Linoleylanilide , CAS No.19878-10-5

CAS: 19878-10-5 Cat. No.: L970159 Formula: C₂₄H₃₇NO Molecular Weight: 355.600

Storage

Room temperature

Specifications

Storage

Room temperature

Names and Identifiers

• Canonical Smiles: CCCCC/C=C\C/C=C\CCCCCCCC(=O)NC1=CC=CC=C1
• IUPAC Name: (9Z,12Z)-N-phenyloctadeca-9,12-dienamide
• InChIKey: HFRLHSQAZLWVEE-HZJYTTRNSA-N
• INCHI: 1S/C24H37NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-24(26)25-23-20-17-16-18-21-23/h6-7,9-10,16-18,20-21H,2-5,8,11-15,19,22H2,1H3,(H,25,26)/b7-6-,10-9-
• Molecular Weight: 355.600

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Anilides

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Anilides
• Intermediate Tree Nodes: Not available
• Direct Parent: Anilides
• Alternative Parents: N-arylamides Fatty amides Secondary carboxylic acid amides Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Anilide - N-arylamide - Fatty amide - Fatty acyl - Secondary carboxylic acid amide - Carboxamide group - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxygen compound - Carbonyl group - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
• External Descriptors: anilide - fatty amide

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

Chemical and Physical Properties

• Molecular Weight: 355.600 g/mol
• XLogP3: 8.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 15
• Exact Mass: 355.288 Da
• Monoisotopic Mass: 355.288 Da
• Topological Polar Surface Area: 29.100 Ų
• Heavy Atom Count: 26
• Formal Charge: 0
• Complexity: 380.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1

Application Protocols

No validated bioanalytical application protocols (e.g., WB, IHC, IF, FC) are provided in the Product Data for this small molecule. Typical usage is as a research chemical in organic synthesis or materials/biophysical studies. For solution preparation and assay incorporation, see “Solvent Selection” and “Storage & Reconstitution.”

Biological Roles

• Item-specific biological data: Not specified for this item; for research use only.

• General context (biochemistry; no clinical claims)

  • Linoleylanilide is a synthetic fatty acid amide featuring the linoleoyl moiety (derived from linoleic acid, an essential ω-6 fatty acid). While endogenous fatty acid amides (e.g., oleamide, anandamide) are known signaling lipids, anilide derivatives are non-natural and primarily used as hydrophobic probes or model compounds.
  • Its amphiphilic topology (hydrophobic C18 chain with an amide/aryl headgroup) suggests partitioning into lipid bilayers and micellar phases; such compounds can be used to study membrane association, diffusion, and the influence of aromatic headgroups on interfacial behavior.
  • Amide hydrolysis and oxidative pathways can be explored enzymatically or chemically to model stability versus more biologically prevalent ethanolamides or primary amides, without implying endogenous activity for the anilide itself.
  • Spectroscopic incorporation: the aromatic ring offers a UV chromophore, aiding quantification in partitioning and binding experiments.

Note: Any biological testing should be performed under appropriate laboratory approvals and is strictly for research applications.

Buffer Applications

This compound is a highly hydrophobic amide and is not typically used as a buffering agent or buffer component. It lacks acid–base pairs in the physiological pH range suitable for maintaining pH. For experiments requiring aqueous handling, prepare stock solutions in compatible organic cosolvents (e.g., DMSO, EtOH, or EtOAc) and dilute into buffered aqueous media with surfactants or carriers as appropriate.

Green Alternatives

• Solvent strategy (general guidance)

  • Prefer ethyl acetate, 2-MeTHF, CPME, or toluene over chlorinated solvents when feasible; they often dissolve long-chain amides adequately while reducing environmental and safety burdens.

• Processing choices

  • Replace petroleum ether/hexanes with heptane or bio-based alkane blends where possible.
  • Use catalytic hydrogenation (H2, Pd/C) instead of stoichiometric hydride reagents for saturations.
  • Perform epoxidations with in situ generated peracids (e.g., Oxone/ketone systems) or enzymatic epoxidation where compatible, as alternatives to mCPBA.

• Comparison snapshot (general; not product specifications)

  • Metric | Conventional option | Greener alternative | Trade-offs
  • ------------------- | ------------------- | ------------------- | ---------
  • Dissolution | CH2Cl2/CHCl3 | EtOAc/2-MeTHF/CPME | May need mild heating/cosolvent
  • Column eluents | Hexanes/EtOAc | Heptane/EtOAc | Slightly different selectivity
  • Oxidations | mCPBA | Oxone/NaHCO3/AcOEt | Rate/selectivity tuning required
  • Workup drying | Na2SO4/MgSO4 | Brine + minimal drying agent | Similar efficiency; reduce waste

Adopt inert-atmosphere handling to extend material life, reducing waste from oxidative degradation.

Pharmaceutical Uses

• Item-specific pharmacopeial status/grade: Not specified for this item; refer to CoA/Spec Sheet.

• General formulation context (non-clinical)

  • Long-chain amide derivatives are occasionally evaluated as hydrophobic excipient candidates, crystal habit modifiers, or as components of lipid-based delivery systems in pre-formulation research. Linoleylanilide itself is a non-natural anilide and is primarily used as a research chemical rather than a standard excipient.
  • The aromatic amide chromophore facilitates UV-based quantitation in formulation studies compared with fully aliphatic amides.
  • Given its strong hydrophobicity and low melting/softening behavior, it may act as a structurant in semi-solid matrices or as a compatibility probe in lipidic systems.

No therapeutic or clinical uses are claimed. Any pharmaceutical investigations should remain within research and development settings only.

Physical Properties

• Item-specific specs: Not specified for this item; refer to CoA/Spec Sheet.

• General/literature expectations for an acylanilide of linoleic acid (informational, not product specifications)

  • Physical state/appearance: typically a viscous oil or low-melting waxy solid at ambient temperature due to the long aliphatic chain and two cis double bonds.
  • Solubility: insoluble in water; soluble in nonpolar and moderately polar organic solvents (e.g., hexanes, toluene, chloroform, dichloromethane, ethyl acetate). Poor solubility expected in highly polar protic solvents (water, methanol) without heating or cosolvent.
  • Polarity/logP: high hydrophobicity expected from the C18 chain and phenyl ring; amide functionality confers limited polarity and strong hydrogen-bond donor/acceptor character localized at the amide.
  • Volatility: very low; negligible vapor pressure at room temperature typical of long-chain amides.
  • Thermal behavior: long-chain unsaturated amides often soften near room temperature and can form glassy or semi-crystalline phases upon cooling. Avoid overheating that can accelerate oxidative degradation of the double bonds.
  • Spectroscopic signatures: strong IR amide I (C=O) band near ~1630–1680 cm⁻¹ and amide II near ~1540 cm⁻¹ (literature, solvent-dependent); aromatic C–H stretches ~3030 cm⁻¹; aliphatic C–H ~2850–2950 cm⁻¹; alkene =C–H stretch ~3005 cm⁻¹.

Note: Use these as qualitative guides only; obtain exact values from the CoA/SDS for the supplied lot.

Quality & Grades

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

• Interpreting common grades for context (general guidance)

  • Research/biochemical grade: emphasizes low levels of residual solvents and byproducts; suitable for routine synthesis or biochemical model studies.
  • HPLC grade (if offered for analogous items): targets low UV background and minimal nonvolatile residues for chromatography use.
  • Stabilizers: Unsaturated lipids are sometimes supplied with trace antioxidants (e.g., BHT) to mitigate autoxidation; no stabilizer is specified for this item. If present, it will be declared on the CoA/Spec Sheet.

• Purity considerations specific to linoleylanilide-class materials (general)

  • Typical impurities may include positional/isomeric variants (E/Z isomerization at Δ9/Δ12), residual starting linoleic acid, aniline, and coupling reagents. Oxidation products (peroxides, epoxides) can form on storage if exposed to air/light.
  • Quality control techniques: 1H/13C NMR to confirm amide formation and E/Z content; FT-IR for amide bands; LC–MS or GC–MS for impurity profiling; peroxide value for oxidative status; HPLC for assay.

Refer to the lot-specific Certificate of Analysis for actual assay, impurity profile, and any stabilizer declaration.

Reaction & Applications

• Typical uses in synthesis (general for linoleic acid anilides)

  • Lipid-anchored anilide scaffold for modeling amide bond stability, lipophilicity, and membrane interactions in physical-organic studies.
  • Substrate for transformations at the unsaturated chain:
    • Selective hydrogenation (Z,Z → Z/E or full saturation to stearanilide analog).
    • Epoxidation (peracids/mCPBA) at Δ9/Δ12, followed by ring-opening to diols or halohydrins.
    • Olefin metathesis (Grubbs/Hoveyda catalysts) to tailor chain length or introduce functional handles.
    • Hydroboration–oxidation or halogenation across C=C.
  • Amide bond serves as a handle for acyl transfer or activation (e.g., conversion to imidazolides or Weinreb-like derivatives is generally challenging from secondary amides, but N-acyl activation via CDI or Ghosez reagent is studied in literature).

• Practical notes

  • Oxidation control: purge solvents with nitrogen/argon; include a minimal headspace and protect from light during extended reactions.
  • Purification: silica gel can promote isomerization/oxidation of polyunsaturated chains; work rapidly, pre-saturate with eluent containing 0.1–1% triethylamine if acid sites cause tailing.
  • Analysis: monitor by TLC with KMnO4 or phosphomolybdic acid stains (double bonds visible); confirm E/Z integrity by 1H NMR (allylic and vinylic signals) and GC/LC–MS.

• Application domains (non-clinical)

  • Model compound in lipid oxidation studies, surface modification with hydrophobic amides, and as an intermediate toward functionalized long-chain aromatic amides.

Reaction Conditions

General literature guidance for transformations of linoleic-acid-derived anilides (informational; adjust per substrate and scale):

• Hydrogenation (C=C saturation)

  • Catalyst: 5–10 wt% Pd/C or Raney Ni.
  • Solvent: EtOH, EtOAc, or toluene; deoxygenate prior to use.
  • Conditions: 1–3 bar H2, 20–40 °C, 1–6 h. Monitor to avoid over-reduction of the aromatic ring.

• Epoxidation (peracid)

  • Reagent: mCPBA (1.0–2.2 equiv per C=C) with 4 Å molecular sieves.
  • Solvent: CH2Cl2, 0–25 °C, 1–4 h. Buffer with NaHCO3 to suppress N-acyl migration/over-oxidation.

• Olefin metathesis (cross- or ethenolysis)

  • Catalyst: Grubbs II or Hoveyda–Grubbs II (1–5 mol%).
  • Solvent: toluene, DCM, or 2-MeTHF; 25–60 °C under inert gas. Include ethylene purge for ethenolysis.

• Hydrolysis (amide cleavage; relatively resistant)

  • Acidic: 6 M HCl, reflux, hours–overnight (can lead to double-bond isomerization/oxidation; protect from air).
  • Basic: KOH/EtOH–H2O, reflux, prolonged times; often less effective for secondary amides.

• Oxidative cleavage of alkenes

  • Ozonolysis at −78 to −40 °C in DCM/MeOH, then reductive workup (Me2S) or oxidative (H2O2) to access fragments.

• Analytical controls

  • TLC staining (KMnO4), GC/LC–MS for product distribution, and NMR to assess E/Z retention. Exclude oxygen/light to minimize peroxidation.

Safety & Handling

• Item-specific hazard statements (from Product Data): Not specified; consult the SDS for authoritative classification.

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

• General safety guidance for long-chain fatty amide derivatives (informational)

  • Expected hazards: typically low volatility and low acute inhalation risk; may cause skin/eye irritation. Unsaturated chains can undergo autoxidation—oxidized products may be more irritating/sensitizing.
  • PPE: lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Avoid skin contact; wash thoroughly after handling.
  • Handling: minimize exposure to air, heat, and light to reduce oxidative degradation. Use clean, dry tools. Avoid aerosol generation.
  • Incompatibilities: strong oxidizing agents (risk of exothermic reaction/oxidation), strong acids/bases (can promote hydrolysis), and reactive acylation or nitration systems affecting the aromatic ring.
  • First aid (overview; defer to SDS):
    • Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
    • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
    • Inhalation of mists/particulates: move to fresh air; obtain medical attention if symptoms occur.
  • Fire safety: combustible organic; use CO2, dry chemical, or foam. Thermal decomposition can produce CO/CO2 and nitrogen oxides.

Always consult the product’s SDS for definitive hazard, toxicological, and disposal information.

Solvent Selection

• Polarity/miscibility profile (general for long-chain anilides)

  • Highly hydrophobic; water-insoluble.
  • Good solubility: nonpolar to moderately polar organics (hexanes/heptane, toluene, xylene, CH2Cl2, CHCl3, THF, CPME, EtOAc). Limited solubility in alcohols at room temperature; improves with gentle heating or cosolvents.

• Practical selection tips

  • For weighing/stock solutions: CH2Cl2, toluene, or ethyl acetate provide rapid dissolution; add a small portion of DMSO as a cosolvent if formulating into aqueous systems for assays.
  • For chromatographic purification: normal-phase silica with hexanes/EtOAc or toluene/EtOAc gradients offers good resolution from unreacted aniline/acid. Avoid excessive polar eluents that may broaden the amide.
  • For reactive chemistry on the double bonds: use aprotic, oxygen-free solvents (e.g., dry toluene, DCM, MeCN) depending on transformation (epoxidation, metathesis, hydroboration–oxidation).

• Comparison snapshot (general)

  • Toluene vs DCM: toluene is less volatile and less chlorinated waste; DCM maximizes solubility and cold-temperature operations but requires more stringent exposure controls.
  • EtOAc/CPME: greener alternatives with adequate solubility; CPME tolerates water and strong bases better than Et2O and has low peroxide formation.

Choose solvent grade and type based on intended use and downstream analytics (UV background, residual solvent limits).

Storage & Reconstitution

• Item-specific storage (from Product Data)

  • Storage conditions: Room temperature.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• Practical storage guidance (general for unsaturated long-chain amides)

  • Protect from light and air to limit autoxidation of the linoleoyl double bonds; store tightly closed under inert gas if possible, in amber glass.
  • Keep dry; moisture and acids/bases can promote gradual amide hydrolysis and oxidation.
  • If long-term storage is intended, consider refrigeration (2–8 °C) as a best practice for polyunsaturated materials, while allowing the container to equilibrate to room temperature before opening to prevent condensation. Room temperature per product data is acceptable for routine handling.

• Reconstitution/solution preparation

  • Warm gently (25–40 °C) if semi-solid to facilitate transfer.
  • Prepare concentrated stock solutions in suitable organic solvents (e.g., CH2Cl2, toluene, ethyl acetate, or DMSO as cosolvent) and filter if particulates are present.
  • For use in predominantly aqueous systems, premix with a miscible organic cosolvent and, if necessary, dispersing agents/surfactants; add slowly with vigorous mixing to avoid precipitation.

• Stability on use

  • Minimize repeated freeze–thaw or open–close cycles; aliquot solutions. Monitor for signs of oxidation (odor, color change, peroxide tests) before critical experiments.

• Research use note: For research use only.

Structure & Identity

• Item-specific identifiers (from Product Data)

  • CAS: 19878-10-5
  • Product name: Linoleylanilide (commonly understood as the anilide of linoleic acid; i.e., N-phenyl-9Z,12Z-octadecadienamide)
  • InChIKey: 120296 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

• Structural description (general chemistry/literature)

  • Functional groups: primary amide (–CONH–) attached to a phenyl ring (anilide), and a C18 aliphatic chain bearing two cis (Z) C=C bonds at Δ9 and Δ12 typical of linoleic acid.
  • Ring systems: one benzene ring (aniline-derived) directly bound to the amide nitrogen (acylanilide motif).
  • Stereochemistry: the fatty chain typically derives from linoleic acid (9Z,12Z). No stereocenters are present; C=C geometry is the key configurational feature.
  • 2D depiction in words: benzamide core where the amide nitrogen bears one hydrogen and one phenyl substituent, with the carbonyl bonded to a C18 chain containing two cis double bonds separated by a methylene (–CH=CH–CH2–CH=CH–).

Synthetic Utility

• Functional group leverage

  • Amide: robust handle that confers hydrogen-bonding capability; can be selectively N-alkylated/acylated under strong conditions, though secondary amides are less nucleophilic.
  • Diene (linoleoyl chain): platform for chemoselective transformations—hydrogenation, epoxidation, dihydroxylation, oxidative cleavage (e.g., ozonolysis to generate shorter-chain fragments), and cross-metathesis.
  • Aryl ring: enables electrophilic aromatic substitution (nitration, halogenation), transition-metal-catalyzed C–H activation (directed by the amide), or cross-coupling after installing a suitable leaving group.

• Retrosynthetic value

  • Serves as a convergent intermediate linking an aniline-derived pharmacophore/headgroup to a linoleoyl hydrophobe. Variants with tags (e.g., azide/alkyne on the ring or chain) can be accessed for click-chemistry handles while preserving the lipid length and unsaturation pattern.

• Derivatization ideas (general)

  • Selective mono- versus di-epoxidation at Δ9/Δ12 followed by regioselective openings to introduce hydroxyl topology mimicking oxidized lipids.
  • Hydrogenation series (partial to full) to map the effect of unsaturation on physical properties and membrane partitioning.
  • Installation of isotopic labels (2H, 13C, 15N) on the aniline or amide carbonyl for mechanistic/analytical studies.

• Purification/analysis tips

  • Avoid prolonged exposure to acidic silica; consider neutral/alumina or add 0.1–1% NEt3. Confirm integrity by 1H NMR (allylic multiplets ~1.9–2.2 ppm; vinylic ~5.3–5.5 ppm) and IR amide bands.

Target Specificity

Not applicable. This product is a small-molecule reagent and not an antibody or affinity reagent. No target/epitope specificity is defined in the Product Data.