This compound belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.
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.
Dissolve in anhydrous DMSO to 10–100 mM. Vortex and, if needed, gently warm (≤40 °C) to aid dissolution. Filter through 0.22 µm PTFE if particulates persist.
For ethanol stocks (e.g., 10–50 mM), ensure compatibility with downstream assay components; maintain final organic solvent ≤1–2% v/v in aqueous assays to avoid precipitation.
Working solution dilution
Add stock slowly to stirred buffer/media to the desired final concentration, maintaining constant solvent composition across samples/controls. Inspect for turbidity/precipitation.
Thin-film preparation (materials/optical studies)
Cast from toluene, THF, or chlorobenzene onto clean substrates; control evaporation rate to tune film morphology. Optionally perform post-deposition annealing below any thermal decomposition point (not specified for this item).
Always validate concentration by UV–Vis or quantitative NMR, and confirm stability under your specific assay conditions.
Biological Roles
General biochemical context (literature; not specific to this synthetic derivative)
Chalcones are key intermediates in plant flavonoid biosynthesis. Chalcone synthase (CHS) produces chalcones from p-coumaroyl-CoA and malonyl-CoA, and chalcone isomerase converts them to flavanones. These pathways underpin pigments and defense metabolites in plants.
Phenolic chalcones often exhibit interactions with proteins via Michael acceptor chemistry and π–π stacking; the para-hydroxyl enhances hydrogen bonding, while the butyl substituent increases hydrophobic interactions with lipid/protein environments (qualitative considerations for binding studies).
In cell-free biochemical assays, chalcones are widely used as reactive probes or scaffolds to study thiol-reactive chemistry and conjugate addition kinetics.
Important notes
This product is supplied strictly for research use only (per Product Data). No clinical, diagnostic, or therapeutic claims are made.
Any biological activity reported in literature for related chalcones is context-dependent; users should validate activity and selectivity under their own conditions.
Buffer Applications
This compound is a neutral, hydrophobic aromatic enone and is not used as a buffering agent. It lacks acid/base pairs with pKa values suited for aqueous buffer capacity near physiological pH. For work involving this material in aqueous systems, prepare organic cosolvent stocks (e.g., DMSO or ethanol) and dilute into pre-formed biological buffers (PBS, HEPES) with appropriate solvent controls.
Green Alternatives
Greener considerations center on solvent and reagent choices, as the substrate is fixed.
Preferred solvents (when feasible)
Ethanol or isopropanol for extractions/recrystallizations instead of chlorinated solvents.
2-Methyltetrahydrofuran (2-MeTHF) or cyclopentyl methyl ether (CPME) as alternatives to THF/DCM in conjugate additions or protection steps.
Ethyl acetate and toluene (or xylene) in place of dichloromethane for workups/purifications.
Reagent choices
Organocatalyzed Michael additions or photocatalytic methods can reduce reliance on heavy metals.
Hydrogenation with reusable heterogeneous catalysts (Pd/C, Ni) under low pressure reduces waste; consider transfer hydrogenation (isopropanol, formic acid) as an alternative to H2 cylinders.
Small comparison (general, literature)
THF vs 2-MeTHF: similar polarity and reaction profiles; 2-MeTHF has better renewability and lower peroxide concerns but different miscibility with water (beneficial for separations).
DCM vs EtOAc: DCM offers rapid kinetics for some reactions but is volatile and a suspected carcinogen; EtOAc is less toxic and biodegradable but may alter reaction rates/selectivity.
Trade-offs
Switching to greener solvents may require re-optimization of base/catalyst and temperature to maintain selectivity for Michael vs 1,2-addition. Monitor by TLC/HPLC and adjust reagent equivalents accordingly.
Pharmaceutical Uses
No pharmacopeial/excipient status is indicated for this item. It is provided for research use only.
General formulation context (literature/practice)
Hydrophobic small molecules like para-substituted chalcones are commonly handled as DMSO or ethanol concentrates for in vitro screening or as analytical standards. For any pre-formulation research, consider solubilization aids (cyclodextrins, surfactants) and light protection due to conjugated chromophores.
Compliance note
Do not use in humans or for diagnostic purposes. Consult institutional guidelines for handling investigational research chemicals.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Phase: typically a crystalline solid for para-substituted chalcones.
Solubility (qualitative, literature):
Poorly soluble in water; soluble in polar aprotic and moderately polar organic solvents (e.g., DMSO, DMF, acetone) and in alcohols (ethanol, methanol); also soluble in aromatic solvents (toluene) and moderately in esters (EtOAc).
Partitioning (literature expectation): hydrophobic character increased by the para-n-butyl group; anticipated logP > 3 (qualitative).
Acidity/basicity (literature): phenolic OH weakly acidic (pKa typically ~9–10 for para-phenols; specific value not determined for this derivative).
UV/Vis (literature): chalcones show strong π→π* bands in the near-UV/visible due to extended conjugation; para-hydroxy substitution bathochromically shifts λmax. Exact cutoffs/λmax not specified for this item.
Melting/boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Notes for handling solutions (general)
Prepare concentrated stocks in dry DMSO or ethanol; dilute into working media with mixing to prevent precipitation. Filter if necessary (PTFE/nylon).
Quality & Grades
Item-specific quality information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades (general information)
Research-grade chalcones are typically supplied at high chemical purity suitable for synthetic and analytical work. If designated “analytical” or “HPLC” grade (not specified here), expectations include narrow impurity profiles and low non-volatile residue suitable for quantitative assays.
Phenolic compounds may contain trace inhibitors or stabilize by virtue of their own antioxidant functionality; no stabilizer is indicated for this item.
Verification: confirm identity/purity by NMR (distinct enone signals; para-substitution patterns), HRMS (m/z consistent with C19H20O2), and HPLC/GC as applicable.
What to check on receipt
Appearance and documentation (CoA, Lot-specific purity, water/volatile content if reported). If UV spectral characteristics or residual solvent limits are critical for your application, request an item-specific specification sheet.
Use-case alignment
For photophysical or bioassay work, minimize fluorescent/UV-absorbing impurities (select lots with HPLC purity data). For synthesis, confirm absence of peroxides (rare for solids of this class) and monitor for aldol-derived impurities by NMR.
Reaction & Applications
General reactivity of 4-Butyl-4'-hydroxychalcone (literature)
Michael acceptor: undergoes 1,4-conjugate additions with soft nucleophiles (thiols, amines, malonates, enolates, cuprates, organozinc). Para-hydroxyl can hydrogen-bond, subtly affecting regioselectivity and rates.
Hydrogenation: catalytic reduction (H2/Pd, Pt, or Ni) yields saturated dihydrochalcones; chemoselective C=C reduction (leaving the carbonyl) is achievable with suitable catalysts/conditions.
Cycloadditions: the enone can act as a dienophile in Diels–Alder reactions with electron-rich dienes (often requiring elevated temperatures or Lewis acids).
O-derivatization: the phenolic OH enables etherification (Williamson) or esterification (acyl chlorides/anhydrides), allowing polarity tuning or protecting-group strategies.
Oxidative cyclizations: although classic Algar–Flynn–Oyamada to flavonols requires an ortho-phenol, para-phenol derivatives can still engage in alternative oxidative annulations under tailored conditions (literature-dependent).
Applications (representative, non-exhaustive)
Building block for flavonoid-like libraries, chalcone diversification, and materials with donor–acceptor conjugation.
UV–Vis/photophysical studies leveraging the extended π-system and substituent effects (butyl increases hydrophobicity; phenol modulates electronics).
Practical tips
Maintain dry, oxygen-limited conditions for base-catalyzed conjugate additions to minimize side reactions (e.g., polymerization).
For O-alkylations, pre-form the phenoxide with K2CO3/NaH in dry polar aprotic solvents; avoid over-alkylation or Michael addition of alkoxide under strongly basic conditions.
Reaction Conditions
General, literature-based guidance (not item specifications)
Conjugate (Michael) addition:
Solvents: THF, MeCN, DCM, or toluene; for polar nucleophiles, DMF/DMSO.
Bases/catalysts: secondary amines (organocatalysis), K2CO3/DBU for deprotonated pronucleophiles; Cu(I)/Cu(II) salts for organocuprates.
Temperature/time: 0–25 °C to control 1,4- vs 1,2-addition; reactions typically complete in 2–24 h depending on nucleophile.
Hydrogenation:
Catalyst: Pd/C (5–10%), PtO2, or Raney Ni.
Solvent: EtOH, EtOAc, or THF.
Conditions: 1–5 bar H2, 20–40 °C; monitor to avoid over-reduction of carbonyl.
Epoxidation (Prilezhaev):
Oxidant: mCPBA (1.1–1.5 equiv) in DCM at 0–25 °C.
Workup: aqueous Na2SO3/NaHCO3 to remove peracid; epoxyketone often forms cleanly within 1–4 h.
O-alkylation (ether formation):
Base: K2CO3 or Cs2CO3 in acetone/MeCN; or NaH in THF/DMF for more challenging electrophiles.
Electrophiles: alkyl halides, tosylates; 0–25 °C, 1–16 h.
Monitoring and purification
TLC/HPLC with UV detection (chalcones have strong absorbance in near-UV/vis). Purify by silica gel using hexanes/EtOAc or toluene/EtOAc; add 0.1–1% Et3N if phenol adsorption is problematic.
Expected selectivity notes
Soft nucleophiles favor 1,4-addition; hard nucleophiles (e.g., RMgX) risk 1,2-addition—use cuprates or lower temperatures to bias 1,4-chemistry.
Safety & Handling
Item-specific hazard data
GHS classification, pictograms, signal word, H-statements: Not specified for this item; refer to the SDS.
General safety information for chalcones/phenolic enones (literature/best practice)
Likely hazards: may cause skin/eye irritation; dust may irritate respiratory tract. Phenolic compounds can cause local irritation; α,β-unsaturated ketones are Michael acceptors and may cause sensitization in susceptible individuals.
PPE: lab coat, safety glasses, and chemically resistant gloves (e.g., nitrile). Handle solids in a fume hood to avoid inhalation of dust.
First aid (overview; defer to SDS):
Inhalation: move to fresh air; seek medical advice if symptoms persist.
Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical attention if irritation continues.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Incompatibilities: strong oxidizing agents; strong bases/acids (may promote undesired reactions such as retro-aldol, polymerization, or etherification of the phenol). Avoid prolonged exposure to light/UV which can drive photochemical reactions in conjugated enones.
Hygiene: avoid dust generation; wash thoroughly after handling; do not eat/drink in work area.
Waste: collect organic waste and dispose per institutional and regulatory guidance.
Always consult the current SDS for authoritative hazard classification and response measures.
Poorly soluble: water and highly nonpolar alkanes at ambient conditions.
Polarity and use scenarios
The conjugated enone with a para-phenol and a para-butyl group makes the molecule amphiphilic but overall hydrophobic. For stock solutions in screening or materials work, dry DMSO (10–100 mM) is typically preferred; ethanol is an excellent alternative when DMSO must be minimized.
Choice guidance
For synthesis/transformations: use polar aprotic solvents (THF, MeCN, DMF, DCM) to support nucleophilic conjugate additions and oxidations; aromatic solvents (toluene) are suitable for thermal reactions.
For purification: normal-phase silica with gradients of hexanes/EtOAc or toluene/EtOAc works well; adding a small percentage of MeOH or Et3N can help elute phenolic forms if adsorption is strong.
Brief comparison (general)
DMSO vs EtOH: DMSO affords higher solubility and stability for concentrated stocks; ethanol facilitates rapid evaporation and is more benign for waste considerations.
MeCN vs THF: MeCN offers higher polarity and better control for conjugate additions; THF is advantageous for low-temperature chemistry but requires peroxide monitoring (solvent-level consideration).
Storage & Reconstitution
Item-specific storage
Storage conditions: Room temperature (per Product Data). Store tightly closed in a dry place.
Shipping: Normal.
General recommendations (best practice)
Protect from light to minimize potential photochemical changes in the conjugated enone system.
Keep container tightly sealed with desiccant to avoid moisture uptake and base-catalyzed degradation.
For long-term storage, consider refrigeration (2–8 °C) in the dark if compatible with your workflow, although not required by the product data.
Reconstitution and solution stability
Solvents: DMSO, ethanol, or other dry organic solvents. Prepare concentrated stocks (e.g., 10–100 mM) and aliquot to minimize freeze–thaw and headspace oxygen.
Stability: solutions in aprotic solvents are generally stable for days to weeks at ambient conditions when protected from light; confirm by HPLC before critical use. Aqueous mixtures may show precipitation or slow degradation; prepare fresh as needed.
If any lot-specific specifications (water content, purity, residual solvents) are required, consult the CoA/Spec Sheet for this item.
Structure & Identity
Overview: 4-Butyl-4'-hydroxychalcone is a para/para-disubstituted chalcone (α,β-unsaturated aryl ketone) featuring a phenyl–enone–phenyl framework with a para-butyl substituent on one ring and a para-phenolic hydroxyl on the other.
Item-specific identifiers (from Product Data)
CAS: 385810-21-9
PubChem CID: 11108740
InChIKey: 198162 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers and features (general)
Core functional groups: conjugated enone (α,β-unsaturated ketone), phenolic OH (para to enone), n-butyl substituent (para to enone on the opposite ring).
Structural description (2D): an E-configured cinnamoyl linker (Ph–CO–CH=CH–) conjugated to a second phenyl ring. One aryl ring bears a para-hydroxyl; the other bears a para-n-butyl (–(CH2)3CH3). No stereocenters; one C=C geometric element typically E (literature for chalcones).
Stereochemistry/tautomerism
Enone predominantly in the trans (E) configuration across the C=C (literature for chalcones). Possible keto–enol tautomerism of the enone is minimal for para-hydroxy substitution (literature).
Synthetic Utility
Retrosynthetic and forward-synthesis value (literature)
Electrophilic handle: the α,β-unsaturated carbonyl functions as a versatile Michael acceptor enabling rapid diversification at the β-position (C–C, C–N, C–S bond formation).
Conjugated scaffold: suitable for constructing donor–acceptor materials, tuning optical properties by modifying the O-substituent and/or the enone.
Named/typical transformations
Conjugate addition with malonates (Knoevenagel partners) and soft organometallics (e.g., Gilman reagents) to furnish β-substituted ketones.
Selective hydrogenation (e.g., Pd/C, H2) to dihydrochalcones; subsequent intramolecular cyclizations can give chromanes/chromanones.
Epoxidation (mCPBA) followed by regioselective nucleophilic opening to install β-heteroatoms.
O-alkylation/acylation via Williamson ether synthesis or Steglich acylation.
Protection strategies: convert phenol to benzyl or silyl ethers for base-sensitive steps; deprotect under mild hydrogenolysis/fluoride conditions as appropriate.
Upstream synthesis
Typically prepared by Claisen–Schmidt (aldol) condensation between 4-hydroxyacetophenone and 4-butylbenzaldehyde under basic or acid-catalyzed conditions, followed by E-selective dehydration (literature).
Target Specificity
Not applicable. This product is a small-molecule chemical and does not have antibody/bioreagent target specificity parameters (no antigen, clone, isotype, or species reactivity). For biochemical work, any target engagement must be empirically determined by the user.
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