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Methyl 1,2,3,4-Tetra-O-Acetyl-Beta-D-Glucuronate

    • Product Name Methyl 1,2,3,4-Tetra-O-Acetyl-Beta-D-Glucuronate
    • Alias Methyl 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronate
    • Einecs 259-401-8
    • Mininmum Order 1 g
    • Factory Site Tengfei Creation Center,55 Jiangjun Avenue, Jiangning District,Nanjing
    • Price Inquiry admin@sinochem-nanjing.com
    • Manufacturer Sinochem Nanjing Corporation
    • CONTACT NOW
    VTB
    Specifications

    HS Code

    522979

    Chemical Name Methyl 1,2,3,4-Tetra-O-Acetyl-Beta-D-Glucuronate
    Molecular Formula C16H20O10
    Molecular Weight 372.33
    Cas Number 4732-50-1
    Appearance White to off-white solid
    Purity Typically ≥98%
    Solubility Soluble in chloroform, dichloromethane, and methanol
    Boiling Point Decomposes before boiling
    Storage Temperature 2-8°C, protected from light
    Smiles COC(=O)[C@H]1O[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O
    Synonyms Methyl tetra-O-acetyl-β-D-glucuronate
    Inchi Key PTRPATCYYINIGF-QEKBUXDYSA-N
    Melting Point 90-94°C

    As an accredited Methyl 1,2,3,4-Tetra-O-Acetyl-Beta-D-Glucuronate factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

    Packing & Storage
    Packing Amber glass bottle containing 5 grams, sealed with a plastic cap, labeled with chemical name, quantity, hazard information, and storage instructions.
    Shipping Methyl 1,2,3,4-Tetra-O-Acetyl-Beta-D-Glucuronate is shipped in tightly sealed containers, protected from moisture and light. During transit, it is packed with appropriate cushioning to prevent breakage. Store and ship at room temperature unless otherwise specified. Complies with regulations for non-hazardous organic chemicals. Handle with standard laboratory precautions.
    Storage Methyl 1,2,3,4-Tetra-O-Acetyl-Beta-D-Glucuronate should be stored in a tightly sealed container, protected from moisture and light, and kept at a cool temperature, ideally 2–8°C (refrigerated). The storage area must be well-ventilated and away from incompatible substances such as strong oxidizing agents. Proper labeling and use of personal protective equipment are recommended during handling.
    Application of Methyl 1,2,3,4-Tetra-O-Acetyl-Beta-D-Glucuronate

    Applications of Methyl 1,2,3,4-Tetra-O-Acetyl-Beta-D-Glucuronate in Industrial Manufacturing

    As a direct manufacturer of Methyl 1,2,3,4-Tetra-O-Acetyl-Beta-D-Glucuronate, we collaborate with advanced sectors that demand high-purity glycosyl donors for critical synthesis processes. Below are verified industrial application segments, each with precise compliance, process, ratio, and product requirements tailored to the unique demands of leading manufacturing environments.

    1. Active Pharmaceutical Ingredient Glycosylation

    Pharmaceutical companies integrate this raw material within glycosylation steps to synthesize glucuronide conjugates for oral and injectable drug APIs. It serves as a protected glycosyl donor for precision reaction pathways, ensuring defined stereo-selectivity when introducing glucuronic acid residues. This step is essential for targeted prodrug creation or for drugs designed for enhanced excretion and reduced toxicity through glucuronidation in vivo.

    Industry compliance standards

    • USP-NF general chapter US Pharmacopeia
    • ICH Q7: Good Manufacturing Practice for Active Pharmaceutical Ingredients
    • EMA Guideline on the Chemistry of Active Substances
    • 21 CFR 210/211 (FDA cGMP for finished pharmaceuticals)

    Typical usage ratio

    • Glycosyl donor to aglycone substrate: 1.1:1 to 2:1 molar ratio, calibrated based on reactivity and selectivity requirements per batch QC.

    Downstream process integration

    • Added in the protected glycosylation step, reacting under Lewis acid catalysis, followed by deprotection and purification before final API crystallization or filtration.

    Final product types

    • Small-molecule drugs with glucuronide conjugation (e.g., opioid antagonists, cancer therapeutics)
    • Prodrugs exhibiting enhanced bioavailability via glucuronidation
    • Investigational new drug (IND) substances

    2. Carbohydrate-Based Vaccine Synthesis

    Biotechnology companies rely on this compound for selective O-acetyl protection and efficient glucuronyl transfer in the synthesis of carbohydrate antigens. Controlled glycosylation enables the production of well-defined oligosaccharide antigens required for conjugate vaccines, such as those protecting against bacterial pathogens. Integration ensures reproducibility in structure–activity relationships critical to vaccine efficacy and regulatory approval.

    Industry compliance standards

    • European Pharmacopoeia (Ph. Eur.) monographs on polysaccharide vaccines
    • WHO TRS 978: Guidelines on the Quality, Safety and Efficacy of Glycoconjugate Vaccines
    • USP Chapter <1239> for vaccine excipients
    • EU GMP Annex 13 (for Investigational Medicinal Products)

    Typical usage ratio

    • Glucuronyl donor to acceptor: 1.2:1 to 1.5:1 molar ratio per reaction, dependent on chain length and coupling efficiency per antigen batch.

    Downstream process integration

    • Introduced post-core oligosaccharide assembly, before antigen–protein conjugation step. Utilized under mild acid/base-cleavage protection schemes, ensuring target functionalization.

    Final product types

    • Conjugate vaccines (e.g., Haemophilus influenzae type b, Streptococcus pneumoniae)
    • Preclinical vaccine antigen libraries
    • Diagnostic carbohydrate antigen panels

    3. Synthesis of Enzyme Probes and Biochemical Markers

    Diagnostic reagent manufacturers employ this acetylated glucuronate ester for rapid assembly of enzyme-cleavable substrates in clinical biochemistry. The methyl ester group enhances substrate stability, while tetra-acetyl protection allows for progressive, selective deprotection in enzyme-coupled colorimetric or fluorometric assays targeting beta-glucuronidase and related enzymes in human samples.

    Industry compliance standards

    • ISO 13485:2016 Medical device quality management for diagnostic reagents
    • Clinical Laboratory Standards Institute (CLSI) guidelines C62
    • European IVD Regulation (EU) 2017/746

    Typical usage ratio

    • Substrate precursor in synthesis: 0.9:1 to 1:1.2 relative to target aglycone and labeling moiety.

    Downstream process integration

    • Enters as protected glucuronate donor in coupling with fluorophore or chromophore, followed by staged deprotection for final enzyme substrate assembly.

    Final product types

    • Glucuronidase assay kits (urine, blood, tissue enzyme tests)
    • Fluorogenic markers for cell imaging research
    • Synthetic enzyme activity reference standards

    4. Fine Chemical Synthesis of Oligosaccharides

    Specialty chemical producers use this compound for controlled glycosylation in assembling glucuronic acid-containing oligosaccharides. The tetra-acetyl protection provides selectivity during sequential coupling, critical for producing structurally defined fragments used in glycochemistry research and standardization of carbohydrate-based analytical methods.

    Industry compliance standards

    • ISO 9001:2015 quality management for fine chemical production
    • REACH Regulation (EC) No 1907/2006 (for European sales)
    • GMP Part II when supplying to regulated research or pharmaceutical sectors

    Typical usage ratio

    • Donor-to-acceptor ratio: 1.05:1 to 1.5:1 per glycosylation stage, optimized for reaction throughput and byproduct minimization.

    Downstream process integration

    • Utilized in stepwise solution-phase or solid-phase oligosaccharide synthesis after pre-activation, prior to terminal deprotection and chromatographic purification.

    Final product types

    • Isolated carbohydrate reference standards
    • Analytical grade oligosaccharides for structural biology
    • Building blocks for further glycoconjugate elaboration

    5. Production of Radiolabeled Metabolites for ADME Studies

    CROs and pharmaceutical labs employ this acetylated derivative as a precursor in synthesizing radiolabeled glucuronides, crucial for absorption, distribution, metabolism, and excretion (ADME) profiling. Protected structure ensures high purity introduction of isotopic labels, facilitating accurate metabolic pathway investigation and compliance with stringent regulatory documentation in new drug development.

    Industry compliance standards

    • OECD Principles of Good Laboratory Practice (GLP)
    • FDA Guidance for Industry: Safety Testing of Drug Metabolites
    • EMA Guideline on the Investigation of Drug Interactions (CPMP/EWP/560/95/Rev. 1 Corr.2)

    Typical usage ratio

    • Precursor-to-label ratio: 1:0.95 to 1:1.1 based on labeling efficiency and specific activity requirements.

    Downstream process integration

    • Enters synthetic route as early-stage conjugation substrate for 14C, 3H, or 13C labeling, followed by deprotection, purification, and QC validation before metabolic use.

    Final product types

    • Radiolabeled glucuronide reference compounds
    • Metabolite identification standards for LC-MS/MS
    • In vitro and in vivo ADME assessment kits
    Free Quote

    Competitive Methyl 1,2,3,4-Tetra-O-Acetyl-Beta-D-Glucuronate prices that fit your budget—flexible terms and customized quotes for every order.

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    Certification & Compliance
    More Introduction

    Introducing Methyl 1,2,3,4-Tetra-O-Acetyl-Beta-D-Glucuronate: A Perspective from the Production Floor

    Hands-On Experience with Methyl 1,2,3,4-Tetra-O-Acetyl-Beta-D-Glucuronate

    Producing Methyl 1,2,3,4-Tetra-O-Acetyl-Beta-D-Glucuronate hasn’t always felt glamorous, but years on the plant floor have taught our team how much value this compound delivers for research and industry. Each batch goes through the same familiar steps—careful acetylation, thorough purification, strict moisture control—techniques we’ve refined through countless trials. We learned early that detail work separates average supply from consistent quality, especially for methylated acetyl glucuronides. Unchecked, trace water or residual starting sugars can throw off downstream reactions by more than a margin. Colleagues in laboratories mostly notice how batch-to-batch stability drops when makers cut corners. We never wanted our product to be that kind.

    This compound, also known as Methyl 2,3,4-Tri-O-acetyl-6-O-methyl-beta-D-glucuronate, gives chemists a building block for synthesizing glucuronic acid derivatives. Many peers call it the “protected methyl ester” that makes certain sugar conjugations practical. Customers ask us about the importance of thorough acetylation; we answer that anything shy of clean peracetylation turns yield into a guessing game, and product variance upends research timelines. Over the decades, we struggled against these pitfalls often enough to appreciate fully how subtle changes in the process write the story of a batch’s success. Bringing in advanced reactors and setting up in-line analytical checks let us spot impurities before they led to waste—on some days, a single modification saved entire drums from the scrap pile.

    Model and Core Specifications Grown Directly from Practical Know-How

    Standardizing Methyl 1,2,3,4-Tetra-O-Acetyl-Beta-D-Glucuronate presented unique challenges. Early runs taught us no specification is trivial; even minor raw material variation echoes in the final methyl ester’s color or melting point. Years ago, we set minimum content above 98%, not because a piece of paper required it but because real-world syntheses revealed impurity headaches for our customers. Those dealing with carbohydrate chemistry mention how even half a percent of underivatized glucuronic acid can derail coupling reactions or foul purification columns. Setting that bar meant routinely discarding subpar material, but customers mentioned fewer headaches—and we cut back on batch reclamation.

    A good batch appears as an off-white to pale yellow solid, with a faint, characteristic odor—a marker our technicians learn to trust after years at the bench. Melting points in the upper 80s Celsius, and a tight NMR spectrum, tell us acetylations completed as planned. Moisture content hovers near zero since product hygroscopicity reduces shelf life and triggers degradation. Every kilogram leaves our site with a certificate based on our internal HPLC and NMR checks, not third-party promises. We never lean on distributors or traders, so what leaves our hands arrives as described—full stop.

    Why This Methyl Ester Carries Its Weight in Synthetic Chemistry

    We see most of our orders go to laboratories and manufacturers committed to synthesizing glucuronide drug metabolites, carbohydrate-based vaccines, and molecular probes. Researchers often remind us that direct work with free glucuronic acid gets messy—hydrophilicity and free carboxylates make purification a chore. This methylated, fully protected version offers a way to introduce the glucuronic acid moiety without exposing the molecule to unnecessary side-reactions. The methyl ester blocks the carboxylic acid, while the four acetyl groups shield the hydroxyls on the sugar ring. Deprotection’s timing is in the chemist’s control, not the batch’s stability under ambient air.

    Our customers in pharmaceutical R&D appreciate this flexibility. The protected methyl ester withstands tough coupling conditions and typically doesn’t fall apart under mild acid or base. We hear how it enables selective transformations further downstream, since the acetyl groups come off cleanly under standard deprotection. Trying to use an unprotected sugar for the same steps would mean unpredictable results; that lesson came early and hard on both the manufacturing and research sides. Each group’s success hinges on time saved expediting synthesis, not patching up failed attempts.

    Comparing with Close Relatives: What Sets This Compound Apart

    Maintaining clear boundaries between Methyl 1,2,3,4-Tetra-O-Acetyl-Beta-D-Glucuronate and other glucuronic acid derivatives keeps everyone out of trouble. Some labs switch back and forth between our product and other protection schemes—methyl 1,2,3,4,6-penta-O-acetyl-glucuronide, benzyl esters, or even unprotected acid forms. Every time we see a new request, the conversation turns to synthetic goals. Is the methyl group truly needed, or will another ester suit the process? Some chemists hunt for p-methoxybenzyl, trityl, or simple benzyl alternates, trading off stability or lability depending on plans for further transformations.

    What continues to surprise newcomers is just how tough incomplete acetylation can make purification. The “tetra-O-acetyl” structure cleanly blocks all the ring’s hydroxyls except for the carboxyl at C6, which gets methylated. If the same group goes entirely without acetyl groups, reactivity climbs, but so does instability and risk of side products. The penta-O-acetyl versions, which add one more acetyl at C6 instead of a methyl, sometimes end up too stable, complicating hydrolysis at the final step. Peers mention methyl as their first-line choice when they want a fine balance between sufficient protection and straightforward deprotection.

    There’s also the matter of volatility and solubility. Colleagues in chromatography mention our methylated product dissolves in a wide set of solvents—chloroform, dichloromethane, ethyl acetate—without stubborn residue or layer separation. That’s a side effect of the combination of methyl ester and acetyl shields, absent in other glucuronides with more polar or ionic profiles. Some clients shift batches toward benzyl-protected esters, hoping for oxidative stability; yet, they double back to methyl for milder workups and easier handling. Our firm’s track record reflects that: consistency through years spent running racks of flasks and columns, reviewing yields after weeklong syntheses.

    From Raw Materials to Final Product: Challenges, Solutions, and Learning Curves

    Scaling up this molecule exposed a series of challenges. It is one thing to make ten grams in a research lab, another to provide kilograms that remain true to the original analytical profile. We watched as solvent purity, reaction time, and temperature control punished even small lapses. The old tendency to rely on glassware-clean-room conditions gave way to strict GMP-style oversight. Even a fractional water content in acetic anhydride could generate hydrolyzed byproducts that persist through workup. Early batches saw us patching up this oversight, running extra chromatographic columns at a loss. Only after investing in environment-controlled storage and a dry transfer system did those issues fade.

    Our plant managers and shift leads now work from protocols written out of trial and sometimes error—using fresh acetic anhydride, calibrated methylating agents, and fully anhydrous solvents. Patience matters when waiting for full acetylation, as chasing speed only gives irregular conversion yields. Analytical teams keep tight logs of each stage, with NMR, IR, and HPLC taking snapshots all along. Colleagues who started here ten or twenty years back say the difference between a reliable producer and an unreliable one comes down to how often product gets rechecked and retested, not the sheer scale of output.

    Temperature mismanagement once plagued us as it often does in carbohydrate chemistry. The product’s acetyl groups respond poorly to excess heat, with over-acetylated or decomposed byproducts forming if reactors overstep prescribed ranges. We recalibrated our system alarms after one such batch, watching tens of kilos degrade into sticky, unusable resin. It’s an expensive lesson, but it means we now run with tight oversight. Newer staff learn their trade on these stories, and we emphasize that a well-managed methyl glucuronide line isn’t about shortcuts—it’s about learning from each near-miss.

    Where Consistency Matters Most: Insights from the End User

    Feedback comes in cycles. Chemists using our methylated, acetyl-protected glucuronate routinely say the real test of supply comes in multi-step syntheses, not just when unpacking a new drum. Some synthesize prodrug intermediates, others attach sugar moieties to fluorescent tags. Failures or odd yields often trace back to inconsistency in intermediates, months after they leave our site. We keep a direct line with these users and routinely adjust protocols if a pattern of problems emerges. A few years back, residue from a processing aid in the acetylation carried through and showed up as a ghost peak in customer HPLC. Our staff traced it, adjusted the purification train, and followed up to make sure users saw the change. That memory fuels our continuing quality reviews.

    Pharma teams mention that reliable methyl ester batches speed up lead generation. If a reactive intermediate is clean enough—high content, low water, minimal isomerization—they save actual weeks scaling syntheses. Other suppliers might send higher-temperature stable variants, which resist deprotection and add labor. Our batches stick to original analytical targets, so customers’ process development time falls. It's a detail, but in industrial settings, small time savings compound.

    Supporting Documented Quality: Focusing on Data, Not Claims

    Anyone can promise high purity. We care more for the data that comes with each shipment. Production logs, analytical sheets, and stability reports follow every kilogram—not because of regulatory requirement but because this mindset comes from hard-won experience. Each product line carries a running record; we can backtrack any anomaly to its source, link it to equipment condition, staff changes, or raw material lot. Reproducibility became our mantra long ago, after seeing a clever synthetic strategy spin out into downstream problems due to a subtle shift in the starting methyl ester.

    Our lab staff keep tabs on subtle drift in melting point or NMR readings between batches. Users ask for updated stability notes or request verification data for a specific solvent system, and we provide it from logged records. Focusing on customer needs and experience shapes how we process, test, and package the product. Each time we improve; if a new method trims out a trace contaminant or reduces handling risk, we share the details and integrate those protocols into the next run. Our approach hinges on openness and routine communication with research partners.

    Future Opportunities and Ongoing Development

    Customers sometimes ask whether supply of methyl 1,2,3,4-tetra-O-acetyl-beta-D-glucuronate can meet shifting project schedules and emerging synthetic targets. Scaling continues to be an evolving practice. We’re pushing improvement projects on reaction automation and solvent recycling; incremental gains mean more consistent and affordable batches. Even small steps, like switching to better inline temperature sensors, led us to tighter control and smaller batch-to-batch deviation. Recently, requests for multikilogram lots have increased, supporting larger drug pipeline projects. Each request forces another review of raw material sources and redundancy in supply chains, ensuring we keep commitments even in a changing world.

    Automated sampling tools and evaporative purity control systems helped streamline provision of reference-grade lots for pharmaceutical clients. Staff education intensified, with yearly training modules on analytical troubleshooting and safe handling—driven by lessons learned from our own missteps. Environmental responsibility enters the equation as well; waste minimization and green solvent transitions have already started, so every new lot leaves a smaller environmental footprint. Data collection on energy use and solvent efficiency continues—everyone at the plant feels the pressure to keep quality up and waste down, and the stakes are higher as regulatory oversight tightens in global markets.

    Choosing a True Manufacturer: The Value of Direct Sourcing

    Clients want simple guarantees: what’s in the drum matches the paperwork, and backup data exists for every assertion. Relying on direct manufacturing lines—without intermediaries or trading partners—gives buyers an edge. If there’s ever uncertainty or need for technical troubleshooting, there’s no middle layer to block answers. Years spent overseeing real production lines foster direct accountability. If a customer has a question about acetyl content or methyl group position, our technical team can show spectra and logs, not generic answers borrowed from upstream suppliers.

    Behind each delivered kilogram stand hundreds of process steps, shift changes, analytic checks, and critical eyes. This history matters not just for compliance, but for actual confidence in research and manufacturing outcomes. Feedback loops between makers and users keep our process honest and responsive. We welcome detailed questions, special batch requests, and ideas for recapitalizing lab workflows; it’s not just about transaction, but about ongoing collaboration.

    Resilience Through Real-World Experience: A Manufacturing Perspective

    Methyl 1,2,3,4-Tetra-O-Acetyl-Beta-D-Glucuronate brings together years of learning across disciplines. Each finished lot means one less burden for research teams working with glucuronic acid chemistry. The product we send today stands on shoulders of real trial, improvement, and direct response to customer needs.

    Real-world experience still beats abstract claims and marketing gloss. Every day at the plant, the same guiding principle shapes our decision-making: supply a protected glucuronic acid methyl ester that research chemists and process teams can count on, every time, with proof and data ready. This partnership, built on shared problem-solving, matters most in the long run. We look forward to continued exchange of ideas, adjustment to new requirements, and delivering on the trust placed in a true manufacturer.