This compound belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.
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
Not applicable. No validated immunoassay or cell-based application protocols are provided for this small-molecule reagent in the Product Data. For synthetic or analytical use, refer to the Reaction Conditions and Synthetic Utility sections for general guidance, and consult peer-reviewed procedures tailored to your transformation.
Biological Roles
This product is intended for research use only. No clinical or therapeutic claims are made.
General/literature context
Cinnamaldehyde scaffolds are common in plant secondary metabolites, contributing to aroma and defense chemistry. Substituents such as methoxy and acetoxy tune lipophilicity and electrophilicity of the Michael acceptor (α,β-unsaturated aldehyde) moiety.
The conjugated enal can react with biological nucleophiles (e.g., thiols) in model systems, a property often exploited in chemical biology probes to study redox signaling and covalent ligand interactions. Such reactivity must be handled cautiously to avoid nonspecific modification.
Phenyl acetates can hydrolyze enzymatically to phenols; in vitro, esterases may convert acetoxy groups to hydroxy groups, altering polarity and binding in biochemical assays (general observation for aryl acetates).
Experimental planning notes
For biochemical assays, prepare fresh solutions to limit aldehyde oxidation; include appropriate scavengers or controls to distinguish covalent adduct formation from specific binding.
Validate stability of the compound in assay buffers; the aldehyde can hydrate or form imines with amine-containing buffers (see Buffer Applications).
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare pH buffer systems.
Practical lab notes (general)
Avoid primary amine buffers (e.g., Tris, glycine, HEPES contains tertiary amine but still nucleophilic to some extent) with aldehydes, as imine or enamine formation can occur, altering effective concentration.
If aqueous work is required, use minimal aqueous-organic mixtures (e.g., 5–20% water in acetonitrile or ethanol) and add the compound last. Phosphate or acetate buffers (pH 5–7) are less nucleophilic but can still promote hydrolysis of the acetoxy group under basic conditions; keep to mildly acidic/neutral pH and low temperature.
For spectroscopic measurements, non-nucleophilic buffers and high organic content mobile phases are preferable to preserve the aldehyde integrity.
Green Alternatives
Solvent and process choices (literature/guidance)
Replace chlorinated solvents: use ethyl acetate or 2-MeTHF instead of DCM where kinetics allow; both dissolve this substrate well and are preferable from an EHS perspective.
Prefer bio-derived ethers: 2-MeTHF can substitute for THF in many nucleophilic additions and reductions, offering higher boiling point and improved phase behavior.
Aqueous-organic media: for imine/oxime formation, ethanol or isopropanol with catalytic acid and molecular sieves can minimize hazardous solvent use.
Comparison (general)
DCM vs EtOAc: EtOAc is biodegradable, lower toxicity; DCM offers superior low-temp performance but with higher environmental/health burdens.
THF vs 2-MeTHF: 2-MeTHF has better sustainability metrics (often from hemicellulose), lower peroxide formation rate, and easier separations; THF remains slightly more polar and sometimes enhances rates/selectivity.
NaBH4 vs catalytic hydrogenation: for selective C=O reduction, NaBH4 in green alcohols (EtOH, iPrOH) may avoid high-pressure H2; conversely, catalytic hydrogenation can minimize salt waste when feasible.
Waste minimization
Use catalytic rather than stoichiometric reagents where possible (e.g., organocatalytic Michael additions).
Implement solvent recycling (rotovap recovery) and micro-scale optimization to reduce E-factor prior to scale-up.
Pharmaceutical Uses
No pharmacopeial grade or excipient designation is specified for this item; refer to CoA/Spec Sheet.
General formulation context (non-clinical, literature)
Aromatic aldehydes are occasionally used in discovery chemistry as intermediates toward drug-like scaffolds. The acetoxy and methoxy substituents can modulate lipophilicity and metabolic liability, while the aldehyde serves as a versatile synthon for generating libraries (e.g., via reductive amination, Knoevenagel condensations).
Due to the electrophilic aldehyde/Michael acceptor, such compounds are typically avoided as final drug substances unless specifically designed as covalent modifiers. They are, however, valuable in medicinal chemistry campaigns for SAR exploration.
Handling in formulation development (research only)
If used in preformulation studies, protect from oxidation (argon headspace, antioxidants if compatible) and from hydrolysis of the acetoxy group. Evaluate stability in chosen vehicles (PEGs, ethanol, polysorbates) as aldehydes can react with excipient nucleophiles.
Physical Properties
Item-specific specs
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general values and expectations (for guidance; not item specifications)
Phase: typically a pale solid or viscous oil for substituted cinnamaldehydes; exact state depends on purity and temperature.
Molecular weight: ~222.24 g/mol (from C12H14O4)
Solubility: sparingly soluble in water; soluble in common organic solvents (EtOH, MeOH, acetone, acetonitrile, DCM, ethyl acetate, toluene) due to aromatic and ester functionality; good solubility in DMSO (literature, qualitative).
Polarity/partition: expected moderate hydrophobicity (logP likely in the 2–3 range; literature estimates for analogous methoxy/acetoxy cinnamaldehydes). Exact value not specified for this item.
UV–Vis: strong π→π* absorption in the near-UV due to conjugated aryl–enal chromophore; specific maxima not specified for this item.
Boiling and melting points: Not specified for this item; refer to CoA/Spec Sheet. For planning, substituted cinnamaldehydes often show mp in the 40–90 °C range if crystalline, or boil/decompose >250 °C under reduced pressure (literature, general).
Refractive index/density: Not specified for this item; refer to CoA/Spec Sheet.
Note: Use literature values only as planning guidance; confirm with the product’s CoA for assay-specific parameters.
Quality and Grades
Item-specific details
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting grades (general guidance)
Research/technical grade: suitable for most synthetic and exploratory research; impurity profiles may include trace solvents or isomers.
Purified/assay grades (e.g., ≥95%, ≥98%): indicate tighter control of organic impurities, lower residual solvents, and often LC/HPLC verification. For conjugated aldehydes, higher grades reduce background in spectroscopic assays and minimize side reactions (e.g., polymerization seeds).
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Some aldehydes are shipped under inert gas or with trace acid/base inhibitors; your item is specified as argon-charged (see Storage), which helps limit oxidative degradation.
Documentation and release testing
Request CoA for batch-specific assay, residual solvent profile, and identity confirmation (e.g., 1H/13C NMR, IR C=O ~1670–1690 cm−1 for enal; IR ester C=O ~1730–1750 cm−1; MS [M+H]+ ~223, literature).
For chromatographic work, ask about UV cutoffs and baseline characteristics; if not available, pre-screen with your method.
Choose grade according to your application’s sensitivity to trace acids, peroxides, and isomers; confirm with the current batch CoA.
Reaction and Applications
Functional reactivity (general/literature)
Aldehyde handle: supports imine/oxime/hydrazone formation, reductive amination (on the aldehyde), acetalization, and nucleophilic additions (e.g., cyanohydrin formation).
Conjugated enal: undergoes 1,4-additions (Michael additions) with soft nucleophiles and selective hydrogenations; participates in Horner–Wadsworth–Emmons (as acceptor) and Diels–Alder as a dienophile in some systems.
Aryl acetate: can be hydrolyzed to the corresponding phenol (4-hydroxy-3-methoxy-) enabling onward O-alkylation, O-arylation, or cross-couplings after conversion to aryl triflate/halide.
Methoxy group: directs electrophilic aromatic substitution (EAS) and stabilizes the conjugated system; can be demethylated (e.g., BBr3) to access catechol-like motifs.
Synthesis of substituted stilbenes and cinnamyl derivatives via Wittig/HWE olefination using this aldehyde as electrophile.
Formation of enamines/imines followed by cyclizations to access heterocycles (e.g., dihydropyridines by Hantzsch-type condensations with β-dicarbonyls and ammonia sources).
Michael additions with thiols or malonates to the α,β-unsaturated system, furnishing β-substituted aldehydes.
Reductive transformations: chemoselective reduction of the aldehyde to allylic alcohol (e.g., NaBH4/MeOH) or full saturation (H2, Pd/C) as needed; careful control prevents over-reduction of the double bond.
Practical notes
Maintain inert atmosphere (argon, as shipped) to limit oxidation/polymerization.
Avoid strong base at elevated temperatures to prevent transesterification and self-condensation.
Reaction Conditions
All values below are literature/general guidance for cinnamaldehyde-type substrates; they are not specifications for this item.
Imine/oxime formation
Solvent: EtOH, iPrOH, toluene, or MeCN; add 3 Å molecular sieves or use Dean–Stark in toluene.
Catalyst: AcOH (0.1–1 equiv) or p-TsOH (1–10 mol%).
Temperature/time: RT to 80 °C, 1–16 h. Typical conversions: high with water removal.
NaBH4 reduction (to allylic alcohol)
Solvent: MeOH, EtOH, or THF/MeOH mixtures; 0–25 °C.
Reagent: 1.1–2.0 equiv NaBH4; quench cautiously.
Selectivity: preferential C=O reduction; minimize prolonged times to avoid over-reduction.
Catalytic hydrogenation
Catalyst: Pd/C (5–10 wt%), H2 (1–3 bar).
Solvent: EtOH, EtOAc, or MeOH.
Outcome: sequential C=C, then C=O reduction depending on time/pressure; monitor closely.
Wittig/HWE olefination
Solvent: THF or toluene under inert atmosphere.
Base: n-BuLi or NaH for ylide/phosphonate generation.
Temperature: −78 to 25 °C; 1–6 h; typical good to excellent yields with stabilized ylides (E-selective).
Hydrolysis of acetoxy (to phenol)
Conditions: K2CO3 or Na2CO3 in MeOH/THF/H2O, 0–25 °C; or acid-catalyzed (HCl, aq. MeOH) at mild temperatures.
Note: protect aldehyde (e.g., acetal) if prolonged basic or acidic conditions are required.
Oxidation of aldehyde
Pinnick oxidation: NaClO2, NaH2PO4 buffer, t-BuOH/H2O; RT; 1–3 h to give acid with minimal C=C scrambling.
Safety and Handling
Item-specific hazard information (from Product Data)
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 safety considerations for aromatic α,β-unsaturated aldehydes and aryl acetates (literature/general)
Likely hazards: combustible liquid/solid; skin and eye irritation; may cause respiratory irritation; aldehydes can be sensitizers in susceptible individuals. Avoid inhalation of vapors and contact with skin/eyes.
PPE: lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood.
Incompatibilities: strong bases (can induce aldol/self-condensation or transesterification), strong acids (hydrolysis of acetoxy; polymerization), strong oxidizers (oxidation of aldehyde), strong reducing agents (reduce C=C/CHO). Avoid amines and nucleophiles that can form imines/Schiff bases without control.
First aid (overview; defer to SDS): rinse eyes/skin with water for ≥15 min upon contact; remove contaminated clothing; if inhaled, move to fresh air; if ingested, seek medical attention. Provide SDS to responders.
Stability notes: aldehydes can undergo oxidation to acids and polymerization; phenyl acetate can hydrolyze under moisture/heat. Minimize exposure to air and moisture; keep container tightly closed.
Always consult the product SDS for authoritative hazard classification and response measures.
Solvent Selection
Polarity and miscibility (general)
The compound is moderately nonpolar with polar functional groups; it is soluble in many organic solvents (EtOH, MeOH, acetone, acetonitrile, DMSO, DMF, DCM, EtOAc, toluene) and poorly soluble in water (literature, qualitative).
For moisture-sensitive transformations (e.g., Wittig, enamine formation), use rigorously dried, oxygen-free solvents.
Choosing solvents by task
Nucleophilic additions/reductions to the aldehyde: dry THF, 2-MeTHF, or toluene are typical; DCM for mild hydride donors (NaBH(OAc)3 won’t reduce aldehyde; NaBH4 needs protic solvent mixtures).
Imine/oxime formation: EtOH, MeOH, toluene, or acetonitrile with azeotropic water removal (Dean–Stark in toluene) or molecular sieves.
Ester stability: limit prolonged exposure to strong protic/basic solvents to avoid transesterification/hydrolysis.
Chromatography: normal-phase silica with hexanes/EtOAc or DCM/MeOH gradients separates E/Z side products and deprotected phenols. Protect aldehyde from air during workup to minimize over-oxidation.
Comparison snapshot (literature/guidance)
THF vs 2-MeTHF: 2-MeTHF offers better phase separation and greener profile; both dissolve this substrate well.
DCM vs EtOAc: DCM affords fast reactions at low temp; EtOAc is a greener eluent and often adequate for extractions and column elution.
Storage and Reconstitution
Item-specific storage and shipping (from Product Data)
Keep tightly sealed under inert gas (argon or nitrogen) to limit oxidation of the aldehyde and hydrolysis of the acetoxy group. Store in amber glass away from strong light and moisture.
For long-term storage, consider refrigeration (2–8 °C) as a precaution if compatible with your workflow; allow to warm to ambient before opening to avoid condensation. Verify with CoA/SDS for any temperature constraints.
Reconstitution and solution handling (general)
Prepare stock solutions fresh in dry organic solvents (e.g., DMSO, acetonitrile, ethanol, THF). Typical research stocks: 10–100 mM depending on application. Filter through PTFE (0.2 μm) if particulate is present.
Avoid aqueous basic media and primary amine buffers; if aqueous work is required, limit exposure time and maintain mildly acidic to neutral pH.
Minimize freeze–thaw: aliquot solutions and store under inert atmosphere at low temperature where appropriate. Monitor by TLC/LC–MS for degradation (look for carboxylic acid oxidation or deprotected phenol).
Structure and Identity
Brief description: 4-Acetoxy-3-methoxycinnamaldehyde is an aryl cinnamaldehyde bearing meta-methoxy and para-acetoxy substituents on the phenyl ring; the side chain is an α,β-unsaturated aldehyde (cinnamylidene) conjugated to the ring.
Item-specific (from Product Data)
SKU: A467427
CAS: 83071-67-4
InChIKey: 376901 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers (for reference only; not item specifications)
Molecular formula (literature, inferred): C12H14O4
Molecular weight (literature, calculated from formula): ~222.24 g/mol
The benzene ring bears a methoxy group at the 3-position and an acetoxy substituent at the 4-position relative to the cinnamaldehyde side chain.
The side chain is trans-disubstituted in typical cinnamaldehyde derivatives, providing conjugation across the aryl–vinyl–carbonyl system.
Electron-donating methoxy and electron-withdrawing acetoxy substituents modulate ring electronics and reactivity of the enal.
Synthetic Utility
Retrosynthetic value (literature/general)
The aldehyde enables access to diverse analogs via C=O transformations: imines, oximes, hydrazones, cyanohydrins, and alcohols (selective reduction). It also serves as an electrophile in Wittig/Horner–Wadsworth–Emmons to extend conjugation or install substituted olefins.
The α,β-unsaturated system participates in 1,4-additions providing β-functionalized aldehydes, which can be further oxidized (to acids) or reduced (to alcohols) with orthogonal selectivity.
The aryl acetate can be deprotected to phenol, enabling cross-coupling handles via conversion to aryl triflates, or further O-functionalizations (ethers, carbonates, carbamates).
Named reactions and pathways
Knoevenagel condensations with active methylenes to give extended cinnamates/cinnamides.
Wittig or HWE olefination on the aldehyde to create trans-styryl systems.
Henry (nitroaldol) reaction to introduce β-nitro alcohols (followed by Nef or reductions).
Baeyer–Villiger not applicable directly; however, the aryl acetate can undergo solvolysis/hydrolysis; aldehyde can be oxidized to acid (Pinnick) or alcohol (NaBH4).
Selectivity tips
Use chemoselective reagents (e.g., NaBH4 reduces C=O faster than C=C; Stryker’s reagent or conjugate-selective catalysts target C=C). Protect aldehyde as acetal if conducting base-promoted aromatic substitutions.
Target Specificity
Not applicable. This product is a small-molecule research chemical, not a biologic or affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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