of one enantiomer you have compared to its mirror image. Technically, a value of 100% means you have a single enantiomer, with no contamination from the opposite form. This measure carries big weight in chemical manufacturing and research. Labs commonly use chiral high-performance liquid chromatography (HPLC) and polarimetry to verify purity, since even small traces of the “wrong” enantiomer can spoil a synthesis or skew biological testing.
In practice, the commercial supply of (2S,3S)-(+)-di-O-benzoyltartaric acid boasts high enantiomeric purity — often upwards of 98% ee, and some suppliers guarantee as high as 99%. Analytical certificates generally back that up, reporting [α]D values at standardized concentrations and temperatures that match or slightly exceed reference standards. Having handled this compound in both teaching and research environments, I’ve seen that even minor dips in purity cause all sorts of difficulties. The workup gets messier, and the results can go sideways fast.
Compromised enantiomeric purity matters far beyond just a number in a certificate. If the compound drifts below 95% ee, for example, separation methods deliver less predictable products, wastes rise, and reproducibility drops. For researchers working on new drugs, unchecked enantiomeric contamination can lead to false negatives or positives during screening. In the worst-case scenario, an overlooked impurity could create safety concerns, since biological systems respond in unique ways to each enantiomer. I’ve seen process control teams spend days hunting down the source of a rogue impurity, only to find it traced back to a batch of resolving agent that never got checked for enantiomeric purity.
Maintaining solid enantiomeric purity calls for several strategies. Reliable suppliers remain a must, and every incoming lot needs verification with chiral HPLC. Batch-to-batch consistency reduces risk during large-scale work. In smaller labs, running control experiments alongside actual syntheses helps highlight problems before they snowball. Documentation that tracks impurities and deviations puts everyone on the same page. When budgets allow, investing in modern chiral analytics brings peace of mind. This discipline — sometimes tedious, always essential — ensures that (2S,3S)-(+)-di-O-benzoyltartaric acid lives up to its promise as a trustworthy resolving agent.
This compound shows up a lot in labs where precise stereochemistry matters. It plays a key role in separation techniques and the synthesis of enantiomerically pure compounds. Still, there’s no room for cutting corners with safety just because it’s a common sight on the shelf. Benzoylated tartrates bring a cocktail of hazards, from irritation of the eyes and skin to more serious risks if you ignore proper handling.
Lab coats, gloves made from nitrile or neoprene, and tight-fitting goggles should come out before you ever uncap the bottle. Once, early in my career, I neglected to double-check glove compatibility—only to find a tingling rash from a splash hours later. Not every solvent or acid eats through your gloves the same way, so attention to materials beats regret every time.
This chemical isn’t especially volatile compared to some solvents, but dust and fine powders still linger in the air after weighing. For me, weighing compounds inside a fume hood became non-negotiable after watching residues settle everywhere during an unusually dry winter. Fume hoods don’t just pull vapors out—they drag fine particles with them, keeping both lungs and benchtops cleaner.
If a spill happens—whether a little or a lot—keeping a spill kit nearby, stocked with absorbent materials and pH-neutralizing agents, really limits chaos. Trying to wipe powdered acids with a damp paper towel only spreads the hazard around and wastes time. Sweeping up powders with soft, disposable brushes before chemical neutralization avoids static and airborne dust. Good storage also helps. I keep this acid in tightly closed containers, far from bases, strong oxidizers, and any moisture-prone area. The containers always wear clear hazard labels, avoiding mix-ups during long days testing different derivatives and reactions.
Working with benzoyltartaric acid, it’s important not to ignore small symptoms. Eye redness, coughing, or a burning sensation on skin all signal a possible issue. Washing the area with cool water helps, but sometimes you need to go further if symptoms stick around. More than once I’ve seen colleagues brush off a stinging eye, only to look at irritated bloodshot sclera later. Immediate rinsing—up to 15 minutes—usually works, but safety showers and eyewash stations act as insurance you’ll wish you had, should a larger mishap occur.
After reactions wrap up, every gram of leftover acid and contaminated items heads into specialized chemical waste bins. Long ago, I saw solvents mixed down the drain out of habit. Now, strict rules and training protect not just the person holding the flask, but the groundwater and community as well. Tracking disposal with a proper chemical waste log removes confusion during inspections and helps make sure nothing illegal slips through.
From my experience, casual routines in handling chemicals gradually morph into complacency. It takes updated safety briefings, shared stories of close calls, and personal reminders to nudge folks out of cruise control. Treating every sample as a potential hazard, even after hundreds of uses, makes sure the learning never stops—for yourself and those working beside you.
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