Nsc201545 - ≥98% , CAS No.56412-55-6

CAS: 56412-55-6 Cat. No.: N981821 分子式: C₂₀H₁₆O 分子量: 272.35 EC番号: 653-577-1 PubChem CID: 5708426

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

仕様と純度

≥98%

保管条件

Room temperature

純度

≥98%

名前と識別子

カノニカル・スマイル

CC1=CC=C(C=C1)C(=O)C=CC2=CC=CC3=CC=CC=C32

IUPAC Name

(E)-1-(4-methylphenyl)-3-naphthalen-1-ylprop-2-en-1-one

InChIKey

FWCCLQQDGFXYFH-BUHFOSPRSA-N

INCHI

1S/C20H16O/c1-15-9-11-18(12-10-15)20(21)14-13-17-7-4-6-16-5-2-3-8-19(16)17/h2-14H,1H3/b14-13+

異性体SMILES

CC1=CC=C(C=C1)C(=O)/C=C/C2=CC=CC3=CC=CC=C32

PubChem CID

5708426

分子量

272.35

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • 分類 Linear 1,3-diarylpropanoids
      • Subclass Chalcones and dihydrochalcones

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• 分類: Linear 1,3-diarylpropanoids
• Subclass: Chalcones and dihydrochalcones
• Intermediate Tree Nodes: Not available
• Direct Parent: Retrochalcones
• Alternative Parents: Naphthalenes Styrenes Benzoyl derivatives Aryl ketones Toluenes Enones Acryloyl compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Retrochalcone - Naphthalene - Benzoyl - Styrene - Aryl ketone - Toluene - Benzenoid - Monocyclic benzene moiety - Enone - Acryloyl-group - Alpha,beta-unsaturated ketone - Ketone - Organic oxide - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Aromatic homopolycyclic compound
• 説明: This compound belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

化学的性質と物理的性質

• 分子量: 272.300 g/mol
• XLogP3: 5.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 272.12 Da
• Monoisotopic Mass: 272.12 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 375.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Application Protocols

No vendor-validated application protocols (e.g., WB, IHC, IF, FC) are provided for this product, and none are implied. The following is a general workflow for handling small-molecule screening compounds in biochemical or cell-based assays (non-item-specific guidance):

• Stock preparation: Dissolve to 10–50 mM in anhydrous DMSO. Verify concentration by qNMR (internal standard) or UV if an extinction coefficient is known.
• Sterility: For cell assays, prepare solutions under aseptic conditions. Avoid membrane filtration if adsorption is suspected; use low-binding plastics and glass vials.
• Dosing: Serially dilute in assay buffer or media, maintaining constant vehicle percentage across conditions (typical final DMSO ≤0.1–1% v/v).
• Controls: Include vehicle-only, positive control (mechanism-relevant standard), and orthogonal counter-assays to detect interference.
• Stability checks: Assess precipitation and chemical stability over assay time by HPLC/LC–MS of post-assay supernatants.
• Data integrity: Randomize plate layouts; include inter-plate and intra-plate replicates; monitor Z′ factor where applicable.

Note: Replace these general steps with compound- and assay-specific protocols once the structure, solubility, and stability of NSC 201545 are confirmed from the CoA and internal pilot experiments.

Biological Roles

Item-specific biological functions or targets are not provided for NSC 201545 in the Product Data. No biological activity or mechanism is claimed by the supplier; this material is sold strictly for research use only.

General considerations for NSC-library compounds (non-item-specific, literature-guided):

• NSC numbers originate from the NCI screening program; many entries have sparse or historical assay annotations. Activity, if any, is context-dependent and may not reproduce across modern assay formats.
• Before attributing a biological role, confirm identity and purity, eliminate assay artifacts (fluorescence interference, redox cycling, colloidal aggregation), and determine basic ADME-relevant properties (solubility, stability, permeability) experimentally.
• If literature exists for the exact CAS (56412-55-6) or CID (5708426), compile reported targets, EC50/IC50 ranges, and selectivity panels; validate in-house with orthogonal assays and fresh material.

Best practices:

• Build a target-agnostic profile: cytotoxicity counterscreens, promiscuity filters, and broad selectivity panels (kinases/GPCRs/enzymes as relevant) after verifying chemical stability.
• If used as a tool compound, clearly annotate limitations (solubility, instability, off-target alerts) and avoid over-interpretation without complementary genetic evidence.

Buffer Applications

This product is not a buffering agent and no pKa information is provided. Therefore, buffer formulation applications are not typically applicable.

Practical guidance (if aqueous work is required):

• Prepare concentrated DMSO stocks and dilute into the desired biological buffer (e.g., PBS, HEPES) while maintaining DMSO at assay-tolerated levels (commonly ≤0.1–1% v/v).
• If precipitation occurs, consider gentle warming, sonication, or incremental addition of co-solvent. Do not adjust buffer pH on the assumption of acid/base functionality unless the compound’s pKa is known.
• For analytical work, use volatile buffers (e.g., ammonium formate/acetate) if LC–MS will be employed; avoid non-volatile salts that complicate ionization and source cleanliness.

Summary: No buffer capacity or recipes apply to this item based on the available data; consult the CoA/SDS for any solubility or pKa information relevant to aqueous handling.

Green Alternatives

Because the specific structure and process context are not provided, green chemistry guidance is presented in a general, solvent- and operation-focused manner for handling small-molecule screening compounds.

Greener dissolution and handling strategies (general):

• Prefer aqueous-compatible vehicles: DMSO at minimal final assay percentages (≤0.1–0.5% v/v) reduces organic solvent load; where feasible, use ethanol or propylene glycol as co-solvents within assay tolerance.
• Avoid high-boiling, reproductive-toxicity-flagged dipolar aprotics (NMP, DMF) when DMSO or bioethanol suffice.
• Use micro-scale operations (96/384-well) to minimize solvent volumes and waste generation.

Comparison of common vehicles (general; non-item-specific):

| Vehicle | Greenness | Notes | |---|---|---| | DMSO | Moderate | Broad solvency; manage dermal uptake and disposal carefully. | | Ethanol | Higher | Renewable feedstock; limited solvency for very lipophilic compounds. | | 2-MeTHF | Higher | Good for extractions/chromatography; not ideal for aqueous stock prep. | | MeCN | Moderate | Volatile, recyclable; limited solvency for greases; toxic. | | DMF/NMP | Lower | Effective solvents but with regulatory and toxicity concerns. |

Operational improvements:

• Implement solvent recovery where feasible (rotovap with cold traps, closed-loop systems).
• Choose silica-free or low-solvent purification (crystallization, minimalistic flash) once the compound’s properties are known.
• Document waste streams; segregate halogenated vs non-halogenated organics to enable compliant disposal.

Pharmaceutical Uses

No pharmacopeial status, excipient role, or manufacturing use is specified for this item. It is supplied strictly for research use only.

General guidance (non-item-specific):

• If the compound is evaluated as an analytical reference in pharmaceutical QC (e.g., impurity or degradation standard), ensure traceability: document lot, purity, and characterization data (NMR, LC–MS, water/RS content if applicable).
• For pre-formulation or developability studies in discovery research, determine fundamental properties (pKa, logP/logD, pH–solubility profile, chemical stability). Use this information to explore salt formation or prodrug strategies ONLY in a non-clinical research context.
• Adhere to institutional policies for handling non-GMP, non-GLP research chemicals; do not use in human or veterinary applications.

Regulatory note:

• Absence from compendial listings (USP/EP/JP) is typical for NSC screening compounds; any use beyond basic research would require comprehensive CMC development not covered by this product.

Physical Properties

Item-specific physical constants are not supplied in the Product Data and must be obtained from the CoA/SDS or primary literature for this exact registry entry.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet. (literature value should be used only if it matches the same CAS and stereochemistry)
• Boiling point: 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/logD: Not specified for this item; refer to CoA/Spec Sheet.
• pKa: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable unless liquid; not specified for this item.

General/literature guidance for NSC-type screening compounds (non-item-specific):

• Many NSC small molecules are crystalline organics with variable polarity; they are commonly prepared as 10–50 mM DMSO stocks due to broad solubilizing power of DMSO.
• If aqueous use is required, co-solvent systems (e.g., 1–5% DMSO with PBS or cell culture media) are typical.
• Where feasible, determine exact solubility by a miniaturized shake-flask assay and confirm by HPLC area normalization.

Practical notes:

• If the item is a solid, perform a quick differential scanning calorimetry (DSC) screen to identify phase transitions (melting/decomposition), which informs storage and handling.
• Record observed color/appearance upon receipt and compare to CoA images if provided.

Quality and Grades

Item-specific grade/purity and stabilizers are not provided in the Product Data.

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

Interpretation and practical implications (general guidance):

• For screening compounds, suppliers typically provide material meeting research-grade specifications with LC–MS purity (UV, single-wavelength or DAD) ≥95% unless otherwise noted. Always confirm the certified purity on the CoA for this specific lot.
• If low-UV impurities are a concern (bioassays, photometric analytics), request a DAD trace across 200–400 nm and LC–MS TIC. For NMR-sensitive applications, review 1H/13C spectra for residual solvents.
• If a salt form is offered, verify counterion content (e.g., chloride, triflate) and water of crystallization; report concentration as free-base/acid equivalent when preparing stocks.

Recommended quality control on receipt:

• Identity: HRMS (±5 ppm) matched to theoretical (once formula is confirmed from CoA).
• Purity: analytical HPLC on an orthogonal method (e.g., C18 and HILIC if polarity is uncertain).
• Stability: short-term forced degradation screen (acid/base/oxidant, heat, light) to inform handling.

Documentation:

• File CoA, SDS, and any vendor chromatograms in the ELN; capture lot, date received, and storage condition (room temperature per Product Data).

Reaction and Applications

Manufacturer Applications: Not specified in Product Data beyond “For research use only.” The following expands on typical use cases for NSC-library small molecules in research settings (general guidance, not item-specific claims):

• Chemical biology/HTS: Employed as a screening hit or probe candidate in biochemical or cell-based assays to explore pathway modulation. Establish solubility, stability, and assay interference profile (e.g., redox activity, aggregation) before interpreting results.
• Reference standard: If the structure is known from CID 5708426, the compound may serve as an analytical reference for method development (LC–MS retention, fragmentation, stability studies).
• SAR starting point: Utilize the core scaffold (once confirmed) for analog synthesis to map structure–activity relationships; prioritize positions with metabolically soft spots for modification.

Assay fitness filters (recommended):

• Evaluate PAINS and REOS flags (computational, literature) once the structure is confirmed.
• Run orthogonal assays to exclude colloidal aggregation (detergent sensitivity, DLS) and redox cycling (HRP/Amplex Red counter-screens).

Practical workflow:

• Prepare a 10–20 mM DMSO stock; confirm concentration by qNMR or UV if the extinction coefficient is known.
• Track stability under assay conditions (pH, light, temperature) via LC–MS.
• If synthetic modification is intended, acquire or derive a reliable retrosynthesis from the verified structure.

Reaction Conditions

No item-specific reaction conditions can be provided without a confirmed structure and functional group inventory. The following are general, literature-based starting points when modifying small-molecule screening scaffolds after the structure is verified.

General coupling conditions (examples; literature guidance, not item-specific):

• Suzuki–Miyaura: Pd(dppf)Cl2·DCM (1–3 mol%), K3PO4 or Cs2CO3, 2-MeTHF or dioxane/H2O (80–100 °C), 2–8 h.
• Buchwald–Hartwig amination: Pd2(dba)3 (1–2 mol%) with BrettPhos or XPhos ligand, NaOtBu or Cs2CO3, toluene/1,4-dioxane (80–110 °C), 4–16 h.
• Amide coupling: HATU or EDCI/HOBt replacement (e.g., Oxyma), DIPEA in DMF/MeCN, 0–25 °C, 1–4 h.
• Reductive amination: NaBH(OAc)3 in DCE/MeOH or MeCN, 0–25 °C, 2–6 h.

Stability screening:

• Subject the parent compound to small-scale stress (0.1 M HCl, 0.1 M NaOH, 3% H2O2, light, 60 °C) and monitor by LC–MS to define compatible chemistries.

Purification:

• Begin with reverse-phase flash or prep HPLC for polar cores; switch to normal-phase for nonpolar scaffolds. Consider crystallization if a robust solid form is identified.

Note: Replace these generic conditions with structure-tailored protocols once NSC 201545’s functional groups are known from CoA/literature.

Safety and Handling

Safety data specific to this item are not provided in the Product Data and should be taken from the SDS for NSC 201545.

Item-specific hazard information:

• 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 (applicable to small-molecule screening compounds):

• Use in a chemical fume hood; avoid inhalation, ingestion, and skin/eye contact.
• PPE: lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Change gloves frequently when working with DMSO solutions due to enhanced dermal transport potential of DMSO.
• Avoid incompatible reagents until structure-specific incompatibilities are known (strong oxidizers/reductants, strong acids/bases, reactive metals). If the compound contains nitro, azo, or peroxides (unknown here), additional precautions may apply.
• First aid overview: rinse skin/eyes with water for ≥15 min upon contact; move to fresh air if inhaled; seek medical attention per SDS guidance.

Risk management best practices:

• Prepare small aliquots for screening to minimize repeated freeze–thaw or moisture exposure; label with concentration, solvent, date, and operator.
• Conduct a small-scale thermal stability check (TGA/DSC) if the compound will be heated.
• Defer to the SDS and institutional EHS for waste segregation and disposal procedures.

Solvent Selection

Item-specific solubility is not provided. The following is general, literature-based guidance for small-molecule screening compounds and should be adapted once the exact structure/solubility of NSC 201545 is confirmed.

• Primary solvent for stocks: DMSO is typically preferred for NSC-library compounds due to broad solvency across polar/apolar chemotypes.
• Alternative solvents: DMF and NMP offer similar solvency but higher boiling points and greater regulatory burden; ethanol or isopropanol may work for moderately polar organics.
• Aqueous use: Prepare concentrated DMSO stocks (e.g., 10–50 mM) and dilute into buffer or media, keeping final DMSO ≤0.1–1% v/v to limit assay interference.
• Co-solvent systems: DMSO/water, DMSO/MeCN/H2O, or small percentages of surfactant (e.g., 0.01% Tween-80) can mitigate precipitation during dilution.

Comparison (general):

• DMSO: maximal solvency, miscible with water; can enhance dermal absorption and impact some assays.
• MeCN: volatile, low viscosity; limited solubility for highly lipophilic solids.
• 2-MeTHF/EtOAc: greener options for workup or chromatography but seldom used for aqueous stock preparation.

Practical tips:

• Determine kinetic vs thermodynamic solubility by time-course turbidity/HPLC.
• Filter sterilize stock solutions only if validated not to bind to the membrane; PTFE or PES are safer than nylon for hydrophobic compounds.
• Record any observed precipitation post-dilution and adjust vehicle accordingly.

Storage and Reconstitution

Item-specific storage/shipping details are limited in the Product Data.

• Storage Conditions (from Product Data): Room temperature.
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General best practices for small-molecule screening compounds:

• Protect from moisture and light unless data indicate insensitivity; store in tightly sealed amber vials with desiccant. Even at room temperature, humidity control improves shelf life.
• For long-term storage of solutions, keep frozen (−20 to −80 °C) in aliquots to avoid repeated freeze–thaw; DMSO stocks are typically stable for months when dry and oxygen-protected.
• Label all vials with concentration, solvent, lot, and preparation date.

Reconstitution guidance (general):

• If solid: allow vial to equilibrate to room temperature in a desiccator before opening. Weigh quickly to minimize moisture uptake.
• Dissolution: start with anhydrous DMSO to a convenient concentration (e.g., 10–50 mM), then dilute into assay medium as needed while monitoring for precipitation.
• If the CoA specifies a salt form, calculate concentration as free-base/acid equivalents.

Note: In the absence of item-specific specifications (water content, purity, stabilizers), consult the CoA/SDS for authoritative instructions before first use.

Structure and Identity

Brief overview: This catalog entry corresponds to an NSC-library small molecule (screening compound). Item-specific structural identifiers are largely not provided in the Product Data.

• SKU: N981821
• Product Name: Nsc201545 (NSC 201545)
• CAS: 56412-55-6
• PubChem CID: 5708426 (identifier provided; consult PubChem for full structural record)
• InChIKey: 93741 (as provided; appears truncated/incomplete — verify against CoA/SDS)
• 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 features (general guidance):

• Without a provided structure, ring systems, heteroatoms, and stereochemistry cannot be confirmed for this specific item.
• If you access the PubChem record (CID 5708426), export canonical SMILES and InChI to populate ELNs and inventory systems; cross-check against the Aladdin CoA.

2D structure description (general):

• Not determinable from the supplied Product Data. For internal documentation, attach the 2D depiction from a curated database (e.g., PubChem or Reaxys) and confirm that registry numbers (CAS, NSC) match the same compound entry.

Identity verification workflow (best practice):

• Cross-verify CAS, NSC number, and CID across at least two databases; compare calculated HRMS (from formula) with the CoA. Run 1H/13C NMR and LC–MS against the provided reference where available.

Synthetic Utility

Item-specific functional groups and reactivity are unknown from the provided Product Data; thus, no compound-specific synthetic transformations can be asserted.

General strategies if NSC 201545 is used as a scaffold (post-structure verification):

• Diversification: Identify substitution vectors (aryl halides, heteroaryl positions, amide/urea linkages) amenable to cross-coupling (e.g., Suzuki, Buchwald–Hartwig) or heteroatom acylation/sulfonylation to build SAR.
• Late-stage functionalization: If benzylic C–H or heteroaromatic C–H motifs exist, consider Minisci-type C–H functionalization or photoredox-mediated coupling to rapidly explore analog space.
• Polarity tuning: Introduce solubilizing groups (morpholine, tertiary amines) or ionizable handles to improve assay tractability while monitoring permeability and clearance proxies.

Analytical and protection strategies:

• Develop orthogonal purity methods (reverse-phase and HILIC) anticipating polar/ionizable metabolites or analogs.
• If chiral centers are present, employ SFC or chiral HPLC for enantiopurity; consider catalytic asymmetric routes if activity is stereodependent.

Caveats:

• Validate stability of the core under coupling conditions (base/heat/photoredox) before route commitment.
• Avoid over-derivatization without confirming that observed bioactivity is not driven by aggregation or assay artifacts.

Target Specificity

No target, enzyme, receptor, or pathway specificity is provided in the Product Data for NSC 201545. The supplier makes no claims of biological target engagement.

Guidance for researchers (general):

• If literature associates CAS 56412-55-6 or CID 5708426 with a particular target, treat such data as provisional until replicated with authenticated material and orthogonal assays.
• Establish specificity by performing counterscreens across related target families, testing for off-target liabilities (e.g., kinome scan, GPCR panel) as appropriate to the hypothesized mechanism.
• Control for assay artifacts: fluorescence quenching/enhancement, redox activity, metal chelation, and colloidal aggregation can mimic target engagement.

Summary: Target specificity for this item is not established in our catalog; consult primary literature and validate in your laboratory.

よくある質問

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

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

The CAS Number is 56412-55-6, the molecular formula is C20H16O, and the molecular weight is 272.35 g/mol. InChIKey FWCCLQQDGFXYFH-BUHFOSPRSA-N.

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.