Irenolone - ≥98% , CAS No.149184-19-0

CAS: 149184-19-0 Cat. No.: I1018269 Formula: C₁₉H₁₂O₃ Peso molecolare: 288.300

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥98%

Nomi e identificatori

• Sorrisi canonici: C1=CC2=C3C(=C1)C(=O)C(=CC3=C(C=C2)C4=CC=C(C=C4)O)O
• IUPAC Name: 2-hydroxy-4-(4-hydroxyphenyl)phenalen-1-one
• InChIKey: UQMKPTIDKHEGFW-UHFFFAOYSA-N
• INCHI: 1S/C19H12O3/c20-13-7-4-11(5-8-13)14-9-6-12-2-1-3-15-18(12)16(14)10-17(21)19(15)22/h1-10,20-21H
• Peso molecolare: 288.300

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Naphthalenes
      • Subclass Phenylnaphthalenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Naphthalenes
• Subclass: Phenylnaphthalenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylnaphthalenes
• Alternative Parents: Phenalenones Aryl ketones 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Enols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Phenylnaphthalene - Phenalen-1-one - Phenalen - Aryl ketone - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Monocyclic benzene moiety - Ketone - Enol - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homopolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as phenylnaphthalenes. These are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 288.300 g/mol
• XLogP3: 4.300
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 288.079 Da
• Monoisotopic Mass: 288.079 Da
• Topological Polar Surface Area: 57.500 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 475.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No validated application protocols are provided for this item.

• Item-specific (from Product Data)

  • Tested applications, assay dilutions, positive controls: Not specified for this item; refer to CoA/Spec Sheet.

• General starting points (screening compounds)

  • Stock: Prepare 10–50 mM in dry DMSO; store aliquots at −20 °C to maintain integrity (if freeze-thaw tolerance is unknown).
  • Assay dosing: Serially dilute in DMSO, then back-dilute into assay buffer/media to a final DMSO of ≤0.5–1% v/v. Include vehicle controls and, when possible, a known positive control for benchmarking.
  • Analytical QC: Run LC–MS at t0 and post-incubation to confirm chemical stability during the assay window.

Biological Roles

• Item-specific (from Product Data)

  • Biological function/targets: Not specified for this item; refer to primary literature or CoA if available.

• General guidance for small-molecule library members

  • Role in discovery: Such compounds are typically used as test articles to probe pathways, enzymes, receptors, or phenotypes in screening cascades. Any “biological role” is context-dependent and must be determined experimentally.
  • Follow-up characterization: If activity is observed, assess selectivity, off-target profiles (broad kinome, receptor panels, or proteomics as appropriate), and basic ADME properties (solubility, permeability, stability in buffer and microsomes) using standardized protocols.
  • Mechanistic validation: Employ orthogonal assays (biochemical vs cellular), target engagement (CETSA/thermal shift), and, where suitable, chemoproteomics to confirm direct binding versus pathway-level effects.

• Important caveats

  • No medical or clinical claims are made or implied. This material is sold strictly for research use.
  • Without an explicit structure and known liabilities, include PAINS and aggregator filters in your triage workflow and verify concentration-response behavior with fresh material and rigorous controls.

Buffer Applications

Not typically applicable. Irenolone is a small organic compound, not a buffering agent or pH-control reagent.

• Item-specific (from Product Data)

  • Buffering capacity, pKa values, and recommended buffer systems: Not specified for this item; refer to CoA/Spec Sheet if relevant.

• Practical note (general)

  • When dosing into biological buffers, prepare concentrated DMSO stocks and back-dilute into the target buffer while keeping final DMSO ≤0.5–1% v/v. Verify compatibility with buffer components (e.g., avoid precipitation with high-salt PBS if the compound is hydrophobic).

Green Alternatives

With no defined reagent role or solvent identity for Irenolone, “green alternative” discussions focus on handling and process choices rather than replacing the substance itself.

• Minimizing environmental footprint (general)

  • Stock solvents: Prefer MeOH or bio-based ethanol over chlorinated solvents where compatible; for stock solutions, DMSO remains standard but keep volumes minimal and reuse vials when safe.
  • Workup and cleaning: Replace chlorinated wash solvents with EtOAc/heptane or 2-MeTHF where possible. Use aqueous surfactant-enabled workups to reduce solvent usage.
  • Analytics: Favor UHPLC with shorter columns and MeCN/MeOH mobile phases; apply gradient compression to reduce solvent consumption.

• Procurement and scale

  • Order only the quantity required for screening to avoid waste from expired material.
  • If purification is necessary, consider supercritical CO2 or greener flash solvents (heptane/EtOAc) in place of DCM/hexanes where feasible.

• Comparison snapshot (general best practice)

  • DCM/chloroform: High hazard, disposal burden → Prefer EtOAc, MTBE, or 2-MeTHF when compatible.
  • DMF/NMP: Effective but reproductive hazards → Prefer MeCN/MeOH for analytics; 2-MeTHF/EtOAc for synthesis when acceptable.

• Note

  • No substance substitution is suggested here because the compound’s structure and function are not specified.

Pharmaceutical Uses

No pharmacopeial status or excipient role is provided for this item.

• Item-specific (from Product Data)

  • Pharmaceutical/excipient status: Not specified for this item; refer to CoA/Spec Sheet.

• Research/formulation context (general)

  • In preclinical research, small molecules like this are often handled as DMSO stocks for in vitro assays. For in vivo method development (research only), typical vehicles include PEG400/saline, Captisol, or lipid-based systems; however, any such use requires structure-informed safety data—absent here—and institution-specific approval.
  • As an analytical reference, compounds can support method validation (specificity, linearity, precision) in LC–MS workflows when identity and purity are fully verified.

• Compliance reminder

  • This product is supplied strictly for research use only and is not for human or veterinary use, diagnostic procedures, or clinical applications.

Physical Properties

Item-specific values provided: none.

• Item-specific (from Product Data)

  • Physical state/appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Melting/boiling point, density, refractive index, pKa/logP, UV cutoffs: Not specified for this item; refer to CoA/Spec Sheet.
  • Solubility: Not specified for this item; refer to CoA/Spec Sheet.

• Practical guidance (general; establish experimentally)

  • Solubility screening ladder (typical for diverse small molecules): DMSO > DMF > MeCN ≈ MeOH/EtOH > acetone/EtOAc > isopropanol > THF/2-MeTHF > toluene/CHCl3. Begin with DMSO stocks (10–50 mM) for biological screening and back-dilute into assay buffer with ≤1% v/v DMSO.
  • Thermal behavior: If a solid, differential scanning calorimetry (DSC) and melting point (capillary) can establish polymorph/phase data; if an oil, report viscosity qualitatively and determine boiling point by microdistillation or GC.
  • Spectral properties: Record UV–vis spectrum (200–400 nm) in MeCN or MeOH to assess potential interference with optical assays; collect IR (ATR) for functional-group fingerprints once the structure is confirmed.
  • Partitioning: If logP/logD is unknown, estimate chromatographic hydrophobicity by reversed-phase HPLC retention vs standards.

• Note

  • Where exact numerical properties are required (e.g., for formulation/QC), rely on the item’s CoA/Spec Sheet or your in-house characterization.

Quality and Grades

• Item-specific (from Product Data)

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

• Interpreting grade (general guidance)

  • “Screening-grade” or “library-grade” small molecules typically emphasize identity, purity (often ≥90–98% by UPLC/LC–MS), and stability suitable for HTS/HCS. When HPLC-grade or AR-grade terms are used for reagents/solvents, they relate to chromatographic baseline and impurity limits; these terms are not usually applied to screening compounds.

• What to check on the CoA for this item

  • Assay/purity method and result (HPLC/UPLC area %, orthogonal LC–MS if available).
  • Identity confirmation (1H NMR, HRMS, sometimes 13C NMR). Retention time and mass match versus reference.
  • Water content (Karl Fischer), if relevant to stability or mass accuracy. If not listed: Not specified for this item; refer to CoA/Spec Sheet.
  • Residual solvents (GC) and inorganic residue/ash, if applicable.
  • Stabilizer/additives: Not specified for this item; refer to CoA/Spec Sheet.

• Practical advice

  • For SAR or quantitation work, verify purity on your in-house LC–MS system before use. If necessary, repurify by flash or prep HPLC and document the updated purity spectrum with the batch ID.

Reaction and Applications

• Item-specific (from Product Data)

  • Manufacturer Applications: Not specified in this listing beyond membership in a small-molecule/compound library.

• Research usage context (general for library compounds)

  • High-throughput screening (HTS/HCS): Evaluate as a test article against biochemical or cell-based assays to identify preliminary activity; follow with orthogonal counterscreens.
  • Profiling and reference standard: Use as an analytical reference in LC–MS method development or to probe chromatographic selectivity.
  • Mechanism studies: If a target association emerges, deploy thermal shift assays (DSF), SPR/BLI, or microscale thermophoresis with careful vehicle controls.

• Synthetic chemistry note

  • Without a known structure, Irenolone is not recommended as a generic reagent/transform reagent. Treat as a finished test compound rather than a building block unless the CoA provides functional-group details enabling derivatization.

• Practical tips (general)

  • Prepare fresh DMSO stocks and aliquot under dry conditions. Confirm purity by LC–MS immediately prior to screening to avoid false positives from degradation products.
  • If instability is suspected, perform a simple stability-indicating assay (LC–MS at t0/t24 in your intended solvent at RT and 37 °C).

Reaction Conditions

Not applicable in a reagent sense. Without a known structure and functional handles, recommending reaction conditions for transformations involving Irenolone would be speculative.

• Item-specific (from Product Data)

  • Reaction conditions/catalysts/yields: Not specified for this item; refer to CoA/Spec Sheet or primary literature if available.

• Practical note (general)

  • If you plan to derivatize the compound, first establish its stability in common media (acidic, basic, oxidative, reductive) and select conditions accordingly, verifying progress by LC–MS.

Safety and Handling

Safety data specific to this item were not provided. Always consult the product SDS for authoritative guidance.

• Item-specific (from Product Data)

  • Storage conditions: Room temperature.
  • GHS signal word, hazard statements, pictograms, classification: Not specified for this item; refer to SDS.

• General laboratory precautions (small organic molecules)

  • PPE: Safety glasses, lab coat, and appropriate chemically resistant gloves (nitrile as default; verify compatibility after SDS review). Handle in a fume hood to avoid inhalation of vapors or aerosols.
  • Avoid: Skin/eye contact, ingestion, and inhalation. Prevent release to the environment until hazards are known.
  • Incompatibilities: Until functional groups are confirmed, segregate from strong oxidizers and strong acids/bases; avoid reactive metals if halides or acidic functions are suspected.

• First-aid overview (general)

  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical advice.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

• Handling notes

  • For screening compounds, minimize DMSO aerosolization; use sealed plates/vials. If hygroscopicity or photosensitivity is unknown, handle quickly under ambient dry conditions and protect from strong light as a precaution.

• Disposal

  • Collect organic waste according to institutional and local regulations; do not discharge to drains.

Solvent Selection

Because the exact structure and polarity of Irenolone are not provided here, choose solvents empirically, starting with high-donor-number polar aprotics for stock solutions.

• Item-specific (from Product Data)

  • Structural/polarity cues: Not specified for this item; refer to CoA/Spec Sheet.

• General selection strategy (screening compounds)

  • Stock preparation: DMSO (analytical grade, water ≤0.05% if possible) at 10–50 mM; store aliquots to minimize freeze–thaw and moisture uptake.
  • Solubility fallback: DMF or NMP can rescue poorly soluble chemotypes for synthetic operations; for analytical injections, MeCN or MeOH often suffice after dilution.
  • Partition-sensitive assays: For biochemistry, limit final DMSO to ≤0.5–1% v/v. Use co-solvent systems (e.g., 10–20% MeOH in buffer) with prior compatibility testing.

• NMR solvents (general)

  • First-line: CDCl3 for neutral nonpolar organics; DMSO-d6 for polar/ionic; CD3OD as a middle ground; CD3CN for LC–MS comparability; CD2Cl2 for acid-sensitive species.

• Small comparison (general)

  • DMSO vs DMF: DMSO offers better biocompatibility in assays; DMF is harder to remove and more toxic.
  • MeCN vs MeOH: MeCN gives lower backpressure and cleaner baselines in LC; MeOH is greener and protic, aiding ionizable analytes.

• Tip

  • If solubility remains ambiguous, conduct a 8–10 solvent micro-solubility screen (visual + LC–MS) to select a robust vehicle.

Storage and Reconstitution

• Item-specific (from Product Data)

  • Storage conditions: 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 (small molecules)

  • Protect from moisture and strong light until stability is known; store in a tightly closed container with desiccant. For long-term integrity, many users transfer to amber vials and nitrogen/argon blanket upon first opening.
  • Reconstitution for assays: Dissolve in dry DMSO to prepare a 10–50 mM stock. If particulate remains, brief sonication may help. Optionally, 0.2 µm PTFE filtration can clarify solutions for cell-based assays.
  • Aliquoting: Split into single-use aliquots to avoid repeated freeze–thaw and headspace moisture uptake.
  • Short-term working solutions: Keep at 2–8 °C and use within the day. Discard if precipitation or discoloration occurs.

• Notes

  • If specific hydration state, counterion, or stabilizer is applicable, it is not provided here: Not specified for this item; refer to CoA/Spec Sheet.
  • Always defer to the SDS and CoA for definitive handling and storage instructions.

Structure and Identity

Brief overview: This listing is for Irenolone, supplied for research use as a member of a small-molecule/compound library. Item-specific structure details are limited in the provided Product Data; consult the CoA/Spec Sheet for definitive identifiers.

• Item-specific (from Product Data)

  • SKU: I1018269
  • Product name: Irenolone
  • CAS: 149184-19-0
  • PubChem CID: 2754650
  • InChIKey: 366646 (as provided)
  • 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.

• Literature/registry note (general)

  • For small molecules, the preferred identity triad includes a structure-defining string (SMILES or InChI), exact mass, and high-resolution spectroscopic data.

• Structural features (general guidance, not item-specific)

  • Without a provided structure, functional-group and scaffold annotations cannot be summarized here. If you plan to use Irenolone in structure–activity relationship (SAR) work, confirm the exact 2D structure (skeletal formula, stereochemistry) from the primary reference or CoA prior to assay deployment.

• Recommended identity confirmation (general best practice)

  • 1H/13C NMR (solvent chosen per solubility), HRMS (ESI±), and UPLC/LC–MS purity/retention time match to reference.
  • Optional orthogonal methods: IR (for key functional groups), elemental analysis when appropriate.

Synthetic Utility

Because no structure or functional groups are provided for Irenolone, specific synthetic transformations cannot be recommended.

• Item-specific (from Product Data)

  • Functional groups/reactivity: Not specified for this item; refer to CoA/Spec Sheet.

• General guidance (if derivatization is intended)

  • Confirm the exact structure (including stereochemistry) and identify modifiable positions. Plan orthogonal protection where needed, and evaluate chemoselectivity risks by small-scale test reactions.
  • Establish stability domains (acid/base/oxidation/reduction, light) before committing to multi-step sequences. Run spot tests (e.g., TLC/LC–MS) under representative conditions.

• Alternative approach

  • If Irenolone is intended solely as a screening analyte, treat it as a terminal compound and avoid unnecessary chemical modification unless SAR exploration is explicitly desired and structurally justified.

Target Specificity

This section is typically relevant to biological macromolecules (e.g., antibodies, proteins). For this small-molecule library member, no target specificity is provided.

• Item-specific (from Product Data)

  • Target(s), binding constants, selectivity profile, species reactivity: Not specified for this item; refer to CoA/Spec Sheet or published studies.

• Guidance (general)

  • If an activity signal is observed, build a specificity panel early (close homologs/isoforms, key off-target families). Use orthogonal binding and functional assays to deconvolute mechanism.