This compound belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.
External Descriptors
Isoflavonoids
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.
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Application Protocols
No validated application protocols are provided in the Product Data for this small-molecule standard/building block.
General literature practices:
Stock preparation: dissolve in DMSO at 10–50 mM; vortex and sonicate if needed; filter through 0.22 μm PTFE for clarity.
Spectroscopy: record UV–Vis spectra in MeOH with small aliquots of base/acid to map pH-dependent bands; protect from light.
Chromatography: analytical RP-HPLC with water (0.1% formic acid) / acetonitrile gradient; monitor at 270 and 340 nm.
Bioassay inclusion (mechanistic, non-clinical): dilute DMSO stocks into assay buffer with final DMSO ≤1–2%; include vehicle controls and non-specific binding controls (detergent, BSA) to mitigate polyphenol aggregation artifacts.
For any standardized protocol needs, consult primary literature or develop assay-specific SOPs.
Biological Roles
Context for researchers (no medical/clinical claims): 6-Hydroxygenistein is a plant-derived isoflavone analog structurally related to genistein, featuring an additional phenolic OH at C6.
Literature/general roles of isoflavones and relevance of the 6-OH substitution:
Plant metabolism: isoflavones participate in defense and signaling in legumes and related species; additional hydroxylation patterns arise from specific O-hydroxylases and tailoring enzymes.
Chemical biology: multiple phenolic groups enable metal chelation (notably via the 5-OH/4-oxo system and adjacent 6-OH), redox cycling, and radical scavenging. These features impact fluorescence/absorbance and can modulate enzyme assays via redox interactions.
Protein interactions: polyphenols can engage proteins through H-bonding and π–π contacts, sometimes leading to nonspecific binding or aggregation phenomena in biochemical assays—use appropriate controls (detergents, BSA) to rule out artifacts (literature/general best practice).
Membrane affinity: relative to genistein, the extra hydroxyl generally reduces hydrophobicity and may decrease passive partitioning into lipid phases (literature trend).
Spectroscopic behavior: acid–base equilibria shift UV–Vis bands and fluorescence; phenolate formation (at elevated pH) increases conjugation and can be used as a pH-dependent probe in model systems.
For any biological testing, ensure: well-defined solvent systems (e.g., DMSO stocks), matched vehicle controls, light protection, and verification of compound integrity by HPLC prior to use. Research use only.
Buffer Applications
This compound is not a buffering reagent and is not typically used to prepare defined pH buffer systems.
If inclusion in buffered assays is required, prepare concentrated stocks in DMSO and dilute into the target buffer (e.g., phosphate, HEPES) with vigorous mixing to avoid precipitation. Maintain DMSO at the minimal level compatible with solubility (often ≤1–2%, literature practice).
Phenolate formation at elevated pH can alter spectral properties and apparent activity in assays; maintain consistent pH and include vehicle controls.
No item-specific buffer recipes apply.
Green Alternatives
This product is a solid reagent/analyte rather than a bulk solvent. “Green alternatives” therefore focus on greener solvent systems and processing strategies when handling 6-Hydroxygenistein in synthesis or analysis.
Greener handling options (literature/general):
Prefer ethyl acetate, ethanol, or isopropanol over chlorinated solvents for extractions and recrystallizations when solubility allows.
For reactions requiring polar aprotics, consider propylene carbonate or dimethyl sulfone where feasible as replacements for DMF/NMP; recognize tradeoffs in viscosity and workup.
Aqueous co-solvent systems: use minimal DMSO as a co-solvent (≤1–5%) with surfactants or cyclodextrins to enhance aqueous handling in assays, reducing total organic solvent usage.
Solid-phase or mechanochemical methods (ball milling) for O-alkylation/O-acylation steps may reduce solvent volumes; applicability depends on reactivity and selectivity demands.
Comparison snapshot (general):
DMSO vs DMF/NMP: DMSO has a better environmental/health profile and lower volatility; choose DMSO for stock solutions and many coupling/alkylation contexts when compatible.
EtOAc/EtOH vs CH2Cl2/MeCN: EtOAc and ethanol are preferred where chromatographic/selectivity constraints allow.
Tradeoffs:
Greener solvents can alter regioselectivity or reaction rates in phenolic derivatizations; small-scale scouting is recommended.
Highly polar green solvents (e.g., propylene carbonate) may complicate product isolation; plan for antisolvent precipitation or adsorption workups.
Pharmaceutical Uses
No pharmacopeial or excipient grade is indicated for this item, and it is supplied strictly for research use only (per Product Data).
General/literature context relevant to formulation research (non-clinical):
As a polyphenolic solid with low water solubility, 6-Hydroxygenistein is often handled as DMSO or ethanol stock solutions for in vitro studies.
Enabling strategies explored in formulation research for similar flavonoids include cyclodextrin inclusion complexes, amorphous solid dispersions, and nano-suspensions to enhance apparent solubility—useful for preformulation studies but outside the scope of this catalog item’s specifications.
Stability considerations: susceptibility to oxidative discoloration in solution; protect from light and air, and consider inert atmosphere for long incubations.
Regulatory/grade note:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
No USP/EP monograph context provided for this product.
Use limitation: For research and laboratory use only. Not for human or veterinary use, diagnostic, or therapeutic applications.
Physical Properties
Item-specific specifications are not listed in the Product Data; consult the CoA/SDS for authoritative values.
Appearance: yellow to yellow-brown polyphenolic solid is typical for highly hydroxylated isoflavones (literature, general observation). Not specified for this item; refer to CoA/Spec Sheet.
Melting behavior: polyhydroxy isoflavones generally show high melting points (often in the high 200s to >300 °C) with possible decomposition (literature trend; check CoA for exact value if needed).
Solubility profile: very sparingly soluble in water; soluble in polar aprotic solvents (DMSO, DMF) and moderately in hot alcohols (EtOH, MeOH) and acetone; enhanced solubility with mild base due to phenolate formation (literature/general).
Acid–base: multiple phenolic OH groups (pKa values for analogous isoflavone phenols typically in the ~6–10 range depending on position and hydrogen bonding; literature/general trends).
LogP: polyphenolic isoflavones exhibit modest hydrophobicity reduced by multiple OH groups; 6-hydroxylation generally lowers logP vs genistein (literature/general trend).
UV–Vis: strong π→π* absorption typical of isoflavones (around 260–280 nm and 320–370 nm bands; literature/general). Low-UV cutoff is not applicable; this is a solid analyte, not a solvent.
Any numerical specification for this catalog item (mp, solubility, UV cutoffs, metal limits, water, etc.): Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay method (e.g., HPLC), impurity profile, and residual solvent limits.
What to expect in the CoA: professional CoAs for isoflavones typically include HPLC purity, identity confirmation (1H NMR/HRMS or IR), and water content (Karl Fischer) when relevant. UV spectral characteristics may also be provided to benchmark identity.
Implications of polyphenolic structure for quality:
Phenolic oxidation: trace oxidative products can form if exposed to light/air; high-quality material is stored sealed and protected from light to minimize such changes.
Counter-ions/salts: 6-Hydroxygenistein is provided as a neutral free phenol unless otherwise noted; verify no salt form is indicated in the CoA.
Stabilizers: None indicated in Product Data. If stabilizers/antioxidants are used, they will be declared on the CoA; absence of such a note generally implies neat material.
HPLC assay at multiple wavelengths (e.g., ~270 and ~340 nm) to capture isoflavone chromophores.
NMR showing characteristic downfield phenolic OH and H-6/H-8 signals with intramolecular H-bonding patterns.
Selecting grade for use:
For quantitative biochemical assays or as a reference standard, seek ≥95–98% HPLC purity and documented identity.
For synthetic derivatization, slightly lower purity may be acceptable depending on downstream purification.
For item-specific specifications and acceptance criteria: Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
Manufacturer Applications: Not specified in the Product Data.
Expanded research and lab applications (literature/general for 6-hydroxylated isoflavones):
Analytical standard and reference compound in flavonoid profiling, antioxidant capacity assays, and structure–activity relationship (SAR) studies comparing genistein analogs.
Photophysics/UV–Vis studies leveraging the strong isoflavone chromophores and pH-dependent spectral shifts due to phenolate formation.
Metal chelation studies via 5-hydroxyl/4-keto and 6-hydroxyl sites; used to probe complexation stoichiometry and redox behavior.
Precursor for derivatization:
O-alkylation or O-acylation of selected phenolic positions to modulate lipophilicity and stability.
Silyl protection (TBDMS/TBS) to enable regioselective transformations on the isoflavone core.
Redox/antioxidant mechanistic work: kinetics of radical scavenging with DPPH/ABTS and peroxyl radicals (non-clinical, mechanistic chemistry focus).
Practical notes:
Drying: brief drying under vacuum at ambient temperature is often sufficient before moisture-sensitive reactions; avoid prolonged heating that can induce oxidation.
Degassing: not usually required, but limiting oxygen/light can minimize oxidative discoloration in solution.
Workup/purification: normal-phase silica gel chromatography with gradient EtOAc/hexanes or MeOH/CH2Cl2 systems; phenols may tail—add 0.1–1% AcOH to mobile phase or use reverse-phase C18 for analytical separations.
Characterization: monitor by HPLC-UV at dual wavelengths (≈270/340 nm). 1H NMR shows characteristic chelated phenolic OH (downfield, often >12 ppm) and distinct A- vs B-ring patterns.
Reaction Conditions
General literature guidance for typical transformations of polyhydroxy isoflavones; adapt conditions to scale and substrate, and verify by small-scale trials.
O-Methylation: K2CO3 (2–4 eq) in dry acetone or DMF, MeI or Me2SO4 (3–5 eq per OH), 0–25 °C to reflux, 2–24 h. Monitor by TLC/HPLC; quench with aqueous NH4Cl, extract, and purify by silica gel. Regioselectivity can be tuned via protecting groups.
O-Acylation: acyl chloride or anhydride (1.2–3 eq per OH), pyridine or CH2Cl2 with catalytic DMAP, 0 °C to rt, 1–6 h. For labile positions, use mild bases (Et3N) and low temperature to avoid transacylation.
Silylation: TBSCl (1.2–1.5 eq per OH), imidazole (2–3 eq) in DMF, rt, 2–12 h; deprotect with TBAF in THF (0 °C to rt).
Metal complexation/extraction studies: prepare ligand in MeOH or DMSO, titrate metal salts in buffered ethanol–water; track shifts by UV–Vis (bands near 260–280 and 320–370 nm, literature). Maintain pH to control phenolate formation.
Oxidative coupling: catalytic Cu/O2 or Ag2O in alcohol/MeCN mixtures, rt to 50 °C, to access biaryl dimers; yields vary with substitution and conditions (optimize carefully).
Solvent choices: DMSO/DMF/NMP for high solubility; EtOAc, MeOH, or acetone for workup and recrystallization. Protect from light/air during extended reactions.
Yields: strongly dependent on substitution and protection strategy; consult primary literature for specific targets. All values above are general literature guidance, not item-specific specifications.
Safety and Handling
GHS/SDS information for this specific item is not provided in the Product Data. Always consult the product SDS for authoritative hazard classification, pictograms, and response statements.
GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
General hazards (literature/general for polyphenolic flavonoids): low volatility solid; dust may cause mechanical irritation to eyes/respiratory tract. Phenolic compounds may cause skin/eye irritation on contact.
Personal protective equipment (PPE): laboratory coat, safety glasses, and appropriate gloves (e.g., nitrile). Handle powders in a fume hood or with local exhaust to minimize dust inhalation.
First aid (general):
Inhalation: move to fresh air; seek medical advice if symptoms persist.
Skin contact: wash with soap/water; remove contaminated clothing.
Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy; continue rinsing; seek medical attention if irritation persists.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Handling notes: avoid creating dust; prevent contact with oxidizers and strong bases/acids during storage. Polyphenols can undergo oxidation; limit exposure to air and light during weighing and solution preparation.
Fire safety: combustible organic solid; use standard extinguishing media (CO2, dry chemical, foam). Combustion may produce CO/CO2 and irritating fumes.
Waste disposal: dispose according to institutional and local regulations for non-halogenated organic solids/solutions.
Storage per Product Data: store at room temperature; keep container tightly closed, in a dry, well-ventilated place, protected from light. Defer to SDS for detailed guidance.
Solvent Selection
6-Hydroxygenistein is a highly hydroxylated, conjugated isoflavone with low intrinsic water solubility but good solubility in polar organic media.
Polarity class: moderately polar polyphenolic aromatic; forms strong H-bonds as donor/acceptor.
Primary solvents: DMSO and DMF (excellent solubility at millimolar concentrations); NMP also suitable.
Secondary/working solvents: ethanol, methanol, acetone, acetonitrile (heating/sonication may be needed). Solubility improves in alkaline aqueous solutions due to phenolate formation; avoid strong base if phenolic integrity must be preserved.
Aqueous media: very poor at neutral pH; consider co-solvent strategies (e.g., 0.1–1% DMSO in buffer after preparing a concentrated DMSO stock) or cyclodextrin inclusion complexes.
Dielectric considerations: polar aprotics (ε > 30) best disrupt phenolic self-association; protic solvents enable H-bonding and may shift UV spectra.
Comparison (literature/general):
DMSO vs EtOH: DMSO affords higher stock concentrations and superior stability toward precipitation upon dilution; ethanol is preferable when lower boiling point and volatility are desired.
DMF/NMP: good solvents for reactions/protections but less desirable in bioassays; ensure removal after synthesis.
Handling tips:
Prepare concentrated stocks in DMSO (e.g., 10–50 mM, literature practice) then dilute into assay media with vigorous mixing to avoid local supersaturation.
Filter sterilize solutions for biological assays if required (0.22 μm PTFE or PVDF) and protect from light.
Storage and Reconstitution
Storage conditions (Product Data): Room temperature. Keep tightly closed in a dry, well-ventilated place. Protect from light and sources of oxidation. If long-term storage is anticipated, consider desiccation and an inert atmosphere.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Stability notes (literature/general): polyphenolic solids are typically stable when dry and protected from light. In solution, gradual oxidative discoloration can occur, especially in protic solvents and at elevated pH.
Reconstitution and solution handling (literature/general best practice):
Solvents: prepare concentrated stocks in DMSO (e.g., 10–50 mM) or DMF. Ethanol or methanol can be used for shorter-term needs; confirm solubility.
Dilution: add stock slowly to vigorously stirred buffer or media to avoid precipitation. Maintain minimal organic cosolvent consistent with assay tolerance.
Filtration: for analytical or biological work, pass solutions through 0.22 μm PTFE/PVDF filters.
Light/air protection: use amber vials, foil wrap, and minimize headspace oxygen for sensitive studies.
Freeze–thaw: for DMSO stocks, aliquot to avoid repeated freeze–thaw; store aliquots at ≤−20 °C if long-term solution storage is required. Allow to warm to room temperature before opening to prevent moisture uptake.
Any item-specific stabilizers, concentration limits, water/peroxide/metal specifications: Not specified for this item; refer to CoA/Spec Sheet.
Research Use Note: For research use only.
Structure and Identity
Briefly: 6-Hydroxygenistein is a polyphenolic isoflavone (a flavonoid) corresponding to genistein bearing an additional phenolic OH at C6, i.e., 5,6,7,4′-tetrahydroxyisoflavone.
Product name: 6-Hydroxygenistein (SKU: H997237)
CAS: 13539-26-9 (Product Data)
PubChem CID: 6063386 (Product Data)
InChIKey: 118984 (as provided in Product Data)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: C15H10O6 (literature for 5,6,7,4′-tetrahydroxyisoflavone)
Molecular weight: ~286.24 g/mol (literature, computed from C15H10O6)
Structural features (general/literature):
Core scaffold: isoflavone (3-phenylchromen-4-one) with a carbonyl at C4 and an aryl (B-ring) at C3.
Functional groups: four phenolic hydroxyls (5-OH and 7-OH on the A-ring, 6-OH ortho to 5-OH, and 4′-OH on the B-ring), conjugated lactone (flavone carbonyl), and extended aromatic π-system.
2D description: A fused benzopyran (A- and C-rings) bearing phenolic OHs at positions 5, 6, and 7; the B-ring is para-hydroxylated (4′-OH) and attached at C3 of the heterocycle; the C4 carbonyl is conjugated to both rings.
Notes:
The exact connection table/tautomeric representation and stereochemistry are trivial (achiral); depiction follows standard isoflavone numbering.
For definitive identifiers used for this specific lot (e.g., SMILES/InChI), consult the CoA/Spec Sheet.
Synthetic Utility
6-Hydroxygenistein serves as a versatile polyphenolic building block based on the isoflavone scaffold.
Reactivity features (literature/general):
Phenolic O–H groups (5-, 6-, 7-, and 4′-positions):
O-alkylation: MeI/Me2SO4 with base (K2CO3/Cs2CO3) in acetone/DMF affords methyl ethers; stepwise protection enables regioselective patterns.
O-acylation: acyl chlorides or anhydrides with base or DMAP catalysis in pyridine/CH2Cl2.
Silylation: TBS/TBDMS with imidazole in DMF affords acid-labile protections for subsequent cross-couplings or oxidations.
4-oxo–5(6)-dihydroxy chelation motif allows transient metal complexation; can be leveraged for directed ortho-functionalization on the A-ring in certain protocols (literature precedents for flavones).
Electrophilic aromatic substitution: deactivated by the carbonyl; however, activated positions ortho/para to phenols can undergo halogenation/nitration under controlled conditions.
Redox chemistry: phenoxyl radical formation under oxidative conditions enables coupling/polymerization; useful to access biaryl dimers.
Utility in synthesis:
Scaffold diversification: generate libraries of ether/ester pro-derivatives to study SAR and physicochemical tuning.
Late-stage functionalization: selective protection–deprotection sequences exploit differential acidity/hydrogen bonding (5-OH often most acidic due to intramolecular H-bonding with C4=O).
Conjugation: carbonate/urethane linkages to linkers, PEGs, or solid supports for affinity materials or delivery studies.
Not applicable. This product is a small-molecule isoflavone, not an antibody, enzyme, or nucleic acid probe. No target binding specificity, clone, isotype, or species reactivity is provided in the Product Data.
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