Naringenin triacetate - ≥99% , CAS No.3682-04-0

CAS: 3682-04-0 Cat. No.: N650633 Summenformel: C₂₁H₁₈O₈ Molekulargewicht: 398.36 PubChem CID: 14354984

QUALITÄT & REINHEIT ≥99%

Synonyms

[4-(5,7-diacetyloxy-4-oxo-2,3-dihydrochromen-2-yl)phenyl] acetate | DTXSID50559290 | HQZXCNZZVRAEPO-UHFFFAOYSA-N | AKOS022184613 | 2-[4-(Acetyloxy)phenyl]-4-oxo-3,4-dihydro-2H-1-benzopyran-5,7-diyl diacetate | 4',5,7-Triacetoxyflavanone | Naringenin triac

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Übersicht

Naringenin triacetate is a flavonoid isolated from plant, exhibits a good binding affinity with multiple crystal structures of first bromodomain BRD4 (BRD4 BD1).

Form:Solid

Spezifikationen

Synonyme

[4-(5,7-diacetyloxy-4-oxo-2,3-dihydrochromen-2-yl)phenyl] acetate | DTXSID50559290 | HQZXCNZZVRAEPO-UHFFFAOYSA-N | AKOS022184613 | 2-[4-(Acetyloxy)phenyl]-4-oxo-3,4-dihydro-2H-1-benzopyran-5,7-diyl diacetate | 4',5,7-Triacetoxyflavanone | Naringenin triac

Spezifikationen & Reinheit

≥99%

Biochemische und physiologische Mechanismen

Naringenin triacetate is a flavonoid isolated from plant, exhibits a good binding affinity with multiple crystal structures of first bromodomain BRD4 (BRD4 BD1).

Storage

Protected from light,Store at -80°C

Verschickt in

Dry ice packs + Cold packs

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Reinheit

≥99%

Namen und Kennungen

Kanonisches Lächeln

CC(=O)OC1=CC=C(C=C1)C2CC(=O)C3=C(O2)C=C(C=C3OC(=O)C)OC(=O)C

IUPAC Name

[4-(5,7-diacetyloxy-4-oxo-2,3-dihydrochromen-2-yl)phenyl] acetate

InChIKey

HQZXCNZZVRAEPO-UHFFFAOYSA-N

INCHI

1S/C21H18O8/c1-11(22)26-15-6-4-14(5-7-15)18-10-17(25)21-19(28-13(3)24)8-16(27-12(2)23)9-20(21)29-18/h4-9,18H,10H2,1-3H3

Isomere SMILES

CC(=O)OC1=CC=C(C=C1)C2CC(=O)C3=C(O2)C=C(C=C3OC(=O)C)OC(=O)C

Alternative CAS-Nummer

73111-01-0

PubChem CID

14354984

Molekulargewicht

398.36

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Klasse Flavonoids
      • Subclass Flavans

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Klasse: Flavonoids
• Subclass: Flavans
• Intermediate Tree Nodes: Not available
• Direct Parent: Flavanones
• Alternative Parents: Chromones Phenol esters Tricarboxylic acids and derivatives Phenoxy compounds Aryl alkyl ketones Alkyl aryl ethers Carboxylic acid esters Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavanone - Chromone - Chromane - Benzopyran - 1-benzopyran - Phenol ester - Tricarboxylic acid or derivatives - Phenoxy compound - Aryl alkyl ketone - Aryl ketone - Alkyl aryl ether - Monocyclic benzene moiety - Benzenoid - Carboxylic acid ester - Ketone - Oxacycle - Carboxylic acid derivative - Organoheterocyclic compound - Ether - Carbonyl group - Organic oxygen compound - Organic oxide - Organooxygen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as flavanones. These are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.
• External Descriptors: Not available

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

Chemische und physikalische Eigenschaften

• Löslichkeit: DMSO : 100 mg/mL (251.03 mM; Need ultrasonic)
• Molekulargewicht: 398.400 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 398.1 Da
• Monoisotopic Mass: 398.1 Da
• Topological Polar Surface Area: 105.000 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 651.000
• 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

Application Protocols

No vendor-validated bioassay protocols are provided for this item. It is supplied as a small-molecule reagent for research and synthesis.

General laboratory usage examples (non-validated; adapt to your system):

• Preparation of a 10–50 mM DMSO stock for in vitro studies of deacetylation or permeability; dilute into assay buffer keeping final DMSO ≤1–2% v/v to mitigate precipitation.
• Deprotection test: Dissolve in anhydrous MeOH, add catalytic NaOMe at 0°C, monitor by LC–MS to confirm regeneration of naringenin.

For any biological applications, develop and qualify in-house protocols; this product is not intended for diagnostic or therapeutic use.

Biological Roles

No direct endogenous biological role is assigned to naringenin triacetate; it is a synthetic, peracetylated derivative of the natural flavanone naringenin.

General context (biochemistry/literature):

• Naringenin is a central intermediate in plant flavonoid biosynthesis (phenylpropanoid pathway), leading to diverse flavones, flavonols, and anthocyanins.
• Triacetylation masks phenolic hydroxyls, altering polarity and membrane permeability relative to naringenin; in biological systems, esterases can hydrolyze acetates to regenerate phenolic groups (mechanistic note; not a clinical claim).
• Peracetylated flavonoids are often used as pro-forms in chemical biology to facilitate cellular uptake in vitro prior to intracellular deacetylation (research use only).

Assay and mechanistic uses (research context):

• Substrate for esterases/lipases in enzyme kinetics studies, where stepwise deacetylation can be monitored by LC–MS or UV–vis.
• Model compound to evaluate structure–permeability relationships by comparing acetylated vs deacetylated flavonoids.

Note: Any biological evaluation should be performed under appropriate institutional approvals; this product is supplied strictly for research use only, not for diagnostic, therapeutic, or in vivo applications.

Buffer Applications

This compound is a hydrophobic triester and is not typically used as a buffer component. It lacks acid–base functionality suitable for maintaining pH in aqueous systems and shows poor water solubility.

Practical note:

• For aqueous assay preparation, dissolve in a miscible organic cosolvent (e.g., DMSO) to make a concentrated stock, then dilute into buffer with careful control of final organic percentage to avoid precipitation. Keep pH neutral to mildly acidic to limit hydrolysis.

For buffer selection and preparation, consider standard buffering systems (e.g., phosphate, HEPES, acetate) unrelated to this compound.

Green Alternatives

Sustainability considerations focus on solvent choice and protecting-group strategy.

• Greener solvent options (compared to chlorinated solvents):

  • Replace DCM/CHCl3 with EtOAc, 2-MeTHF, CPME, or toluene when reaction/solubility allows.
  • For recrystallization or chromatography, prefer EtOAc/hexanes systems over chlorinated solvents.

• Protecting-group strategy:

  • While acetate groups are atom-efficient and cleavable under mild conditions, alternatives like carbonate (e.g., Boc- or allyl-carbonates) or benzoates may offer differing stability/greenness profiles depending on step economy and deprotection conditions.

• Workup/waste minimization:

  • Use aqueous bicarbonate or brine washes judiciously and minimize basic exposures to reduce hydrolysis byproducts.
  • Consider solvent recovery (EtOAc, 2-MeTHF) and short-path chromatography to cut waste.

Comparison snapshot (general):

• DCM vs 2-MeTHF: 2-MeTHF is biorenewable, higher boiling (better for heated reactions), but still requires drying to protect acetates; DCM offers inertness and fast evaporation but is a chlorinated solvent with higher environmental impact.
• EtOAc: Widely regarded as a greener workup and reaction solvent; compatible with this triacetate, though avoid strong base.

Choose the least hazardous solvent system that meets solubility and stability needs, and design routes to limit protection/deprotection cycles where possible.

Pharmaceutical Uses

No pharmacopeial monograph or excipient designation is provided for this item. It is supplied for research use only.

Research/formulation context (general):

• Triacetylated flavonoids can serve as pro-forms in formulation screening or permeability studies, where esterases may regenerate the parent phenols in vitro. Such use remains strictly preclinical and exploratory.
• Enhanced lipophilicity may aid solubility in non-aqueous vehicles or lipid-based systems for in vitro testing.

Manufacturing/CMC considerations (general):

• Control of residual solvents, assay purity, and solid-state form (amorphous vs crystalline) is important for reproducibility in research settings.
• Avoid exposure to alkaline excipients or aqueous basic media that may result in premature deacetylation.

No therapeutic claims are made; this product is not intended for human or veterinary use.

Physical Properties

Item-specific numerical specifications (melting point, boiling point, density, UV cutoff, trace metals, residual solvents, water, or stabilizers): Not specified for this item; refer to CoA/Spec Sheet.

Literature/general reference values and behavior (for guidance only; not product specifications):

• Molecular weight: ~398.36 g/mol (literature, C21H18O8).
• Physical state/appearance: Typically a pale solid for peracetylated flavonoids (literature expectation; exact appearance not specified for this item).
• Solubility profile (general behavior):
  • Good solubility in non-polar to mid-polar organic solvents (e.g., dichloromethane, chloroform, ethyl acetate, acetone, acetonitrile, THF).
  • Soluble in DMSO and DMF for stock solutions.
  • Very low solubility in water due to triacetylation increasing lipophilicity.
• Partitioning: Triacetates are substantially more lipophilic than their parent phenols; expect a higher logP than naringenin (qualitative guidance; no value claimed).
• Stability considerations (general):
  • Sensitive to base-catalyzed hydrolysis (cleavage of acetate esters).
  • Hydrolysis can also occur under prolonged exposure to moisture; handle under dry conditions.
  • More stable under neutral to mildly acidic conditions.

Refractive index, pKa, and other constants: Not specified for this item; consult literature or CoA/SDS as applicable.

Quality and Grades

Item-specific grade and purity: Not specified for this item; refer to CoA/Spec Sheet.

How to interpret typical grades (general guidance for small molecules):

• Research grade: Suitable for exploratory synthesis, screening, and non-GLP studies; purity often ≥95% by HPLC/GC unless otherwise stated.
• Analytical/Reagent grade (AR): Tight limits on inorganic/organic impurities; supports quantitative analysis.
• HPLC grade solvents/reagents: Low UV background and low non-volatile residue; relevant if compound is supplied as a solution (not the case here).

Impurity considerations for O-acetylated flavonoids (general):

• Potential co-impurities include partial acetates (mono-/di-acetates), parent aglycone (naringenin), and over-acetylated side products if other positions are reactive.
• Hydrolysis during storage can increase parent aglycone content; monitor by HPLC/LC–MS.

What to check on the CoA for this item:

• Assay/purity method (HPLC, NMR integration).
• Identity (1H/13C NMR, HRMS) consistent with tri-O-acetate.
• Residual solvents and water content (where applicable).
• Confirm storage and light protection conditions match this listing.

Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

This compound serves primarily as a protecting-group derivative of naringenin, enabling transformations that would otherwise be impeded by phenolic hydroxyl reactivity and hydrogen bonding.

Key applications (general/literature guidance):

• Protection strategy: The 5-, 7-, and 4′-OH groups are masked as acetates, reducing polarity and increasing solubility in nonpolar media for downstream synthetic steps.
• Selective derivatization: With phenols protected, reactions at the C-8 (A-ring) or on the B-ring (e.g., halogenation, formylation, metalation) may proceed with improved control.
• Glycosylation precursors: Phenolic O-acetates can be chemoselectively deprotected to expose a targeted phenol for glycosylation or etherification.
• Enzymatic studies: Used as a substrate in esterase/lipase assays to probe selective O-deacetylation (literature context for peracetylated flavonoids).
• SAR libraries: Enhanced lipophilicity facilitates cell-based screening of pro-forms or masked phenols in chemical biology workflows (research-use only).

Practical tips:

• For clean deprotection back to naringenin, employ mild base (e.g., NaOMe/MeOH, K2CO3/MeOH) at low temperature; quench carefully to avoid overreaction or acyl migration.
• Maintain anhydrous conditions during multi-step sequences to prevent premature hydrolysis.
• On silica, add a trace of acid (e.g., AcOH) to curtail base-triggered cleavage; minimize high-pH conditions.

Representative transformations: O-deacetylation → phenolic functionalization (etherification, carbonate/urethanation), electrophilic aromatic substitutions, and late-stage diversification on the flavanone backbone.

Reaction Conditions

General literature-style conditions for common operations on O-acetylated flavonoids (non-binding guidance; verify experimentally):

• O-Deacetylation (regeneration of naringenin):

  • NaOMe (0.05–0.2 eq) in MeOH, 0–25°C, minutes to hours; quench with acetic acid and concentrate. Monitor for stepwise deprotection if partial acetates are desired.
  • K2CO3 (1–2 eq) in MeOH or MeOH/THF, 0–25°C; slower and milder; useful for selective removal.
  • Enzymatic: Lipase/esterase in buffered aqueous–organic mixtures at ambient temperature; offers selectivity at particular positions depending on enzyme.

• Electrophilic aromatic substitution (on protected scaffold):

  • Halogenation (e.g., NBS/NCS) in DCM/AcOH or MeCN, 0–25°C; protect from base.

• Couplings on pre-halogenated derivatives:

  • Suzuki–Miyaura: Pd(0/II) catalyst (e.g., Pd(PPh3)4), base (K2CO3 or Cs2CO3), toluene/EtOH/H2O or 1,4-dioxane/H2O, 60–100°C; ensure acetate stability (prefer neutral, avoid prolonged strong base).

• Oxidation/reduction on the C-ring:

  • Careful with strong hydrides or oxidants; acetates generally stable to mild DIBAL-H at low T or DDQ under controlled conditions, but confirm experimentally.

Typical yields: Highly route- and substrate-dependent; monitor by TLC/HPLC and adjust conditions to minimize acetate cleavage.

Note: Keep processes anhydrous and avoid extended exposure to basic aqueous media to prevent unwanted deacetylation.

Safety and Handling

Authoritative safety classification for this specific item:

• Signal word: Not specified for this item; refer to SDS.
• H-statements: Not specified for this item; refer to SDS.
• GHS classification/pictograms: Not specified for this item; refer to SDS.

General laboratory handling guidance (non-authoritative; for planning):

• Avoid inhalation of dust and contact with skin/eyes. Use appropriate PPE: lab coat, safety glasses, nitrile gloves.
• Handle solids and weigh-outs in a fume hood to minimize dust exposure.
• This triacetate ester is susceptible to base-catalyzed hydrolysis; avoid strong bases and aqueous alkaline media unless deprotection is intended.
• Protect from moisture and light to prevent hydrolysis and degradation.
• Keep containers tightly closed under dry, inert atmosphere if possible.

First-aid overview (consult SDS for full guidance):

• Inhalation: Move to fresh air; seek medical attention if symptoms persist.
• Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical advice if irritation persists.
• Ingestion: Rinse mouth; do not induce vomiting; obtain medical attention.

Incompatibilities and special risks (general):

• Strong bases, strong nucleophiles, and prolonged aqueous exposure can cleave acetate esters.
• Strong oxidants should be avoided.

Waste: Dispose according to institutional and local regulations; organic solvent rinses may contain hydrolysis products.

Solvent Selection

Naringenin triacetate is a moderately lipophilic, neutral triester. Select solvents that balance solubility, stability (against hydrolysis), and downstream compatibility.

• Polarity/miscibility (general behavior):

  • Highly soluble in chlorinated solvents (CH2Cl2, CHCl3) and good in ethyl acetate, acetone, MeCN, THF.
  • Soluble in polar aprotics (DMSO, DMF) for concentrated stocks; avoid extended exposure to wet DMSO/DMF.
  • Poorly soluble in water and aqueous buffers.

• When to choose:

  • For rapid workups and extractions: EtOAc or MTBE to partition away from aqueous phases while minimizing hydrolysis time.
  • For chromatography: Hexanes/EtOAc or DCM/MeOH (≤2%) systems; keep silica slightly acidic (add 0.1% acetic acid) to suppress on-column deacetylation.
  • For reactions requiring anhydrous conditions: Dry DCM, THF, toluene, or MeCN are typical.

• Comparison notes (general):

  • DCM vs EtOAc: DCM gives higher solubility and inertness; EtOAc is greener but can participate in transesterification under strong base.
  • THF vs 2-MeTHF: 2-MeTHF offers greener profile and water tolerance but ensure dryness to limit hydrolysis.
  • DMSO stocks: convenient for biological assays of pro-forms; limit water content and freeze–thaw cycles.

Always minimize residence time in basic aqueous media to avoid acetate cleavage.

Storage and Reconstitution

Storage (item-specific from Product Data):

• Store at −80°C, protected from light.
• Shipped on dry ice packs + cold packs to maintain low temperature and limit hydrolysis.

Handling best practices (general, aligned with above):

• Allow container to equilibrate to room temperature in a desiccator before opening to avoid moisture condensation.
• Work swiftly under dry, inert atmosphere if possible. Reseal tightly with desiccant present.

Reconstitution (general guidance):

• Prepare concentrated stocks in anhydrous DMSO, DMF, or dry DCM/MeCN depending on application.
• Typical in vitro stock concentrations: 10–50 mM in DMSO (research-use context). Filter through 0.22 µm PTFE if particulate is present.
• For aqueous assays, dilute organic stocks into buffer with vigorous mixing, maintaining neutral to mildly acidic pH and limiting organic cosolvent to avoid precipitation.

Stability notes:

• Avoid repeated freeze–thaw cycles; aliquot stocks and store at −80°C, protected from light and moisture.
• Exposure to bases or wet conditions accelerates deacetylation to naringenin; minimize time in basic aqueous media.

For definitive stability/shelf-life information and any item-specific specifications, consult the product’s CoA and SDS.

Structure and Identity

Naringenin triacetate is the fully O-acetylated derivative of the flavanone naringenin, bearing acetate protecting groups on the 5-, 7-, and 4′-hydroxy positions of the flavonoid scaffold.

• Product name: Naringenin triacetate
• CAS: 3682-04-0
• PubChem CID: 14354984 (literature)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: C21H18O8 (literature for naringenin triacetate)
• Molecular weight: ~398.36 g/mol (literature)

Structural description (general chemistry):

• Core scaffold: Flavanone (2,3-dihydro-2-phenyl-4H-1-benzopyran-4-one).
• Functional groups: One conjugated ketone (flavanone C4 carbonyl); three aryl/phenolic acetates (O–COCH3) at typical 5-, 7- (A-ring) and 4′- (B-ring) positions.
• Ring systems: Chromanone ring fused to an A-ring, and a pendant B-ring (typical flavonoid A–C fused, B pendant via C2).
• Stereochemistry: Flavanones can exhibit a stereocenter at C2; commercial naringenin derivatives are commonly racemic unless otherwise specified (no stereochemical specification provided for this item).

2D structure in words (general): A benzopyranone (chromanone) fused system (A/C rings) bearing two acetate esters on the A-ring (positions 5 and 7) and an additional acetate on the para position of the phenyl B-ring (4′). The C-ring features the characteristic flavanone carbonyl at C4 and a saturated C2–C3 bond.

Synthetic Utility

Naringenin triacetate is a versatile protected intermediate enabling selective transformations on the flavanone core while suppressing phenolic reactivity.

Key utilities (general/literature guidance):

• Phenol protection: Acetates reduce hydrogen bonding and enhance solubility in organic media, facilitating reactions such as electrophilic aromatic substitutions on the A- or B-rings.
• Orthogonal deprotection: Stepwise O-deacetylation can be tuned by base strength, solvent, and temperature to reveal targeted phenols for subsequent etherification, carbamate/carbonate formation, or glycosylation.
• Late-stage diversification: With phenols masked, operations like halogenation, Friedel–Crafts-type acylations (on suitably activated positions), or metal-catalyzed couplings (after prior halogenation) are more manageable.
• Probing reactivity/stability: Comparison of reactivity vs naringenin in oxidation, reduction, or photochemical steps without interference from free phenols.

Guidance for use:

• Maintain neutral to mildly acidic conditions during non-deprotection steps; exclude moisture to prevent adventitious hydrolysis.
• For deprotection, employ NaOMe/MeOH, K2CO3/MeOH, or enzymatic cleavage (lipases/esterases) for selectivity; monitor closely by TLC/HPLC.
• Purification is typically achieved by flash chromatography (hexanes/EtOAc or DCM/EtOAc), buffering silica with a trace of acetic acid to minimize on-column deacetylation.

Target Specificity

Not applicable for this small-molecule reagent. No antibody/biologic target specificity, clone, isotype, or species reactivity is associated with this product.

Häufig gestellte Fragen

What is the purity of this product?

This product is supplied at ≥99% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?80 °C, protected from light. The material is light-sensitive — keep it in its original opaque or amber container.

How is this product shipped?

This product ships frozen with dry ice and cold packs. Unpack on arrival and transfer it to the storage condition stated above; handle dry ice with insulated gloves in a ventilated area.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 3682-04-0, the molecular formula is C21H18O8, and the molecular weight is 398.36 g/mol. InChIKey HQZXCNZZVRAEPO-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.