Eicosyl ferulate , CAS No.133882-79-8

CAS: 133882-79-8 Cat. No.: E1023837 PubChem CID: 6440080

Storage

Room temperature

Specifications

保管条件

Room temperature

名前と識別子

• カノニカル・スマイル: CCCCCCCCCCCCCCCCCCCCOC(=O)C=CC1=CC(=C(C=C1)O)OC
• IUPAC Name: icosyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• InChIKey: UBNJQWYYWIBSGN-ZNTNEXAZSA-N
• INCHI: 1S/C30H50O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25-34-30(32)24-22-27-21-23-28(31)29(26-27)33-2/h21-24,26,31H,3-20,25H2,1-2H3/b24-22+
• 異性体SMILES: CCCCCCCCCCCCCCCCCCCCOC(=O)/C=C/C1=CC(=C(C=C1)O)OC
• 代替CAS番号: 64190-82-5
• PubChem CID: 6440080

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • 分類 Cinnamic acids and derivatives
      • Subclass Hydroxycinnamic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• 分類: Cinnamic acids and derivatives
• Subclass: Hydroxycinnamic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Coumaric acids and derivatives
• Alternative Parents: Fatty alcohol esters Cinnamic acid esters Methoxyphenols Styrenes Phenoxy compounds Methoxybenzenes Anisoles Fatty acid esters Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Enoate esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Coumaric acid or derivatives - Fatty alcohol ester - Cinnamic acid ester - Methoxyphenol - Anisole - Phenoxy compound - Phenol ether - Styrene - Methoxybenzene - Phenol - Alkyl aryl ether - Fatty acid ester - 1-hydroxy-2-unsubstituted benzenoid - Fatty acyl - Benzenoid - Monocyclic benzene moiety - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Carboxylic acid ester - Ether - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organooxygen compound - Carbonyl group - Organic oxide - Hydrocarbon derivative - Organic oxygen compound - Aromatic homomonocyclic compound
• 説明: This compound belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
• 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

化学的性質と物理的性質

• 分子量: 474.700 g/mol
• XLogP3: 11.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 23
• Exact Mass: 474.371 Da
• Monoisotopic Mass: 474.371 Da
• Topological Polar Surface Area: 55.800 Ų
• Heavy Atom Count: 34
• Formal Charge: 0
• Complexity: 490.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Application Protocols

No vendor-tested bioassay protocols are specified for this item; refer to CoA/Spec Sheet. As a small molecule, typical “WB/IHC/IF/FC” style protocols do not apply.

General literature-based handling suggestions:

• Stock preparation: 10–50 mg/mL in chloroform, ethyl acetate, or DMSO. Filter if needed using PTFE membranes.
• Enzymatic assays: Deliver via minimal DMSO (<1–2% v/v final) or emulsify with nonionic surfactants. Include vehicle controls due to strong UV absorbance.
• Thin-film studies: Cast from EtOAc or CHCl3 onto substrates; evaporate under nitrogen; condition films in the dark to constant mass.

Always validate conditions in your laboratory context and consult the SDS before designing experiments.

Biological Roles

This product is supplied strictly for research use only.

Literature context for ferulate esters:

• Plant biochemistry: Alkyl ferulates occur in the suberin and cuticular wax fractions of plant cell walls, where long-chain ferulate esters contribute to barrier properties and oxidative stability. The ferulate moiety can also form radical-mediated cross-links with polysaccharides and lignin-related phenolics.
• Pro-phenolic behavior: Alkyl ferulates can act as pro-forms of ferulic acid; enzymatic or chemical hydrolysis releases ferulic acid, a phenolic antioxidant, enabling studies of controlled release into lipid phases or emulsions.
• Membrane/lipid interactions: The long aliphatic chain embeds in lipid bilayers or oil phases, positioning the ferulate chromophore at the interface, a geometry useful for probing interfacial radical chemistry.
• Enzymology: Substrates for lipases/esterases (e.g., Candida, porcine, or microbial enzymes) to compare chain-length preferences, turnover numbers, and regioselectivity.

No medical or clinical claims are made. Any discussion of biological behavior is for mechanistic or analytical research only. If biological assays are planned, ensure appropriate solvent vehicles (e.g., minimal DMSO) and controls for UV-absorbing compounds, as ferulate chromophores can interfere with spectrophotometric readouts.

Buffer Applications

Eicosyl ferulate is a hydrophobic neutral ester and does not function as a buffering agent. It is essentially insoluble in water and lacks ionizable groups in the working pH range. Consequently, there are no standard buffer recipes or buffering roles for this compound.

Practical note: When introducing eicosyl ferulate into aqueous systems (e.g., enzyme assays), use an appropriate co-solvent (small volumes of DMSO or ethanol) and/or formulate as emulsions or micelles with nonionic surfactants in a separate buffered medium selected for the biological system (e.g., phosphate, Tris). Optimize the delivery vehicle independently of the buffer.

Green Alternatives

While eicosyl ferulate itself is the target analyte/reagent, greener choices primarily concern the solvent system and processing aids used with it.

Greener solvent substitutions (literature guidance):

• Replace dichloromethane/chloroform with ethyl acetate or 2-methyltetrahydrofuran (2-MeTHF) for dissolution, film casting, or extraction.
• For nonpolar media, favor heptane over hexane (lower toxicity, similar solvency), or employ bio-based isoparaffins.
• For high-boiling aromatic solvents (toluene/xylene), consider anisole or p-cymene as higher-T, lower-toxicity aromatics depending on application.

Comparison (general, literature):

• Chlorinated solvents vs. EtOAc/2-MeTHF:
  • Environmental: chlorinated > worse; EtOAc/2-MeTHF > better
  • Solvency for ferulate esters: all good; minor adjustments in concentration may be needed
  • Workup: EtOAc/2-MeTHF simplify aqueous workups and waste segregation

Process considerations:

• Use room-temperature operations when possible (low vapor pressure of the solute already aids handling).
• Implement closed-vessel photochemistry with LED sources (energy-efficient, narrowband) for cinnamate reactions.
• Explore biocatalytic transesterification/hydrolysis (lipases in green solvents or solvent-free systems) to adjust chain length while reducing hazardous reagents.

Note: Selection should be balanced against performance, regulatory constraints, and downstream analytical requirements.

Pharmaceutical Uses

No pharmacopeial or excipient grade is specified for this item; refer to CoA/Spec Sheet. The following are general, literature-based research contexts without therapeutic claims:

• Oil-phase antioxidant/UV-absorbing additive: The ferulate chromophore provides UV absorption and radical-scavenging potential, while the C20 tail promotes retention in hydrophobic excipient matrices (oils, waxes). Useful for formulation research on oxidative stability of lipid vehicles.
• Pro-phenolic in lipid systems: Serves as a model for controlled release of ferulic acid via enzymatic or chemical hydrolysis in emulsions or semi-solids.
• Film/coating component: Long-chain cinnamate esters can enhance hydrophobicity and film formation; explored in coating systems and packaging materials research.

Regulatory note: This listing is for research use only. It is not intended for human or veterinary use, not a drug substance, and not certified to any pharmacopeial monograph. For any development work, establish material specifications (identity, impurities, residual solvents, stabilizers) independently and confirm compatibility with other excipients by stress testing (light/heat/oxidants).

Physical Properties

• Appearance: Not specified for this item; refer to CoA/Spec Sheet. (Long-chain alkyl ferulates are typically waxy solids at ambient temperature; literature expectation.)
• Molecular Weight: ~474.72 g/mol (literature, from C30H50O5)
• Molecular Formula: C30H50O5 (literature)
• Boiling point / Decomposition: Not specified for this item; refer to CoA/Spec Sheet. (Long-chain esters commonly decompose before boiling at 1 atm; literature.)
• Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Waxy ferulate esters often melt between ~40–70 °C depending on chain packing; literature.)
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable for solids; if molten/oil phase is measured, value not specified for this item.
• LogP: High (strongly lipophilic; qualitative, literature for C20 aliphatic esters).
• pKa: Not applicable (no free acid; phenolic proton is blocked as –OMe; literature).
• Solubility (qualitative, literature):
  • Water: essentially insoluble.
  • Organic solvents: good solubility in nonpolar/aprotic media (e.g., hexane, toluene, chloroform, dichloromethane, ethyl acetate). Variable solubility in alcohols; generally soluble in hot ethanol/isopropanol. Soluble in DMSO.

Important: All numeric item-specific specifications (mp, bp, density, UV cutoff, trace impurities) are Not specified for this item; refer to CoA/Spec Sheet. Use literature values only for preliminary planning and confirm with small-scale trials.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Ferulate esters generally do not require inhibitors; protection from light/oxygen is a best practice (literature).

Interpreting common grades (general guidance):

• Analytical/AR grade: Tight controls on inorganic/organic impurities; suitable for analytical workflows.
• Synthesis grade: Suitable for preparative chemistry; trace UV-absorbing/bg components may be higher than HPLC grade.
• HPLC grade (solids): For UV-sensitive applications, low background absorbance upon dissolution; certified low residue on evaporation.

Item-specific considerations for eicosyl ferulate:

• The conjugated cinnamate chromophore gives strong UV absorbance (near 320–330 nm; literature), so low-UV impurities are important for spectroscopic experiments.
• Water content and residual solvents can influence hydrolytic stability and crystallinity; these are Not specified for this item; refer to CoA/Spec Sheet.
• Long-chain esters can exhibit polymorphism/semicrystalline behavior; melting characteristics may vary with thermal history (literature). If crystallinity is critical (e.g., materials science), request detailed thermal analysis from the CoA.

Always rely on the shipped batch’s Certificate of Analysis for exact assay, impurity profile, and recommended analytical methods.

Reaction and Applications

As a long-chain ferulate, eicosyl ferulate serves both as a model substrate and a functional material incorporating the antioxidant ferulate motif into hydrophobic matrices.

Representative research applications (literature):

• Model for ester hydrolysis and lipase specificity: Useful for studying enzymatic saponification and chain-length effects in esterase/lipase-catalyzed reactions.
• Antioxidant delivery into lipids: The ferulate chromophore (phenolic methoxy-substituted cinnamate) can scavenge radicals; the C20 tail anchors it in oils, surfactant micelles, and polymer films for oxidative stability testing in materials/food chemistry.
• Photochemical studies: Cinnamate esters undergo [2+2] photodimerization and E/Z isomerization under UV; the long alkyl chain influences film morphology and photoreactivity.
• Polymer and surface modification: Transesterification or grafting onto polymer backbones generates ferulate-functional materials with UV-absorbing and antioxidant properties.
• Metathesis and hydrogenation models: The α,β-unsaturated ester can participate in cross-metathesis (Grubbs/Ru catalysts) and selective hydrogenation to the saturated ester (literature conditions).

Practical tips:

• Dry, neutral conditions help minimize background hydrolysis in solution. Include BHT or work under inert gas if oxidative stability is a concern (general best practice; not item-specific).
• For photochemical work, standardize path length and light dose due to strong UV absorbance of the ferulate chromophore.
• For enzymatic assays, prepare stock solutions in minimal DMSO or emulsify with nonionic surfactants to ensure consistent substrate delivery.

Reaction Conditions

Representative literature-style conditions for the ferulate framework (optimize for your setup; verify by small-scale trials):

• Saponification (to ferulic acid + eicosanol): KOH or NaOH (1–2 equiv) in EtOH/H2O or THF/MeOH, 25–60 °C, 1–4 h. Quench into water, extract alcohol, acidify aqueous to pH ~2 to precipitate ferulic acid. Typical yields: high for both fragments with careful phase handling.
• Enzymatic hydrolysis: Lipase (e.g., Candida antarctica B) in biphasic buffer/organic or solvent-free at 30–50 °C; monitor by HPLC/UV (λ ~320–330 nm, literature for ferulates).
• Hydrogenation of C=C: 5–10 wt% Pd/C (1–5 mol% Pd relative to substrate), H2 (1–3 bar), EtOAc, EtOH, or heptane/EtOAc mixtures, 20–40 °C, 1–6 h. Work under subdued light to limit isomerization.
• Cross-metathesis: 2–5 mol% Hoveyda–Grubbs II, toluene or DCM (0.05–0.2 M), 40–60 °C, 2–12 h; remove ethylene under slight vacuum/inert sweep if needed. Additives (CuI) can suppress isomerization (literature practice).
• Photodimerization: UV-A (320–365 nm), degassed films or solutions in nonpolar solvents, 0.1–1 mM, 10–60 min; monitor by UV–vis and LC–MS for dimer formation vs E/Z isomerization.

Analytics and workup:

• Use UV–vis (ferulate band near 320–330 nm, literature) and HPLC with nonpolar stationary phases. Avoid strongly basic silica unless neutralized; ferulate esters can tail under acidic conditions. Protect from intense light during chromatography.

Safety and Handling

• GHS Classification / Signal Word / H-Statements / Pictograms: Not specified for this item; refer to the product SDS for authoritative safety information.

General safety guidance for long-chain aromatic esters (literature-based):

• Hazards: Typically low volatility and low acute inhalation hazard; can cause skin/eye irritation on contact. Dust generation is minimal for waxy solids but avoid aerosolization. Not classified as a peroxide former.
• Incompatibilities: Strong oxidizers; strong bases and acids can induce saponification or hydrolysis. Avoid prolonged exposure to high heat and strong UV which may promote oxidation or E/Z isomerization of the cinnamate double bond.
• PPE: Lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a chemical fume hood when weighing/dissolving to prevent exposure to solvent vapors.
• Handling tips:
  • Warm gently (30–40 °C) to facilitate transfer if waxy/solid.
  • Use dry glassware/solvents if hydrolysis-sensitive operations are planned.
  • Minimize light exposure; cinnamate chromophores strongly absorb UV.
• First aid (overview; consult SDS):
  • Skin: Wash with soap and water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; seek medical advice if irritation persists.
  • Ingestion/Inhalation: Rinse mouth; move to fresh air; obtain medical attention as needed.
• Waste: Dispose according to institutional and local regulations for non-halogenated organic chemicals. Segregate from oxidizers and caustics.

Solvent Selection

Eicosyl ferulate is highly hydrophobic with a single polar ester linkage and aromatic headgroup; dissolution favors nonpolar and moderately polar organic solvents.

• Polarity class: Nonpolar to weakly polar solute; favors apolar organic media (literature).
• Recommended solvents (literature): hexane, heptane, toluene, xylene, chloroform, dichloromethane, ethyl acetate; soluble in DMSO and hot alcohols (ethanol, isopropanol). Poorly soluble in acetonitrile and extremely poor in water.
• Dielectric context: Choose solvents with low-to-moderate dielectric constants (ε ~2–10) to maximize solubility of the C20 chain while accommodating the ester/aryl headgroup.
• When to choose which:
  • Hexane/heptane: nonpolar environments, lipid blending, crystallization control.
  • Toluene/xylene: higher boiling for thermal reactions or photochemistry in aromatic media.
  • CH2Cl2/CHCl3: rapid dissolution, room-temperature processing, thin-film casting.
  • Ethyl acetate: greener alternative to chlorinated solvents with good solvency for cinnamate esters.
  • DMSO: small-volume stock solutions for bioassays or antioxidant tests (then dilute into lipid phase or emulsions).

Comparison (literature):

• Eicosyl ferulate vs. Ethyl ferulate: The C20 ester shows markedly lower polarity and higher oil-phase affinity; choose the eicosyl ester to maximize lipophilicity, film formation, and compatibility with waxy matrices; choose shorter esters for higher volatility/solubility in polar media.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature (per Product Data). Store in a tightly closed container, dry environment, and protect from light to preserve the cinnamate chromophore. Avoid prolonged exposure to heat and air.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution/solubilization (literature guidance):
  • Prepare stock solutions in chloroform, dichloromethane, ethyl acetate, toluene, heptane, or DMSO. Warm gently (≤40 °C) if needed to aid dissolution.
  • For aqueous systems, deliver via co-solvent (DMSO/EtOH) at minimal percentages or as emulsions with nonionic surfactants.
• Freeze–thaw: Not typically applicable for a solid/waxy ester. If solutions are prepared, store aliquots to minimize repeated freeze–thaw; keep light-protected amber vials.
• Shelf-life considerations: No item-specific shelf-life is provided. As a best practice, monitor by HPLC/UV for signs of oxidation or isomerization over time, especially in solution. Use inert atmosphere for long-term solution storage.

For exact specifications (appearance, purity, stabilizers, residual solvents), consult the CoA/Spec Sheet accompanying your lot.

Structure and Identity

Eicosyl ferulate is a long-chain alkyl ester of ferulic acid, comprising a C20 linear alkyl group (eicosyl) linked via an ester to the trans-cinnamate scaffold bearing 3-methoxy and 4-hydroxy substituent patterns typical of ferulic acid derivatives.

• CAS: 133882-79-8
• SKU: E1023837
• CID (PubChem): 6440080 (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: C30H50O5 (literature, eicosyl ester of ferulic acid)
• Molecular Weight: ~474.72 g/mol (literature, calculated from formula)
• Category: Small molecules and compound library (小分子和化合物库)

Structural features (descriptive):

• Core motif: trans-3-methoxy-4-hydroxycinnamate (ferulate) linked to an eicosyl (C20H41) chain through the carboxylate as an alkyl ester.
• Functional groups: aryl methoxy, phenolic ether (–OMe), conjugated alkene (–CH=CH–) with E-geometry (typical for ferulates; literature), and an aliphatic long-chain (hydrophobic) segment.
• 2D description: a substituted anisole ring (1,3-disubstitution by –OMe and –O–C(=O)–CH=CH–), where the ester carbonyl connects to a linear C20 alkyl tail. The molecule is amphiphilic in a broad sense (polar ester/aryl headgroup, nonpolar C20 tail) but overall highly hydrophobic.

Notes:

• Where registry identifiers (InChIKey/SMILES) are needed for informatics, consult the product CoA/Spec Sheet or PubChem CID for literature reference. Product-specific identity testing is covered by Aladdin’s QC release criteria.

Synthetic Utility

Eicosyl ferulate integrates a conjugated α,β-unsaturated ester with a C20 alkyl chain, offering a versatile platform for transformations and materials design (literature):

• Hydrogenation: Selective reduction of the C=C affords saturated eicosyl 3-methoxy-4-hydroxyphenethyl ester (retaining the ester). Conditions: Pd/C or Pd(OH)2/C, H2, ambient–50 psi, EtOAc or ethanol; monitor to avoid over-reduction.
• Cross-metathesis: The cinnamate double bond participates in Ru-catalyzed metathesis to diversify the side chain; solvent choices include toluene or DCM, 30–60 °C, Grubbs II or Hoveyda–Grubbs II.
• [2+2] Photodimerization: Typical of cinnamates under UV (300–365 nm), enabling dimeric structures and cross-linked networks in films.
• Transesterification/Interfacial polymerization: Exchange with polyols or diols (chemical or lipase-catalyzed) to introduce ferulate motifs into polyesters, urethanes, or alkyds; the long chain aids hydrophobicity and film properties.
• Saponification/Hydrolysis: Base- or enzyme-catalyzed cleavage yields ferulic acid and eicosanol, enabling access to the acid for further coupling strategies (e.g., amide formation) while recovering the alcohol.

Retrosynthetic perspective:

• Disconnection at the ester bond gives ferulic acid and eicosanol, both readily sourced or prepared. The E-cinnamate geometry is accessible via esterification of ferulic acid using DCC/DMAP or via acid chloride routes under mild conditions to preserve configuration.

Target Specificity

Not applicable. This product is a small-molecule ester, not an antibody or affinity reagent. No antigen/epitope specificity, clone information, or species reactivity applies.