This compound belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position.
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
422.500 g/mol
XLogP3
5.500
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
6
Exact Mass
422.173 Da
Monoisotopic Mass
422.173 Da
Topological Polar Surface Area
107.000 Ų
Heavy Atom Count
31
Formal Charge
0
Complexity
736.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
1
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
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Recensioni
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Application Protocols
Item-specific validated protocols are not provided in the Product Data. The following generic procedures support common research uses of poorly water-soluble small molecules; adjust to your assay/system.
DMSO stock preparation (general)
Allow vial to equilibrate to room temperature in the dark. Centrifuge briefly to settle contents.
Add anhydrous DMSO to achieve a target concentration (e.g., 10, 25, or 50 mM), vortex until fully dissolved. Gentle warming (≤37 °C) or brief sonication can assist.
Aliquot into amber microtubes to minimize freeze–thaw and light exposure.
Aqueous assay dilution
Add the DMSO stock slowly into vigorously mixing buffer or media to a final DMSO content typically ≤0.5–1% v/v. Inspect for precipitation; if present, reduce concentration or include acceptable cosolvent (e.g., 0.1–0.5% Tween 80 or 1–5% PEG 400 as assay-compatible).
Analytical QC on receipt (recommended)
Record appearance and mass. Run a quick HPLC-DAD purity check (two orthogonal gradients if possible) and LC–MS for identity. Document retention time(s) and spectral maxima for future comparability.
Solid-phase storage aliquoting
If material is received as a solid, split into small, inert-atmosphere aliquots (amber vials) to limit repeated air/light exposure during use.
Biological Roles
Context (general literature; not product-specific or clinical)
Chemical class: isoflavones are plant polyphenols derived from the phenylpropanoid pathway (via chalcones and isoflavone synthase). They function as phytoalexins and signaling molecules in legumes (e.g., Derris, Glycine, Pueraria).
Molecular interactions: phenolic and conjugated systems engage in hydrogen bonding, π–π interactions, and metal chelation; many isoflavones bind to protein pockets with preference for hydrophobic and H‑bonding sites.
Receptor engagement: numerous isoflavones exhibit affinity for nuclear receptors (e.g., estrogen receptors) and enzymes (topoisomerases, kinases) in biochemical assays; binding is structure-dependent (substitution pattern, planarity, phenol positioning).
ADME-relevant features: limited aqueous solubility, potential for glucuronidation/sulfation, and transporter interactions are frequently reported for isoflavone scaffolds. Phenolic conjugation modulates cellular uptake and stability in biological media.
Appropriate use statement
As supplied, this product is for research use only (per Product Data). Any biological roles discussed are general properties of the isoflavone class and are not claims about this specific item’s activity or suitability for any in vivo use.
Buffer Applications
Not typically applicable.
Derrisisoflavone B is a neutral, poorly water-soluble small molecule; it is not a buffering agent and does not define a useful pH range in aqueous systems.
Practical note: when used in aqueous assays, prepare a concentrated DMSO stock and dilute into pre-made biological buffers (e.g., PBS, HEPES) ensuring final DMSO content is compatible with the assay system. Gentle heating (≤37 °C) and sonication can assist solubilization, followed by filtration (0.22 µm) if precipitates form.
Green Alternatives
Greener handling strategies for isoflavone-type compounds (general guidance)
Solvent choices (comparison; not product-specific)
Stock solutions: DMSO is effective but has high E-factor at scale; consider bio-based solvents for processing/purification.
| Use case | Conventional option | Greener alternative | Trade-offs |
|---|---|---|---|
| Normal-phase chromatography | CH2Cl2/hexanes | EtOAc/heptane or toluene/EtOAc | Slightly lower resolution; less toxicity and halogen-free |
| Aqueous workup/extractions | CHCl3 or CH2Cl2 | EtOAc or 2-MeTHF | Higher water co‑solubility; easier solvent recovery |
| Recrystallization | Acetone/CH2Cl2 | EtOAc/EtOH, MeTHF/EtOAc | Solubility may be lower; safer profiles |
| Hydrogenation solvent | THF/DMF | 2‑MeTHF, CPME, bio‑EtOH | Catalyst compatibility must be checked |
Process considerations
Favor reversed‑phase chromatography with water/MeCN (or water/EtOH) gradients to minimize VOC impact.
Minimize light/air exposure to extend shelf life, reducing waste from degradation.
Evaluate mechanochemistry (ball milling) for O‑alkylation/acylation steps to reduce solvent use (method development required).
Waste reduction
Use microplate-based assays and micro-scale reactions for SAR and screening to cut solvent consumption.
Implement solvent recycling (rotary evaporation with proper fraction collection) for common eluents such as EtOAc and heptane.
Pharmaceutical Uses
Formulation/analytical context only (no therapeutic claims)
Typical roles for isoflavone reference materials in pharmaceutical and natural-products labs include:
Reference standard for QC of botanical extracts and dietary-ingredient materials (HPLC/UPLC–MS, DAD quantitation, identity confirmation).
System suitability and retention-time markers in chromatographic methods for flavonoid-rich matrices.
Tool compound for pre-formulation studies exploring solubilization strategies (cosolvents, cyclodextrins, lipid vehicles) and stability indicating methods under ICH conditions.
Regulatory status
No pharmacopeial monograph is indicated for Derrisisoflavone B in this listing. Pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet.
Practical guidance
For assay development, establish calibration ranges using gravimetrically prepared DMSO or MeOH stocks and validate linearity, precision, and recovery in your target matrix.
For forced-degradation studies, probe oxidative (H2O2), thermal, photolytic, and pH stress to develop stability-indicating analytical methods. Note: conduct on small scale and verify degradation pathways via LC–HRMS and, where feasible, NMR.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Melting point, boiling point, density, refractive index, UV cutoff, water content, metals: Not specified for this item; refer to CoA/Spec Sheet.
General/literature expectations for isoflavones (for planning only; not product specifications)
Physical state: typically crystalline solids with high aromatic content; often light yellow to tan if phenolic.
Melting point: many isoflavones melt in the ~200–330 °C range (literature, compound-dependent).
Solubility: poor in water (often <0.1 mg/mL); soluble in polar organics (DMSO ≫ MeOH/EtOH ≈ Acetone > EtOAc) and in basic aqueous solutions due to phenolate formation.
logP/logD: frequently moderate to high lipophilicity (cLogP ~2–4; literature ranges).
UV/Vis: strong absorbance in 240–280 nm (π–π*) and 300–380 nm (extended conjugation) regions; substituents shift bands (literature).
pKa: phenolic OH typically pKa ~7.5–10 depending on substitution; multiple phenols may show distinct pKa’s (literature).
Practical notes (general)
Prepare stock solutions in anhydrous DMSO (e.g., 10–50 mM) and dilute into assay media with vigorous mixing to minimize precipitation.
For analytical characterization, reversed-phase HPLC with acidified aqueous/MeCN gradients and diode-array detection at ~254/280/330 nm is typical.
Quality and Grades
Item-specific grade/purity
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and practical implications (general guidance)
Without a declared grade (e.g.,
“Analytical/Reference Standard Grade” typically emphasizes identity confirmation (NMR/HRMS), tight purity by HPLC/UPLC (often ≥95–98%), and low residual solvents.
“Screening/Library Grade” commonly targets purity suitable for biological screening (e.g., ≥90–95% by HPLC) with identity confirmed by MS/1H NMR.
“Preparative/Synthetic Grade” may be suitable as a starting material where trace impurities are acceptable.
For this listing (compound library category), expect use in screening or method development; verify suitability with the current Certificate of Analysis (CoA) for:
Purity assay method and result (e.g., HPLC area %), acceptance limits, residual solvents.
Identity confirmation (MS, NMR, possibly HRMS or elemental analysis).
Water content (KF) and inorganic residue if relevant to your application.
Stabilizers/antioxidants
Stabilizers or additives: Not specified for this item; refer to CoA/Spec Sheet. If none are used, store under inert atmosphere/light protection to mitigate slow oxidation or photodegradation typical for polyphenolic conjugated systems.
Recommendation
Request and retain the exact CoA lot-matched to your vial. For trace-analysis or photometric work, consider performing an in-house purity check (HPLC-DAD, qNMR) before use.
Reaction and Applications
Use context for this catalog item
Category: Small-molecule/compound library member (suitable for screening, reference, and method-development applications).
Manufacturer application text: Not provided beyond category; typical uses are expanded below.
Applications (general to isoflavones; not product-specific claims)
Chemical biology and screening: evaluate as a reference chemotype for phenolic isoflavones in enzyme assays, receptor-binding screens, redox/antioxidant models, and phenotypic assays.
Analytical standards: develop/validate HPLC/UPLC-DAD/LC–MS methods for plant extract profiling or metabolomics where isoflavones are markers.
Derivatization studies: phenolic OH groups allow prodrug-like masking (O‑acyl/O‑alkyl) to modulate solubility and lipophilicity; halogenation or O‑arylation for SAR.
Reactivity notes (general)
Phenolic functions: undergo O‑alkylation (alkyl halides, base), O‑acylation (acyl chlorides/anhydrides, DMAP/base), and Mitsunobu etherification (with caution for polyphenols).
Core transformations: hydrogenation of C2=C3; electrophilic substitution on activated aromatic rings; demethylation of aryl methyl ethers with BBr3 or AlCl3/thiols.
Metal-catalyzed couplings: if halogenated derivatives are prepared, Suzuki/Heck/Buchwald–Hartwig reactions extend the scaffold.
For parallel chemistry or library expansion, protect phenols (e.g., MOM, Bn, TBDMS) prior to C–C/C–N bond-forming steps, then deprotect under mild conditions.
Reaction Conditions
Typical conditions for transformations of isoflavone scaffolds (general literature guidance; not item-specific specifications)
O‑alkylation of phenols
Base: K2CO3 or Cs2CO3 (DMF/MeCN), or NaH (THF/DMF) at 0–25 °C, 1–6 h.
Electrophiles: alkyl halides, dialkyl carbonates; catalytic KI can accelerate less reactive halides.
O‑acylation/Carbamate formation
Reagents: acyl chlorides/anhydrides or chloroformates with Et3N/DIPEA; DMAP (5–10 mol%) in DCM/EtOAc at 0–25 °C, 0.5–4 h.
Demethylation of aryl methyl ethers (to reveal phenols)
BBr3 (1–3 equiv per OMe) in DCM at −78→0 °C, 1–3 h; or AlCl3/thiols under milder conditions for sensitive substrates.
Hydrogenation/partial saturation
Catalyst: Pd/C (5–10 wt%) in EtOH/EtOAc or 2‑MeTHF at 1–3 bar H2, 25–40 °C, 2–12 h; selectively reduces C2=C3 in many cases.
Electrophilic halogenation (for coupling handles)
NBS/NCS in AcOH/DMF at 0–25 °C, 0.5–3 h; regiocontrol depends on ring activation.
Analytical/Prep guidance
Monitor by HPLC-DAD at 254/280/330 nm; LC–MS provides rapid mass balance. Expected isolated yields for well-optimized steps often 60–90% depending on substitution.
Note: Optimize conditions for the specific substituent pattern of Derrisisoflavone B once fully characterized. Protect phenols when incompatible with bases/acids used in C–C couplings.
Safety and Handling
Item-specific hazard data
GHS classification, pictograms, signal word, H-statements: Not specified for this item; refer to SDS.
General safety guidance for phenolic, polyaromatic small molecules (not product-specific; consult SDS for authoritative instructions)
Likely hazards: may cause skin/eye irritation and respiratory tract irritation; dust can be an inhalation nuisance. Some isoflavones are photosensitive.
Personal protective equipment (PPE): lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Handle powders in a fume hood or ventilated enclosure to control dust.
Handling: avoid generating dust; prevent exposure to light and moisture. Use clean, dry tools; cap vials promptly. Dissolve in compatible solvent (DMSO/MeOH/EtOH) before dilution into aqueous systems to prevent precipitation.
Incompatibilities: strong oxidizers; strong bases can induce phenolate formation and possible degradation or polymerization upon prolonged exposure. Avoid strong acids and high-temperature conditions that may induce hydrolysis or rearrangement.
First aid (overview):
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; seek medical advice if irritation continues.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Waste: collect solutions/solids as halogen-free organic waste unless otherwise mandated; follow institutional and local regulations.
Polarity/solubility profile (typical for isoflavones)
Water: very low solubility at neutral pH; solubility increases in basic media (phenolate formation) but may risk degradation.
DMSO: excellent solvent for stock solutions (10–50 mM commonly achievable).
Alcohols (MeOH, EtOH, i-PrOH): moderate solubility; suitable for HPLC sample prep and UV/fluorescence assays with attention to precipitation on aqueous dilution.
Ketones/esters (acetone, EtOAc): moderate solubility; useful for extractions and recrystallizations.
Nonpolar solvents (toluene, hexanes): generally poor solubility unless the structure is heavily methoxylated.
Selection tips
Screening assays: prepare concentrated DMSO stock; final assay DMSO usually kept ≤0.5–1% v/v to protect cells/enzymes.
Purification: reversed‑phase C18 with MeCN/H2O (0.05–0.1% formic acid) is robust; normal‑phase silica with toluene/EtOAc/MeOH mixtures also common for polyphenols.
Spectroscopy: MeOH or DMSO yields well-defined UV bands near 254–280 and 300–360 nm; verify linearity to avoid inner-filter effects.
Small comparison (general)
DMSO vs MeOH: DMSO maximizes solubility but may interfere in bioassays; MeOH is greener and volatile but offers lower solubility.
2‑MeTHF/EtOAc vs CH2Cl2: for extractions or workups, greener ethers/esters can replace chlorinated solvents where polarity permits.
Storage and Reconstitution
Item-specific storage
Storage conditions: Room temperature (per Product Data). Protect from light and moisture. Store in a tightly closed container.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General stability guidance for isoflavone solids (not product-specific)
Keep desiccated and under inert gas (e.g., nitrogen/argon) if long-term storage is anticipated, as polyphenolics can slowly oxidize or discolor under air/light.
Avoid prolonged exposure to elevated temperatures; room temperature storage is typically adequate when dry and dark.
Reconstitution (general procedure)
For stock solutions, dissolve in anhydrous DMSO to 10–50 mM. Mix thoroughly by vortexing and brief sonication if needed. Filter through 0.22 µm PTFE if particulate persists.
For short-term working solutions in alcohols (MeOH/EtOH), prepare fresh daily and protect from light.
Freeze–thaw guidance (solutions)
If frozen stocks are desired, aliquot DMSO solutions and store at −20 °C to −80 °C in amber vials. Minimize freeze–thaw cycles; thaw at room temperature and vortex to ensure homogeneity.
Expiration and verification
Retest/expiration date: Not specified for this item; refer to CoA/Spec Sheet. Periodically recheck purity by HPLC/LC–MS for long-stored materials.
Research use note
For research use only (per Product Data).
Structure and Identity
Brief overview: Derrisisoflavone B is an isoflavone-type natural product reported from Derris spp. As supplied here, only minimal identifiers are provided; use the CoA/SDS for definitive structure-specific details.
Item identifiers (Product Data)
CAS: 246870-75-7
PubChem CID: 10812165
InChIKey: 388078 (as provided)
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 class (general/literature)
Isoflavone scaffold: 3-phenylchromen-4-one (1,2-benzopyran-4-one) core with the B-ring attached at C3 of the heterocycle (distinct from flavones where it is at C2).
Common features in isoflavones: one or more phenolic OH groups on A- and/or B-rings; conjugated carbonyl at C4; C2=C3 olefin within the heterocycle.
2D description (general)
A fused benzopyran ring system (A/C rings) bearing a C4 ketone, with an exocyclic phenyl (B-ring) at C3. Substituent pattern (number and position of OH/O-Me groups) defines the specific isoflavone; for Derrisisoflavone B these positions are not specified in this listing.
Stereochemistry
Isoflavones of this type are generally achiral (planar aromatic system) unless bearing chiral substituents; no stereochemical information is provided for this item.
Synthetic Utility
Functional-group perspective (general to isoflavones)
Phenolic OH groups (if present):
Protection: MOM, Bn, TBDMS to enable downstream C–C and C–N couplings.
Derivatization: O‑alkylation (alkyl halides, carbonate reagents), O‑acylation (acyl chlorides/anhydrides) to modulate solubility and bioavailability in SAR efforts.
Conjugated 4‑oxo chromen backbone:
Electrophilic aromatic substitution on activated rings; regioselectivity governed by phenol pattern.
Hydrogenation or 1,4‑additions can reduce/functionalize the C2=C3 unit.
Late-stage diversification:
Directed metalation on appropriately protected derivatives; cross-coupling of halogenated analogs (Suzuki, Heck, Sonogashira) to elaborate the B‑ring.
Retrosynthetic value (general)
Access via deoxy‑Baker–Venkataraman rearrangement, Algar–Flynn–Oyamada oxidation, or cyclization of 2'-hydroxychalcones using DDQ/I2 or base-induced methods. Substituent pattern is introduced from substituted salicylaldehydes and acetophenones.
Utility in research workflows
Serves as a benchmark chemotype in libraries to probe phenolic H‑bonding and planar aromatic interactions. Modifying phenolic count/position tunes pKa/logP and target engagement.
For conjugation chemistry, phenolic handles allow linker installation (carbonates/carbamates) to attach to resins, probes, or reporter tags.
Target Specificity
Not applicable for this listing.
No antibody, enzyme, or biologic target specificity is provided in the Product Data. Derrisisoflavone B is supplied as a small-molecule library member; any binding profiles would be determined empirically in your assay system.
Target specificity data: Not specified for this item; refer to primary literature or generate in-house binding/functional data.
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