(±)-Taxifolin-C - ≥99% , CAS No.T1423527

CAS: T1423527 Cat. No.: T1423527 Formula: C₁₂₁₃C₃H₁₂O₇ Peso molecolare: 307.23

GRADE & PURITY ≥99%

Storage

Store at 2-8°C

Shipped In

Wet ice

Panoramica

(±)-Taxifolin-13C3 ((±)-Dihydroquercetin-13C3) is a derivative of (±)-Taxifolin, labeled with 13C3. (±)-Taxifolin is the racemate of Taxifolin. Taxifolin exhibits important anti-tyrosinase activity. Taxifolin exhibits significant inhibitory activity against collagenase with an IC 50 value of 193.3 μM. Taxifolin is an important natural compound with antifibrotic activity. Taxifolin is a free radical scavenger with antioxidant capacity.

Specifications

Specifiche e purezza

≥99%

Condizioni di conservazione di stoccaggio

Store at 2-8°C

Spedito in

Wet ice

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Tipo di azione

INHIBITOR

Purezza

≥99%

Nomi e identificatori

Peso molecolare

307.23

Application Protocols

No tested or recommended application protocols are provided for this SKU.

• General guidance (for small-molecule screening/chemistry workflows):
  • Prepare a DMSO stock (e.g., 10–50 mM) under low light and inert atmosphere if feasible. Vortex and, if necessary, warm gently to aid dissolution. Filter through 0.22 µm for cell-free assays to remove particulates.
  • For biochemical assays, titrate into buffer to keep final DMSO ≤ assay tolerance; include controls for redox activity and metal chelation where relevant.
  • For synthetic derivatization, plan protection/deprotection of phenols and monitor by LC-MS/UPLC.

Refer to the CoA/Spec Sheet for any lot-specific notes on solubility, impurity profile, or handling precautions that might affect protocol choices.

Biological Roles

No item-specific biological characterization is provided. The notes below reflect general, literature-based roles of taxifolin (dihydroquercetin) and structurally related flavanonols, and are offered for research design context only.

• Chemical biology context (general):

  • Polyphenolic scaffolds act as hydrogen-bond donors/acceptors and metal chelators, enabling modulation of redox-active pathways in vitro. They are often evaluated in antioxidant and enzyme-inhibition assays.
  • Catechol/resorcinol motifs can undergo autoxidation to quinones, potentially forming covalent adducts with nucleophilic residues (Cys, Lys) in proteins under certain conditions.

• ADME-relevant features (general):

  • Multiple phenols imply high polarity and low passive permeability in neutral form; conjugation (glucuronidation, sulfation, methylation) is common in metabolic studies.

• Experimental caveats:

  • Polyphenols may exhibit assay interference (redox cycling, metal chelation, fluorescence quenching). Employ counter-screens and control metals/antioxidants (e.g., EDTA present/absent) to deconvolute mechanisms.
  • Avoid over-interpretation of broad-spectrum activity; adhere to PAINS-aware screening workflows.

Research use only: These remarks are for in vitro and mechanistic study planning, not for medical or nutritional claims. Verify the exact structure and purity of “(±)-Taxifolin-C” via the CoA before drawing biological conclusions.

Buffer Applications

This compound is not a conventional buffering agent. No item-specific pKa or buffer system data are provided.

• Practical guidance (general):
  • If used in biochemical assays, prepare concentrated stocks in DMSO or ethanol and dilute into your chosen buffer (e.g., phosphate, HEPES, Tris) while keeping the final organic cosolvent within assay tolerance.
  • Avoid strongly basic buffers if compound stability is a concern; phenolic deprotonation can promote oxidation.

For routine buffering needs, use established buffer systems with defined pKa values. Refer to the CoA/Spec Sheet for any item-specific solubility notes relevant to buffer preparation.

Green Alternatives

Where solvent use or derivatization chemistry is involved with taxifolin-like compounds, greener choices can reduce environmental impact. The guidance below is general and should be adapted to your specific procedure.

• Solvent substitutions (general):

  • Replace DMF with safer polar aprotics where possible (e.g., Cyrene, propylene carbonate) recognizing differences in basicity and viscosity.
  • Prefer ethanol or isopropanol over methanol where compatible with solubility and reaction kinetics.
  • For extractions, consider ethyl acetate or 2-MeTHF instead of dichloromethane.

• Energy and process intensity:

  • Phenolic acylations/alkylations often proceed at mild temperatures. Microwave or flow techniques can shorten reaction times and reduce solvent volumes.

• Protection strategies:

  • Use carbonate coupling (e.g., dimethyl carbonate) for green O-methylations where applicable, acknowledging reactivity limitations versus classical MeI/Me2SO4.

• Comparative snapshot (general guidance; trade-offs apply):

  • DMF vs. Cyrene: Cyrene reduces reproductive toxicity concerns but is more viscous and less base-stable.
  • DCM vs. EtOAc/2-MeTHF: Greener alternatives lower halogenated waste; may affect phase behavior and solubility.
  • MeOH vs. EtOH/i-PrOH: Slightly lower toxicity and better sustainability metrics for EtOH/i-PrOH; may reduce solubility for highly polar analytes.

Always validate performance (solubility, rate, selectivity) when substituting. For regulated EHS goals, document solvent selection using established guides (e.g., CHEM21 or GSK Solvent Sustainability Guide).

Pharmaceutical Uses

No pharmacopeial status, excipient role, or formulation grade is provided for this SKU. It is supplied for research use only.

• Context (general/literature for related polyphenols):

  • Polyphenolic flavonoids are sometimes explored in preformulation studies for antioxidant capacity in model systems, but they are not standard pharmaceutical excipients.
  • Solubility limitations and potential instability under basic conditions often necessitate derivatization (e.g., prodrugs, salt/complex formation) in research settings.

• Guidance:

  • Do not use in human or veterinary products. If your work involves formulation screening or stability modeling, confirm exact identity, polymorph/solvate state, and purity via the CoA.
  • For analytical method development (e.g., stability-indicating HPLC), consider photostability and oxidative stress conditions as part of forced-degradation studies, noting that these are general best practices rather than specifications for this SKU.

Physical Properties

Item-specific physicochemical properties are not provided in the Product Data.

• Item-specific properties (this catalog entry):

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Melting point, boiling point, density, refractive index, pKa, logP, UV/Vis cutoff, water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.

• General/literature context for taxifolin (dihydroquercetin) and related flavanonols (for planning only; not product specifications):

  • Typical molecular formula (taxifolin): C15H12O7; MW ~304.25 g/mol (literature).
  • Physical form: Often a yellowish to off-white crystalline solid (literature); tends to be poorly water-soluble and freely soluble in DMSO, moderately in ethanol or methanol (literature).
  • Acid-base/ionization: Multiple phenolic OH groups with pKa values typically in the ~7–10 range depending on position and solvent; carbonyl is non-ionizable (literature).
  • Stability: Phenolic compounds can undergo oxidative discoloration; light/air/alkali can accelerate degradation (literature).

Practical note: Use the literature values only as orientation for method development. For any quantitative work, chromatography, or release testing, obtain the exact item-specific data from the CoA/Spec Sheet and SDS accompanying this SKU.

Quality and Grades

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

Interpretation and context:

• Research use only: This SKU is supplied strictly for research and laboratory applications. It is not intended for human or veterinary use, food, cosmetic, or household purposes.
• When the exact grade/purity is unspecified, rely on the provided CoA for batch-specific purity determination (e.g., HPLC area %, NMR purity), residual solvents, and any known stabilizers.
• UV specifications, heavy metals, water/peroxide content, and chromatographic suitability are not provided here. Do not assume suitability for analytical calibration or regulated work without reviewing the CoA/Spec Sheet.
• Stabilizers: None are listed. If present, they will be disclosed on the CoA/SDS; phenolic compounds generally need no stabilizer but can benefit from protection from light/air.

Practical guidance:

• If you require defined grades (e.g., bioactive screening grade vs. synthetic intermediate grade), contact technical support for available lots that meet your performance criteria.
• For library screening, document the exact purity basis (area % vs. weight %) and analytical method. If LC-UV is used, note that polyphenols can exhibit strong UV absorbance and potential baseline drift depending on mobile-phase pH.
• If using in quantitative bioassays, verify counterion/solvate state and moisture content where relevant; this information is batch-dependent and should be confirmed via CoA.

Reaction and Applications

Manufacturer Applications: Not specified in the Product Data. The following are general applications for taxifolin-like flavanonols in research workflows; validate relevance for this SKU.

• Screening and probe development (general):

  • Used as polyphenolic chemotypes in small-molecule libraries for biochemical screening and structure–activity relationship (SAR) exploration. Phenolic motifs enable rapid derivatization to explore H-bonding and chelation effects.

• Chemical reactivity (general):

  • Phenolic O-acylation and O-alkylation provide prodrugs or solubility-tuned analogues; selective protection strategies differentiate catechol vs. resorcinol sites.
  • Carbonyl at C4 allows derivatization (e.g., oxime/hydrazone formation), though sterically and electronically deactivated compared to simple aryl ketones.
  • Metal chelation via catechol groups can be leveraged in materials/coordination studies.

• Analytical applications (general):

  • Antioxidant capacity assays (DPPH, ABTS, FRAP) where taxifolin is used as a reference chemotype; not a product specification.

• Practical tips:

  • Protect from light/air during reactions to minimize oxidative side products. Inert atmosphere and anhydrous conditions help, especially during base-mediated steps.
  • For selective mono- vs. di-alkylation/acylation on catechols, use stoichiometry and base choice (e.g., K2CO3 vs. Cs2CO3) to tune outcomes; consider silyl protection (TBS) on more reactive phenols.
  • Monitor by LC-MS; phenolic isomers can co-elute—use orthogonal methods (HILIC or phenyl-hexyl phases) if needed.

Reaction Conditions

Without item-specific data, the following are general laboratory conditions commonly used with taxifolin-like polyphenolic scaffolds (literature/practice). They are not specifications for this SKU.

• O-Acylation/O-alkylation of phenols:

  • Base: K2CO3, Cs2CO3, or NaH (for more reactive conditions); phase-transfer catalysts can aid selectivity.
  • Solvents: Acetone, acetonitrile, DMF, or DMSO.
  • Temperature: 20–60°C typically; higher temps increase risk of oxidation.

• Protection strategies:

  • Silylation: TBSCl/TBDMSCl with imidazole in DMF; 0–25°C, inert atmosphere.
  • Benzylation: BnBr/NaH in DMF; room temp to 40°C, followed by hydrogenolysis for deprotection.

• Carbonyl transformations:

  • Oxime formation: Hydroxylamine·HCl, pyridine or acetate buffer, rt–50°C.
  • Reduction: NaBH4 or catalytic hydrogenation; monitor to avoid over-reduction of aromatic rings.

• Analytical control:

  • LC-MS with acidic aqueous-organic mobile phases (e.g., 0.1% formic acid in MeCN/H2O) for clean peak shapes; consider phenyl-hexyl phases for resolving closely related regioisomers.

• Stability precautions:

  • Minimize exposure to strong base, light, and air. Conduct sensitive steps under nitrogen/argon; add antioxidants (e.g., BHT) only if compatible and documented for your application.

Adjust conditions based on the exact substitution pattern and protection state confirmed for this SKU via CoA.

Safety and Handling

No item-specific GHS hazard data are provided in the Product Data for this SKU. Always consult the product SDS for authoritative safety information.

• Item-specific hazard fields:

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

• General handling guidance for polyphenolic flavonoids (literature/practice; not product-specific):

  • PPE: Wear lab coat, safety glasses, and appropriate chemically resistant gloves. Handle powders in a fume hood to minimize inhalation of particulates.
  • Incompatibilities: Strong oxidizers, strong bases (can promote oxidative/air degradation and phenolate formation), and prolonged exposure to light and air.
  • Hygiene: Avoid dust generation; prevent contact with eyes/skin; wash thoroughly after handling.
  • First aid (general): If inhaled, move to fresh air; if on skin/eyes, rinse with water for several minutes; if ingested, rinse mouth. Seek medical attention as needed. Follow SDS instructions.
  • Fire safety: Many organic solids are combustible. Use CO2, dry chemical, or foam as appropriate; firefighters should wear SCBA.

• Waste: Collect in organic solid or solution waste per institutional and local regulations.

Note: Absent item-specific hazard evaluation, treat as a laboratory chemical of unknown toxicity. For research use only.

Solvent Selection

No item-specific solubility data are provided. The following guidance reflects general behavior of taxifolin-like polyphenolic flavanonols (literature), and should be validated for this SKU.

• Expected solubility profile (general/literature):

  • Water: Low intrinsic solubility at neutral pH; solubility may increase in basic aqueous media due to phenolate formation (may risk degradation/oxidation).
  • Polar aprotic: DMSO — typically high solubility and preferred for stock solutions. DMF — often soluble; consider toxicity and hygroscopicity.
  • Polar protic: Methanol/ethanol — moderate solubility; may be adequate for analytical sample prep.
  • Nonpolar solvents (hexanes, toluene): Poorly soluble.

• Polarity considerations:

  • Multiple phenolic groups confer high H-bonding capacity; Hansen profile skews toward hydrogen-bonding and polar interactions. Choose solvents that can donate/accept hydrogen bonds (DMSO, MeOH, EtOH, acetone to a lesser extent).

• Practical tips:

  • Prepare concentrated DMSO stocks (e.g., 10–50 mM) and dilute into assay buffer with vigorous mixing; keep final DMSO below assay tolerance (commonly ≤0.5–1% v/v) if doing biochemical work.
  • For chromatography, aqueous-acetonitrile or aqueous-methanol with 0.1% formic acid or ammonium acetate buffers are common. Beware of strong adsorption on bare silica; end-capped C18 generally works well.
  • Avoid strong base if analyte integrity is critical; phenolate formation can promote oxidative changes.

• Quick comparison (general):

  • DMSO: Highest solvency; ideal for stocks.
  • MeOH/EtOH: Convenient for prep/analytical; moderate solvency.
  • Water: Limited unless pH-adjusted; potential instability when basic.

Storage and Reconstitution

• Storage (item-specific):

  • Store at 2–8°C (per Product Data). Protect from light and moisture for optimal stability.
  • Shipped on wet ice; upon receipt, promptly return to 2–8°C storage.

• Container/atmosphere (general best practice for polyphenols):

  • Keep tightly closed in an inert atmosphere if possible (nitrogen/argon) to limit oxidative degradation. Use amber vials to minimize light exposure.

• Reconstitution (general guidance; not a specification):

  • For stock solutions, dissolve in anhydrous DMSO to a convenient concentration (e.g., 10–50 mM). Sonication or brief warming (≤40°C) can assist dissolution. Record exact concentration gravimetrically where precision is required.
  • If aqueous use is required, dilute the organic stock into buffer with vigorous mixing. Avoid strong base and prolonged ambient exposure. Prepare fresh working solutions and store aliquots at 2–8°C when short-term use is intended.

• Freeze–thaw and stability:

  • If frozen stocks are prepared, aliquot to avoid repeated freeze–thaw. Assess stability by periodic LC before critical experiments.

Note: No item-specific stabilizers, hydrate/solvate state, or shelf-life are provided. For definitive guidance, consult the lot-specific CoA and SDS. Research use only.

Structure and Identity

This item is labeled “(±)-Taxifolin-C,” suggesting a racemic taxifolin (dihydroquercetin) analogue or form within a small-molecule library. Item-specific structural identifiers are not provided in the Product Data.

• Item-specific identifiers (this catalog entry):

  • CAS: T1423527 (catalog placeholder)
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

• Structural class and features (general/literature for taxifolin, a flavanonol):

  • Core scaffold: Flavanonol (dihydroflavonol) framework with a chroman (2,3-dihydro-2-phenylchromen-4-one) nucleus bearing multiple phenolic OH groups.
  • Typical ring system: A (resorcinol-like), B (catechol-like), and heterocyclic C ring with a 4-keto group.
  • Stereocenters: Two adjacent stereocenters at C2 and C3; “(±)” denotes racemate in many contexts. Specific configuration for this item is not provided.
  • Hydrogen-bond donors/acceptors: Multiple phenolic OH groups (donors) and a conjugated carbonyl (acceptor).

• 2D descriptive sketch (general): A bicyclic benzopyran bearing an additional phenyl ring at C2; the C ring carries a 4-ketone, and the A/B rings carry several hydroxyl substituents.

Note: Because no definitive identifiers are supplied for this catalog SKU, treat the above structural details as general context for taxifolin-like flavanonols. Consult the CoA/Spec Sheet for the exact structure of “(±)-Taxifolin-C.”

Synthetic Utility

Although this SKU lacks item-specific structural data, a taxifolin-like flavanonol offers a versatile platform for derivatization. The following outlines general synthetic utility of such scaffolds.

• Functional handles:

  • Multiple phenolic OH groups enable selective protection (e.g., TBS, benzyl, acetyl) and subsequent O-alkylation/acylation to tune lipophilicity and stability.
  • The 4-keto group enables formation of oximes/hydrazones and reduction to secondary alcohols, expanding the accessible chemical space.

• Divergent synthesis:

  • Differential protection of catechol vs. resorcinol rings allows regioselective elaboration, enabling libraries of ethers/esters and late-stage diversification.
  • Transition-metal-catalyzed cross-couplings are applicable on suitably functionalized analogues (e.g., halogenated aryl derivatives prepared from the parent scaffold).

• Retrosynthetic considerations:

  • Access via flavanone oxidation/reduction sequences or oxidative cyclization from 2′-hydroxychalcones, followed by stereoselective reductions to set C2/C3.

• Practical points:

  • Employ inert atmosphere for base-mediated steps to curb oxidative byproducts. Use mild bases (K2CO3, Cs2CO3) and phase-transfer catalysts when appropriate.
  • Monitor regioisomer formation; orthogonal protecting groups and stepwise deprotection strategies improve selectivity.

These strategies are general for flavanonols and should be adapted once the exact structure of “(±)-Taxifolin-C” is confirmed from the CoA.

Target Specificity

No target, epitope, or binding specificity data are provided for this SKU. As a small-molecule library compound, “(±)-Taxifolin-C” is not an antibody or biologic, and no target selectivity claims are made.

• Item-specific data:
  • Target/epitope: Not specified for this item; refer to CoA/Spec Sheet.
  • Species reactivity, clone/isotype: Not applicable.

If using in biochemical assays, determine apparent potency and selectivity empirically with appropriate counter-screens and orthogonal assays, noting the potential for polyphenolic assay interference (general literature caution).

Domande frequenti

What is the purity of this product?

This product is supplied at ≥99% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at 2–8 °C. Refrigerated storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is T1423527, the molecular formula is C1213C3H12O7, and the molecular weight is 307.23 g/mol.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.