This compound belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.
External Descriptors
Not available
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
652.600 g/mol
XLogP3
6.000
Hydrogen Bond Donor Count
8
Hydrogen Bond Acceptor Count
12
Rotatable Bond Count
1
Exact Mass
652.158 Da
Monoisotopic Mass
652.158 Da
Topological Polar Surface Area
214.000 Ų
Heavy Atom Count
48
Formal Charge
0
Complexity
1350.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
3
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
Calcolatori di soluzioni
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Recensioni
Recensioni dei clienti
Application Protocols
No validated application protocols are provided in the Product Data for this item. For common research uses, consider the following general starting points (literature; adapt to your system):
Analytical standard preparation: Weigh accurately, dissolve in anhydrous DMSO to 1–10 mg/mL; prepare serial dilutions in MeCN or MeOH for LC–UV/HRMS calibration; store aliquots at −20 °C protected from light.
In vitro assay dosing: Prepare 10–50 mM DMSO stock; dilute into assay buffer to ≤0.5–1% DMSO final; verify absence of precipitation by visual inspection and UV–vis.
Spectroscopic studies: Record UV–vis in MeOH or MeCN (scan 200–500 nm). For fluorescence, assess excitation around typical xanthone bands (literature) and optimize empirically.
Always verify solubility, stability, and compatibility in your exact assay matrix. These are general research guidelines, not item-specific validated protocols.
Biological Roles
Context for research only. No medical or clinical claims.
Natural origin (literature): Griffipavixanthone is a dimeric xanthone reported from Garcinia species. Xanthones are plant secondary metabolites involved in chemical defense and pigmentation.
Biochemical properties (literature/general):
Polyphenolic framework supports redox activity and radical-scavenging behavior in chemical assays
Multiple hydrogen-bond donors/acceptors enable interactions with proteins and membranes in biophysical studies
Conjugated xanthone chromophores absorb strongly in the near-UV, enabling spectroscopic tracking and binding studies
Research applications (literature):
In vitro enzyme modulation screening as a phenolic scaffold; binding often driven by π–π stacking and H-bond networks
Studies on aggregation propensity and colloidal behavior of polyphenols near aqueous solubility limits; importance for assay design
Model system for metabolism-mimicking transformations (O-methylation, glucuronidation, sulfation) in microsomal/chemical systems
Practical notes:
Maintain low final DMSO (≤0.5–1% v/v) in biochemical assays to avoid solvent effects
Confirm actual free concentration by monitoring precipitation or adsorption to plastics; use low-bind labware
Control for redox cycling and non-specific assay interference (e.g., employ counterscreens, detergent controls) when profiling phenolic natural products.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare biochemical buffers. For experiments involving Griffipavixanthone, choose buffers based on the biological target (e.g., phosphate, HEPES, Tris) and ensure sufficient co-solvent (e.g., ≤1% DMSO) to keep the compound in solution. Validate solubility and stability in the chosen buffer by UV–vis or HPLC prior to critical assays.
Green Alternatives
Griffipavixanthone is a target compound, not a process solvent. Green chemistry considerations thus focus on solvent and reagent choices used alongside it (literature):
Greener media options (for dissolution/processing):
Prefer ethanol or methanol over chlorinated solvents for routine handling when solubility permits. Employ gentle warming/sonication to aid dissolution.
For chromatography, use water–acetonitrile gradients instead of water–acetonitrile–chloroform systems; minimize buffer salt load to improve solvent recyclability.
O-Acylation: Use acid anhydrides with catalytic DMAP in EtOAc or 2-MeTHF rather than acid chlorides in DCM.
O-Alkylation: Dimethyl carbonate or green alkyl carbonates under base can replace alkyl halides in some cases.
Illustrative comparison (literature):
DCM/CHCl3 vs 2-MeTHF/EtOAc: Chlorinated solvents offer higher solubility but poorer EHS profile; 2-MeTHF/EtOAc provide reduced toxicity and are bio-based/biodegradable with possible tradeoffs in solubility and separation efficiency.
Operational practices:
Scale experiments to need; minimize excess solvent volumes
Recycle HPLC solvents where validated; use inline solvent purification and fraction triggering to reduce waste
Employ solid-phase extraction (SPE) to cut down on large-volume liquid–liquid extractions.
Pharmaceutical Uses
No pharmacopeial/excipient status or formulation role is provided in the Product Data, and this product is sold strictly for research use only.
General research context (literature):
Natural-product scaffold for medicinal chemistry exploration, enabling SAR via O-acylation/O-alkylation and modification of the dimeric linkage.
Analytical reference material for natural product sourcing and quality research on Garcinia-derived materials.
Formulation tips for research assays (literature; not for human use):
Prepare DMSO concentrates and dilute into aqueous media with rapid mixing; consider inclusion of solubilizing excipients (e.g., 0.01–0.05% polysorbate 80) if compatible with the assay.
For solid dispersion studies, PVP or HPMC matrices and solvent casting can improve apparent solubility; characterize by DSC/XRPD.
No therapeutic claims are made or implied. This product is not intended for food, drug, cosmetic, or household use.
Physical Properties
Item-specific numeric specifications are not provided in the Product Data for this catalog entry.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Bixanthones are typically high-melting solids; literature)
Solubility (general guidance; literature):
Poorly soluble in water due to extensive aromatic surface and limited ionizable groups
Soluble in polar aprotic organic solvents such as DMSO and DMF; moderately soluble in acetone, acetonitrile, ethyl acetate, and chlorinated solvents; sparingly to moderately soluble in alcohols (MeOH/EtOH)
LogP/cLogP: Polyphenolic xanthones often exhibit moderate-to-high hydrophobicity offset by phenolic hydrogen bonding (literature); specific value not specified for this item; refer to CoA/Spec Sheet.
UV–vis absorbance (literature): Xanthone chromophores typically show strong absorption in the near-UV (ca. 240–280 nm and 320–380 nm), useful for analytical quantitation; exact maxima not specified for this item; refer to CoA/Spec Sheet.
Density, refractive index, pKa values: Not specified for this item; refer to CoA/Spec Sheet.
Notes for use (literature): Prepare concentrated stock solutions in anhydrous DMSO (e.g., 10–50 mM) and dilute into assay media with vigorous mixing to avoid precipitation. Gentle warming and sonication can aid dissolution. Filter (0.22 µm PTFE) if needed for analytical work.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Research use note: For research use only (as stated in Product Data).
Interpretation and guidance:
Natural product reference standard: Griffipavixanthone is commonly employed as a reference/analytical standard and as a probe compound in discovery chemistry. When purity is specified on the CoA, it is typically determined by HPLC/UPLC with UV detection and may be supported by NMR and MS identity.
Impurity profile: For bixanthones, typical related substances include monomeric xanthones, O-acylated/alkylated congeners, oxidative dimers/oligomers, and residual extraction/synthesis byproducts (literature). Review chromatograms and spectral data on the CoA.
UV behavior: The xanthone chromophore gives strong UV absorption; HPLC-grade solvents and low-UV backgrounds are recommended for quantitative analysis. If a “HPLC grade” designation is present on the CoA for the solvent used in analysis, this supports low baseline drift; it is not a property of the solid itself.
Stabilizers: None indicated in Product Data. If stabilizers or desiccants are included in packaging, they will be listed on the CoA/Spec Sheet.
Recommendation: For quantitative assays, verify purity by orthogonal methods (qNMR, HPLC, HRMS) and confirm identity via diagnostic 1H/13C NMR signals of the xanthone cores.
Reaction and Applications
As a purified natural product, Griffipavixanthone is primarily used as a reference compound, probe, and starting point for structure–activity studies rather than as a bulk reagent. Nonetheless, its functional handles (phenolic OH groups and conjugated carbonyls) permit diverse derivatizations (literature).
Analytical and discovery uses (literature):
Reference standard for profiling Garcinia-derived xanthones by LC–UV/HRMS
Positive control in phenolic antioxidant/radical-scavenging assay development (e.g., DPPH/ABTS), strictly for research screening
Photophysical studies of xanthone chromophores (triplet formation, fluorescence quenching)
Chemical transformation space (literature):
O-alkylation/O-acylation of phenols to tune solubility and lipophilicity (e.g., MeI/K2CO3 in acetone; acyl anhydrides with DMAP/base)
Protection as acetates/benzoates for multistep manipulations
Ether formation (Mitsunobu-type) from phenols for prodrug-like derivatives in discovery campaigns
Metal chelation and complexation studies via catechol-like submotifs; reversible binding assessed by UV–vis shifts
Selective oxidation or oxidative coupling at activated phenolic positions (hypervalent iodine, Ag/Fe salts) for analogue synthesis
Practical tips:
Work under subdued light and inert gas when feasible to minimize slow oxidative darkening
Use dry, oxygen-poor solvents for sensitive steps; add BHT or ascorbate scavengers only if compatible with the study objective
Verify positional selectivity by 2D NMR; bixanthone symmetry can complicate signal assignment.
Reaction Conditions
General, literature-informed conditions for common manipulations of polyphenolic xanthones; adjust based on your specific route and verify on small scale.
O-Acylation: Ac2O (1.5–3.0 eq) or acyl anhydride with catalytic DMAP (5–10 mol%) and Et3N/pyridine in EtOAc, CH2Cl2, or 2-MeTHF; 0–25 °C, 0.5–4 h; typical isolated yields 70–95% for peracetates (literature).
O-Alkylation: Alkyl halide (1.2–2.0 eq) with K2CO3 or Cs2CO3 in acetone/ACN/DMF, 25–60 °C, 2–16 h; yields depend on sterics (50–90%, literature). Mitsunobu (DEAD/DIAD, PPh3) enables challenging ethers but with poorer EHS profile.
Carbonate formation: Dialkyl carbonates (e.g., DMC) with base (DBU/K2CO3) at 80–120 °C in MeCN/acetone or solvent-free, catalytic; greener alternative to alkyl halides (literature).
Oxidative coupling/dearomatization: PIDA/PIFA (1.2–2.0 eq) in HFIP/CH2Cl2 at 0–25 °C; or Ag/Fe/Cu salts under O2; reaction outcome sensitive to substitution; monitor by LC–MS (literature).
Purification: Reverse-phase flash or normal-phase silica with gradient of EtOAc/hexanes or MeOH/CH2Cl2; protect phenols to sharpen bands. Final polishing by prep-HPLC.
Stability notes:
Phenolic acetates/benzoates are moisture-sensitive to hydrolysis; store under inert atmosphere.
Avoid strong base and prolonged light exposure to limit oxidative coloration/polymerization.
These conditions are provided as general guidance from literature on polyphenolic xanthones and related systems, not as item-specific specifications.
Safety and Handling
Hazard information is not provided in the Product Data for this item. Always consult the product-specific SDS for authoritative safety guidance.
GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to SDS.
Likely hazards (general for polyphenolic natural products; literature): Low volatility solid; dust may cause mechanical irritation to eyes/airways. Avoid inhalation of dust and contact with skin/eyes.
Personal protective equipment (PPE):
Lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile)
Work in a fume hood when weighing to minimize dust exposure
Handling tips:
Avoid prolonged exposure to light and air; phenolics can undergo slow oxidative darkening
Use dry tools/containers; hygroscopicity is typically low but phenolic materials can adsorb moisture
Storage incompatibilities (general): Strong oxidizers, strong bases (can promote phenolate formation and oxidation), and strong acids for prolonged contact.
First-aid overview (general):
Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; seek medical attention if irritation persists
Skin: Wash with soap and water; remove contaminated clothing
Inhalation: Move to fresh air; seek attention if symptoms develop
Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel
Defer to the SDS and your institutional EHS policies for detailed spill, fire-fighting, and disposal procedures.
Solvent Selection
This product is a polyphenolic, moderately lipophilic solid. Selection focuses on dissolution and compatibility for analysis/assays.
Polarity profile (literature): Limited aqueous solubility; good solubility in high-donor-number polar aprotics (DMSO, DMF). Moderate solubility in acetone, MeCN, EtOAc; improved in chlorinated solvents (CHCl3, DCM). Alcohols may dissolve upon warming.
Recommended stock solvent: Anhydrous DMSO (analytical grade). Prepare 10–50 mM stocks for bioassays or analytical calibration; store aliquots to minimize freeze–thaw.
Mobile phases (analytical, literature): Reverse-phase HPLC/UPLC with water (0.1% formic acid or ammonium formate) and acetonitrile or methanol. Gradient elution helps resolve congeners.
Avoid: Pure aqueous media and strongly basic aqueous buffers at high concentration (risk of phenolate formation and oxidative degradation). If aqueous delivery is required, co-solvent systems (≤1% DMSO + 10–50% MeOH/ACN) or surfactant-assisted systems can be used.
Comparison (literature):
DMSO: Highest solvating power; biologically compatible in small volumes.
DMF/NMP: Strong solvents but less favored in biological contexts; higher toxicity, harder to remove.
Methanol/ethanol: Green(er) options; may require warming/sonication and higher volumes to achieve target concentrations.
EtOAc/CHCl3: Good for extraction/partitioning and sample cleanup; less suitable for aqueous assay introduction.
Recommended best practices (literature/general for phenolic natural products):
Keep tightly closed in the original container, desiccated, and protected from light to minimize slow oxidative discoloration
For long-term storage or to preserve analytical integrity, consider cool, dry storage (e.g., 2–8 °C) in the dark; allow to equilibrate to room temperature before opening to avoid moisture condensation
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution and working solutions (literature):
Prepare concentrated stocks in anhydrous DMSO (e.g., 10–50 mM). Vortex and, if needed, gently warm (≤40 °C) or sonicate to aid dissolution.
For aqueous systems, dilute DMSO stock into buffer with vigorous mixing; keep final DMSO at ≤0.5–1% v/v to limit solvent effects; include co-solvent (MeOH/ACN) or surfactant if required by your assay.
Filter working solutions through 0.22 µm PTFE for analytical applications.
Shelf-life and stability: Not specified for this item; refer to CoA/Spec Sheet. As a precaution, prepare small aliquots to minimize repeated freeze–thaw/light exposure and periodically re-check by HPLC or LC–MS.
Structure and Identity
Griffipavixanthone is a dimeric xanthone (bixanthone) natural product typically isolated from Garcinia spp., featuring two xanthone cores connected through a carbon–carbon linkage and bearing multiple phenolic hydroxyl groups (literature). Its architecture combines polyoxygenated aromatic rings with conjugated carbonyls, giving a rigid, planar polycyclic framework.
Chemical name: Griffipavixanthone (natural product; bixanthone class)
CAS: 219649-95-3
PubChem CID: 60151566
InChIKey (as provided in Product Data): 175090
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.
Stereochemistry: Typically none at the xanthone cores; substituent patterns and dimeric linkage define the topology (literature).
Structural features (literature):
Two xanthone (9H-xanthen-9-one) units linked via aryl–aryl or aryl–alkyl C–C bond
Multiple phenolic –OH groups enabling hydrogen bonding and derivatization (O-acylation/O-alkylation)
Conjugated diketone/phenone system supporting strong UV–vis absorbance
2D description in words (literature): Two planar, polyoxygenated tricyclic xanthone scaffolds joined through a carbon–carbon bond, each ring system bearing phenolic hydroxyls and carbonyl groups; overall a rigid, highly conjugated polyphenolic dimer.
Synthetic Utility
From a synthetic perspective, Griffipavixanthone offers multiple phenolic sites and conjugated carbonyls that can be selectively transformed to access analog libraries and probe structure–property relationships (literature).
Key functional groups and reactivity (literature):
Phenolic OH groups: O-alkylation (MeI/Me2SO4, carbonate electrophiles), O-acylation (Ac2O/AcCl with base or DMAP catalysis), carbonate/carbamate formation; temporary protection as MOM/benzyl/acetates for multistep routes.
Xanthone carbonyls: Participation in hydrogen bonding and potential for nucleophilic addition under forcing conditions is limited; more commonly, reduction to dihydroxanthones or derivatization via imine/enamine is atypical.
Aromatic rings: Electrophilic substitution at activated positions; oxidative coupling and dearomatization with hypervalent iodine or metal-mediated protocols for analogue synthesis.
Dimer linkage: Strategic cleavage is generally challenging; most campaigns modify periphery rather than the core linkage.
Retrosynthetic value (literature):
Serves as a benchmarking target for oxidative dimerization methodologies of polyprenylated xanthones
Useful substrate for late-stage diversification to tune solubility, permeability, and photophysics
Analytical considerations: Diversification often collapses symmetry; full 2D NMR (HSQC/HMBC/NOESY) and HRMS are recommended to establish substitution patterns.
Target Specificity
Not applicable. This product is a small-molecule natural product, not an antibody or affinity reagent. No target specificity data are provided for this item in the Product Data.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
