Chemists started paying attention to the peculiar arrangement of hydroxy groups on the benzaldehyde ring long before analytical instruments made things easy. 2,3,4-Trihydroxybenzaldehyde, thanks to those three closely set hydroxy groups, caught the eye of organic researchers who wanted to probe phenolic chemistry. In the early 20th century, interest in phenolic aldehydes spiked thanks to work with natural product extraction, especially from bark and roots where these compounds show up during tannin analysis. Over time, lab syntheses took over plant extraction, and process chemists focused efforts on setting up reliable, practical methods to get this compound in the lab and at pilot scale.
2,3,4-Trihydroxybenzaldehyde stands out by packing both the reactivity of an aldehyde and the strong hydrogen-bonding potential of three hydroxy groups. The molecule takes the benzene core and tacks on hydroxy groups at adjacent positions—2, 3, and 4—then stakes an aldehyde at the 1-position. This combination brings a lot of versatility. Folks in dye chemistry, coordination chemistry, and biochemistry all use this building block, and the breadth of possibilities grows year by year.
This compound appears as a yellowish, crystalline substance once isolated, and you can spot its distinct color even in crude extracts. Its melting point lands in the 120–130 °C range, which comes in handy for purification and quality checking. Water solubility tends toward moderate—not as friendly as the dihydroxy relatives, but enough for formulation in buffered media. Multiple hydroxy groups make the molecule engage in strong hydrogen bonding. The aldehyde group gives it the familiar scent, probably noticed by every chemist who cracked a bottle after an afternoon of synthetic work. 2,3,4-Trihydroxybenzaldehyde does not stay inert. Under the right acidic or basic conditions, the aldehyde quickly enters condensation reactions, and those hydroxy groups can chelate metals or act as handles for further functionalization.
Laboratories and manufacturers offer this compound at varying purities. For research grade, specifications often earmark purity above 98%, checked by HPLC or melting point analysis. Storage guidance calls for cool, dry conditions, usually sealed under nitrogen or argon to keep air and moisture out. Labels list the chemical formula (C7H6O4), batch, production date, storage temperature, and safety icons. Any batch with higher water content or contamination (detected by NMR or IR) gets flagged, so anyone pursuing analytical or biological work only starts from a solid, trustworthy base chemical.
Early synthesis relied on the oxidation of natural aryl compounds such as catechols and gallic acid. Later, Friedel-Crafts-type acylations and directed ortho-formylations gave chemists better access. Practically, a common route begins with pyrogallol. Selective formylation under Vilsmeier-Haack conditions (using DMF and POCl3) sets the aldehyde in the correct spot. This reaction needs temperature control, careful quenching, and multiple extractions with organic solvents. After the reaction, a slow crystallization, sometimes over days, purifies the product. For pilot-scale runs, liquid–liquid extraction and fine filtration stand at the core of processing. Industrial setups usually swap in greener solvents as waste management standards tighten.
The chemistry of 2,3,4-Trihydroxybenzaldehyde revolves around the rival personalities of the aldehyde and phenolic groups. That aldehyde plays well in Schiff base formation with primary amines, stretching synthetic access to imine-based ligands and intermediates for pharmaceutical synthesis. The phenolic positions welcome acylation, alkylation, and sometimes even regioselective sulfonation. In oxidative settings, the compound helps make benzofurans and xanthones—key scaffolds in medicinal chemistry and natural product synthesis. The hydroxy groups bind easily to transition metals such as Cu(II), Fe(III), and Co(II), which paved the way for studies in catalysis and enzyme mimicry.
Over the decades, 2,3,4-Trihydroxybenzaldehyde has picked up several alternate labels in the literature. Folks might run into names like Protocatechualdehyde-4-ol, Benzene-1,2,3-triol-4-carbaldehyde, and Pyrogallol-4-carboxaldehyde. Some catalogues simply shorten it to Trihydroxybenzaldehyde, but noting those exact positions (2,3,4) proves crucial for both buying and referencing—mistakes in the substitution pattern change the whole game in downstream applications.
Working with this compound calls for basic laboratory controls. The aldehyde group means eye and respiratory irritation risks, so running reactions or weighing powder in a fume hood is common practice. Nitrile gloves protect from skin contact, as phenolic compounds sometimes sensitize skin or cause dermatitis over repeated exposure. Labels flag it as Combustible, Irritant, and Environmentally Hazardous, which means any waste gets collected as organic, halogen-free solvents. Spills need prompt cleanup with absorbent materials. Researchers share logs about accidental skin contact on online forums, warning about lingering, tingling discomfort that takes hours to fade. Fire control teams keep CO2 extinguishers handy for storage areas.
2,3,4-Trihydroxybenzaldehyde works its way into projects spanning dye synthesis, pharmaceutical intermediates, metal chelation, and the study of radical scavenging. Researchers in the pigment industry use it to access polyphenolic dyes with high stability to light and heat. Drug discovery teams explore Schiff base derivatives as leads for enzyme inhibition, antimicrobial, and anti-inflammatory properties. Plant physiologists use it for probing polyphenol pathways. Those preparing metal-organic frameworks and coordination complexes turn to this compound as a straightforward ligand with three anchor points. Analytical chemists sometimes build sensors around its redox-active structure for gadgets measuring trace metals or environmental toxins.
Current research often builds on the versatility of the tri-hydroxy setup. Teams focus on derivatization of the aldehyde group to create heterocyclic rings, often yielding potent antibacterial and antioxidant molecules. Some groups report success in using these compounds to modify surfaces on nanoparticles, pushing applications in drug delivery and catalysis. R&D teams inside pigment manufacturing companies fine-tune the purity and particle size to control coloring power for textiles and plastics. On the academic side, groups publish on ways to tweak the formyl group for selective sensing of biothiols and heavy metals. My peers ask a lot about green chemistry improvements, since producing these aldehydes sometimes burdens wastewater streams. Trials for enzymatic oxidative techniques are surfacing in the research pipeline, as they promise cleaner, enzyme-based oxidation routes.
Toxicology studies published in recent years cover a spectrum from acute exposure in laboratory animals to cell culture assays tracking cytotoxicity. The aldehyde moiety reacts with cellular nucleophiles, which means some caution about genotoxicity and mutagenicity comes into play. Academic and industrial researchers both report mild but consistent irritation on contact with mucous membranes in animal models. No large-scale, chronic exposure studies show carcinogenicity, but reviews keep a careful tone and encourage safe handling, limiting exposure and spills. Biodegradation studies show it does not linger for long in soil or water, breaking down under both aerobic and anaerobic processes after days to weeks, yet concentrations in outflow remain a concern for aquatic systems. Teams working on alternatives track both acute and chronic effects in small vertebrates and invertebrates, so regulatory agencies hold off on classifying it as a high-concern chemical for now.
Innovation drives new uses for 2,3,4-Trihydroxybenzaldehyde. Teams aim to scale up greener production, switching to biocatalysts and milder oxidants. Synthetic chemists keep pushing modification chemistry further, expanding into new functional groups and metal complexes. Sensing applications look set to grow as electrochemical and fluorescence-based tools embrace this compound’s tunable redox properties. Pharmaceutical researchers expect a bigger role in antitumor and anti-infective fields, especially as more structure-activity data emerges from global screening efforts. Regulators and chemical producers collaborate on streamlining waste handling and downstream processing, pushing for closed-loop systems and low-impact effluent management. In teaching labs, the compound remains a favorite example of balancing multiple reactive groups on a single molecule—a lesson in both safety and creativity for the next generation of scientists.
2,3,4-Trihydroxybenzaldehyde often skips the limelight, but this little molecule works quietly behind the scenes in several places that matter. I’ve watched research labs and manufacturers lean on it for both specialty uses and routine syntheses—an important role I don’t see discussed much outside of chemistry circles. Understanding those applications helps highlight why even the unassuming chemicals deserve our attention.
Pharmaceutical chemistry stories usually involve big names, but many successful medicines rely on supporting players like 2,3,4-Trihydroxybenzaldehyde. This compound sits at the foundation for synthesizing a whole class of biologically active molecules—especially those with antioxidant properties. If a research team explores new therapies for inflammation or oxidative stress, there’s a good chance they use this molecule to build more complex drug candidates. The trihydroxy structure matches up perfectly with phenolic antioxidants, letting chemists quickly tweak and optimize leads before ever moving to animal studies.
Drug discovery has never been a fast process. Every shortcut makes a difference, and 2,3,4-Trihydroxybenzaldehyde brings a quick path to forming unique flavonoids and polyphenols. A few years back, a team looking at cancer prevention agents used this aldehyde to generate a library of related compounds—only possible because the basic structure gave them a head start. Using one starting material to reach several analogues accelerates both patent filings and research publications.
Beyond medicine, this compound plays a strong role in producing dyes. Those rich, complex shades seen in textile or paper industries can owe their depth to specialty benzaldehyde derivatives. The three attached hydroxyl groups allow for a cascade of chemical reactions, giving chemists flexibility to attach vivid color centers or modify the hue for a particular effect.
Printers and dye houses don’t just need color—they need stability. That’s where 2,3,4-Trihydroxybenzaldehyde earns its keep, contributing to the intensity and fastness of dyes. I’ve seen its use pop up in patents for advanced inks and pH indicators, taking advantage of its stable yet reactive core. The chemistry here ties together with the growing demand for eco-friendly dyes and laboratory reagents, since this molecule can be a base for synthesizing less hazardous colorants.
Nutrition science and agricultural research keep circling back to phenolic compounds. This one in particular attracts attention for its natural antioxidant potential. Food chemists study it to build better preservatives, looking for ways to extend shelf life without synthetic chemicals. In this application, purity and sourcing matter. Laboratories sourcing this compound for these tests regularly cite efficacy in blocking cellular oxidation, making it a valid reference compound in bioassays.
Environmental chemists also use it as a tool in detecting free radicals and tracing pollution’s effects on biological material. Because its structure reliably scavenges reactive oxygen species, experiments offer clearer results and fewer unwanted reactions in the mix.
There’s room to improve how this compound is made, especially in reducing by-products and boosting yields. As demand for tailored antioxidants and greener synthetic dyes rises, developing more efficient methods because both an economic and environmental push. Some startups focus on biosynthetic routes, using engineered microbes to produce benzaldehyde derivatives safely—a move that’s worth following for industries that want both reliability and lower carbon footprints.
Chemistry often faces criticism for complexity, but stories like this one show that even modest molecules unlock big advances in medicine, manufacturing, and food safety. Keeping these pathways open and improving them lays the groundwork for smarter, safer products down the road.
Every time I hear about 2,3,4-Trihydroxybenzaldehyde, I’m reminded of the smells in organic chemistry labs during undergrad research. It stands out not only by scent but by its shape and usefulness. Its molecular formula, C7H6O4, hints at a compact but powerful structure: a benzene ring hosting three hydroxyl groups at the 2, 3, and 4 positions, alongside an aldehyde group at position 1.
Picture a hexagonal ring, each point representing a carbon, looped together by alternating double bonds—a classic benzene core. At carbon 1, an aldehyde group (-CHO) hooks onto the ring. From there, carbons 2, 3, and 4 each deliver a hydroxyl group (-OH). Chemists draw it with extra care, knowing those hydroxyls sit in a neat row, forming what’s often called a “catechol” motif expanded by one more hydroxyl.
There’s a deeper significance hiding in this molecule’s structure. I often think back to my readings on phenolic compounds and how those spare hydrogen atoms from hydroxyl groups open so many doors. These -OH arms let the molecule snatch up free radicals, donate hydrogen, or form hydrogen bonds with enzymes, which gives 2,3,4-Trihydroxybenzaldehyde a real role in antioxidant research. In a world swept up by talk of oxidative stress—from pollution to everyday metabolism—finding compounds that intercept radical damage matters. The arrangement of these groups influences how the molecule fits into biological pathways, interacts with proteins, and serves as a scaffold for drug developers.
In the lab, I watched researchers eye this compound for its reactivity. The extra hydroxyl means higher water solubility and more spots for chemical modification. This is a dream for medicinal chemists trying out substitutions or bolt-ons, chasing better potency in anti-inflammatory or antimicrobial agents. Chemists studying natural products come across this structure regularly, since it's close to plant secondary metabolites known for bitterness, defense, and color.
Not every day is smooth. Those vivid hydroxyls provide utility but also complicate synthesis. Extra steps for protection and deprotection add hours to projects and push up costs. In scale-up, factories meet bottlenecks—waste streams grow, yields shrink, and purity can slip. Spending for greener, more efficient synthetic routes must become a focus. Green chemistry practices, like using water as a solvent and biocatalysts, can cut down hazards and carbon footprints, pointing toward a safer way to scale lab insights into industry.
Tools such as AI-assisted retrosynthesis and open-access databases open new doors. They help scientists trim steps, swap out rare catalysts, and slash overall costs. It’s a fresh approach to staple chemistry, letting pharmaceutical, cosmetic, and material scientists trial greener paths from substrate to product. Spurring innovation here doesn’t just aid bench scientists; it supports all downstream users clamoring for sustainable, cost-sensitive chemistry.
The quest for better chemicals isn’t just about filling flasks—it’s about matching function with safety and sustainability. Every new insight into molecules like 2,3,4-Trihydroxybenzaldehyde enriches the toolkit of health, materials, and environmental scientists. Bringing its promise beyond notebooks to real-world impact depends on tackling challenges in synthesis and safety, while always keeping an eye on the structure-property relationships at the heart of chemical discovery.
2,3,4-Trihydroxybenzaldehyde looks like a simple aromatic compound, but working with it brings home the reality of lab and warehouse safety. This powder comes packed with three hydroxyl groups, which means it absorbs moisture and reacts pretty easily. Left open on a bench, it’ll draw water from the air and start to clump, making it tough to weigh or handle precisely.
I once saw a jar stored without a tight seal inside a humid storeroom. Within days, the sample became sticky and unusable—the loss stung more because it could have been avoided with a bit more care. Contact with water doesn’t just ruin your supply, it can also change its chemical profile. That means every batch needs checking before use, wasting time and money.
Breathing in the fine dust has its own hazards. The aldehyde group might irritate the nose or eyes, and skin contact can trigger allergic reactions. Anyone handling this material day in, day out wants gloves and a mask, or they risk headaches and chronic irritation. Fume hoods aren’t optional luxuries for this sort of work—they prevent small mistakes from turning into bigger health problems.
Keeping 2,3,4-Trihydroxybenzaldehyde dry matters just as much as temperature control. Store it in airtight containers. A glass bottle with a solid PTFE-lined cap beats plastic jugs because it stops air, and with it, the gradual buildup of moisture. Silica gel packets go a long way inside storage cabinets—they pull in stray humidity before the powder can absorb it.
Lab freezers or cool, shaded cabinets slow down spontaneous degradation. I always choose a shelf out of direct light. Strong UV exposure changes the color and chemical activity of this aldehyde.
Labeling matters, especially after a few years in storage. Every jar should show the date received and last opened, not just the product name and batch number. That way, whoever pulls the next sample knows its history. Old stock brings risks: clumping, hydrolysis, or even contamination. Every batch past its prime demands testing before use, and that only happens if it’s clearly tracked.
2,3,4-Trihydroxybenzaldehyde’s dust travels easily. Transfer powders inside a certified fume hood, always on a spill tray, and never over an open desk. I’ve seen scientists cough through a tiny cloud that lingered after a rushed weighing job. So, a habit of slow, deliberate movement only seems fussy until it saves the hassle of wide cleanup and wasted product. If a spill happens, scoop solids onto wet paper towels, seal everything in a polyethylene bag, and dispose of it as hazardous waste. Scrubbing with dry paper just spreads fine particles around—wet cleanup traps dust.
Training every new staff member matters more than posting warnings. Make sure everyone understands the risks, not just the rules. Pairing written procedures with real-life demos—showing how clumped powder turns unusable or the way a mask actually blocks smells—sticks better than instructions alone.
Routine audits help. Check labels, inspect desiccant packs, and test old stock. Every time I find a leaky lid or a forgotten jar, it’s a reminder that shortcuts in handling add up to bigger costs or real danger. Taking time upfront saves resources and keeps everyone safer.
Most folks have never heard of 2,3,4-Trihydroxybenzaldehyde unless their work sticks them next to lab benches or chemical formulas. In short, this compound puts together a benzene ring, three hydroxyl groups, and an aldehyde. Some chemists lean on this substance for building blocks in making dyes, pharmaceuticals, or antioxidants.
Looking up whether it’s truly toxic or hazardous grabs attention quick. Data from standard safety sheets and scientific journals draw a mixed picture. Direct human studies just don’t exist. Instead, researchers look at chemical cousins and animal studies when giving advice.
Individuals running experiments with 2,3,4-Trihydroxybenzaldehyde notice skin irritation if they forget gloves. Breathing in powdery dust can irritate lungs or eyes. Chemical structure offers clues: the aldehyde group reacts easily with proteins, which hints at possible skin or respiratory effects. Extended exposure in a cramped or poorly ventilated lab could make matters worse for someone with sensitive lungs.
No big alarm bells for extreme toxicity blare out, but absence of evidence isn’t evidence of absence. Plenty of chemicals, including ones handled safely every day, turn out riskier after years of study. This compound isn’t on government blacklists for environmental harm or cancer, but long-term effects haven’t been ruled out. Being careful doesn’t mean treating every chemical like nerve gas—it means not shrugging off unknowns.
I’ve stood in labs where people grew careless with gloves and fume hoods. One researcher ignored a slow, persistent cough until it became a nagging health problem. Even substances marked “low hazard” can build up risk without proper ventilation, gloves, or cleanup habits. Folks new to handling fine powders may miss the irritation that kicks in with certain compounds. The lesson here? Respect every substance, especially when dust or vapors coat the air.
Most chemical safety regulations still lag behind real scientific discovery. Companies sometimes focus on flashy hazards while older compounds slip through unnoticed. For students or startups tight on money, it feels tempting to cut corners with safety instead of ponying up for new fume hoods or goggles.
A practical solution starts with honest safety training, not lectures. People learn best with reminders and role models—they see a senior chemist suit up, they follow along. Keeping safety data sheets by the bench, not locked in an office, makes a difference. Managers need to refresh training regularly, not just check a box once a year.
Lab leaders can swap out riskier chemicals with safer substitutes in teaching and prototyping. For 2,3,4-Trihydroxybenzaldehyde, using it only in well-ventilated labs slashes most risks. Workers should double check for up-to-date gloves, uncracked goggles, and clear cleanup steps for spills. Emergency wash stations should never get blocked with boxes or unused equipment.
No chemical needs to turn into a health scare if respect and caution stay part of lab routine. Communities using these compounds for research, making new products, or even teaching have an obligation: never trade safety for speed or convenience. Science has always lived side by side with risk, but there’s a big difference between taking smart chances and making avoidable mistakes.
2,3,4-Trihydroxybenzaldehyde stands as a specialty chemical with direct use in research labs and niche industrial processes. This molecule supports the groundwork for synthesizing fine chemicals, pharmaceuticals, and often crops up in pathway studies linked to natural product chemistry. Genuine demand mostly arises from universities, contract research labs, and R&D divisions at pharmaceutical or biotech firms.
Large chemical suppliers like Sigma-Aldrich (now part of MilliporeSigma in North America), Alfa Aesar (a Thermo Fisher brand), and TCI provide this compound. They list the product with specifications down to purity, batch numbers, and spectral data. These suppliers vet their products for contamination and offer clear tracking from order to delivery. Ordering through them is straightforward—provided you belong to an institution with the legal right to receive and handle research-grade chemicals.
Some smaller labs and boutique providers in Europe and Asia also offer the compound, often with regional delivery advantages. These outfits sometimes work closer with emerging research teams or tight-budget startups. The essential step is to always verify accreditation, customer reviews, and regulatory standing before placing an order.
In my time assisting researchers, I've seen procurement go off the rails because of blind trust in online vendors. Adulterated compounds, substituted reagents, delayed customs clearance—these hiccups erode budgets and timelines. Trustworthy suppliers provide Certificates of Analysis and Material Safety Data Sheets. Both documents matter far more than a good price or slick website. If your grant funding or experimental data runs on razor-thin margins, you can't afford error from a questionable source.
Also, strict regulations wrap these transactions. U.S. buyers hit with DEA, EPA, or state regulations will need to clarify intended use and maybe even file import documents with customs. The EU employs REACH registration rules. Skipping due diligence opens up projects to product confiscation or legal headaches that nobody needs piled on top of research pressure.
High-purity 2,3,4-Trihydroxybenzaldehyde reduces strange results in your experiments. Side reactions and contaminants shift baselines and can sabotage whole research runs. If you need reliable, reproducible data (especially for synthesis or bioassays), lower-purity alternatives set you up for frustration. Look for purity above 98 percent, and scrutinize the provided spectra for unexpected peaks—those signs can flag poor purification, even if the label insists otherwise.
Open communication with vendors remains overlooked. Once, a chemist I worked with phoned two suppliers and dug into their packaging and traceability practices. Not glamorous work, but they ended up picking the more transparent company, and follow-up orders consistently produced reproducible results. Working relationships with suppliers outlast a one-off quote from the lowest bidder.
Batch testing on delivery gives an immediate check against the vendor's stated quality. Storing a reference sample from each order, with annotated chromatography results, arms you against disputes if strange data emerges later. These steps don't cost much, yet they shore up confidence in the chemical stockroom—saving time, arguments, and research dollars down the line.
For scientists, investing the effort up front, building supplier trust, and double-checking quality pays off. The alternative—cutting corners—almost always creates more work, and often more expense. Do your homework, ask questions, and let quality lead purchasing decisions.
| Names | |
| Preferred IUPAC name | 2,3,4-trihydroxybenzenecarbaldehyde |
| Other names |
2,3,4-Trihydroxybenzenecarbaldehyde
Calseochin 2,3,4-Trihydroxybenzal 2,3,4-Dihydroxy-salicylaldehyde |
| Pronunciation | /ˌtuːˌθriːˌfɔːr traɪˌhaɪdrɒksi bɛnˈzældɪˌhaɪd/ |
| Identifiers | |
| CAS Number | 38895-02-4 |
| Beilstein Reference | 1109554 |
| ChEBI | CHEBI:32198 |
| ChEMBL | CHEMBL20260 |
| ChemSpider | 121348 |
| DrugBank | DB04202 |
| ECHA InfoCard | 7f782a28-683e-4dde-bf75-89c9bdfdf6c8 |
| EC Number | 1.10.3.2 |
| Gmelin Reference | 76680 |
| KEGG | C05584 |
| MeSH | D017910 |
| PubChem CID | 11601345 |
| RTECS number | DD1925000 |
| UNII | ZJ6CB7Z8L6 |
| UN number | 2811 |
| CompTox Dashboard (EPA) | DTXSID5042610 |
| Properties | |
| Chemical formula | C7H6O4 |
| Molar mass | 154.12 g/mol |
| Appearance | yellow crystalline powder |
| Odor | odorless |
| Density | 1.525 g/cm³ |
| Solubility in water | Soluble in water |
| log P | 0.94 |
| Vapor pressure | 6.71E-7 mmHg at 25°C |
| Acidity (pKa) | 7.56 |
| Basicity (pKb) | 11.52 |
| Magnetic susceptibility (χ) | -70.0·10⁻⁶ cm³/mol |
| Refractive index (nD) | 1.661 |
| Viscosity | Viscosity: 2.52 cP (25°C) |
| Dipole moment | 2.52 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 137.6 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | -468.6 kJ/mol |
| Std enthalpy of combustion (ΔcH⦵298) | -1201 kJ/mol |
| Hazards | |
| Main hazards | May cause respiratory irritation. Causes serious eye irritation. Causes skin irritation. |
| GHS labelling | GHS07, GHS06 |
| Pictograms | GHS07 |
| Signal word | Warning |
| Hazard statements | H302, H315, H319, H335 |
| Precautionary statements | Precautionary statements for 2,3,4-Trihydroxybenzaldehyde: "P260, P262, P264, P270, P272, P273, P301+P312, P302+P352, P305+P351+P338, P330, P332+P313, P337+P313, P362+P364, P501 |
| Flash point | > 222°C |
| Autoignition temperature | Autoignition temperature: 593 °C |
| Lethal dose or concentration | LD50 (oral, rat): >2000 mg/kg |
| LD50 (median dose) | LD50 (median dose): >2000 mg/kg (rat, oral) |
| NIOSH | SN3676000 |
| PEL (Permissible) | Not established |
| REL (Recommended) | 0.5 mg/m3 |
| IDLH (Immediate danger) | Unknown |
