alpha,beta-Dihydroxanthohumol - ≥98% , CAS No.102448-00-0

CAS: 102448-00-0 Cat. No.: A1023943 Formule: C₂₁H₂₄O₅ Poids moléculaire: 356.400

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Spécifications et pureté

≥98%

Conditions de stockage de stockage

Room temperature

Pureté

≥98%

Noms et identifiants

• Sourires canoniques: CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)CCC2=CC=C(C=C2)O)O)C
• IUPAC Name: 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)propan-1-one
• InChIKey: SVTCZHIDEDUTBH-UHFFFAOYSA-N
• INCHI: 1S/C21H24O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-6,8-9,12,22,24-25H,7,10-11H2,1-3H3
• Poids moléculaire: 356.400

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Classe Linear 1,3-diarylpropanoids
      • Subclass Chalcones and dihydrochalcones

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Classe: Linear 1,3-diarylpropanoids
• Subclass: Chalcones and dihydrochalcones
• Intermediate Tree Nodes: Not available
• Direct Parent: 2'-Hydroxy-dihydrochalcones
• Alternative Parents: Cinnamylphenols Alkyl-phenylketones Butyrophenones Methoxyphenols Anisoles Aryl alkyl ketones Benzoyl derivatives Resorcinols Phenoxy compounds Methoxybenzenes Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Vinylogous acids Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: 2'-hydroxy-dihydrochalcone - Cinnamylphenol - Alkyl-phenylketone - Butyrophenone - Methoxyphenol - Phenylketone - Anisole - Benzoyl - Phenoxy compound - Phenol ether - Resorcinol - Aryl ketone - Aryl alkyl ketone - Methoxybenzene - 1-hydroxy-2-unsubstituted benzenoid - Phenol - 1-hydroxy-4-unsubstituted benzenoid - Alkyl aryl ether - Monocyclic benzene moiety - Benzenoid - Vinylogous acid - Ketone - Ether - Organic oxide - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position.
• External Descriptors: Chalcones and dihydrochalcones

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

Propriétés chimiques et physiques

• Poids moléculaire: 356.400 g/mol
• XLogP3: 4.900
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 356.162 Da
• Monoisotopic Mass: 356.162 Da
• Topological Polar Surface Area: 87.000 Ų
• Heavy Atom Count: 26
• Formal Charge: 0
• Complexity: 477.000
• 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, item-specific protocols are provided for this SKU.

• General guidance (research use only)

  • Analytical standard preparation: Accurately weigh, dissolve in HPLC-grade methanol, acetonitrile, or DMSO to prepare a stock solution (e.g., 1–10 mg/mL). Filter (0.22 µm PTFE) if needed. Store aliquots protected from light.
  • Bioassay stock solutions: Dissolve in anhydrous DMSO or ethanol; vortex and sonicate if necessary. Dilute into buffered assay media with rapid mixing. Maintain consistent vehicle % across controls and treatments.
  • Synthetic use: For O-alkylations, dry glassware/solvents; add base, then substrate, then electrophile. Monitor by TLC/HPLC and quench cautiously.

• Notes

  • Adsorption and light sensitivity can affect recovery; use amber vials and low-binding plastics or glass. Validate concentration by UV or quantitative NMR where critical.

Biological Roles

• Context (literature/general; no clinical claims)

  • Alpha,beta-dihydroxanthohumol is described as a hop-derived prenylated polyphenolic dihydrochalcone. Prenylation often increases lipophilicity and membrane association of phenolics, influencing in vitro biochemical behavior.

• Research interests (non-clinical)

  • Antioxidant/ROS scavenging assays: Phenolic OH groups can donate H•/e–, enabling standard in vitro antioxidant measurements (DPPH, ABTS, ORAC). Results depend strongly on solvent, pH, and assay design.
  • Metabolic biotransformation: Serves as a substrate in studies of phase I/II metabolism (e.g., O-glucuronidation/sulfation), oxidative prenyl modifications, and microbial conversions relevant to food chemistry.
  • Target engagement screens: Used in exploratory binding or modulation studies involving enzymes that interact with polyphenols (kinases, oxidoreductases) or with transporters; any findings are assay- and context-specific and not generalizable.

• Practical notes for biochemical work (general)

  • Solubilization: Prepare concentrated DMSO or ethanol stock; dilute into assay buffer with vigorous mixing. Use minimal organic cosolvent (typically ≤0.1–1% v/v) and include vehicle controls.
  • Adsorption/light: Polyphenols can adsorb to plastics and degrade under UV; use low-binding labware and amber vials.
  • pH effects: Ionization of phenolic groups alters solubility and reactivity; maintain controlled pH and include appropriate buffer capacity.

• Item-specific biological specifications

  • None provided in Product Data; refer to CoA/Spec Sheet for any available characterization or recommended use parameters.

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare buffer systems.

• Practical handling in buffers (general guidance)

  • Prepare a concentrated stock in DMSO or ethanol, then dilute into the working buffer immediately before use. Maintain final organic cosolvent ≤0.1–1% v/v as assay permits.
  • If higher aqueous solubility is needed, consider limited basification (e.g., addition of minimal NaOH to form phenolates) but note that pH elevation can alter biochemical outcomes and compound stability.
  • Common assay buffers: Phosphate-buffered saline (PBS), Tris, or HEPES are suitable vehicles once the compound is premixed with an organic cosolvent; avoid strong oxidants in the buffer.

• Item-specific buffer data

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

Green Alternatives

While alpha,beta-dihydroxanthohumol itself is a substrate/standard rather than a process solvent, greener choices can be made for its handling and transformations.

• Solvent selection (literature/general)

  • Prefer bio-based or lower-toxicity solvents: Ethanol, isopropanol, 2-MeTHF, CPME, ethyl acetate, propylene carbonate where compatible with solubility and reactivity.
  • Minimize chlorinated and high-VOC solvents unless required for selectivity or workup.

• Example comparisons (general guidance; not product specifications)

  Greener option | Typical use | Trade-offs vs conventional --- | --- | --- Ethanol (bio-based) | Stock solutions, recrystallization | Lower solubility than DMSO; volatility may complicate long incubations 2-MeTHF | O-alkylations, extractions | Water content control needed; different dielectric than THF may change rates CPME | Lewis-acid cyclizations, extractions | Higher bp slows concentration; good peroxide stability Ethyl acetate | Workups, chromatography | Limited solubility for highly hydrophobic solids; miscible with alcohol cosolvents

• Process considerations

  • Use catalytic rather than stoichiometric reagents for redox/cyclization steps where possible.
  • Apply microwave or flow chemistry to reduce reaction times and energy.
  • Choose solid-supported bases/acids to simplify workup and reduce aqueous waste.
  • Recover and recycle solvents with azeotrope-aware distillation where composition permits.

Pharmaceutical Uses

No pharmacopeial or excipient role is specified for this item.

• Research/formulation context (general, non-clinical)

  • May be employed as a reference standard for quality control of botanical ingredients (e.g., hop extracts) and food chemistry studies.
  • Can serve in pre-formulation research exploring solubilization strategies for hydrophobic polyphenols (cosolvents, cyclodextrins, lipid vehicles), strictly for laboratory investigation.

• Regulatory status

  • No pharmacopeial monograph or GMP grade is indicated. For any regulated use, users must qualify the material independently. Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• Stability considerations in formulation trials (general)

  • Protect from light and oxygen; include antioxidants only if compatible with study goals. Monitor by stability-indicating HPLC.
  • Avoid strong alkaline or acidic vehicles that can drive O-derivatization or prenyl rearrangements.

Physical Properties

• Item-specific physico-chemical specifications

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Melting point: Not specified for this item; refer to CoA/Spec Sheet.
  • Boiling point: Not applicable; compound expected to decompose before boiling under ambient pressure (literature/general for polyphenolic solids). Exact value not specified for this item; refer to CoA/Spec Sheet.
  • Density: Not specified for this item; refer to CoA/Spec Sheet.
  • Solubility: Not specified for this item; refer to CoA/Spec Sheet.
  • LogP, pKa, refractive index: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general guidance for prenylated dihydrochalcones (informative; not product specifications)

  • Physical state: Typically a pale amorphous solid or low-melting crystalline solid for related hop polyphenols.
  • Solubility behavior: Sparingly soluble in water; soluble in polar aprotic and protic organic solvents such as DMSO, DMF, methanol, ethanol, acetone, and ethyl acetate; enhanced solubility upon mild basification due to phenoxide formation.
  • Acid–base: Phenolic OH groups exhibit weak acidity (typical phenol pKa ~9–10; prenylated phenols can be slightly less acidic). Exact pKa for this compound is not specified for this item.
  • Stability: Phenolic compounds can be sensitive to strong oxidants, prolonged UV exposure, and high temperature; store protected from light and moisture for best integrity (see Storage tab).

Quality and Grades

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

• Guidance on grades (general)

  • Research grade: Suitable for discovery chemistry, reference studies, screening, and synthetic transformations. Typical emphasis is on identity and assay purity rather than trace inorganic/UV-absorbing impurities.
  • HPLC/Analytical grade (if applicable to a future lot): Emphasizes low non-volatile residue and low UV background, enabling accurate quantitation in chromatographic workflows.
  • Natural product standards: For use as reference materials, look for documentation covering assay purity by HPLC/UPLC, residual solvents, water content, and identity confirmation (NMR/HRMS). Metals/UV cutoff/peroxide content: Not specified for this item; refer to CoA/Spec Sheet.

• Stabilizers/inhibitors

  • Not specified for this item; refer to CoA/Spec Sheet. Phenolic compounds typically do not require added stabilizers but benefit from protection from light and air.

• Documentation and release testing

  • For each lot, consult the CoA/Spec Sheet for assay purity, identity (NMR/MS/IR), residual solvents, and any additional tests used to qualify the material for research use.

Reaction and Applications

• Research applications (general)

  • Natural products chemistry: Used as a reference standard and substrate when probing prenylated phenolic metabolism, oxidative transformation, and structure–activity relationships of hop-derived polyphenols.
  • Analytical chemistry: Calibration standard in HPLC/UPLC-MS workflows analyzing hop extracts, beer matrices, or prenylflavonoid panels. Emphasize light protection and minimal adsorption to plastics.

• Representative transformations with prenylated dihydrochalcones (literature/general; not item-specific specifications)

  • O-Functionalization: Phenolic O-alkylation or O-acylation under mild base (e.g., K2CO3/acetone or DMF) to access prodrugs, protecting groups, or analog libraries.
  • Oxidative cyclization: Lewis acid or iodine-mediated annulations can convert chalcone/dihydrochalcone motifs to flavanones or related heterocycles, modulating scaffold rigidity.
  • Prenyl manipulations: Epoxidation (mCPBA) of the prenyl double bond, followed by ring opening to install additional functionality; hydroboration–oxidation to generate primary alcohols; radical additions for side-chain diversification.
  • Carbonyl chemistry: Typical aryl ketone reactivity—formation of oximes/hydrazones; reduction (NaBH4) to secondary alcohols; Baeyer–Villiger oxidation to aryl esters/phenols.

• Practical notes

  • Drying: Use anhydrous conditions for base-mediated O-alkylations; phenolate generation is moisture-sensitive.
  • Protection: Temporary protection of phenols (e.g., MOM, Bn, silyl) may be necessary for selective transformations on the prenyl chain.
  • Analysis: Monitor by HPLC-UV (280–330 nm typical for polyphenols) and LC-MS; confirm structures with 1H/13C NMR given characteristic aromatic and benzylic signals.

Reaction Conditions

The following are literature/general conditions relevant to prenylated dihydrochalcones; they are guidance only and not specifications for this item.

• O-Alkylation / O-Acylation of phenols

  • Base: K2CO3, Cs2CO3, or NaH (for more challenging electrophiles)
  • Solvent: Acetone, DMF, MeCN; 0.05–0.2 M
  • Temperature/time: rt to 60 °C, 1–16 h
  • Notes: Exclude water; use phase-transfer catalysis for milder conditions.

• Reduction of aryl ketone

  • Reagent: NaBH4 (MeOH/EtOH/THF)
  • Temperature/time: 0 °C to rt, 0.5–3 h
  • Outcome: Secondary benzylic alcohol; monitor to avoid over-reduction of sensitive side chains.

• Prenyl epoxidation and opening

  • Oxidant: mCPBA (DCM or toluene, 0 °C to rt)
  • Follow-up: Nucleophilic opening (ROH, H2O, amines) with acid/base catalysis

• Oxidative cyclization to flavanone-like scaffolds

  • Promoters: I2, Br2, or Lewis acids (AlCl3, BF3·OEt2)
  • Solvents: CH2Cl2, toluene, or CPME
  • Temperature/time: 0 °C to reflux, 1–12 h
  • Notes: Protect phenols if overreaction occurs; control halogen equivalents.

• Analytical monitoring

  • HPLC-UV (280–330 nm) and LC-MS are standard; confirm structure by NMR (distinct benzylic signals in dihydrochalcones).

• Expected yields

  • Transformation-dependent; 50–90% often reported for clean O-alkylations and NaBH4 reductions on related systems. Optimize on small scale first.

Safety and Handling

• GHS/Classification (item-specific)

  • Signal word: Not specified for this item; refer to SDS.
  • Hazard statements (H-codes): Not specified for this item; refer to SDS.
  • GHS classification and pictograms: Not specified for this item; refer to SDS.

• General laboratory safety for polyphenolic, prenylated dihydrochalcones (literature/general; not a substitute for SDS)

  • Expected hazards: May cause skin and eye irritation; dust may cause respiratory irritation. Avoid inhalation of powders and contact with skin/eyes.
  • PPE: Safety glasses, lab coat, and disposable nitrile gloves as a minimum. Use dust control (weighing hood) when handling solids.
  • Handling: Avoid generation of dust. Use in a well-ventilated area or fume hood. Prevent exposure to strong oxidizers and strong bases/acids that can degrade phenolic structures.
  • Incompatibilities: Strong oxidizing agents; strong bases can induce O-alkylation/acylation or degrade; strong acids may cause polymerization or dehydration of prenyl groups.
  • First aid (overview): If on skin/eyes, rinse with water for several minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention. Always consult the SDS for authoritative instructions.
  • Fire: Combustible organic solid. Use CO2, dry chemical, or foam. Combustion may produce CO/CO2 and phenolic fumes.

• SDS: For definitive hazard classification and exposure limits, consult the product-specific SDS provided by Aladdin Scientific.

Solvent Selection

Alpha,beta-dihydroxanthohumol is a hydrophobic polyphenolic dihydrochalcone; solvent choice governs solubility, stability, and compatibility with assays.

• Polarity/miscibility (literature/general)

  • Water: Poor intrinsic solubility expected. Solubility can increase under mildly basic conditions (phenolate formation) but may affect downstream biology assays.
  • Good solvents: DMSO, DMF, acetone, ethyl acetate, methanol, ethanol, acetonitrile. For bioassays, DMSO or ethanol stock solutions are common.
  • Nonpolar solvents: Limited solubility in hexanes; increased in toluene or MTBE due to aromatic/prenyl interactions.

• Practical selection by application

  • Analytical standards: Prepare concentrated stocks in HPLC-grade methanol, acetonitrile, or DMSO; dilute into mobile phase to avoid precipitation.
  • Synthetic chemistry: Use polar aprotic solvents (THF, MeCN, DMF) for O-alkylation/acylation; aromatic solvents (toluene) for Lewis-acid mediated cyclizations; alcohols for hydrogen-transfer or protection steps.
  • Bioassays (research use only): Prepare 10–50 mM stocks in dry DMSO/ethanol; final assay DMSO typically ≤0.1–1% v/v to minimize solvent effects. Exact solubility for this item is not specified; verify empirically.

• Short comparison (general)

  • DMSO vs ethanol: DMSO affords higher solubility and stability; ethanol is more volatile and often better tolerated in enzyme/cell-free systems.
  • MeCN vs MeOH for LC: MeCN often provides sharper peaks; MeOH can improve ionization in ESI-MS. Choose based on method development.

Storage and Reconstitution

• Storage conditions (item-specific)

  • Storage temperature: Room temperature (from Product Data).
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• General storage guidance for phenolic, prenylated dihydrochalcones

  • Keep tightly closed in a dry place. Protect from light and prolonged exposure to air to minimize oxidative degradation and prenyl side-chain reactions.
  • For long-term stability, consider desiccated storage and inert atmosphere (e.g., argon) in amber glass.

• Reconstitution

  • Solvents: DMSO, ethanol, methanol, or acetonitrile are typical choices. Exact solubility for this item is not specified; verify empirically.
  • Procedure: Allow vial to equilibrate to room temperature before opening to prevent moisture condensation. Add calculated volume of dry solvent, vortex, and, if needed, sonicate briefly. Filter through 0.22 µm PTFE for analytical use.
  • Aliquoting: Prepare single-use aliquots to avoid repeated freeze–thaw or repeated opening to air.

• Stability after reconstitution (general)

  • DMSO and MeCN stocks are often stable for days to weeks at 2–8 °C when protected from light; verify by HPLC. For longer storage, keep frozen (–20 to –80 °C) in airtight amber vials. Exact stability for this item is not specified; refer to CoA/Spec Sheet.

• Research Use Note

  • For research use only.

Structure and Identity

Alpha,beta-Dihydroxanthohumol is commonly described in the literature as the fully hydrogenated (α,β-dihydro) analogue of the hop chalcone xanthohumol, placing it in the prenylated dihydrochalcone family.

• Item-specific identifiers

  • CAS: 102448-00-0 (from Product Data)
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data field provided is not a valid InChIKey)
  • 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 and features (literature/general)

  • Class: Prenylated dihydrochalcone (saturated chalcone backbone, i.e., 1,3-diphenylpropan-1-one core)
  • Functional groups: phenolic hydroxyl groups; aryl ketone (propiophenone motif); isoprenyl (C5) side chain on one aromatic ring.
  • α,β-Dihydro designation: the Cα–Cβ double bond of the parent chalcone is reduced, giving a saturated linker between the two aryl rings.
  • 2D description: two substituted phenyl rings connected by a three-carbon chain bearing a carbonyl at C1; one ring carries a prenyl substituent and phenolic OH groups; the other ring possesses additional phenolic OH substitution.

• Stereochemistry (literature/general)

  • The core dihydrochalcone typically has no stereocenter unless the prenyl side chain is further transformed; alpha,beta-dihydrogenation removes the E/Z geometry of the chalcone.

Synthetic Utility

• Functional group handles (literature/general)

  • Phenolic OH: amenable to O-alkylation, O-acylation, carbonate/carbamate formation, and protective group strategies (Bn, MOM, silyl). Phenoxide intermediates enable selective elaboration.
  • Aryl ketone: participates in reductions (NaBH4 → secondary alcohol), oxime/hydrazone formation, and Baeyer–Villiger oxidation to phenolic esters.
  • Prenyl side chain: electrophilic additions (HX), epoxidation, hydroboration–oxidation, radical additions, and cross-metathesis with suitable catalysts.

• Scaffold edits (general)

  • Cyclizations: Lewis acid or iodine-promoted annulations can transform dihydrochalcones into flavanones/flavanols, offering access to related prenylflavonoid families.
  • Late-stage diversification: Site-selective C–H activation on the aromatic rings (e.g., Cu/Ag-assisted O-directed arylation) reported for phenolic systems may extend to this scaffold after protection.

• Retrosynthetic value

  • Serves as a saturated reference point for SAR vs. the parent α,β-unsaturated chalcone (xanthohumol). Comparative reactivity enables mapping of Michael acceptor-dependent vs. phenol-driven transformations.

• Practical workflow

  • Protect phenols when functionalizing the prenyl chain to prevent competitive O-reactions.
  • Use non-nucleophilic bases (Cs2CO3, K2CO3) in polar aprotic solvents for clean O-alkylations; monitor by LC-MS and quench carefully to avoid transesterification or over-alkylation.
  • For oxidative steps, include radical inhibitors if necessary and control temperature to prevent polymerization of the prenyl moiety.

Target Specificity

Not applicable. This product is a small-molecule research chemical, not an antibody or affinity reagent.

• Item-specific target data: None provided.
• For receptor/enzyme studies, any interaction profiles are assay- and context-specific and must be established by the end user under their own conditions.