Dehydrodanshenol A , CAS No.1444618-61-4

CAS: 1444618-61-4 Cat. No.: D1438631 分子式: C₂₁H₁₈O₄ 分子量: 334.37

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

概要

Dehydrodanshenol A is a non-competitive inhibitor of Protein tyrosine phosphatase 1B (PTP1B), with an IC 50 value of 8.5 μM. Dehydrodanshenol A can be used in diabetes-related research.

Specifications

保管条件

Store at -20°C

入荷

Ice chest + Ice pads

この製品は冷冷この冷このこの製品の運送が必要です。地上およびその他の経済サービスは利用できません。

アクションタイプ

INHIBITOR

名前と識別子

分子量

334.37

Application Protocols

No validated application protocols are provided in the Product Data for this item. The following general procedures are offered as non-binding guidance for research use only:

• Preparation of stock solutions (general):

  • Weigh compound quickly to minimize air/light exposure. Dissolve in dry DMSO to 10–50 mM. Sonicate briefly if needed. Filter through 0.2 μm PTFE if particles remain. Aliquot into amber vials or plates, flush with inert gas if available, and store at −20 °C.

• LC–MS reference standard workflow (general):

  • Prepare 1 mg/mL in MeCN or MeOH. Dilute to 0.5–5 μg/mL for method development. Use C18 RP gradient (e.g., 5–95% MeCN/H2O with 0.1% formic acid over 10–20 min). Record UV spectrum and MS/MS fragments for library building. Adjust based on compound behavior.

• Plate-based screening (general):

  • Dilute DMSO stock into assay buffer to the desired final concentration, keeping DMSO ≤0.5–1% v/v unless assay-tolerated. Mix thoroughly and check for precipitation. Include vehicle controls.

These are generalized workflows; adapt conditions to your instrumentation and assay constraints. For any quantitative or regulated work, establish fit-for-purpose validation and refer to lot-specific CoA.

Biological Roles

No biological targets or roles are specified in the Product Data for this item. The following is general, literature-based context for phenolic diterpenoids and should not be interpreted as item-specific claims:

• Origin and biosynthesis (general): Many “danshenol” congeners are reported from Salvia miltiorrhiza and related species. Diterpenoids arise from the mevalonate (MVA) or MEP/DOXP pathways to geranylgeranyl diphosphate (GGPP), followed by cyclization and oxidative tailoring to yield abietane or related skeletons.
• Chemical biology properties (general): Phenolic diterpenoids often exhibit redox activity, radical-scavenging capacity, metal chelation via phenolic oxygens, and membrane interactions due to hydrophobic frameworks. These properties influence assay behavior (e.g., potential for redox cycling in certain detection systems).
• ADME considerations (general): Typically lipophilic (higher logP), with limited aqueous solubility; metabolic liabilities can include phenol conjugation (glucuronidation/sulfation) and aromatic oxidation.

Research guidance:

• When using in biochemical or cell-based assays, pre-validate DMSO tolerance, adsorptive losses to plastics, and light sensitivity. Consider including detergents or cyclodextrins to enhance apparent solubility, while checking for assay interference.

Important: No therapeutic or clinical claims are made. This product is supplied strictly for research use only, as indicated in the Product Data.

Buffer Applications

This product is a hydrophobic small molecule and is not typically used to prepare buffer systems. No buffer-related specifications or recipes are provided for this item.

Practical guidance (general):

• If incorporating into aqueous buffers for assays, use a co-solvent strategy (e.g., prepare a concentrated DMSO stock and dilute into the buffer ensuring final DMSO ≤0.5–1% v/v for most biochemical assays). Alternatively, use solubilizing agents (cyclodextrins, non-ionic surfactants) as compatible with your system.
• Verify compound stability in the chosen buffer (pH, ionic strength, presence of metals or oxidants) and monitor for precipitation over time.

For buffer selection itself, defer to the application (enzyme kinetics, binding assays, etc.). Common biological buffers (PBS, HEPES, Tris, acetate) can be used provided the compound remains in solution at the working concentration.

Green Alternatives

While Dehydrodanshenol A is itself the analyte/target rather than a solvent or reagent, greener choices often relate to solvent use during its handling, purification, and analysis. The following are general, literature-based suggestions (not item-specific):

• Prefer greener solvents where feasible:

  • Replace dichloromethane/chloroform with ethyl acetate, 2-MeTHF, or CPME for extractions and normal-phase chromatography.
  • Use MeOH or bio-derived EtOH instead of acetonitrile where chromatographic performance allows.
  • For reversed-phase prep-LC, consider water/EtOH or water/MeOH gradients with CO2-assisted evaporation to reduce solvent load.

• Practical tradeoffs:

  • 2-MeTHF/CPME offer lower peroxide formation than ethers like THF and better hydrophobic solvency than EtOAc, but can retain water and have distinct odors.
  • Ethanol is greener than MeCN but can broaden peaks or interact with stationary phases differently; method re-optimization may be needed.

• Small comparison (general):

  • Ethyl acetate: biodegradable, low toxicity; moderate polarity; easy removal.
  • 2-MeTHF: bio-based option; good for extractions; denser than water variants exist; check peroxides periodically.
  • MeOH/EtOH: low toxicity relative to MeCN; fully miscible with water; compatible with many LC methods.

Implement source reduction: concentrate fractions efficiently, reuse solvent where purity allows, and scale chromatography judiciously to minimize waste.

Pharmaceutical Uses

No pharmacopeial status, excipient role, or formulation guidance is specified for this item in the Product Data. This product is supplied for research use only and is not intended for human or veterinary use.

General research/formulation context (not item-specific):

• As a reference standard: may be used in QC or analytical development related to botanical materials containing structurally related diterpenoids. Establish validated methods (identity, purity, content) using appropriate reference standards and system suitability.
• Preformulation studies: for exploratory work, solubility and stability screening across pH, co-solvents (DMSO, PEG 400), and complexing agents (cyclodextrins) can inform suitability for in vitro assays. Note: these are research-only activities and not instructions for clinical formulation.
• Solid-state characterization: when purity and amount permit, XRPD/DSC/TGA can characterize polymorphism and thermal behavior for research comparability across lots.

Compliance note:

• Avoid implying therapeutic intent. Follow institutional and regulatory guidelines for handling investigational chemicals in non-clinical research settings.

Physical Properties

Item-specific specs (from Product Data):

• 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 (MP): Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point (BP): Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• LogP, pKa, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general expectations for phenolic diterpenoids (not item-specific):

• Physical state: typically a crystalline solid or amorphous powder; often light-yellow to off-white when pure.
• Solubility profile: sparingly soluble in water; soluble in polar aprotic and protic organic solvents such as DMSO, DMF, methanol, ethanol, acetone, acetonitrile, and ethyl acetate; hexanes/toluene solubility varies with substitution.
• Acid–base properties: presence of phenolic OH often gives weak acidity (phenolic pKa commonly ~9–11 in water; literature range varies by substitution).
• Chromatography: aromatic/phenolic chromophores typically provide UV detectability around 210–280 nm (literature/general). Exact λmax depends on conjugation.

Notes for method development:

• If developing HPLC/UPLC methods, scout MeCN/H2O or MeOH/H2O gradients with acid modifiers (e.g., 0.1% formic acid) for improved peak shape; confirm stability at chosen pH.
• Verify all quantitative values with the item’s CoA/SDS; do not treat the above generalities as product specifications.

Quality and Grades

Item-specific quality details:

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers or additives: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and best practices (general guidance):

• For small-molecule library members and natural-product analogs, common quality indicators include purity by HPLC/UPLC (>95% typical for screening), residual solvent limits, water content (KF), and identity confirmation (1H/13C NMR, HRMS, sometimes IR/UV).
• If used as an analytical reference, confirm purity and assign a reference value using an orthogonal method (e.g., qNMR or calibrated HPLC with purity balance).
• UV behavior: If destined for LC-UV quantification, preference is typically given to lots with low baseline noise and clean UV spectra.
• Trace metals and peroxides: Not applicable to most natural products unless specified; values are Not specified for this item; refer to CoA/Spec Sheet.

What the listed storage/shipping imply (item-specific):

• Storage at −20°C and shipment on ice pads suggest the material benefits from reduced thermal exposure to maintain integrity. On receipt, allow to equilibrate to room temperature in a sealed state to avoid condensation, then promptly return to freezer after aliquoting.

Documentation:

• Always consult the lot-specific CoA and SDS for definitive grade, purity, and analytical data before critical applications.

Reaction and Applications

Manufacturer Applications (verbatim): Not provided.

Item context: Listed under “small molecules and compound libraries,” suggesting primary use in discovery research, screening, analytical reference work, and method development rather than as a general-purpose reagent.

General research applications (not item-specific):

• Reference standard: use as a marker in profiling of Salvia/danshen extracts by LC–UV/HRMS. Establish retention time and MS fragmentation for targeted or untargeted metabolomics.
• Screening: inclusion in natural-product-like libraries for target-agnostic phenotypic screening or biochemical assays; prepare DMSO stocks and adhere to plate-handling best practices.
• Stability studies: assess susceptibility to oxidation or photodegradation; develop protective handling (amber vials, low oxygen).
• Derivatization for SAR: phenolic OH can be masked (O-acyl/O-alkyl) to evaluate effects on potency, permeability, and metabolic stability.

Analytical method notes (general):

• LC conditions: RP-C18 with MeCN/H2O or MeOH/H2O plus 0.05–0.1% formic acid; monitor at 210–280 nm and MS in positive/negative ESI depending on ionization.
• Sample preparation: SPE (polymeric reversed phase) or liquid–liquid extraction from complex matrices.

Important: No item-specific reaction performance data are provided. Confirm identity and purity via the lot CoA prior to quantitative or regulatory-facing work.

Reaction Conditions

No item-specific reaction performance data are provided. The following general conditions apply to transformations commonly performed on phenolic and terpenoid motifs (literature guidance, not specifications):

• O-Acylation/O-alkylation of phenols:
  • Base: K2CO3, Cs2CO3, or NaH (anhydrous); Solvent: acetone, acetonitrile, THF, or DMF; Temp: 0–60 °C; Time: 1–16 h. Monitor by TLC/LC–MS.
• Hydrogenation of conjugated double bonds (if present):
  • Catalyst: Pd/C (5–10%); Solvent: EtOH/EtOAc; H2: 1–3 bar; Temp: rt–40 °C; Time: 2–24 h. Watch for over-reduction.
• Oxidations (benzylic/allylic or phenolic to quinone-like species):
  • Reagents: DDQ, MnO2, or TEMPO-based systems for alcohols; ensure controlled conditions to prevent degradation. Perform under inert gas and low light when needed.
• Protection strategies:
  • Phenol protection: BnBr/K2CO3 or TBDMS-Cl/imidazole; deprotect via hydrogenolysis (Bn) or TBAF (TBDMS). Verify stability of the core skeleton to these conditions.
• Purification:
  • Normal-phase silica (hexanes/EtOAc) or reversed-phase C18 (MeOH/H2O or MeCN/H2O with 0.1% acid); protect from light/air during workup.

Always confirm reaction compatibility with a small-scale pilot, as natural-product-like scaffolds may contain sensitive sites. Optimize under inert atmosphere and avoid strong acids/bases for extended periods unless stability is demonstrated.

Safety and Handling

Authoritative safety data for this item are not provided in the Product Data; defer to the SDS.

Item-specific safety fields (from Product Data):

• 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 laboratory precautions for small-molecule phenolic diterpenoids (literature/practice, not item-specific):

• PPE: use lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Handle powders in a fume hood to avoid inhalation/ingestion.
• Avoid dust formation; minimize aerosol generation during weighing and transfers.
• Incompatibilities: strong oxidizers may degrade phenolic structures; strong bases/acids can promote undesired reactions (e.g., O-acyl/alkyl migration, oxidation). Avoid prolonged exposure to light, heat, and air if the compound is conjugated and/or phenolic.
• First-aid overview: if inhaled, move to fresh air; if on skin or in eyes, rinse with water for at least 15 minutes; if ingested, seek medical attention. Always follow institutional protocols and the SDS.
• Waste: collect organic solutions/contaminated disposables as halogenated or non-halogenated organic waste per your solvent composition and local regulations.

Special notes:

• Natural-product-like phenolics can exhibit air/light sensitivity. Store sealed, under inert gas if feasible, and protect from light. Confirm specific precautions with the SDS.

Solvent Selection

Item-specific solvent data are not provided; guidance below reflects general behavior of hydrophobic, phenolic diterpenoid-like small molecules (not item-specific).

• Likely polarity class: low-to-moderate polarity; expect better solubility in organic solvents than in water (general literature).
• Common stock solvents for screening/assay:
  • DMSO: most reliable for concentrated stocks (e.g., 10–50 mM); miscible with aqueous buffers upon dilution. Filter if needed.
  • Ethanol or methanol: alternative vehicles for biochemical assays or analytical injections; watch for solubility limits and assay compatibility.
  • Acetonitrile: useful for LC method development and sample prep; often blended with water and an acid modifier for RP-HPLC.
• Less polar media: ethyl acetate, acetone; toluene may dissolve some congeners but is less assay-friendly.
• Aqueous systems: expect poor water solubility without co-solvent, surfactant (Tween 80, Pluronic), or cyclodextrin. Validate compatibility with the intended biological or analytical system.

Small comparison (general):

• DMSO: maximal solubilization; potential to affect bioassays above 0.5–1% v/v.
• MeOH/EtOH: good analytical compatibility; volatility can aid drying, but may alter protein assays.
• MeCN: excellent for LC; lower proticity avoids esterification/acetals but can be harsher for cells/enzymes.

Practical tips:

• Warm gently (≤40 °C) and sonicate to dissolve; avoid prolonged heating. Filter through 0.2 μm PTFE/NYLON if particulates persist.
• Record exact solvent composition for reproducibility.

Storage and Reconstitution

Item-specific conditions (from Product Data):

• Storage: Store at −20 °C.
• Shipped in: Ice chest + Ice pads.

General best practices for small, phenolic diterpenoid-like molecules (not item-specific):

• Protect from light and moisture; store in tightly closed amber vials. If feasible, backfill headspace with inert gas (N2/Ar) to limit oxidation.
• Upon receipt: allow the sealed container to reach room temperature before opening to prevent condensation. Immediately aliquot solids or concentrated solutions to minimize freeze–thaw cycles.
• Reconstitution:
  • For analytical or screening use, dissolve in anhydrous DMSO (typical 10–50 mM stocks). Alternative solvents: MeOH, EtOH, or MeCN depending on use case. Mix and, if required, gently warm (≤40 °C) and sonicate. Filter (0.2 μm PTFE) to remove particulates.
• Working solutions:
  • Prepare fresh dilutions in compatible media just prior to use. Maintain final DMSO content within the tolerance of your assay or instrument. Monitor for precipitation during incubation.
• Stability checks:
  • Track storage time and conditions; periodically assess by HPLC/UPLC for degradation products. Avoid repeated light exposure; use amber glassware and foil wrapping as needed.

Research Use Note: For research use only.

Structure and Identity

Brief overview: Dehydrodanshenol A is listed as a small-molecule library member. Item-specific structural identifiers are not provided in the product data.

• Item-specific identifiers (from Product Data):

  • CAS: 1444618-61-4
  • 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.

• Literature/general context (not item-specific):

  • “Danshenol” congeners are typically phenolic diterpenoids reported from Salvia miltiorrhiza (danshen) chemistry literature. Dehydro- variants generally denote increased unsaturation relative to the parent “danshenol” scaffold.
  • Structural features commonly associated with this class include: a polycyclic diterpenoid framework, one or more phenolic hydroxyl groups, and conjugated double bonds. Exact substitution pattern and stereochemistry must be confirmed against the CoA/SDS for this specific lot.

• 2D structural description (general, literature-level):

  • Polycyclic carbon skeleton with an aromatic/phenolic ring fused or appended to a terpenoid core; phenolic OH can act as a hydrogen-bond donor/acceptor; conjugation may support UV absorbance useful for analytical detection. The precise ring fusion pattern, double-bond positions, and stereocenters are not specified for this item.

Synthetic Utility

The Product Data present Dehydrodanshenol A as a library small molecule rather than a reagent; nonetheless, natural-product-like phenolic diterpenoids can serve as useful synthetic substrates in research. The following are general, literature-based considerations (not item-specific):

• Functional group handles (typical for phenolic diterpenoids):
  • Phenolic OH: O-alkylation (Williamson ether), O-acylation (acyl chlorides/anhydrides), carbonate/carbamate formation; protective groups (Bn, MOM, TBDMS) for multistep work.
  • Aromatic ring: electrophilic substitutions limited by substitution pattern; cross-coupling possible if a halide handle is introduced.
  • Allylic/olefinic sites (if present): epoxidation, dihydroxylation, hydroboration–oxidation, or selective hydrogenation for SAR exploration.
• Late-stage diversification:
  • SuFEx-based phenol activation (e.g., to aryl fluorosulfates) followed by cross-coupling (literature).
  • Mitsunobu to invert or derivatize secondary alcohols if present on the scaffold; assess steric constraints and redox sensitivity.
• Analytical tracking:
  • Use LC–MS and 1H/13C NMR to monitor conversions; phenolic/terpenoid scaffolds often show diagnostic aromatic and isoprenoid resonances.

Caveats:

• Phenolic cores can undergo undesired oxidation; include antioxidants (ascorbate/BHT) or inert atmosphere as needed.
• Regiochemical control on polyfunctional scaffolds can be challenging; consider protecting-group strategies and chemoselective conditions.

Target Specificity

Not applicable. This product is a small molecule without antibody/biologic target attributes, and the Product Data provide no target-binding or mode-of-action information.

• Item-specific target data: Not specified for this item; refer to primary literature if pursuing target identification.
• Research guidance (general): If investigating biological targets, consider unbiased profiling approaches (thermal shift assays, CETSA, affinity capture with immobilized analogs, chemoproteomics) and orthogonal validation. Ensure appropriate negative controls and assess assay interference potential (e.g., redox activity, aggregation).

よくある質問

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. 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 1444618-61-4, the molecular formula is C21H18O4, and the molecular weight is 334.37 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.