3-Hydroxycarbofuran-d , CAS No.1794759-59-3

CAS: 1794759-59-3 Cat. No.: H1451660 Summenformel: C12H12D3NO4 Molekulargewicht: 240.27

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

3-Hydroxycarbofuran-d 3 is a deuterium labeled compound.

Specifications

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Namen und Kennungen

Molekulargewicht

240.27

Application Protocols

No item-specific, validated application protocols are provided for this product. The following outlines a general LC–MS/MS workflow for using a deuterated internal standard for quantification of 3‑hydroxycarbofuran (general guidance only):

• Preparation: Thaw an aliquot of the internal standard (IS) on ice. Prepare calibration standards by spiking known amounts of native 3‑hydroxycarbofuran into blank matrix or solvent, adding a constant IS concentration to all calibrators and samples.
• Sample spiking: Add the IS to samples prior to extraction (e.g., before QuEChERS salting‑out or SPE). Vortex thoroughly and allow brief equilibration.
• Extraction/cleanup: Perform matrix‑appropriate cleanup (QuEChERS or SPE). Elute with MeOH/ACN. Evaporate gently under nitrogen if concentration is required; reconstitute in initial LC mobile phase.
• LC–MS/MS: Inject onto a reversed‑phase column (e.g., C18). Use a water/ACN or water/MeOH gradient with volatile buffer (e.g., 0.1% FA or 5 mM ammonium acetate). Monitor paired MRM transitions for native and d‑analog.
• Quantitation: Calculate response ratios (analyte/IS) vs calibration curve. Include QC samples at low/medium/high levels. Evaluate recovery, matrix effects, and carryover.

Adjust parameters to your instrumentation and regulatory requirements. Refer to the product’s CoA/SDS for any item-specific constraints.

Biological Roles

General/literature context (not item-specific):

• 3‑Hydroxycarbofuran is reported as a primary oxidative metabolite of the carbamate insecticide carbofuran in environmental and biological systems (plants, soil microbes, and animals). Hydroxylation increases polarity and can facilitate further phase II conjugation (e.g., glucuronidation, sulfation) in higher organisms.
• Carbofuran and related carbamate esters act as acetylcholinesterase inhibitors; metabolite toxicities vary by species and structure. 3‑Hydroxycarbofuran retains the carbamate functionality and may contribute to observed toxicity profiles, though often with altered potency relative to the parent compound (literature, qualitative).
• In environmental matrices, 3‑hydroxycarbofuran formation reflects biotransformation and can serve as a marker of degradation pathways and exposure.

Role of the deuterated analog:

• The deuterated isotopologue has no distinct biological role per se; it is a tracer/standard enabling accurate quantification of the native metabolite in complex matrices via isotope‑dilution mass spectrometry.

Important limitations:

• No medical or clinical uses are implied. Any discussion here is for mechanistic and environmental biochemistry context only. Always consult primary literature and regulatory documents for definitive metabolic and toxicological assessments.

Buffer Applications

This compound is not used as a buffering agent. It does not define a conventional pKa pair suitable for preparing biological or chromatographic buffers.

Practical guidance:

• For LC–MS analyses involving this analyte, employ standard mobile phase buffers/modifiers (e.g., 0.1% formic acid or ammonium formate/acetate at low millimolar concentrations) chosen for ionization efficiency and chromatographic performance. These are applied to the method, not to this compound specifically.
• Avoid strong alkaline buffers that can promote carbamate hydrolysis or phenolate formation during extended exposures, which could bias quantification.

Green Alternatives

While the compound itself is a specific isotopically labeled standard, greener practices can be adopted in its use and in solvent choices for analytical workflows.

Greener analytical choices (general):

• Prefer acetonitrile–water or methanol–water mobile phases with minimal additives; avoid halogenated solvents.
• Where feasible, implement microflow or capillary LC–MS to reduce solvent consumption by 10–100× compared with conventional flows.
• Use solid-phase extraction (SPE) or dispersive SPE (d‑SPE, QuEChERS) to minimize solvent volumes in cleanup.
• Prepare concentrated stock solutions and small working aliquots to reduce waste from repeated thaw/freeze cycles and expired standards.

Comparison of mobile phase choices (general):

• ACN/water: lower viscosity and energy cost for pumping; widely recyclable via distillation.
• MeOH/water: renewable feedstock origin potential; slightly higher viscosity but broadly available and lower toxicity than many alternatives.

Trade‑offs:

• ACN has favorable chromatographic performance but is petrochemical‑derived; MeOH is less hazardous but can increase backpressure. Selecting columns optimized for MeOH can mitigate this.

Note: The deuterated label has no direct “green” substitute if isotopic internal standardization is required; however, efficient method design can markedly reduce overall environmental footprint.

Pharmaceutical Uses

Not applicable. 3‑Hydroxycarbofuran‑d is an isotopically labeled research chemical intended for analytical and laboratory use only.

Context (general, non-therapeutic):

• Isotopically labeled small molecules are sometimes employed as process controls or analytical standards in pharmaceutical quality control laboratories to validate residue, impurity, or extractables/leachables methods. Any such use would be within analytical testing workflows, not as an excipient or active ingredient.
• There is no pharmacopeial monograph known for the deuterated analog of 3‑hydroxycarbofuran. If a compendial context is required for a method, a qualified reference standard and documented traceability should be established internally.

Physical Properties

Item-specific numerical properties have not been provided for this catalog entry. Consult the CoA/Spec Sheet for definitive specifications.

• Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Melting/Boiling Point (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Density/Refractive Index (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (item-specific): Not specified for this item; refer to CoA/Spec Sheet.

General/literature context for analogous non-deuterated 3‑hydroxycarbofuran and related carbofuran metabolites:

• Typically isolated as solids or viscous oils with moderate polarity due to the phenolic OH and carbamate moieties (literature, qualitative).
• Show good solubility in polar organic solvents used in LC–MS workflows (e.g., methanol, acetonitrile) and poor solubility in nonpolar hydrocarbons (literature, qualitative).
• Phenolic OH may engage in hydrogen bonding; pKa of phenolic functions is often in the range ~9–10 (general literature, not specific to this item).

Important: Deuterium substitution minimally perturbs bulk physical properties but can slightly shift spectroscopic signatures (MS, NMR) and isotopic patterns—this is the basis for use as an internal standard.

Quality and Grades

• Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.

Context and expectations for isotopically labeled analytical standards:

• Suppliers of deuterated pesticide metabolites typically control for both chemical purity and isotopic enrichment (e.g., %D at specified site[s]). The exact enrichment pattern and any minor isotopologue distribution should be stated on the CoA for this lot.
• For quantitative LC–MS/MS applications, low levels of unlabeled (d0) analyte are important to minimize back‑contribution to native channels; look for documentation of residual unlabeled content and isotopic purity.
• If offered as “analytical standard” or “LC–MS grade” (not specified here), that generally implies tight control of nonvolatile residues and known solvent content in ampulized solutions; for neat solids, purity is typically established by HPLC/GC and high‑resolution MS.
• Stabilizers: Not specified for this item. If present for some lots, stabilizers can affect UV or MS responses; verify on CoA and account for them in calibration.
• Recommended acceptance checks on receipt: verify identity by LC–MS (exact mass/isotopic pattern) and purity by LC with UV/MS detection; compare retention and MS/MS transitions against a reference spectrum.

Reaction and Applications

This deuterated standard is primarily intended for analytical applications rather than synthetic transformations.

Analytical applications (general/best practices):

• Internal standard for LC–MS/MS quantification of 3‑hydroxycarbofuran in environmental, food, and biological matrices. The isotopic label provides co‑elution with near‑identical ionization efficiency, correcting for matrix effects and recovery.
• Calibration strategies: use isotope‑dilution calibration with matched transitions (e.g., MRM for native vs deuterated analyte). Validate linearity, LOD/LOQ, and check for isotopic cross‑talk into native channels at high native concentrations.
• Sample preparation: typical workflows include QuEChERS or SPE cleanup for complex matrices. Spike the deuterated IS early (pre‑extraction) to correct for procedural losses.
• Confirmation of identity: use concordant retention time and diagnostic MS/MS fragments of both native and d‑labeled analyte with expected isotopic mass shift.

Additional laboratory uses (general):

• Stability studies of 3‑hydroxycarbofuran (e.g., pH or temperature effects) using the d‑analog as a tracer or internal reference.
• Method transfer and proficiency testing as a control material.

Note: The precise deuteration site(s) and enrichment level affect the magnitude of mass shift and potential for H/D back‑exchange. Confirm labeling details on the CoA and avoid conditions that promote exchange (strong acid/base, aqueous protic solvents at elevated temperature).

Reaction Conditions

As an analytical standard, this compound is not typically subjected to synthetic reaction conditions. The following guidance pertains to handling in LC–MS sample preparation and analysis (general, literature-informed):

• Stock solutions: Prepare at 0.1–1.0 mg/mL in MeOH or ACN. Store aliquots at −20 °C; protect from light and moisture. Verify stability over time by periodic QC injections. (Concentrations are general practice suggestions; not item-specific specs.)
• Working solutions: Dilute into mobile phase (e.g., water/ACN or water/MeOH with 0.1% formic acid or 5 mM ammonium formate/acetate). Keep organic content sufficient to prevent precipitation.
• LC–MS/MS detection: Electrospray ionization (ESI+, ESI−) can both be viable depending on method; many carbamate metabolites respond well in ESI− due to phenolic character, while ESI+ can target carbamate fragments. Optimize source parameters empirically.
• Derivatization (optional for GC–MS): Phenolic OH can be derivatized (e.g., silylation) to improve volatility; validate that derivatization does not induce H/D exchange.
• Stability: Carbamate linkages may hydrolyze under strong basic conditions or elevated temperatures in aqueous media. Maintain neutral to mildly acidic conditions during processing and minimize long incubations at high temperature.

Always confirm final method parameters, MS transitions, and retention times with the native analyte and the labeled internal standard.

Safety and Handling

• GHS Classification (item-specific): Not specified for this item; refer to SDS.
• Signal Word / H‑Statements / Pictograms (item-specific): Not specified for this item; refer to SDS.

General safety guidance (not a substitute for SDS):

• 3‑Hydroxycarbofuran is a metabolite of the carbamate insecticide carbofuran. Carbamate esters can inhibit cholinesterases; while toxicity of a specific metabolite/labeled analog may differ, handle this material as toxic/harmful unless data indicate otherwise. Avoid inhalation, ingestion, and skin/eye contact.
• PPE: lab coat, safety glasses or splash goggles, and suitable chemical-resistant gloves (e.g., nitrile). Work in a certified fume hood during weighing and solution preparation.
• Incompatibilities (general): strong oxidizers, strong acids/bases (which may hydrolyze carbamate linkages), reactive acylating agents, and isocyanates. Avoid prolonged exposure to moisture that can promote hydrolysis.
• First aid (overview): If inhaled—move to fresh air; seek medical attention if symptoms develop. Skin/eye contact—rinse with water for ≥15 min; remove contaminated clothing; seek medical advice. If swallowed—rinse mouth; do not induce vomiting; seek medical attention. Provide SDS to responders.
• Environmental precautions: Prevent release to drains; carbamate-derived substances and metabolites are of environmental concern—collect spills with inert absorbent and dispose of as hazardous waste.
• Always consult the product’s SDS for authoritative hazards, exposure limits, and spill/fire-fighting guidance.

Solvent Selection

Item-specific solubility is not provided; the following is general guidance for 3‑hydroxycarbofuran analogs and deuterated standards used in LC–MS workflows.

• Primary diluents (general): methanol (MeOH) and acetonitrile (ACN) typically dissolve carbofuran metabolites well and are compatible with LC–MS.
• Aqueous miscibility: stock solutions in MeOH/ACN can be diluted with water or mobile phase (e.g., water + 0.1% formic acid) to prepare working standards, minimizing precipitation by keeping organic content ≥20–40% during initial dilution.
• Stability considerations: avoid strong base in solution (phenolic deprotonation and potential carbamate hydrolysis). Slightly acidic conditions (0.1% FA) are commonly used for LC–MS mobile phases and are generally benign for short-term handling.
• When to choose MeOH vs ACN:
  • MeOH may better solubilize more polar phenolic metabolites; useful for preparing high-concentration stocks.
  • ACN offers lower viscosity for UHPLC and can sharpen peaks; mixtures (e.g., ACN:water) are widely used.
• Avoid: nonpolar solvents (hexanes) where solubility is often poor; strongly protic acids or concentrated bases that can degrade carbamates.

Comparison (general):

• MeOH: highly polar, protic; excellent solubility, broader chemical compatibility for stocks.
• ACN: polar, aprotic; optimal for LC–MS, lower backpressure, good for working solutions.
• DMSO: strong solvent for challenging solubility but may suppress ESI signals; reserve for special cases.

Storage and Reconstitution

• Storage Conditions (item-specific): Store at −20 °C.
• Shipped In (item-specific): Ice chest + Ice pads.
• Research Use Note (item-specific): For research use only.

General guidance for handling isotopically labeled small‑molecule standards:

• Upon receipt, allow the container to equilibrate to room temperature in a desiccator before opening to minimize condensation. Open under dry conditions.
• If provided neat, dissolve to prepare a primary stock in dry MeOH or ACN (typical 0.1–1.0 mg/mL). Filter through a low‑binding PTFE syringe filter if particulate is observed. Record exact concentration gravimetrically.
• Aliquot into amber vials to avoid repeated freeze–thaw cycles. Store sealed at −20 °C (or as specified on CoA). Protect from light and moisture.
• For working solutions, dilute into initial LC mobile phase just prior to use. Discard working solutions after a defined period (e.g., days to weeks depending on stability studies); verify by QC injections.
• Avoid prolonged exposure to strong acids/bases or elevated temperatures that may cause carbamate hydrolysis or H/D exchange at labile positions.

For any lot-specific reconstitution solvent, concentration, water content, or stabilizer information, consult the CoA/Spec Sheet.

Structure and Identity

This product is an isotopically labeled analog of 3-hydroxycarbofuran, designed for research and analytical use (e.g., as an internal standard).

• Product Name: 3-Hydroxycarbofuran-d (isotopically labeled)
• SKU: H1451660
• CAS: 1794759-59-3
• Molecular Formula (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• SMILES (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey (item-specific): Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general/literature, for context):

• 3‑Hydroxycarbofuran is a known oxidative metabolite of the carbamate insecticide carbofuran and retains the N‑methylcarbamate functional group linked to an aromatic/benzodioxole-type system present in carbofuran metabolites.
• The “‑d” suffix denotes incorporation of deuterium (2H). The exact labeling site(s) and degree of deuteration are not specified for this item and should be confirmed on the CoA/Spectrum.
• Expected functional groups (by analogy to 3‑hydroxycarbofuran, literature): a phenolic or benzylic hydroxy group, an aryl–O–carbamate linkage, and a benzodioxole or related methylenedioxy ring system typical of carbofuran derivatives.

2D description (general): an aryl core bearing a methylenedioxy ring system, substituted by an O‑linked N‑methylcarbamate and an additional hydroxy substituent (“3‑hydroxy” position), with selected hydrogen(s) replaced by deuterium in the labeled analog.

Synthetic Utility

This material is not typically used as a synthetic reagent; its primary value is as an isotopically labeled reference for quantitative analysis.

Nevertheless, deuterated analogs can inform synthesis and mechanistic studies (general):

• Isotope tracing and kinetic isotope effects (KIE): Deuterium incorporation at specific positions may allow interrogation of reaction pathways and rate‑limiting steps in transformations of carbofuran metabolites (oxidation, hydrolysis, conjugation) under controlled conditions.
• Spectroscopic assignment: The d‑label can simplify 1H NMR spectral interpretation by attenuating specific proton signals and can confirm site assignments via 2H NMR.
• Method development: Serves as a surrogate to optimize derivatization or stabilization protocols (e.g., silylation of phenolic OH for GC–MS) while monitoring recovery and artifact formation.

Caveats:

• The exact position and extent of deuteration determine its utility in KIE or mechanistic work; verify labeling via CoA and supporting spectra (2H NMR, HRMS).
• Avoid conditions that provoke H/D exchange at labile positions (acid/base, high temperature, protic solvents) if preservation of the label is required.

Target Specificity

Not applicable. This product is a small-molecule isotopically labeled standard, not an antibody or affinity reagent. There is no antigen, epitope, clone, isotype, or species reactivity associated with this item.