This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
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.
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Application Protocols
Not applicable. No bioassay or immunoassay protocols (WB, IHC, IF, FC, etc.) are associated with this small-molecule building block. For synthetic applications, refer to the Reaction & Applications and Reaction Conditions sections for general laboratory guidance.
Biological Roles
This product is supplied strictly for research use. No medical or clinical claims are made.
General biochemical perspective (literature/chemical reactivity based):
α,β-Unsaturated aldehyde/esters are electrophilic Michael acceptors that can react with nucleophilic residues in proteins (e.g., cysteine, lysine) in vitro, forming adducts; this underlies their use as chemical probes or for bioconjugation method development under controlled conditions.
Not known as a natural metabolite; rather, it is a synthetic intermediate modeled on conjugated carbonyl motifs common in nature (e.g., enals, enones).
The aldehyde can form reversible imines with primary amines (Schiff bases) under near-neutral aqueous-organic conditions, which can be trapped or reduced for stable linkages (research context).
Practical lab notes:
For any work in complex biological matrices, maintain low concentrations and quench residual electrophile (e.g., with excess thiol or amine scavenger) to prevent nonspecific modification.
Avoid high-pH buffers that can trigger aldol/self-condensation and polymerization.
Assess protein compatibility and off-target reactivity empirically; no target specificity is implied for this item.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare defined pH buffer systems. It is reactive toward nucleophiles and bases and can degrade in aqueous buffers.
Practical guidance if aqueous handling is unavoidable (general):
Use mixed aqueous–organic media with low water content and minimal base/acid to limit hydrolysis and polymerization.
For transient imine formation with biomolecules, employ mildly acidic to neutral conditions (pH ~5.5–7) and organic cosolvent (e.g., MeCN) with molecular sieves; promptly quench or reduce imines to stabilize.
For robust and defined buffering capacity, select dedicated buffers (e.g., phosphate, acetate, HEPES) instead.
Green Alternatives
As a reactive building block (not primarily a solvent), greenness considerations focus on solvent/catalyst choices and safer process design rather than replacing the reagent itself.
Greener process options (literature/general):
Solvent substitution: choose biorenewable or lower-toxicity solvents (2-MeTHF, CPME, EtOAc, propylene carbonate) over chlorinated solvents where compatible.
Catalysis: employ organocatalysts or earth-abundant metal catalysts for Michael additions and aldol/Wittig-type chemistry; avoid stoichiometric toxic reagents where possible.
Reductive steps: prefer transfer hydrogenation (e.g., HCO2H/Et3N, isopropanol–Ru) or electrosynthesis to minimize H2 handling and metal waste.
In-line inhibitor removal: rather than thermal distillation, use short inhibitor-scavenging columns at ambient temperature to reduce energy input.
Illustrative comparison (process choices):
Conventional: DCM solvent for reductive amination with NaBH3CN (cyanide waste, chlorinated solvent).
Greener: 2-MeTHF or EtOAc with hydrogenation over Pd/C (carefully controlled) or borohydride alternatives lacking cyanide; aqueous work-up minimized by solvent swapping.
Trade-offs:
Replacing DCM with greener ethers may alter selectivity/solubility; validate on small scale.
Some green solvents (e.g., alcohols) can promote acetalization/transesterification; protect or monitor for byproducts.
Note: No item-specific stabilizer or inhibitor content is provided; if present, account for their removal and disposal in process mass intensity (PMI) calculations.
Pharmaceutical Uses
No pharmacopeial or excipient status is provided for this item, and none should be inferred. It is offered for research use only.
General formulation/manufacturing context (literature/industry practice):
Role as a synthetic intermediate: The bifunctional aldehyde–acrylate motif enables convergent assembly of fragments en route to active pharmaceutical ingredient (API) candidates, especially where sequential aldehyde and Michael chemistries are leveraged.
Derivatization potential: The aldehyde can be converted to oximes/hydrazones or reduced to alcohols; the acrylate can be diversified via Michael addition or hydrogenation, facilitating SAR libraries.
Impurity control: For GMP development, residual monomer, polymer, and acetalization products require orthogonal analytical methods (GC, HPLC-UV, NMR). Stabilizer carryover (if any) should be qualified.
Caveats:
Not intended for human or veterinary use.
No claims of therapeutic activity, safety, or efficacy are made or implied.
Any use in regulated manufacturing would require independent qualification of specifications and vendor CoA.
Physical Properties
Item-specific specifications are not provided in the Product Data. Where appropriate, general/literature information is included for context only.
Item-specific (this listing):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties for methyl (E)-3-formylacrylate (reference only):
Physical state: typically a colorless to pale yellow, low- to mid-boiling liquid with a pungent aldehydic odor.
Functionality: bifunctional Michael acceptor (acrylate) and aldehyde; prone to self-aldol/polymerization under basic/acidic conditions.
Solubility: miscible with many polar aprotic organics (e.g., EtOAc, THF, MeCN); limited solubility in water; soluble in alcohols (literature).
Estimated parameters (for planning only; verify in primary sources/CoA):
• Formula (literature): C5H6O3
• MW (literature): ~114.10 g/mol
• Refractive index, density, bp/mp, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Practical notes:
The conjugated system can undergo polymerization; stabilizers are sometimes used commercially for related acrylates, but none are specified here.
Minimize exposure to moisture/base/acid and heat to retain monomeric purity.
Use amber glass and inert atmosphere to reduce peroxidation/oxidation of the aldehyde functionality.
Quality and Grades
Item-specific quality details are not listed in the Product Data for this SKU.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizer/ inhibitor: Not specified for this item; refer to CoA/Spec Sheet.
Water, peroxide, metal limits, acidity/alkalinity, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting possible grades (general guidance):
Research/technical grade (typical for building blocks) emphasizes assay by GC/1H NMR and limits for common impurities (residual solvents, aldehyde hydration/polymer content).
HPLC grade (when applicable to solvents) targets low UV absorbance; not typically relevant to reactive monomers such as this.
“Stabilized” lots (if present) may contain ppm-level radical inhibitor (e.g., MEHQ/BHT) to suppress polymerization; confirm presence/level on CoA if your synthesis is inhibitor-sensitive.
Quality control considerations for α,β-unsaturated aldehydes/esters (general):
Identity: 1H/13C NMR (diagnostic aldehyde singlet ~9–10 ppm; trans-olefinic coupling J typically ~15–16 Hz, literature), IR (νC=O ~1720–1740 cm−1 ester; ~1680–1720 cm−1 aldehyde), GC-MS.
Purity tracking: monitor for acetalization (in alcohols), hydration (gem-diol), aldol dimers, and polymeric tails by GC.
If trace inhibitors are present, a short alumina plug or washing protocol can remove them prior to use (validate to avoid product loss).
Reaction and Applications
Methyl Fumaraldehydate (literature synonym: methyl (E)-3-formylacrylate) is a versatile, bifunctional electrophile combining an aldehyde with an α,β-unsaturated ester. This enables orthogonal or sequential transformations.
Aldehyde-selective transformations:
• Reductive amination to β-aminated acrylates (NaBH3CN, H2/Pd, or borohydrides; protect C=C where needed).
• Wittig or HWE olefinations to extend the conjugated system; E-selective HWE conditions commonly favored.
• Aldol condensations/Knoevenagel couplings with stabilized methylenes (use mild base; manage competing Michael pathways).
Conjugate additions (Michael):
• Soft nucleophiles (thiols, malonates, amines) add at β-carbon; organocatalytic or base-catalyzed variants.
• Conjugate reduction to saturated aldehyde or further to alcohol (e.g., Stryker’s reagent or catalytic hydrogenation).
Cycloadditions:
• Acts as a potent dienophile in Diels–Alder reactions with electron-rich dienes; the pendant aldehyde enables subsequent diversification (e.g., intramolecular aldol, acetalizations).
Protecting group manipulations:
• Aldehyde can be trapped as acetals/oximes/hydrazones to direct selectivity toward the Michael acceptor.
Practical guidance:
Control chemoselectivity via protecting groups, solvent polarity, base/acid strength, and temperature.
In reactions sensitive to polymerization, include trace inhibitor scavenging steps immediately before use and run at lower concentrations.
For multistep telescoped sequences, sequence aldehyde chemistry before strongly basic Michael additions to minimize self-aldol.
Reaction Conditions
The following conditions are general literature guidance for aldehyde–acrylate substrates; adapt to your substrate and scale. Always run small-scale pilots.
Reductive amination (aldehyde):
• Solvent: MeCN, DCM, toluene, or 2-MeTHF; 3 Å sieves recommended.
• Reagents: amine (1.1–1.5 eq), AcOH (0–0.5 eq) to catalyze imine formation, then NaBH(OAc)3 or H2/Pd.
• Temp/time: 0–25 °C, 1–16 h.
• Notes: Monitor for conjugate addition of amine; using less basic amines and lower temperatures favors imine pathway.
Wittig/Horner–Wadsworth–Emmons (on –CHO):
• Solvent: THF or toluene, rigorously dry.
• Base: NaHMDS, t-BuOK, or K2CO3 (HWE, stabilized ylides).
• Temp: −78 to 25 °C; 1–6 h typical.
• Notes: E-selectivity common with HWE; avoid conditions promoting double addition/polymerization.
Michael additions (on acrylate):
• Nucleophiles: malonates, 1,3-dicarbonyls, thiols, secondary amines.
• Solvent: MeCN, DMF, or alcohols (careful—acetal/transesterification risk).
• Catalyst: tertiary amines, DBU, or organocatalysts (e.g., thioureas).
• Temp: 0–50 °C, 1–24 h.
• Notes: Use inert atmosphere; run dilute to suppress polymerization.
Diels–Alder (as dienophile):
• Diene: electron-rich (e.g., cyclopentadiene, Danishefsky’s diene).
• Solvent: toluene, CH2Cl2, or 2-MeTHF.
• Temp: 0–110 °C (thermal) or Lewis acid-mediated at lower T.
• Notes: Aldehyde may coordinate to Lewis acids; protect as acetal if needed.
Yields: Strongly substrate- and condition-dependent; consult primary literature for your transformation class.
Safety and Handling
Authoritative safety data are defined by the SDS. The following are general precautions for α,β-unsaturated aldehyde/ester reagents.
GHS/Regulatory (item-specific):
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 hazards (literature/analogous substances):
Likely causes skin/eye/respiratory irritation; aldehydes can be sensitizers.
α,β-Unsaturated systems are electrophilic and may alkylate biological nucleophiles; avoid exposure.
Combustible liquid; vapors may be irritating.
PPE and engineering controls:
Use in a certified fume hood. Wear safety glasses or splash goggles, nitrile gloves, and lab coat.
Avoid inhalation; consider respirator per institutional risk assessment if aerosol/vapor unavoidable.
Handling and incompatibilities:
Protect from air and moisture; store under inert gas (argon) as specified.
Incompatible with strong bases/acids (polymerization, aldol), strong oxidizers/reducers, amines, and nucleophiles.
Avoid prolonged heating and light exposure.
First aid (overview; defer to SDS):
Skin/eye contact: rinse with water for ≥15 min; remove contaminated clothing; seek medical attention.
Inhalation: move to fresh air; support breathing; seek medical attention.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Waste management:
Collect organic waste containing unsaturated aldehydes/esters in designated halogen-free organic waste; do not mix with strong base/acid in waste containers.
Solvent Selection
This compound is a low-molecular-weight, polar, conjugated aldehyde–acrylate expected to dissolve well in common organic solvents.
Polarity and miscibility (literature/general):
Good solubility: ethyl acetate, acetone, THF, DCM, toluene, MeCN; soluble in lower alcohols (risk of acetalization/transesterification under acidic/basic conditions).
Limited solubility in water; hydrolysis/polymerization risk increases in aqueous media.
Choosing a solvent by task:
Nucleophilic additions to the aldehyde (e.g., reductive amination): MeCN, DCM, or toluene with molecular sieves to suppress imine hydrolysis.
Conjugate (Michael) additions to the acrylate: polar aprotic solvents (DMF, DMSO, MeCN) to enhance nucleophile reactivity; or alcohols for phase/solubility control with careful base choice.
Wittig/Horner–Wadsworth–Emmons (HWE) at the aldehyde: THF or toluene under rigorously anhydrous, inert conditions.
Comparative notes:
THF vs 2-MeTHF: 2-MeTHF offers higher hydrophobicity and better water partitioning (green advantage); both solvate organometallics well.
DCM vs toluene: DCM provides better polarity for aldehyde chemistry at low temperatures; toluene is higher-boiling and less dense, facilitating phase separations.
Avoid prolonged residence in methanol/ethanol with acid/base catalysts to prevent acetalization or transesterification.
Practical tips:
Dry solvents (molecular sieves 3 Å for aldehyde chemistry) and maintain inert atmosphere to limit polymerization and hydration.
For moisture-sensitive sequences, pre-sparge with argon and conduct syringe/Schlenk transfers.
Storage and Reconstitution
Item-specific storage (from Product Data):
Store at 2–8 °C, argon charged.
Shipped on wet ice.
General handling guidance for α,β-unsaturated aldehyde/esters:
Keep tightly sealed under inert gas (argon) to minimize oxidation and polymerization.
Use amber containers or protect from light.
Minimize headspace and temperature cycling; consider aliquoting into septum vials for glovebox/Schlenk withdrawal.
If a stabilizer/inhibitor is present (not specified for this item), remove immediately before use (e.g., short alumina pass) and proceed without delay.
Reconstitution/use:
Typically supplied as a neat liquid or concentrated solution; if solidification/crystallization occurs at low temperature, gently warm to ambient under argon and swirl to homogenize.
For moisture-sensitive operations, pre-dry with 3 Å molecular sieves (if dissolved) and handle in a dry box or via syringe under inert atmosphere.
Shelf-life and QC:
Periodically check by GC or 1H NMR (aldehyde proton ~9–10 ppm; vinyl J ~15–16 Hz, literature) to confirm integrity.
Discard if significant polymerization, acetalization, or discoloration is observed.
Research use only.
Structure and Identity
Brief overview: This item name indicates an α,β-unsaturated bifunctional building block bearing both an aldehyde and an acrylate ester (commonly referred to in the literature as methyl (E)-3-formylacrylate, i.e., the methyl ester of fumaraldehydic acid).
SKU: M158237
Product Name: Methyl Fumaraldehydate
CAS: 5837-72-9 (literature assignment for methyl (E)-3-formylacrylate)
PubChem CID: 5364747 (literature)
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Literature structural depiction for the commonly cited isomer: COC(=O)/CH=CH/CHO (E-configured C=C)
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
• Literature (for methyl (E)-3-formylacrylate): C5H6O3
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Literature (for C5H6O3): ~114.10 g/mol
Structural features (literature description):
Contains an α,β-unsaturated carbonyl system (acrylate, strong Michael acceptor) conjugated to an aldehyde (–CHO) at the β′-terminus.
Functional groups: aldehyde, ester, and conjugated C=C (E-geometry commonly reported).
2D layout (words): a terminal aldehyde (–CHO) double-bonded to a vinyl carbon that is E to a vinylic proton adjacent to an ester carbonyl (–C(=O)–OMe).
Notes:
The exact stereochemistry/identifier for THIS catalog item is not specified in the Product Data; consult the Aladdin CoA/Spec Sheet for definitive identity markers used for release testing.
Synthetic Utility
Functional group ensemble and strategic value (literature):
α,β-Unsaturated ester: serves as a strong Michael acceptor, dienophile in Diels–Alder, and handle for conjugate reduction or hydrofunctionalization.
Conjugation: electronic activation enables cascade sequences; chemoselectivity can be tuned by protecting groups and conditions.
Typical transformations:
Reductive amination then Michael addition (two-directional diversification).
First Michael addition (e.g., with malonates or thiols), then aldehyde elaboration (e.g., intramolecular cyclizations, acetal-guided steps).
Wittig/HWE on the aldehyde to extend conjugation, followed by hydrogenation to access saturated frameworks.
Retrosynthetic logic:
Serves as a masked 3-carbon synthon bearing differentiated termini: an aldehyde terminus and an ester terminus.
Useful in assembling α-substituted propionate motifs, cinnamaldehyde analogs, and heterocycle precursors via cycloaddition followed by functional group interconversions.
Practical pointers:
To avoid self-aldol/polymerization, run at lower concentrations, under inert gas, and add base catalysts last.
If inhibitor is present (not specified here), remove just-in-time via basic alumina or inhibitor scavengers to minimize repolymerization risk.
Target Specificity
Not applicable. This product is a small-molecule chemical building block, not a biological targeting reagent (e.g., antibody, enzyme inhibitor with defined biological target, or probe with validated selectivity). No item-specific target, epitope, clone, or species reactivity is provided or implied.
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