Sinapyl alcohol-d , CAS No.934634-29-4

CAS: 934634-29-4 Cat. No.: S1433669 Fórmula: C₁₁H₁₁D₃O₄ Peso molecular: 213.24

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

Visão geral

Sinapyl alcohol -d 3 is the deuterated labeled Sinapyl alcohol. Sinapyl alcohol is an orally active anti-inflammatory and antinociceptive agent. Sinapyl alcohol reduces the expression level of inducible NO synthase and COX-2.

Specifications

Condições de armazenamento de armazenamento

Store at 2-8°C,Protected from light,Argon charged

Enviado em

Wet ice

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Nomes e identificadores

Peso molecular

213.24

Application Protocols

No item-specific, validated protocols are provided for this SKU. The following general workflows are commonly used with deuterated sinapyl alcohol; adapt to your system and consult primary literature.

• LC–MS internal standard preparation:

  • Prepare a 1–10 mg/mL stock in MeOH or ACN. Store aliquots at 2–8 °C, protected from light, under inert gas.
  • Spike samples prior to extraction at a fixed concentration to correct for recovery and matrix effects. Monitor M+H (Δm = +1 per D) and characteristic fragments.

• Plant feeding (isotope tracing) – bench-scale:

  • Dissolve in minimal EtOH, dilute into water or growth medium to low µM–mM range. Apply to cut stems or hydroponic roots. Maintain controls without tracer.
  • After incubation (hours–days), extract cell walls/tissues and analyze monolignol-derived units by thioacidolysis/DFRC followed by GC–MS/LC–MS to quantify D-incorporation (literature).

• Enzymatic oxidative coupling (model dimerization):

  • Dissolve substrate in 10–20% MeOH in phosphate buffer (pH 6.5). Add HRP and sub-stoichiometric H2O2 at 20–25 °C. Quench at set intervals with catalase and analyze products by HPLC/LC–MS.

Caution: If the deuterium resides on exchangeable sites (e.g., OD/phenolic D), minimize aqueous exposure or accept partial back-exchange. Always validate isotopic integrity by NMR/MS.

These are general, literature-informed procedures and are not product-specific certifications.

Biological Roles

General (literature) context for the unlabeled parent compound sinapyl alcohol:

• Monolignol precursor: Sinapyl alcohol is one of the three principal monolignols (with coniferyl and p-coumaryl alcohols) used by plants to biosynthesize lignin, forming syringyl (S) units upon oxidative radical coupling.
• Biosynthetic pathway: Derived from the phenylpropanoid pathway via methylation steps (COMT/CCoAOMT) on caffeic/ferulic intermediates, followed by reduction of the corresponding aldehyde (sinapaldehyde) to the alcohol.
• Polymerization: Incorporation into lignin occurs through peroxidase or laccase-mediated one-electron oxidation to phenoxy radicals, which couple to form linkages (β–O–4 dominantly, alongside β–5, 5–5, β–β, etc.).
• Physicochemical influence: Higher sinapyl (S) content often correlates with more linear lignin and improved delignification properties compared to guaiacyl (G)-rich lignin (literature).

Use of deuterated analogs (research practice):

• Stable-isotope tracing enables mapping of monolignol transport and deposition, elucidating cell wall assembly. Deuterium labels facilitate MS-based detection without radioactivity.
• Kinetic isotope effects and position-specific labels help dissect enzymatic steps (e.g., peroxidase H-abstraction, laccase oxidation) and radical coupling pathways.

Note: These are general biological insights and do not imply any clinical or therapeutic use. For item-specific labeling patterns and suitability for biological feeding experiments, consult the CoA and SDS and validate against your model system.

Buffer Applications

This compound is a small, largely hydrophobic phenylpropanoid alcohol and is not a buffering reagent. It does not form a defined conjugate acid/base pair with a practical buffering range under typical biochemical conditions.

Practical notes (if using in aqueous systems):

• Solubilization: Prepare concentrated stocks in water-miscible organics (e.g., ethanol, methanol, DMSO), then dilute into buffer with vigorous mixing. Maintain final co-solvent typically ≤1–2% v/v for biochemical assays, verifying no precipitation.
• pH considerations: The phenolic OH has a pKa around 9.5–10.5 (literature, parent compound). At basic pH the phenolate is more water-soluble but may alter reactivity and can accelerate H/D exchange at exchangeable sites.
• Surfactants: Nonionic surfactants (e.g., 0.01–0.05% Tween-20) can improve dispersion in assay buffers if compatible with the biological system.

For buffering needs, select canonical buffers (HEPES, phosphate, Tris, MOPS) appropriate for your pH and ionic strength. This section is provided only for handling context; the compound itself is not intended as a buffer.

Green Alternatives

Perspective on greener experimentation with deuterated sinapyl alcohol (general guidance):

• Isotopic vs radiolabeled tracers: Using deuterated sinapyl alcohol instead of radioisotopes (e.g., 3H- or 14C-labeled monolignols) reduces radiological hazards, specialized waste, and regulatory burden. Tradeoff: requires sensitive MS/NMR and careful control of H/D exchange.

• Solvent choices for handling and analysis: Comparison (literature-based):

  • Methanol vs Ethanol: Ethanol is generally preferable from a green metric standpoint (renewable sourcing, lower toxicity), though both are protic and can promote H/D exchange at phenolic/OD sites.
  • DCM vs Ethyl acetate/2-MeTHF: Replace chlorinated solvents with EtOAc or 2‑MeTHF when feasible for extractions and reactions; polarity may differ, impacting solubility and reaction rates.
  • DMF/DMSO vs Cyrene/gamma-valerolactone (GVL): For polar aprotic needs, consider bio-based solvents if compatibility with deuterium labeling and substrate stability is confirmed.

• Energy and protection: Product guidance already specifies 2–8 °C storage and light protection; consolidate cold shipments and use amber vials to minimize repeat cooling cycles and photodegradation, lowering waste.

• Workup/waste minimization: Use microscale reactions/analyses, LC–MS-compatible mobile phases to avoid halogenated waste, and solid-phase extraction (SPE) for cleanup instead of large-volume liquid–liquid extractions.

Caveat: Any switch in solvent system should be validated for isotopic integrity (avoid conditions that cause H/D back-exchange if the label is on exchangeable positions).

Pharmaceutical Uses

No pharmacopeial or excipient status is provided for this item.

General research-related roles (non-clinical):

• Analytical internal standard: Deuterated small molecules are commonly used as mass spectrometry internal standards in complex matrices to correct for extraction efficiency and ionization variability. Sinapyl alcohol-d may serve this role in plant, biomass, or food-related phenolic profiling.
• Reference material: Can be used to assign or confirm chromatographic retention and MS/MS fragmentation patterns of monolignols and related phenylpropanoids.

Manufacturing/formulation context: Not typically used as a pharmaceutical excipient or API. No compendial monographs known for sinapyl alcohol or its deuterated forms (literature context).

Regulatory note: The product is labeled “For research use only” per Product Data and is not intended for human or veterinary use, diagnostic procedures, or clinical applications.

If a regulated or validated analytical method is planned, obtain a lot-specific CoA stating isotopic purity/distribution, residual solvents, and chromatographic purity to meet documentation requirements.

Physical Properties

Item-specific physical property data:

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Storage/handling from Product Data:

• Store at 2–8 °C, protected from light, under argon; shipped on wet ice.

Literature values (unlabeled parent, for context only):

• Typical physical form: pale solid or viscous oil depending on purity and temperature (literature).
• Melting point (parent sinapyl alcohol): reported ~71–74 °C (literature, varies by polymorph/purity).
• Solubility: sparingly soluble in water; soluble in polar organics (MeOH, EtOH, acetone), and moderately in less polar solvents (EtOAc, dichloromethane) (literature).
• UV/Vis: conjugated phenyl–propenyl chromophore; λmax often observed in the 280–330 nm range depending on solvent and pH (literature).
• pKa (phenolic OH, parent): typically ~9.5–10.5 (literature, solvent-dependent).
• LogP: estimated moderate (reflecting two methoxy groups and one phenolic OH) (literature/estimation).

Important: Isotopic substitution with deuterium generally has negligible effect on bulk thermophysical properties at ambient conditions, but may shift vibrational spectra and NMR signals. For specifications applicable to this SKU (purity, water content, etc.), consult the CoA/Spec Sheet.

Quality and Grades

Item-specific grade/purity details:

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

Context for deuterated small molecules (general):

• Isotopic enrichment: For “-d” labeled materials, a key quality attribute is deuterium incorporation (atom % D) at each specified position. Vendors typically report overall isotopic enrichment and labeling pattern. Verify by 1H/2H NMR and HRMS. For kinetic isotope effect or tracer studies, positional fidelity matters as much as global %D.
• Impurity profile: Common impurities include unlabeled parent (H-isotopologue), partially labeled isotopologues, methoxy deprotection products, and oxidative dimers. Chromatographic purity (HPLC/GC) and spectral purity (NMR) are both relevant.
• Water/peroxide/metal limits, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilization: The listing specifies argon headspace and light protection, indicating susceptibility to oxidative or photochemical change; this is typical of conjugated phenolic allylic alcohols.

Practical guidance:

• Request CoA lots with explicit isotopic distribution and residual solvent data if your application is quantitative (e.g., internal standard work). For polymerization/biomimetic studies, the percentage of unlabeled isotopologue can influence mass balance and MS pattern deconvolution.
• If using as an internal standard, match the labeling pattern to the analytical transition (e.g., LC–MS/MS MRM) to minimize back-exchange and coelution artifacts.

Reaction and Applications

Item-specific application notes provided by the manufacturer: Not specified for this item; see below for expanded general uses of deuterated sinapyl alcohol in research.

Deuterated sinapyl alcohol is primarily employed as:

• Isotopic tracer in lignin biosynthesis studies (in planta feeding or cell-suspension experiments) to probe monolignol incorporation, transport, and coupling patterns using LC–MS/MS or NMR (literature).
• Mechanistic probe for peroxidase/laccase-mediated oxidative coupling and radical cross-coupling selectivity (β–O–4, β–β, β–5 linkages) via kinetic isotope effects and isotopologue-resolved MS (literature).
• Internal standard in quantitative analysis of monolignols and related phenylpropanoids in biomass pretreatment and depolymerization studies, enabling accurate mass-balance and recovery calculations (literature).
• Model substrate for studying photochemical/oxidative stability of conjugated phenolic allylic alcohols and for benchmarking antioxidant assays.

Practical tips:

• Preserve labeling: If the label is on exchangeable positions (OD/phenolic D), minimize exposure to protic solvents or buffer salts that catalyze H/D exchange. For nonexchangeable C–D labels, standard conditions are generally compatible.
• Sample workup: Use deoxygenated, light-protected conditions to limit oxidative dimerization/polymerization. Argon sparging and amber glassware are recommended (consistent with product storage guidance).
• Analytical: Monitor characteristic mass shifts (Δm = +1 per D) and isotopic envelopes; correct for natural 13C/2H contributions.

Note: Exact labeling positions and enrichment for this SKU are Not specified for this item; consult the CoA to align methods with your experimental goals.

Reaction Conditions

There are no item-specific, validated reaction conditions provided for this SKU. The following are general literature practices for sinapyl alcohol and deuterated analogs; adapt to your labeling constraints and consult primary sources.

• Oxidative coupling (lignin model reactions):

  • Catalyst: Horseradish peroxidase or laccase; co-oxidant H2O2 (peroxidase) or O2 (laccase).
  • Solvent: Aqueous buffer (pH 6–7) with 5–20% v/v co-solvent (MeOH/EtOH/acetone) to aid solubility; low light, O2 control as needed.
  • Temp/time: 20–30 °C; minutes to hours depending on loading; monitor by HPLC/LC–MS.
  • Note: Exchangeable deuterium (OD/phenolic D) may back-exchange in aqueous media.

• Selective oxidations:

  • Alcohol → aldehyde: TEMPO/NaOCl in biphasic CH2Cl2–buffer or Dess–Martin in CH2Cl2/EtOAc at 0–25 °C; 0.5–2 h (literature). Protect phenol if chemoselectivity is poor.
  • Allylic manipulations: mCPBA epoxidation in CH2Cl2 (0–5 °C to rt); subsequent opening under Lewis/Brønsted acid catalysis. Monitor for rearrangements.

• Protection/derivatization:

  • Phenol methylation: MeI/K2CO3 in acetone or dimethyl sulfate (handle with extreme caution) to give trimethoxy analogs (literature). Greener: dimethyl carbonate with base under pressure.
  • Esterification: Acetylation with Ac2O/pyridine or catalytic DMAP in EtOAc/DCM; rt to 50 °C.

• Hydrogenation:

  • C=C reduction: H2, Pd/C in EtOAc/EtOH at rt–40 °C; hours. Beware of potential H/D scrambling at benzylic/allylic positions under acidic/metal-catalyzed conditions.

Always verify compatibility with the deuterium labeling pattern (Not specified for this item; refer to CoA/Spec Sheet).

Safety and Handling

Item-specific hazard information:

• Signal word: Not specified for this item; refer to SDS.
• H-statements / GHS classification / pictograms: Not specified for this item; refer to SDS.

General safety considerations (literature/good practice for phenolic allylic alcohols):

• Hazards: Phenolic compounds may cause skin/eye irritation; avoid inhalation of dust/aerosols. Allylic alcohols can be irritating and may be harmful if swallowed. Handle in a fume hood.
• PPE: Safety glasses or face shield, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). Use splash protection when preparing solutions.
• Incompatibilities: Strong oxidizers (risk of exotherm/oxidation), strong bases (can form phenolate; increased reactivity), strong acids (possible dehydration/side reactions). Avoid prolonged exposure to air and light to limit oxidative discoloration/polymerization.
• Special risks: Phenolic/allylic systems can undergo slow air oxidation; argon headspace and light protection (as specified) mitigate degradation. Dry ice/acetone cooling not generally required unless for reactive transformations.
• First aid (overview): In case of skin contact, wash with soap/water. Eye exposure—rinse cautiously with water for several minutes; remove contacts. If inhaled—move to fresh air; seek medical advice if symptoms persist. If ingested—rinse mouth; do not induce vomiting; seek medical attention.
• Spill response: Absorb with inert material, collect for disposal as organic waste. Prevent discharge to drains.

Always consult the product-specific SDS for authoritative hazard and response information.

Solvent Selection

Item-specific solubility data are not provided; refer to CoA/Spec Sheet.

General solvent behavior (literature, parent sinapyl alcohol):

• Polarity class: moderately polar, H-bond donor/acceptor (phenol + primary alcohol), aromatic/conjugated character.
• Miscibility/solubility: Good in MeOH, EtOH, isopropanol, acetone, acetonitrile, DMF/DMSO; moderate in ethyl acetate and chlorinated solvents; limited in nonpolar alkanes; low in water at neutral pH but more soluble as phenolate in basic aqueous media.
• Dielectric/ionization considerations: Phenolic pKa ~9.5–10.5 (literature). For aqueous work, co-solvents or cyclodextrin encapsulation can assist. Avoid strong base if preserving the native isotopic pattern at exchangeable positions (e.g., OD/OH).

When to choose which solvent (practice tips):

• NMR prep: Use CD3OD, DMSO‑d6, or acetone‑d6 to maintain deuteration at non-exchangeable positions; avoid protic solvents if the label is on an exchangeable hydrogen (OD), unless intentional back-exchange is acceptable.
• LC–MS sample prep: MeOH or ACN with 0.1% formic acid for positive/negative ESI; minimize aqueous fraction to maintain solubility. For phenolate anion detection, add a trace base (e.g., ammonium hydroxide), noting potential H/D exchange at phenolic OH.
• Synthetic transformations: Anhydrous EtOAc, THF, or toluene for esterifications/etherifications; polar aprotic (DMF/DMSO) for SNAr/alkylations on protected derivatives.

Comparison notes:

• Versus coniferyl alcohol analogs, sinapyl derivatives are typically slightly more polar due to the additional methoxy group (literature).

Storage and Reconstitution

Item-specific storage conditions (from Product Data):

• Store at 2–8 °C.
• Protect from light (use amber vials, minimized exposure).
• Argon charged (maintain inert headspace after each use; gently purge vial with argon or nitrogen before recapping).
• Shipped on wet ice.

Reconstitution and handling (general guidance):

• Solvents: Prepare stock solutions in dry, oxygen-free methanol, ethanol, acetonitrile, acetone, or DMSO, depending on downstream use. For NMR or to minimize H/D exchange, choose appropriate deuterated/aprotic solvents and avoid aqueous buffers if the label is on exchangeable positions.
• Concentration: Common analytical stocks are 1–10 mg/mL. Filter through 0.2 µm PTFE if particulate is present.
• Aliquoting: Divide into single-use amber vials or cryovials to reduce freeze–thaw and headspace oxygen exposure. Backfill with argon after each use.
• Stability: Protect from air and light to limit oxidative dimerization/polymerization typical of monolignols. Store tightly sealed at 2–8 °C as specified. For long-term storage, refrigeration with inert gas is preferred; avoid repeated warming cycles.

Specifications not provided:

• Appearance, exact solubility limits, and shelf-life: Not specified for this item; refer to CoA/Spec Sheet.

Always consult the lot-specific CoA and SDS for definitive guidance on stability, compatibility, and safety before use.

Structure and Identity

Item-specific identifiers (from Product Data):

• CAS: 934634-29-4
• Product name: Sinapyl alcohol-d (deuterium-labeled sinapyl alcohol)
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

General structural description (literature, for the unlabeled parent “sinapyl alcohol”):

• Core scaffold: a substituted phenyl ring bearing phenolic OH at para (4‑position) relative to the propenyl side chain, and methoxy groups at 3‑ and 5‑positions (3,5-dimethoxy-4-hydroxyphenyl-2-propen-1-ol).
• Functional groups: phenol (Ar–OH), allylic primary alcohol (–CH2–CH=CH–OH), two anisole-type methoxy substituents (–OCH3), and a conjugated C6–C3 cinnamyl system.
• Conjugation: extended π-system across the aromatic ring and the trans-propenyl chain typical of monolignols.
• Deuterium labeling (general): “-d” indicates replacement of one or more hydrogens with deuterium (2H). Common labeling sites for sinapyl alcohol include the benzylic/allylic methylene, the hydroxyl hydrogen (OD), or ring/side-chain positions; the exact labeling pattern for this catalog item is Not specified for this item; refer to CoA/Spec Sheet.

Notes for identification in the lab:

• Verify isotopic enrichment and labeling positions by 1H/2H NMR and high-resolution MS (literature practice). Use the CoA for definitive item-specific identity parameters.

Synthetic Utility

General synthetic value (literature, parent sinapyl alcohol):

• Functional handles: phenolic OH (for protection/etherification/esterification), primary allylic alcohol (oxidation to aldehyde/acid, Mitsunobu reactions, ester formation), activated aryl ring (electrophilic substitution limited by methoxy/phenol directing effects).
• Conjugated side chain: amenable to selective hydrogenation (C=C), dihydroxylation/epoxidation (e.g., mCPBA epoxidation of the allyl), and cross-metathesis. Radical pathways lead to dimerization/polymerization (model lignin formation) under oxidative conditions (peroxidase/laccase, metal–oxo systems).
• Protecting group strategies: Phenolic OH can be protected as methyl/benzyl/THP silyl ethers; primary alcohol protected as acetate or carbonate to modulate reactivity and solubility. Protecting groups help prevent undesired oxidative coupling.
• Access to analogs: From sinapyl alcohol, one can prepare sinapaldehyde (oxidation, e.g., TEMPO or Dess–Martin) and downstream syringyl derivatives of interest in lignin chemistry and materials research.

Deuterated variant considerations:

• Position-specific C–D bonds serve as mechanistic probes and allow isotope effect studies. Avoid conditions that scramble labels (acid/base-catalyzed H/D exchange at benzylic/allylic positions if activated) when the deuterium site is critical.
• In isotopic dilution experiments, maintain accurate mass balance by quantifying the unlabeled isotopologue fraction.

Note: For this SKU, exact labeling positions are Not specified for this item; refer to CoA/Spec Sheet for planning position-sensitive transformations.

Target Specificity

Not applicable. This product is a small-molecule chemical (deuterated sinapyl alcohol), not an antibody, enzyme, or affinity reagent. There is no antigen/epitope or species reactivity associated with the item.

For biochemical studies, any “specificity” pertains to enzyme–substrate preferences in phenylpropanoid/lignin-related pathways (e.g., peroxidases, laccases), which are model-system dependent and not inherent target-binding properties of this reagent.