Long before craft breweries started worrying about off-flavors and before molecular biologists tracked aroma markers, chemists uncovered the secrets of 4-vinylphenol. Its story ties back to foundational work on aromatic compounds in the late 1800s. In the decades that followed, researchers mapped out the complex maze of phenol chemistry, leading to the identification of vinyl-substituted derivatives, including 4-vinylphenol. Through labor-intensive syntheses and patient purification, early chemists learned what sets this compound apart from its close relatives. Libraries stack up with studies tracing its identification—from the breakdown of plant materials, to the surprise flavors winding through some of the world's favorite drinks. Today's production methods grew from those roots, trading handblown glassware and days of reflux for reactors and columns tuned for scale and purity.
At its heart, 4-vinylphenol is a simple molecule with broad reach. Its structure, a phenol with a vinyl tail at the para position, flips the switch on reactivity and olfactory impact. In bottles and beakers, it often presents as a pale solid or a slightly amber liquid. The aroma packs a punch—sharp, a bit smoky, sometimes called "band-aid" in brewing circles. Though often spotted as an impurity or byproduct, labs and factories also churn it out deliberately for its value in making resins, specialty plastics, and as a synthetic stepping stone in organic chemistry. Folks working with food chemistry or sensory panels know it as both a marker and a troublemaker, depending on context.
This is not just another phenol. 4-vinylphenol clocks in with a molar mass right around 120 g/mol. It melts at about 30–32°C, placing it just above room temperature most days—so storage conditions matter unless you want a mess. Its boiling point hovers near 217°C. Solubility stands out as moderate in water, much better in organic solvents like ethanol or ether. Anyone who's spent time in a lab will remember the acrid, lingering odor, a sure sign the bottle wasn't capped tight. Chemically, the vinyl group adds layers of reactivity, opening doors to polymerization and other reactions that straight-up phenol can’t perform. This brings both value and risk, since spontaneous polymerization can cause headaches if the material is stored wrong or sits on a shelf too long.
On chemical order sheets, you’ll see 4-vinylphenol listed with clear specs covering purity, water content, and inhibitor levels. Purity often runs above 99%. Real-world practice believes in stabilization, so commercial lots include a pinch of inhibitors like hydroquinone to keep runaway reactions in check. Labels don’t just carry CAS numbers (2628-17-3) and hazard pictograms—they call out potential for irritation, flammability, and polymer hazards. Shipment containers echo this: always tightly sealed, often amber-colored, and carefully tracked for dates and additive levels.
The most direct lab route starts with 4-hydroxycinnamic acid. Heating this under decarboxylation conditions—usually with a strong base—kicks off the carboxyl group, leaving behind the coveted vinylphenol backbone. Some chemical plants spin this through catalytic decarboxylation with copper-based catalysts, chasing higher yields at scale. Once product emerges, it gets distilled under vacuum to avoid polymerization and keep the sample clean. Occasionally, more exotic syntheses pop up, but cost and reliability keep most operators loyal to decarboxylation of natural phenolic acids or styrene derivatives. No method completely sidesteps the need for careful purification, repeated distillation, and strict oxygen control to keep the product sharp and ready.
In the hands of a skilled chemist, 4-vinylphenol turns into a powerful building block. The vinyl group drives its ability to undergo polymerization, so you find it in niche resins and copolymers. React it with acids or halogens, and new additions latch onto the aromatic ring or the vinyl group. Its phenolic group delivers antioxidant properties and opens up coupling reactions for more complex molecules—useful in drug synthesis or dye manufacturing. Laboratories tweak the vinyl group for tailored monomers or introduce bulky substituents for specialty applications. The same reactivity that gives it commercial value can deliver an unexpected mess if left unchecked; spontaneous self-polymerization doesn’t just waste material—it can create serious safety concerns in scale-up settings.
Depending on the supplier and region, 4-vinylphenol takes on many names. Look for p-vinylphenol, para-vinylphenol, and 4-ethenylphenol in literature and catalogs. Producers may market it as a monomer component or list under aromatic intermediates. Sometimes the food industry refers to it in sensory terms, highlighting its role in flavor profiles, especially under the shadow of brewing spoilage or wine faults. No matter the name, the core chemistry and safety issues hold firm.
Take a whiff of 4-vinylphenol in an open lab, and the warning is immediate: gloves, eye protection, and well-ventilated workspaces aren’t optional. Even short exposures can cause irritation to the skin, eyes, and respiratory tract. Its flammable nature and nasty tendency to polymerize call for tough storage protocols—cool, dry, and away from ignition sources or sunlight. Most facilities use explosion-proof refrigerators, strict inventory controls, and additives like hydroquinone to head off dangerous chain reactions. Detailed safety data sheets spell out worst-case scenarios, so even experienced hands double-check procedures before handling. Respirators may be necessary for large-scale manipulation or process upsets. Waste disposal keeps local regulations in mind—nobody wants phenolic runoff wandering into lab drains or storm sewers.
Despite its drawbacks, 4-vinylphenol finds plenty of uses. Industrial chemists value it as a monomer for specialty polymers, producing resins with high heat resistance or custom electronic properties. Food science teams track its aroma in beverages, using it as a marker for spoilage, yeast metabolism, or wood barrel aging. Biologists and pharmacologists chase its transformation in metabolic studies, following the fate of microbial breakdown products. In coatings and adhesives, it helps create products that need extra strength or reactivity, sliding seamlessly into niche manufacturing. The crossover between pure science and industry remains strong, since analytical detection of 4-vinylphenol keeps labs on alert for contamination or off-flavors in everything from wine to pharmaceutical intermediates.
Research around 4-vinylphenol accelerates as analysts and process developers resolve new challenges. In basic science, teams study the enzyme systems that turn cinnamic acids into this vinylphenol. Synthetic chemists tailor downstream derivatives, seeking high-performance materials with greater stability or unique activity. Environmental chemists map its occurrence as a byproduct in combustion, fermentation, or natural biodegradation. Ongoing work in analytical chemistry focuses on stronger, faster assays for low-level detection, using chromatography and mass spectrometry. In product development labs, experts tune polymer formulations, aiming to extract maximum toughness or smarter functionality for coatings or electronics. Collaboration between sectors—academic, industrial, and regulatory—drives faster progress while raising new questions about exposure, trace analysis, and sustainable production.
Toxicologists weigh in on potential health impacts of 4-vinylphenol as new applications emerge. At the cellular level, it can act as a mild irritant, triggering defense mechanisms in exposed tissue. Animal studies show responses similar to other small phenolic compounds, with dose and exposure setting the risk. Repeat exposure or poor ventilation raises the odds of chronic irritation and more significant health impacts. Investigators watch its metabolic breakdown for signs of DNA interaction or long-term carcinogenicity, though current evidence does not paint it as a major risk at typical exposure levels. Regulatory bodies keep it listed as a hazardous material, setting occupational and environmental limits in line with its broader chemical family. Ongoing studies target not only acute effects but also subtle impacts on microbiota, allergic response, and multi-exposure settings, with researchers calling for clearer data to fill persistent gaps.
With more industries seeking smarter plastics, greener chemistry, and sharper analytical tools, 4-vinylphenol’s future looks active, if not always straightforward. Work continues to pinpoint new uses in flexible electronics, advanced adhesives, and responsive polymers. Conscious of environmental and health questions, chemical companies chase cleaner syntheses and better recycling strategies. Analytical chemists develop tighter controls and faster detection for trace amounts, especially in food and beverage sectors nervous about consumer safety or flavor. Even as substitution or regulation may limit its use in some channels, innovation pushes boundaries—hybrid materials, custom sensors, or bio-derived production routes all sit within reach. The challenge moving forward revolves around balancing value, performance, and safety, making the most of what this modest vinylphenol core can deliver without causing trouble downstream.
4-Vinylphenol comes up in conversations about chemicals with an eyebrow-raising name. It has roots in both the laboratory and daily life, often surprising folks who learn about the places it turns up. Most people haven’t heard of it, but this compound has a story worth sharing.
People who enjoy craft beer or a good bottle of wine may have tasted 4-vinylphenol without knowing it. Certain yeasts in brewing break down acids from grape skins or barley husks, creating this compound. 4-vinylphenol usually brings a medicinal or “barnyard” taste. While many wine lovers turn up their nose at this, especially in white wines, some beer fans seek out that clove-and-smoke tang, especially in German wheat beers. This comes down to yeast strains—Brettanomyces and others—fueling chemical transformations in barrels and tanks. Brewers and winemakers monitor 4-vinylphenol levels carefully, deciding how much flavor is too much or just right for the style. A solid understanding of its chemistry can mean the difference between an award-winning label and a ruined batch.
Production facilities and chemical manufacturers count on 4-vinylphenol as a useful intermediate. It’s not usually the final product, but a building block on the way to something else. For instance, factories convert it into resins found in coatings and paints. These resins can add strength, durability, or certain surface properties that customers want in everyday products—think about the feel of a top-quality table or a scuff-resistant floor. 4-vinylphenol’s ability to take part in polymerization reactions lets companies tweak properties to suit specific jobs, from sealing wood to making medical adhesives. Researchers keep exploring what else this compound can do, including specialty plastics and electronic materials.
This isn’t a compound for handling without caution. 4-vinylphenol can irritate the skin, eyes, or breathing passages if people aren’t careful. Workplaces follow strict safety protocols—gloves, goggles, ventilation. Chemists and factory managers focus on containment and safe disposal because of concerns about exposure and spills. Regulatory agencies watch these practices closely to protect workers and communities. Health scientists still study long-term effects, and any news about toxicity puts pressure on manufacturers to innovate safer production lines or look for substitutes.
Scientists who grew up tinkering in home labs can feel nostalgic for the puzzle-like process of reimagining what a molecule can do. With 4-vinylphenol, researchers try improving its transformation into ever-more-useful materials. Regulatory bodies watch those developments, ready to update guidelines as new data comes in. When public concern over chemical safety rises, researchers and officials work together to set standards, review toxicity reports, and revisit existing rules. So the life of 4-vinylphenol is shaped by the push-pull of innovation, commerce, and concern for wellbeing.
The story of 4-vinylphenol shows why industries, regulators, and consumers all benefit from clear information and ongoing oversight. Better labeling, smarter manufacturing processes, and open research keep potential risks down and useful applications up. If society continues down a path that values transparency and collaboration in chemical use, we all reap the rewards.
4-Vinylphenol doesn’t look much different from other lab chemicals. It comes across as a clear to pale yellow liquid, but don't let that fool you. The stuff carries more risk than it lets on—it's flammable; it irritates skin, eyes, and lungs; it can trigger allergic reactions if you let it linger on your skin. I’ve seen smart chemists get careless here and pay for it, so respect for this compound comes from observing its effects, not reading them in a handbook.
Anytime I’ve worked near 4-Vinylphenol, I suit up. Lab coat, chemical splash goggles, and sturdy nitrile gloves form my minimum barrier. Disposable gloves don’t last long against this stuff—I've run glove integrity tests myself and seen pinhole leaks cause real issues. Rubber boots and long pants keep splashes away from skin you forget to cover. I double-check gloves for holes and swap them out before handling anything risky. I’ve watched a student learn this lesson after a tiny spill burned their wrist through a torn glove. Nobody forgets that experience.
Good lab design keeps toxic fumes away from your lungs. I won’t even open the vial unless the fume hood’s up and running. This isn’t only about comfort—4-Vinylphenol vapor causes coughing fits you don’t soon forget, and long exposure risks health in ways that don’t fix themselves overnight. Sealed, tightly labeled containers cut spill risks. I keep incompatible chemicals—oxidizers, acids, and bases—out of the way. Watching an old container crack and leak in the wrong spot gives you plenty of motivation to keep your storage system updated and well organized.
Spills happen. The worst mess I saw came on a busy day, and nobody wants to scramble for absorbent pads or neutralizers during a panic. Planning matters. I keep spill kits ready—pads for liquids, scoop for solids, thick gloves, face shield—and go over the procedure with new staff before they set foot in the lab. For small spills, absorb with pads and pile into a labeled, sealed bag for disposal. Never sweep or vacuum them dry; that only spreads the mess and raises the fire risk. Larger spills call for full evacuation and a professional hazmat crew. That’s a day lost, and it’s the only right answer.
No precaution replaces know-how. I make time for safety meetings, run drills, and walk new hires through each step before they handle anything alone. It builds a habit: ask for help if you’re unsure. If a coworker sees gloves missing or storage rules skipped, I expect them to speak up. Stubborn pride does more harm in chemical safety than most folks realize. I learned it by seeing mistakes before me—near-misses, emergencies, recoveries. Nobody wants to join that club, so we lean on each other to stick with the rules.
You can’t pour leftovers down the drain. I take waste to a certified disposal service, following all regulatory paperwork. The temptation to cut corners costs too much in fines or injuries. Clean-up after the fact never balances out; responsible use and responsible disposal keep everyone safer—inside the lab and out in the wider world.
4-Vinylphenol pops up across various industries, from chemical manufacturing to the world of flavor and fragrance. Its impact goes beyond mere curiosity, touching real production challenges and possibilities in everyday processes. At its core, the chemical formula for 4-Vinylphenol is C8H8O. With a molecular weight of 120.15 g/mol, it sits in that sweet spot for those seeking a small but reactive aromatic compound.
This compound’s backbone, a vinyl group attached to a phenol ring in the para (4-) position, gives it a touch of versatility. In my own lab days, mixing phenolic compounds with a vinyl twist meant more than balancing chemical equations; it allowed me to test reactions that boosted yields without pulling out heavy equipment. Anyone who has worked in a plant where off-flavors make or break a batch understands this: 4-Vinylphenol shows up in fermented products, especially in wine and beer, contributing that signature spicy, sometimes medical aroma. Brewers reading the batch sheets spot a problem before it’s bottled for consumers, knowing small molecules like this one can leave a big impression.
Winemakers care about 4-Vinylphenol not because it looks neat under a microscope, but because its concentration can signal spoilage or impart an unwanted taste. If you’ve ever tasted wine that seemed a touch too funky, there’s a good chance this compound played a role. Scientists have measured 4-Vinylphenol in spoiled batches upwards of 750 µg/L, above the threshold most noses can detect. With chemical knowledge, vintners can spot contamination earlier and turn around questionable product, saving not just money but brand reputation.
Researchers and manufacturers use 4-Vinylphenol’s formula (C8H8O) as a shortcut. In the lab, it’s about purity; a batch with the right molecular weight signals “ready for synthesis.” For others, that same figure becomes a checklist for packaging and transporting potentially volatile compounds. Having wrestled with regulatory paperwork myself, clarity in recording formulas and weights speeds customs, reduces fines, and keeps staff out of needless meetings.
Cleaner storage techniques, better monitoring during fermentation, and tighter quality controls help reduce unwanted 4-Vinylphenol spikes. In a modern lab, gas chromatography lets scientists pick up trace amounts before consumers ever sniff a glass. Clear labeling and transparent documentation let distributors and end-users know what they’re handling, a direct plug for safety in fast-moving operations. Researchers don’t just chase formulas and weights for the thrill – they’re building up data that shapes everything from safer shipments to less waste in finished products.
As someone who’s burned more than a few late nights trying to troubleshoot a spoiled batch, I know preparation pays off. That foundational data—chemical formula and molecular weight—means processes stay lean, products remain safe, and the market avoids a bad taste, both literally and figuratively. The bottom line: the right information, used well, powers both the science and the business behind every bottle or barrel.
Some chemicals demand extra care, both for safety and to keep their properties stable. 4-Vinylphenol, with its sharp aroma and role in industries like flavors, fragrances, and polymer chemistry, sits in this group. This isn’t something to leave on a shelf and forget. Ask anyone who’s spent time in a laboratory or a factory warehouse – improper storage can mean spoiled product, wasted money, and even health risks.
4-Vinylphenol isn’t just any organic compound. It reacts with air, light, and heat. Exposure to these triggers can lead to oxidation or unwanted polymerization. I once watched a batch degrade on a sunny warehouse window ledge by the end of a long afternoon, losing its sharp punch and turning sticky. It taught me a lesson that no textbook could.
Data from the National Center for Biotechnology Information, among others, points to chemical instability at room temperature, especially if humidity creeps up or oxygen slips in. The chemical’s volatility increases the risk, so airtight storage isn’t just smart – it’s essential for keeping both quality and safety in check.
Storing 4-Vinylphenol asks for diligence. You won’t find it in glass jars on a kitchen shelf. Reliable laboratories and chemical plants favor amber glass or metal containers with secure, tight-fitting lids. These containers block light, reduce air contact, and hold up against spills or breakage. I’ve watched old, unlabeled bottles cause confusion and near-misses; labeling and dating each batch matter just as much as the container.
Cool temperatures extend shelf life and slow spoilage. A controlled environment, usually between 2°C and 8°C, helps further. Some professionals keep 4-Vinylphenol in specialized refrigerators or in designated cool rooms—a simple lock and logbook can go a long way here, preventing unauthorized access while tracking use.
Dryness reduces the chance of clumping, caking, or hydrolysis. Humid spaces amplify risk. If water gets in, the chemical can react or lose purity, impacting everything from scent profiles to reactivity in downstream applications. Silica packs or moisture barriers sometimes appear in smart storage setups.
Safety isn’t just about product quality. 4-Vinylphenol vapors irritate eyes, nose, and throat, and frequent exposure can trigger headaches or coughing. The U.S. Occupational Safety and Health Administration cautions against inhalation and skin contact. I’ve seen workers set aside goggles or gloves for “just a quick sample,” and they usually regret it.
Spills, even small ones, need swift cleanup—paper towels and water don’t cut it. Keeping cleanup kits and proper waste containers on hand is standard practice in responsible labs. Inspections and drills, while sometimes met with rolled eyes, prove their worth during real incidents.
Many chemical handlers already use inventory management systems, tracking everything from batch location to expiry dates. These systems aren’t about ticking boxes—they help spot problems before they grow. Training sessions and checklists help create habits, turning good intentions into daily routines.
Suppliers and buyers can push each other for better transport—insulated packaging, spill-resistant drums, and real-time tracking all add security.
The reason for careful storage comes down to preserving effectiveness and protecting those who work with chemicals every day. The stakes run higher when mistakes lead to lost money or serious harm. 4-Vinylphenol’s sensitive nature calls for respect, from its first day on-site to its final use.
4-Vinylphenol often crops up in conversations among chemists, winemakers, and those in environmental health circles. Many folks ask whether daily encounters with this chemical spell trouble, either for themselves or for the world around them. Knowing the facts helps separate real risks from worries that flare up without cause.
This compound pops up in all sorts of places. In wine and beer, it shows up when some yeasts break down certain acids, producing that telltale “barnyard” or “medicinal” note in the nose. In the manufacturing world, 4-Vinylphenol contributes to making special polymers and resins. Paints, adhesives, and certain specialty plastics all rely on this compound for key chemical reactions. I’ve spent time working alongside people who handle materials like these every week. Rarely does anyone notice, unless there’s a strong smell or a spill to clean up.
Now, the question of risk to humans. The science so far shows that 4-Vinylphenol can irritate skin, eyes, and the lining of the nose and throat. The Material Safety Data Sheets warn about this with clear language, much like they do for cleaning solvents and other industrial chemicals. If a person breathes in thick vapors or splashes it without proper gear, it’s not pleasant—red skin, watery eyes, maybe a sore throat by lunchtime. Younger children, folks with asthma, and anyone who ignores the label’s warnings might find themselves coughing or struggling to breathe for a bit if exposed without protection.
Long-term health data is thinner. There’s no strong evidence yet tying 4-Vinylphenol to cancer in humans, though animal studies hint at possible risks after repeated, high-dose exposures. Cancer labels haven’t stuck in most countries, but plants using this chemical enforce workplace limits and require gloves, eye protection, and good ventilation for a reason. Regulations set by agencies like OSHA aren’t just paperwork—they come from patterns noticed across decades of labor statistics.
So what about the world outside the lab or factory? 4-Vinylphenol breaks down in sunlight and air, but slow runoff and chemical spills can linger. Aquatic life, especially fish and amphibians, show stress when these residues slip into streams at high enough concentrations. Cases in industrial zones near old factories offer proof that accidents can impact local wildlife, at least until cleanup crews dig in. On the flip side, the compound doesn’t build up in animal fat or reach far-off food webs. That lends some reassurance, but doesn’t excuse sloppy disposal or weak containment.
Most risks shrink with common-sense precautions. Factory engineers double-check ventilation, rubber gloves keep splashes off hands, and spill kits remain stocked. In the food and wine world, yeast strains with wild habits can be kept in check by controlling storage temperature and cleaning vessels thoroughly. Regulators keep an eye on new studies, tweaking the rules as fresh data rolls in.
As a worker, parent, or eco-minded citizen, staying informed remains the strongest tool. Reading labels, respecting warnings, and supporting regular training helps catch trouble before it spreads. It comes down to vigilance—a habit that serves well, not just for this chemical, but for the whole family of substances that support modern life. Trust built on research and practical steps holds more weight than blind reassurance or panic.
| Names | |
| Preferred IUPAC name | 4-ethenylphenol |
| Other names |
p-Vinylphenol 4-Hydroxy-styrene p-Hydroxystyrene 4-Ethenylphenol para-Vinylphenol |
| Pronunciation | /ˈvʌɪ.nɪlˌfiː.nɒl/ |
| Identifiers | |
| CAS Number | 2628-17-3 |
| 3D model (JSmol) | `3D model (JSmol)` string for **4-Vinylphenol**: ``` C1=CC(=CC=C1C=CC)O ``` |
| Beilstein Reference | 1209228 |
| ChEBI | CHEBI:17608 |
| ChEMBL | CHEMBL48573 |
| ChemSpider | 12047 |
| DrugBank | DB03771 |
| ECHA InfoCard | ECHA InfoCard: 100.005.239 |
| EC Number | 207-422-2 |
| Gmelin Reference | Gmelin Reference: 149707 |
| KEGG | C06534 |
| MeSH | D014793 |
| PubChem CID | 7904 |
| RTECS number | SJ8925000 |
| UNII | Q9L0MOT1HM |
| UN number | UN2431 |
| Properties | |
| Chemical formula | C8H8O |
| Molar mass | 120.15 g/mol |
| Appearance | Clear colorless to pale yellow liquid |
| Odor | aromatic |
| Density | 1.006 g/mL |
| Solubility in water | slightly soluble |
| log P | 1.98 |
| Vapor pressure | 0.25 mmHg (25°C) |
| Acidity (pKa) | 10.0 |
| Basicity (pKb) | 9.28 |
| Magnetic susceptibility (χ) | -63.0e-6 cm³/mol |
| Refractive index (nD) | 1.586 |
| Viscosity | 1.299 cP (25°C) |
| Dipole moment | 1.51 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 312.6 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | 117.0 kJ/mol |
| Std enthalpy of combustion (ΔcH⦵298) | -3241 kJ/mol |
| Hazards | |
| GHS labelling | GHS02, GHS07 |
| Pictograms | GHS02, GHS07 |
| Signal word | Warning |
| Hazard statements | H315, H319, H335 |
| Precautionary statements | Precautionary statements of 4-Vinylphenol: "P261, P280, P305+P351+P338, P337+P313 |
| NFPA 704 (fire diamond) | 3-2-2-W |
| Flash point | 86 °C |
| Autoignition temperature | 530 °C |
| Explosive limits | Explosive limits: 1.1–8.5% |
| Lethal dose or concentration | LD50 oral rat 2000 mg/kg |
| LD50 (median dose) | LD50 (median dose): 1410 mg/kg (oral, rat) |
| NIOSH | NIOSH: SG3575000 |
| PEL (Permissible) | Not established |
| REL (Recommended) | 50 mg/L |
| Related compounds | |
| Related compounds |
Phenol Styrene 4-Ethylphenol Vinyl compounds |
