Ugaxanthone - ≥98% , CAS No.13179-11-8

CAS: 13179-11-8 Cat. No.: U1018072 PubChem CID: 5321880

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: CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C3=C(O2)C(=C(C=C3)O)O)C
• IUPAC Name: 1,3,5,6-tetrahydroxy-4-(3-methylbut-2-enyl)xanthen-9-one
• InChIKey: ZZUFNBISWJNCEE-UHFFFAOYSA-N
• INCHI: 1S/C18H16O6/c1-8(2)3-4-9-12(20)7-13(21)14-15(22)10-5-6-11(19)16(23)18(10)24-17(9)14/h3,5-7,19-21,23H,4H2,1-2H3
• Isomeri SMILES: CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C3=C(O2)C(=C(C=C3)O)O)C
• CAS alternativo: 13179-11-8
• PubChem CID: 5321880

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Benzopyrans
      • Subclass 1-benzopyrans
        • Level5 Dibenzopyrans
          • Level6 Xanthenes
            • Level7 Xanthones
              • Level8 4-prenylated xanthones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Benzopyrans
• Subclass: 1-benzopyrans
• Intermediate Tree Nodes: Dibenzopyrans - Xanthenes - Xanthones
• Direct Parent: 4-prenylated xanthones
• Alternative Parents: Chromones Pyranones and derivatives 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Vinylogous acids Heteroaromatic compounds Polyols Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 4-prenylated xanthone - Chromone - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Pyranone - Pyran - Benzenoid - Heteroaromatic compound - Vinylogous acid - Polyol - Oxacycle - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone 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: 328.300 g/mol
• XLogP3: 4.000
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 328.095 Da
• Monoisotopic Mass: 328.095 Da
• Topological Polar Surface Area: 107.000 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 514.000
• 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 item-specific tested applications or protocols are provided in the Product Data.

General handling protocols for small-molecule screening materials (not item-specific)

• Stock solution preparation
  • Weigh accurately in a low-humidity environment. Prepare 10–50 mM stocks in anhydrous DMSO; record exact concentration by weight-in/volume-out or by quantitative NMR if required.
  • Aliquot into inert-lined microvials (amber) to minimize freeze–thaw and light exposure.
• Plate formatting
  • For HTS: dispense with acoustic or positive-displacement systems; cap or seal plates to limit DMSO evaporation.
  • Aim for final assay DMSO ≤0.5–1.0% v/v unless your biology supports higher levels; include vehicle controls.
• Analytical confirmation
  • Verify identity/purity by LC–MS before critical experiments; monitor stability of working dilutions over assay timelines.

Adjust these practices to the exact solubility and stability of Ugaxanthone once item-specific data are reviewed.

Biological Roles

Scope and limitations

• Item-specific biological/biochemical roles are not provided in the Product Data. The following is general information about xanthone scaffolds and does not imply any particular biological activity of Ugaxanthone.

General context for xanthones (literature/scaffold-level)

• Origin: many xanthones are plant-derived secondary metabolites (e.g., Clusiaceae, Gentianaceae), often bearing polyphenolic substitution patterns.
• Biochemical interactions: phenolic xanthones can engage in hydrogen bonding and π–π stacking with proteins and nucleic acids; the conjugated carbonyl may participate in polar interactions.
• Assay considerations: phenolic content can cause redox activity in certain assay formats (e.g., peroxidase-coupled readouts) and potential fluorescence interference. Employ orthogonal detection (MS-based endpoints) to de-risk artifacts.
• Metabolic liabilities: free phenols are prone to Phase II conjugation (glucuronidation, sulfation) in biological systems; methoxy groups can undergo O-demethylation (literature, scaffold-level observations).

Research-only statement

• This product is intended strictly for research use. Do not use in humans or diagnostics. Any evaluation of biochemical activity should be validated with appropriate controls and counter-screens.

Buffer Applications

Not typically applicable. Ugaxanthone is a neutral/weakly acidic small molecule rather than a buffering reagent. It does not constitute a defined buffer system.

Practical notes for assay buffers (general guidance)

• Prepare concentrated DMSO stocks and dilute into assay buffers at low final DMSO percentages (commonly ≤0.5–1%) to minimize cosolvent effects.
• To mitigate precipitation in aqueous media, consider adding solubilizing excipients (≤1% Tween-80, 0.5–1% Pluronic F-127) or complexing agents (hydroxypropyl-β-cyclodextrin) as appropriate to your biological system.
• Filter or centrifuge assay plates if precipitation is suspected; verify compound presence by LC–MS of supernatants.

Green Alternatives

Greener handling and solvent choices for xanthone-type compounds (general guidance; not item-specific)

Comparison of common and greener options (qualitative)

• Dissolution/stock preparation
  • Conventional: DMSO (excellent solvency; high boiling point; readily recyclable but not bio-based).
  • Greener alternatives: Cyrene (dihydrolevoglucosenone) or GBL alternatives where compatible; note potential reactivity with strong nucleophiles and differing miscibility profiles.
• Synthetic transformations
  • Replace DMF/NMP with safer polar aprotics: acetonitrile, propylene carbonate, sulfolane, or dimethyl carbonate when feasible.
  • Use 2-MeTHF or CPME instead of THF/diethyl ether for extractions or O-alkylation workups, acknowledging different peroxide formation tendencies and water miscibility.
• Workup and purification
  • Favor EtOAc/heptane systems over chlorinated solvents when chromatographing; switch from DCM to toluene/EtOAc blends if resolution permits.
• Energy and waste
  • Explore mechanochemistry (ball milling) for O-alkylation of phenols to reduce solvent use.

Trade-offs to consider

• Solubility of polyaromatic phenolics can be more limited in bio-based solvents; small-scale solubility screens are advised.
• Some green solvents (e.g., Cyrene) are more viscous and can complicate handling at scale.

Note: No item-specific solvent restrictions or stabilizers are provided for Ugaxanthone; validate greener options for compatibility with your method.

Pharmaceutical Uses

No item-specific excipient status, pharmacopeial monograph, or formulation use is provided for this product.

General research/formulation context (not therapeutic claims)

• Role in discovery: small-molecule natural products and analogs like xanthones are frequently included in screening decks for SAR exploration and hit validation.
• Reference material: may be used as an analytical reference in method development for natural product quantification in plant matrices.
• Preformulation guidance: if studying delivery in model systems, create DMSO master stocks and evaluate solubility in pharmaceutically acceptable cosolvents (e.g., PEG-400, propylene glycol) and lipid vehicles; assess stability under light/air.

Important

• For research use only. Not for use as a drug substance, excipient, or in clinical applications.

Physical Properties

Item-specific (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.

Literature/general properties for xanthone scaffolds (not item-specific; use as context only)

• Physical state: many natural xanthones are yellow to orange crystalline solids due to extended conjugation.
• Solubility profile: typically sparingly soluble in water; soluble in polar aprotic organic solvents (DMSO, DMF) and moderately in alcohols (MeOH, EtOH). Solubility strongly depends on substitution (number/location of phenols/methoxy groups).
• UV–Vis: xanthone chromophore shows strong absorption bands in the near-UV (ca. 240–280 nm, 310–360 nm) with substituent-dependent bathochromic shifts (literature, scaffold-level).
• Fluorescence/photophysics: the xanthone core often exhibits efficient intersystem crossing with detectable phosphorescence at low temperature and moderate fluorescence in certain solvents (literature, scaffold-level).
• Melting point, density, logP, pKa, refractive index: Not specified for this item; consult the CoA or primary literature for Ugaxanthone specifically.

Practical handling notes (general)

• Prepare concentrated DMSO stocks (e.g., 10–50 mM) to aid dispensing; dilute into assay media last to minimize precipitation.
• Warm (25–40 °C) and sonicate briefly to dissolve recalcitrant samples; avoid prolonged heating that could promote oxidative darkening of polyphenols.

Quality and Grades

Item-specific (from Product Data)

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Category: Small molecules and compound libraries (小分子和化合物库). Research use only.

General guidance on grades and characterization (not item-specific)

• Research grade small-molecule standards are typically accompanied by identity confirmation (e.g., 1H/13C NMR, HRMS, HPLC purity). When exact purity is not stated, consult the CoA for chromatographic assay, residual solvent, and water content.
• Library suitability: Compounds offered for screening collections prioritize identity and stability. Verify solubility in your assay matrix and consider pre-aliquoted DMSO stocks to reduce freeze–thaw.
• Spectral data: For structural analogs like xanthones, diagnostic signals include a deshielded carbonyl (δC ~175–182 ppm by 13C NMR) and phenolic OH (variable δH; often exchangeable). UV–Vis bands in near-UV support the xanthone chromophore.

What to confirm on receipt

• Appearance check vs. CoA description, single major HPLC peak at stated wavelength, and matching MS isotopic pattern.
• If LC–MS methods are assay-critical, verify that mobile phase and detection wavelengths are suitable for polyaromatic chromophores to avoid purity underestimation due to limited UV response of impurities.

Reaction and Applications

Research context (general; expand as relevant for xanthone-type small molecules)

• Screening/standards

  • Use as a reference standard in analytical methods profiling natural product extracts or in target-based/phenotypic screening panels featuring xanthone chemotypes.
  • The extended aromatic system affords robust UV detection and often MS-friendly ionization (ESI− for phenolates, ESI+ for protonated species depending on substitution).

• Synthetic derivatization motifs (scaffold-level)

  • Phenolic O–H: amenable to O-alkylation/O-acylation (e.g., Mitsunobu, Williamson) to tune lipophilicity and permeability.
  • Aromatic ring: electrophilic substitution (nitration, halogenation) guided by phenolic activation; cross-coupling possible after halogen installation (Suzuki, Buchwald–Hartwig if amination).
  • Carbonyl at C9: nucleophilic additions are less common due to conjugation; however, acylation or formation of imines/Schiff bases with appropriate derivatives may be explored.

• Photophysical/photochemical studies (scaffold-level)

  • Xanthone cores serve as triplet sensitizers and fluorescence probes; useful in studying energy transfer, intersystem crossing, or as standards in photoredox method development.

• Practical tips

  • Dry polar aprotic solvents (DMSO-d6, DMF, MeCN) often required for clean O-alkylations; include base (K2CO3, Cs2CO3) and exclude water.
  • Protect phenols when pursuing metal-catalyzed couplings to avoid catalyst inhibition; consider carbonate or silyl protections.

Item-specific application statements are not provided in the Product Data; tailor usage to your experimental design and verify reactivity with small-scale trials.

Reaction Conditions

General conditions for common xanthone derivatizations (literature/scaffold-level; not item-specific)

• O-Alkylation of phenols

  • Conditions: K2CO3 or Cs2CO3 (2–3 equiv), alkyl halide (1.2–2 equiv), dry acetone/MeCN/DMF, 25–60 °C, 2–16 h.
  • Notes: Exclude water; for hindered substrates, use phase-transfer catalysis (TBAB) or stronger base (NaH) in THF/DMF.

• O-Acylation/Carbamate formation

  • Conditions: Acyl chloride/anhydride (1.1–1.5 equiv), pyridine or Et3N, DCM/MeCN, 0–25 °C.
  • Notes: Phenolic selectivity vs. carbonyl reactivity typically favorable; monitor by TLC (UV 254 nm).

• Electrophilic aromatic halogenation

  • Conditions: NBS/NCS (1.0–1.2 equiv) with catalytic acid, MeCN/DMF, 0–25 °C.
  • Notes: Directing effects of phenols/methoxy groups govern regioselectivity; protect phenols if overreaction occurs.

• Cross-coupling (after aryl halide installation)

  • Suzuki–Miyaura: Pd(PPh3)4 (1–3 mol%), K2CO3, dioxane/H2O or toluene/EtOH/H2O, 60–100 °C, 2–12 h.
  • Buchwald–Hartwig amination: Pd2(dba)3 (1–2 mol%), BINAP/BrettPhos, NaOtBu, toluene or dioxane, 80–110 °C.

• Purification

  • Reversed-phase prep-LC or silica gel chromatography using EtOAc/hexane or MeOH/DCM gradients; detect at 254–330 nm.

Yields and exact parameters are substrate-dependent. Verify conditions on small scale with the specific Ugaxanthone substitution pattern (not provided in the Product Data).

Safety and Handling

Item-specific hazard information (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/pictograms: Not specified for this item; refer to SDS.

General laboratory precautions (applicable to polyphenolic/aromatic small molecules; not item-specific)

• PPE: lab coat, nitrile gloves, safety glasses. Handle powders in a fume hood to avoid inhalation of particulates.
• Incompatibilities: strong oxidizers may degrade phenolic xanthones; strong bases can induce O-alkyl cleavage or promote autoxidation. Avoid prolonged exposure to light and air for sensitive phenolic materials.
• Spill/cleanup: gently cover solids, collect with disposable spatula; decontaminate with ethanol or acetone followed by detergent and water.
• First aid overview: eye/skin contact—rinse with water for ≥15 min; inhalation—move to fresh air; ingestion—rinse mouth. Seek medical attention as per SDS guidance.
• Waste: collect organic solutions and contaminated disposables as halogen-free organic waste unless solvent system dictates otherwise.

Notes

• Without item-specific SDS data, treat as a substance of unknown hazard. Implement conservative exposure controls and minimize dust/aerosol generation.
• Always refer to the official Aladdin Scientific SDS for authoritative hazard classifications and response procedures.

Solvent Selection

Context: Ugaxanthone is a xanthone-type aromatic polyphenolic compound; such scaffolds are generally hydrophobic to amphiprotic, with limited aqueous solubility.

• Practical dissolution strategy (general, not item-specific)

  • Primary solvent: DMSO (high solubilizing power; typical stock 10–50 mM).
  • Secondary solvents: DMF or NMP for synthesis; MeOH/EtOH for analytics; acetone and acetonitrile sometimes effective.
  • Aqueous systems: use cosolvent strategies (≤1–2% DMSO final) and/or cyclodextrins or surfactants for bioassays if precipitation is observed.

• Polarity/miscibility (scaffold-level)

  • Xanthones possess a conjugated carbonyl and may bear phenolic OH groups, enabling hydrogen bonding; nonetheless, bulk hydrophobic surface often limits water solubility.
  • Partitioning: expect moderate to high logP depending on substitution; verify experimentally for Ugaxanthone.

• Tips for analytics

  • LC: reversed-phase (C18), gradients from aqueous 0.1% formic acid to acetonitrile or MeOH. Monitor at 254–330 nm for xanthone chromophore.
  • Sample prep: filter 0.2 µm PTFE if in strong organic; avoid nylon for phenolics due to potential adsorption.

• When to choose alternatives

  • If DMSO is incompatible with the assay, try PEG-400 or 2-methyltetrahydrofuran (for synthesis) and formulate aqueous dilutions with gentle heating/sonication.

Note: No item-specific solubility values are provided; consult the CoA or perform a solubility screen under your conditions.

Storage and Reconstitution

Item-specific (from Product Data)

• Storage conditions: Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General best practices (not item-specific)

• Protect from light and moisture. Store in tightly capped amber vials. If the compound bears free phenolic groups, limit air exposure to reduce gradual oxidation (potential darkening over time).
• For long-term storage, many users prefer 2–8 °C or −20 °C for polyphenolic solids to maximize stability, even when room temperature is acceptable; equilibrate to ambient before opening to avoid condensation.

Reconstitution guidance

• Prepare initial stock in dry DMSO (common starting point 10–50 mM). If using alcohols (MeOH/EtOH), confirm stability and avoid prolonged exposure to basic conditions.
• If aqueous working solutions are required, dilute the organic stock into buffered media as the last step with vigorous mixing to prevent precipitation; use immediately or within the demonstrated stability window.

Freeze–thaw

• If maintaining DMSO aliquots at −20 °C, minimize freeze–thaw cycles by single-use aliquoting (e.g., 50–200 µL). Inspect for precipitation or color change before use.

Always defer to the product’s CoA/SDS for definitive storage and handling specifications.

Structure and Identity

Brief overview: Ugaxanthone is a small-molecule member of the xanthone family (dibenzo-γ-pyrone core), typically isolated from plant sources. Item-specific identifiers are limited for this SKU; literature context is provided for the scaffold.

• Item-specific (from Product Data)

  • Product name: Ugaxanthone
  • CAS: 13179-11-8
  • SKU: U1018072
  • InChIKey: 470750 (as provided; note this does not follow the usual 27-character InChIKey format)
  • 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 structural features (for xanthone scaffolds; not item-specific)

  • Core motif: xanthone (9H-xanthen-9-one), a tricyclic system formed by two benzene rings fused to a central pyranone.
  • Typical functional groups: phenolic hydroxyls and/or methoxy substituents on the aromatic rings; conjugated carbonyl at C9.
  • 2D structure description: two para-fused benzene rings connected via an oxygen-bearing central ring with a ketone at the bridgehead; planarity enables π–π interactions and distinct photophysics.
  • Stereochemistry: xanthones are generally achiral unless bearing chiral side chains (no item-specific stereochemical information provided).

Notes

• Any exact structural assignment (substitution pattern, SMILES, elemental formula) must be confirmed from the item’s CoA or spectral data. The above “general” description pertains to xanthone frameworks and may not reflect the precise substitution pattern of Ugaxanthone.

Synthetic Utility

Scaffold-driven reactivity (general; not item-specific)

• Phenolic functionalization (if present)
  • O-alkylation and O-acylation enable rapid property modulation; carbonate or silyl protections facilitate metal-catalyzed couplings.
  • Ether cleavage strategies (BBr3, AlCl3) can unmask phenols from methoxy groups on xanthone rings.
• Aromatic diversification
  • Directed metalation or electrophilic substitution affords halogenated intermediates suitable for Suzuki, Heck, or Buchwald–Hartwig couplings.
  • Late-stage C–H functionalization (e.g., Ru/Ir photoredox or Minisci-type if heteroatom introduction is viable) has been demonstrated on related polyaromatics.
• Carbonyl chemistry at the xanthone core
  • While conjugated and less nucleophile-reactive, the 9-one can participate in condensations or act as an acceptor in photoredox processes.

Retrosynthetic utility

• Xanthones arise from intramolecular acylations (Friedel–Crafts) of diaryl salicylates, oxidative coupling of benzophenone derivatives, or cyclization of benzoyl salicylic acid frameworks—routes that enable installation of tailored substitution patterns.

Analytical leverage

• The strong UV chromophore simplifies reaction monitoring by TLC/LC at 254–330 nm; MS typically shows [M−H]− for phenolic xanthones and [M+H]+ for less acidic variants.

Note: The precise functional groups of Ugaxanthone were not provided; adapt the above tactics to the actual substitution pattern from CoA/spectral data.

Target Specificity

Not applicable. Ugaxanthone is a small molecule and not an affinity reagent or biological macromolecule.

• No antigen/epitope, clone, isotype, or species reactivity applies.
• If used in biochemical assays, any target engagement should be empirically determined and validated with orthogonal methods; no item-specific target data are provided.