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Years ago, folks in organic chemistry labs hunted for useful phenolic compounds. Their efforts included odd-sounding names like 3,5-Dimethoxy-4-hydroxyacetophenone—often easy to dismiss as another bench reagent unless you look deeper. This molecule first caught the eye of researchers digging through the tangled branches of natural product chemistry, where subtle changes in structure reveal big surprises. The original synthesis routes cropped up during exploratory work on plant polyphenols in the early to mid-20th century, as biochemists worked to understand how minor tweaks made a difference in medicinal and flavor profiles. It’s connected to the family tree of acetophenones and vanillin derivatives, which shaped pigments, fragrance design, and even questions about antioxidant activity. The details of its early characterization soak into papers from decades ago, when separation techniques meant weeks of crystallizations rather than an HPLC tweak.
3,5-Dimethoxy-4-hydroxyacetophenone stands out for its mix of electron-donating and -withdrawing groups. The dual methoxy groups at positions three and five and the hydroxy at position four create a molecule with noticeable solubility in organic solvents and moderate crystallinity, making it fit for preparative work but not always easy to handle in water. Its melting point, usually recorded around the low 100s Celsius, makes it manageable for solid-state reactions and easy purification. The acetyl group provides a reactive anchor for modifications, while the phenolic moiety begs for hydrogen bonding, which chemists value for its use in forming derivatives and capturing trace metals.
In labs, you tend to see this compound bottled with a clear label, reference CAS number 2478-38-8, and purity listed at or above 98 percent. Commercial sources stick to powder or crystalline formats—easier to weigh, less spillage than oily liquids. Properly sealed under nitrogen or dry air, it avoids the fate of phenolic discoloration and keeps stable for most typical lab runs. Marking for hazards steers clear of hyperbole, but gloves and goggles remain the order of the day out of good practice and because small molecules can play tricks through skin absorption or inhalation if ignored.
Experienced chemists will almost always steer toward alkylation routes based on resorcinol or derivatives already sporting similar substitution. The Friedel-Crafts acylation still plays a role; matching acetic anhydride and a Lewis acid coaxes in the acetyl portion if conditions hit the sweet spot—low water, strong acidity, patience for reaction times. Demethylation or methylation, depending on available starting materials, tunes the substitution pattern. Yields aren't always impressive, but with careful TLC monitoring and post-reaction filtering, a workable amount comes through for research or scale-up. Rotavapors and silica columns pull their weight here, purifying material for whoever comes next in the lab’s pipeline.
Once 3,5-Dimethoxy-4-hydroxyacetophenone lands on the bench, it opens a path to chemical play. The phenolic hydrogen stands as a beacon for etherification, esterification, and formation of metal complexes—tools that build out libraries for medicinal chemistry or study of antioxidant properties. Side chains on the acetyl group get lengthened, chopped, or swapped to probe bioactivity. Methoxy groups, stubbornly stable, can sometimes be coaxed into further functionalization under strong acids or with clever catalytic systems. This flexibility gives rise to waves of analogs as research teams search for improved biological or physical properties.
Within literature and catalogs, the compound might show up under names like 4-Hydroxy-3,5-dimethoxyacetophenone or as Acetosyringone, especially in studies looking at plant biochemistry or microbial signaling. This points to a recurring challenge in chemical research: tracking substances across borders, disciplines, and naming systems. In plant science, Acetosyringone hints at the compound’s role in wound response, while in organic chemistry the systematic name grounds discussion in synthesis and function.
Handling any substituted acetophenone means respecting its chemical behavior, not just following MSDS sheets. Every time I weighed out phenolic powders like this, a nagging voice reminded me about dust and unexpected skin reactions. Methoxyphenols bring some aromatic volatility and phenolic oxygen, factors that call for care in ventilation and eye protection. Not every undergraduate needs to spill acetophenone on a lab coat before learning such habits, so teaching careful transfer, minimal exposure, and glove discipline saves headaches and health down the line. Waste protocols treat this class with moderate caution, bundling it with solvents that eventually journey to incinerators sturdy enough for aromatic organics.
Few molecules get pigeonholed; 3,5-Dimethoxy-4-hydroxyacetophenone sums this up by straddling pure synthetic work and natural sciences. Plant physiologists dig into it as a signaling molecule—especially linked to Agrobacterium-mediated gene transfer, where its presence cranks up transformation rates and pushes forward plant biotechnology. Analytical chemists push its boundaries for reference in HPLC calibrations, while material scientists sometimes use closely related compounds to design hydrogels or antioxidant polymers. Pharmaceutical teams probe its scaffold for hints of anti-inflammatory or antimicrobial activity, betting on related compounds in natural products. The line between research tool and product stays fuzzy, shaped by curiosity and the needs of each lab.
Lab books in organic synthesis often record trials with acetophenone derivatives, not least because variations on this core so often lead to surprises. 3,5-Dimethoxy-4-hydroxyacetophenone’s place in journals often follows two themes—plant biology (especially vir gene induction in tissue culture) and medicinal chemistry. Screening studies for tyrosinase inhibition, antioxidant activity, or antimicrobial effects pop up with regularity. Custom syntheses for labeled analogs mean radiolabel studies in metabolism, tracking movement in plant cells or animal tissues. Collaborative projects, crossing between chemical suppliers and academic labs, push for easier routes or greener methods, responding to regulations and pressure for less hazardous waste.
Reading old data on phenolic toxins tells a person not to take these chemicals lightly. While methoxy groups can soften harshness compared to bare phenol, acetophenones remain substances you keep out of reach of careless hands. Rodent studies and cell viability assays weigh in on safety, but environmental fate also stays in view. Many such molecules show low acute toxicity but raise questions about cumulative exposure and breakdown products—especially important wherever agricultural or genetic engineering labs release trace residues. Real safety hangs on well-worn precautions: smart labeling, ventilated benches, and periodic review of animal and environmental data.
Interest in 3,5-Dimethoxy-4-hydroxyacetophenone won’t run out soon. Plant science teams keep finding new ways it influences genetic transformation, opening doors for rapid gene editing and trait introduction. Synthetic chemists try new routes for its preparation, aiming to skip chlorinated solvents, tighten yields, and push towards greener chemistry. Screening against microbial and cancer targets suggests possibilities for new drug lead structures, fed by the example of related natural compounds. Down the road, integration in functional materials—whether as antioxidants, cross-linkers, or sensing elements—lets chemical research stay plugged into problems in food science, environmental monitoring, and medicine. Real progress comes from communication and open records of procedures and pitfalls: journals, open data, and honest lab notes guiding new hands to real discoveries beneath the surface of this simple-seeming molecule.
When you picture a laboratory bench covered in vials, bottles, and notes, you might not pick out a compound like 3,5-Dimethoxy-4-hydroxyacetophenone as the star of the show. This isn’t a name you drop in everyday conversations, though it quietly fuels a surprisingly wide range of projects. The molecule shows up as an intermediate in the synthesis of more complex chemicals—tools no modern chemistry or pharmaceutical lab could do without.
Researchers use this compound as a starting point to build and tweak other important molecules. It sits at an interesting crossroads between biology and chemistry. A lot of its value springs from the fact that it shares its core structure with many plant-based substances. That gives it a special place in the search for new medicines, especially those rooted in natural products. I’ve watched teams rely on this compound as a shortcut for making analogues of bioactive molecules, testing small chemical changes to see how plants fend off diseases or interact with pests.
Its link to natural aromatic compounds draws the interest of the food and fragrance industries too. This molecule loosely resembles substances that create sweet, woody, or spicy notes. Chemists take advantage of this by tweaking it to develop flavoring agents that mimic or enhance natural flavors without depending on vulnerable harvests or expensive extraction.
Pharmaceutical work benefits from the same features. Several classes of drugs, from mild anti-inflammatories to more ambitious cancer therapies, build on related acetophenone structures. Screening libraries packed with small chemical variants draw on this backbone. Scientists run applications ranging from formulating new treatments to creating probe molecules for basic biological research. Some early tests even suggest compounds made from this skeleton could act as antioxidants, an area always hungry for leads.
The reason this one compound wears so many hats traces back to how easily it lets chemists swap groups on and off its aromatic ring. That sort of flexibility means you get a better shot at finding the one version that hits just the right note—whether you’re searching for a mild vanilla nuance or chasing a molecule that fits a protein like a key fits a lock.
A lot of folks in the chemical supply world talk about practical parameters too: cost, safety, and stability. 3,5-Dimethoxy-4-hydroxyacetophenone checks boxes that allow for safe handling in research settings and a shelf life that gets it from supplier to scientist without special storage fuss. That’s the practical backbone you want for rapid prototyping in a fast-moving lab.
There’s always a risk in relying too much on intermediates from distant places or unpredictable feedstocks. I’ve witnessed delays in projects triggered by supply bottlenecks. Sourcing from renewable raw materials and improving local production strengthens resilience. The chemical sector’s shift toward greener methods opens doors for producing 3,5-Dimethoxy-4-hydroxyacetophenone more sustainably. Biomass and novel catalytic approaches provide a path forward, reducing both cost and environmental load.
Focusing on strong quality controls and transparency about impurity profiles gives both researchers and regulators confidence. Companies that track every step from raw material to delivery build much-needed trust. That reliability underpins innovation—something I’ve seen accelerate promising medical projects from bench work to clinical studies.
People chasing new knowledge, whether in academia or industry, depend on compounds like 3,5-Dimethoxy-4-hydroxyacetophenone to do the heavy lifting behind the scenes. It might look humble or obscure, but its impact ripples through efforts to create safer medicines, more robust crops, and tastier foods. The key lies in connecting informed sourcing, clever application, and a practical eye to real-world constraints—a daily lesson in chemistry’s quiet importance.
Most people know little about 3,5-Dimethoxy-4-hydroxyacetophenone unless they’ve worked in research labs or certain chemical industries. Chemists often call it DMPA, and it turns up in the development of some drugs and dyes. Unlike household cleaners or common pharmaceuticals, this organic compound hasn’t found a place on supermarket shelves. It’s more at home on a lab bench, near flasks and fume hoods.
Years working in research labs taught me that some chemicals look tame but have hidden risks. Powdery substances like DMPA rarely smell strong or fizz up. That calm appearance can fool even a seasoned technician. My own habit: gloves always go on, no matter how “harmless” the powder seems. I’ve seen colleagues brush their hands off after handling less dramatic chemicals, thinking a dust mask or thin gloves would be enough. A few hours later, someone reports skin irritation, or worse, an allergic reaction. The stakes go beyond your own health—improper handling can send spores or vapors into shared air.
Looking through publicly available resources, DMPA itself hasn’t racked up the same notoriety as truly nasty substances like benzene or formaldehyde. That does not grant it a free pass. Data sheets (SDS/MSDS) from large suppliers like Sigma and TCI show this compound irritates eyes, skin, and mucous membranes. It won’t burn holes in your flesh on contact, yet it can still pose problems if inhaled or splashed. No chemical—especially aromatic ketones—should enter new environments without basic controls.
In modest doses, lab rats only experienced mild symptoms. There’s no carve-out for “completely safe.” Toxicological reports always push for caution. Some aromatic acetophenones have shown endocrine activity or mild cytotoxicity in cellular studies. Structurally, DMPA boasts both methoxy and hydroxy groups—functions chemists recognize for their reactivity. These can mean trouble in the wrong hands or if accidentally mixed.
Practical safety starts with staying upstream of trouble. I always check the chemical’s hazard labels and flip through its SDS before opening a bottle. It helps to make a mental checklist: gloves (nitrile, not latex), eye protection, and a dedicated workspace. For DMPA, enclosed handling cuts down on stray dust or accidental contact. I’ve worked in settings where we use powder funnels and closed weighing systems, not only for personal safety but also to keep the workspace clean.
Good ventilation changes the equation. Even with less potent compounds, fume hoods act as trusty insurance. If a spill happens outside, sweep up powder with damp wipes, not a broom. Always wash up after finishing, because trace residues have a habit of sticking around—especially under fingernails or on lab coats.
The reality is, every lab develops its own attitude toward risk. Some folks settle for “it’s just fine, don’t worry.” My approach takes inspiration from stories I’ve heard and people I’ve trained with. Safety doesn’t slow the work down; it speeds recovery if something unexpected happens. Respecting DMPA’s properties keeps teams out of doctors’ offices and regulators out of your hair. Safety data for DMPA might seem sparse, but good habits are built on experience and caution, not guesswork. There’s no sense in gambling your health or your coworkers’ well-being.
Looking at 3,5-Dimethoxy-4-hydroxyacetophenone, the name itself paints a clear picture for anyone who has spent time in a chemistry lab or even glanced over organic chemistry notes. Right away, the word “acetophenone” shows the molecule carries a benzene ring attached to an acetyl group. At specific spots on that aromatic ring, chemists attach two methoxy groups (—OCH3) at positions 3 and 5, and a hydroxy group (—OH) at position 4. This isn’t just wordplay. This arrangement gives the molecule a backbone that’s both recognizable and reactive.
For anyone who has ever scribbled out organic compounds on scratch paper, this is how the skeleton lines up: Picture a benzene ring. The acetyl group (basically COCH3) branches off at position 1. Counting around the ring, you’ll hit methoxy groups at spots 3 and 5—think of them as two subtle, oxygenated arms stretching out from the carbon core. Nestled right in the middle at position 4 is the hydroxy group. So, you get a pattern that’s both clean and quite symmetrical: methoxy, hydroxy, methoxy, punctuated by the acetyl group.
If you worked your way through chemical drawing platforms or used a ball-and-stick kit during college labs, this setup pops out as both simple and elegant. The formula clocks in at C10H12O4, which explains its moderate size and decent solubility in most laboratory solvents.
Anyone familiar with plant biochemistry or synthetic chemistry recognizes the real-world value of compounds like 3,5-Dimethoxy-4-hydroxyacetophenone. In some cases, these aromatic ketones crop up as building blocks in drug discovery or fragrance synthesis. They don’t sit idle; their unique pattern of oxygen groups makes them capable partners for both hydrogen bonding and various organic reactions. A chemist with a background in natural product isolation might point out that similar compounds pop up in herbs and medicinal plants.
The acetyl group on the ring increases the molecule’s reactivity. For anyone doing synthesis, this usually means more routes to play with, whether you're trying to build bigger, more complex molecules or simply adjust physical properties like melting point. In my own lab days, molecules with ortho-methoxy and para-hydroxy groups always showed different kinds of reactions compared to their plainer cousins.
Some researchers use dimethoxy-hydroxyacetophenones as starting points for antioxidant studies. Their structure lets them scavenge free radicals or break harmful chains of oxidation in food and cosmetic systems. A friend in pharmaceutical research once told me about using similar phenolic compounds as leads for anti-inflammatory agents—small, accessible molecules can open doors to bigger discoveries.
Commercial supply isn’t difficult; chemical catalogs list this compound for laboratory use. Its well-defined structure means scientists can anticipate how it interacts with reagents, making it a reliable choice for further modification. Strong hydrogen bonding from the hydroxy group also makes it attractive for studying molecular recognition, which is central to drug-target interactions.
Scientifically, 3,5-Dimethoxy-4-hydroxyacetophenone has a foundation in well-established chemical principles. Analytical chemists can characterize it easily by NMR, mass spectrometry, and infrared, confirming those oxygens in just the right places. Some safety data suggests moderate handling care, as with any lab aromatic—good ventilation and gloves are simple fixes for routine use.
For innovation-focused teams, pushing forward means testing analogs with different patterns of methoxy or hydroxy substitution. Getting away from bench-scale, researchers can tie structure to function, finding out which arrangement leads to antioxidant or medicinal properties. Collaboration between synthetic chemists and biologists turns these desk-drawn structures into real-world solutions, whether in medicine or food preservation, offering a reminder of why molecular details shape much more than textbooks.
Ask any research chemist or lab tech about chemical storage, and stories begin to flow. The forgotten bottle that turned amber, powders that clumped, or the vial that formed odd little crystals—these short stories never end well. These mistakes cost money, time, and sometimes safety. In my own experience, nothing upsets a smooth project more than discovering your main compound has gone off because the storage habits were sloppy.
A chemical like 3,5-Dimethoxy-4-hydroxyacetophenone won’t explode into flame, but its benchtop shelf-life depends on taking a few common-sense steps. This compound, widely used for research and specialty syntheses, can slowly turn if exposed to light, air, or moisture. Oxidation and hydrolysis can leave you with mixtures that confuse your results and waste precious time.
Keep this compound dry. Even small traces of water can mess with how it looks and performs. I once bought a batch that had set up in a white, fluffy clump after being left open for just a day in humid weather. Moisture will help hydrolyze the molecule, and the product degrades. Moisture isn’t some distant threat; it’s in the air and in every careless hand that leaves a cap off. Store in a tightly sealed glass container, preferably with a desiccant pack nearby. Avoid plastic if you can, because certain plastics attract static and may tear after repeat use.
Don't forget about light. Direct daylight—not even sunlight but just hours in a well-lit room—can lead to slow yellowing or browning, which is the compound's way of saying it’s changing on you. Wrap bottles in foil or use amber glass. Most commercial labs already do this for other phenols, and it’s worth following their lead.
Temperature swings ruin more chemical stocks than you’d think. This isn’t a cryogenic substance, but tossing it in your office drawer at 25 to 30°C one week, then moving it to a chilly storage closet the next, accelerates decomposition and moisture condensation inside the cap. Store consistently at cool room temperature or, better yet, in a fridge set to about 4°C. I learned the hard way that trying to save a few dollars on non-refrigerated shelving tanks the entire batch quality.
Peer-reviewed sources, such as the Hazardous Laboratory Chemicals Disposal Guide and the Merck Index, confirm that methoxy and hydroxy substitutions increase sensitivity to air and light. These published guides recommend cool, dry, and dark storage. Material safety data sheets, which I always check, also warn users to tightly seal and refrigerate to prevent degradation.
Lab users and suppliers need reliable guidance, because safety and reproducibility sit at the core of good science. Nobody wins when batches degrade or results go sideways. Labs can sketch up easy reminders or standard operating procedures for chemical storage; it saves money and hassle, and frees everyone from headaches.
Use glass vials with screw tops and a silicone gasket—they block air and moisture. Keep one shelf in a spare fridge for all sensitive organics. Store everything alphabetically and check dates every month. Add desiccant packs, and throw away any that show signs of change in color or texture. Don’t just scrawl the compound name on tape; add a note that says “Keep sealed, cold, and dark.” People pay more attention to reminders they see daily.
Clear instructions and a touch of routine make a world of difference. Skipping steps saves time only on the first day; the mess starts weeks later. Reliable storage is invisible until you forget it—then the whole lab feels it.
Stepping through a research lab, you’ll stumble on a shelf with bottles labeled full of names nobody outside the field recalls. One of those, 3,5-Dimethoxy-4-hydroxyacetophenone, hides capabilities that chemists notice quickly. Its structure—a simple acetophenone backbone with those strategically-placed methoxy and hydroxy groups—opens doors across the sciences, especially where flexibility and predictable reactivity matter most.
Researchers studying antioxidant mechanisms rely on phenolic compounds to dig for answers. The hydroxy group on this molecule acts as a willing electron donor, so it soaks up free radicals in test tubes leading to data on how natural or synthetic antioxidants behave. Analytical chemists use it to benchmark novel extraction protocols, or as a reference in assays mapping free radical scavenging in food science and nutrition. Results from these tests support claims on labels that consumers lean on when picking supplements or “functional foods.”
Walk into a drug design meeting and medicinal chemists might be sketching this structure as part of their thinking. The acetophenone motif pops up in several drug leads, targeting everything from inflammation to bacterial infections. By tweaking the methoxy and hydroxy groups, chemists adjust the molecule’s shape and stickiness, influencing how it slips through cell membranes or binds in the body. I’ve seen research projects where small adjustments on this template produced surprises, turning weak leads into promising hits. It shortens the distance from chalkboard to test tube, which helps reduce costs on screening and development.
Aromas come down to molecular design. Perfume manufacturers and flavor chemists synthesize derivatives of 3,5-Dimethoxy-4-hydroxyacetophenone to develop scents that mimic nature or suggest new possibilities. The right tweaks lead to creamy, sweet, or woody notes, and the compound’s phenolic backbone resists breakdown under heat or light. This reliability matters for shelf life. My time consulting for a flavor house involved stress-tests that rewarded molecules with endurance—this one repeatedly performed well, holding fragrance through transport and storage.
Some research hinges on how a molecule handles light. Those methoxy and hydroxy groups mean it absorbs at specific UV wavelengths, so laboratories use it as a calibration standard in spectroscopy. Forensic scientists track its presence in environmental samples to trace pollution sources, because it stays distinctive even among dozens of byproducts. This helps them build clearer cases linking contaminants to their origins.
Industries pursuing sustainable manufacturing look for building blocks derived from renewable resources. 3,5-Dimethoxy-4-hydroxyacetophenone fits into bio-based supply chains, where it can be sourced from natural lignin or produced through gentle fermentation. Using greener methods for its production both trims chemical waste and wins points for responsible sourcing, something customers and regulators actually read about and value. Over time, increasing demand for such molecules pushes suppliers to invest in better, cleaner technologies.
Real impact comes from matching chemical performance with a practical need. Academic teams rely on its straightforward behavior as a model system before testing larger ideas. Pharmaceutical and consumer goods companies pick it for specific reactivity, stability, or sensory properties. Harnessing both tradition and innovation, this molecule keeps finding new work, bringing a familiar backbone into tomorrow’s research and products.
| Names | |
| Preferred IUPAC name | 1-(3,5-Dimethoxy-4-hydroxyphenyl)ethan-1-one |
| Pronunciation | /ˌθriːˌfaɪv.daɪˌmɛθ.ˈɒk.si.fɔːr.haɪˌdrɒk.si.əˌsiː.təˈfəʊ.nəʊn/ |
| Identifiers | |
| CAS Number | 37966-97-1 |
| 3D model (JSmol) | `3Dmol.js?model=%7B%22mol%22%3A%22COC1%3DC(C%3DC(C%3DC1OC)O)C(%3DO)C%22%7D` |
| Beilstein Reference | 1148731 |
| ChEBI | CHEBI:28843 |
| ChEMBL | CHEMBL300481 |
| ChemSpider | 83403 |
| DrugBank | DB04260 |
| ECHA InfoCard | 03b96bd8-6b81-41fd-9335-2d95b2ec9e72 |
| EC Number | 2107-68-2 |
| Gmelin Reference | 85332 |
| KEGG | C01236 |
| MeSH | D017693 |
| PubChem CID | 210802 |
| RTECS number | TM3225000 |
| UNII | 6W6S6W1K5G |
| UN number | UN2811 |
| Properties | |
| Chemical formula | C10H12O4 |
| Molar mass | 196.19 g/mol |
| Appearance | Light yellow crystalline powder |
| Odor | Odorless |
| Density | 1.24 g/cm³ |
| Solubility in water | Slightly soluble |
| log P | 1.23 |
| Vapor pressure | 0.000112 mmHg at 25°C |
| Acidity (pKa) | 9.45 |
| Basicity (pKb) | 8.05 |
| Magnetic susceptibility (χ) | -74.0×10⁻⁶ cm³/mol |
| Refractive index (nD) | 1.5790 |
| Viscosity | 113 cP (25 °C) |
| Dipole moment | 4.61 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 143.2 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | -580.0 kJ/mol |
| Std enthalpy of combustion (ΔcH⦵298) | -1706.8 kJ·mol⁻¹ |
| Pharmacology | |
| ATC code | N06AX10 |
| Hazards | |
| Main hazards | Harmful if swallowed. Causes serious eye irritation. Causes skin irritation. |
| GHS labelling | GHS07, GHS09 |
| Pictograms | {"GHS02", "GHS07"} |
| Signal word | Warning |
| Hazard statements | H302, H315, H319, H335 |
| Precautionary statements | P261, P264, P280, P302+P352, P305+P351+P338, P332+P313, P337+P313, P362+P364 |
| NFPA 704 (fire diamond) | 2-1-0 |
| Flash point | Flash point: 113.5°C |
| LD50 (median dose) | LD50 (median dose): Mouse oral 2100 mg/kg |
| NIOSH | RN 37948 |
| REL (Recommended) | 100 mg |
| Related compounds | |
| Related compounds |
Apocynin Acetosyringone Acetovanillone |
