This compound belongs to the class of organic compounds known as wax monoesters. These are waxes bearing an ester group at exactly one position.
External Descriptors
Wax monoesters
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Poids moléculaire
530.900 g/mol
XLogP3
14.800
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
31
Exact Mass
530.506 Da
Monoisotopic Mass
530.506 Da
Topological Polar Surface Area
26.300 Ų
Heavy Atom Count
38
Formal Charge
0
Complexity
546.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
3
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
3
Covalently-Bonded Unit Count
1
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Application Protocols
No vendor-validated biological assay protocols are provided for this SKU. Typical research uses are chemistry/formulation oriented. General, non-item-specific guidance includes:
Preparation of stock solutions:
Dissolve in hexane, toluene, DCM, EtOAc, or ethanol to desired concentration (e.g., 10–100 mg/mL). For antioxidant-sensitive studies, pre-sparge solvent with N2 and include 50–200 ppm BHT in the diluent (optional, literature practice).
Thin-film hydration (for lipid-additive studies):
Dissolve oleyl linoleate with other lipids in chloroform:methanol (2:1). Evaporate under reduced pressure to form a thin film. Dry under high vacuum (≥2 h). Hydrate with buffer at 40–60 °C under agitation; probe-sonicate or extrude to size as required.
Oxidation assays (conjugated diene method):
Incubate samples at set temperature with/without antioxidant; periodically dilute in isooctane and record UV at 234 nm to monitor conjugated diene formation (literature method). Maintain identical pathlengths and concentrations.
For any application requiring specific purity, isomeric composition, or low-peroxide status, obtain the lot CoA and perform incoming QC prior to use.
Biological Roles
Oleyl linoleate is not a native single molecular species in vivo but is structurally analogous to neutral lipids and esterified fatty acids found in biological systems.
Structural analog of wax esters and neutral lipids: composed of a long-chain fatty alcohol esterified to a polyunsaturated fatty acid, akin to natural wax esters in marine organisms and plant cuticles.
Membrane interaction (literature): highly hydrophobic and non-ionic; partitions into lipid bilayers and oil phases, altering fluidity and packing when used as an additive in model membrane systems.
Metabolic processing (biochemistry): hydrolyzable by lipases/esterases to release linoleic acid (an essential ω-6 fatty acid) and oleyl alcohol (convertible to oleic acid). Enzymatic specificity can be studied using this ester as a probe substrate.
Oxidation behavior: the presence of three cis double bonds makes it a sensitive reporter for lipid peroxidation mechanisms, conjugated diene formation, and antioxidant efficacy in vitro.
Self-assembly/formulation: in the presence of suitable surfactants, supports nanoemulsion and lipid nanoparticle formation; used to model oil-phase partitioning and interfacial transport.
Note: All statements above are for research/biochemistry context only. This product is supplied strictly for research use; it is not intended for human or animal consumption or clinical applications.
Buffer Applications
This product is a hydrophobic neutral ester and does not function as an acid/base buffer. It is not typically used to prepare aqueous buffer systems.
Practical note for experiments involving buffers:
When incorporating oleyl linoleate into aqueous buffers (e.g., for emulsions or liposomal additives), dissolve first in a compatible organic solvent (e.g., ethanol, isopropanol, or a small volume of DMSO/THF), or pre-form an oil-in-water emulsion with appropriate surfactants. Add slowly to the aqueous phase under high shear to ensure dispersion.
Avoid high concentrations of water-miscible co-solvent if they interfere with downstream assays; perform solvent exchange or evaporation after forming the desired colloidal system.
Green Alternatives
When choosing media and processes for working with oleyl linoleate, greener solvent and energy options can reduce environmental impact without compromising performance.
Greener solvent choices (literature/guidance):
Prefer bio-based or lower-toxicity solvents for dissolution and processing:
Heptane (biobased) or isoparaffins over hexane (reduced neurotoxicity concerns).
Ethyl acetate or 2-methyltetrahydrofuran (2-MeTHF, from hemicellulose) instead of chlorinated solvents for extractions and reactions.
Supercritical CO2 for extraction/processing of lipid mixtures; tunable solvency via pressure/temperature.
Illustrative comparison (general):
Hexane vs Heptane: similar solvency; heptane often rated preferable in solvent guides; slightly higher bp aids recovery.
DCM vs EtOAc: DCM excellent solvency but high EHS footprint; EtOAc is biodegradable, low toxicity, and effective for many lipid operations.
Toluene vs CPME/2-MeTHF: toluene is effective for high-temp reactions; CPME/2-MeTHF provide good hydrophobic solvency with improved safety/greenness and water tolerance.
Process intensification:
Use flow hydrogenation or packed-bed enzymatic reactors to limit solvent volumes and improve selectivity.
Employ solvent-free (neat) transesterifications where feasible; the substrate is liquid, enabling reduced solvent usage.
Tradeoffs:
Greener solvents may change rates/selectivity (e.g., epoxidation kinetics differ in EtOAc vs DCM); validate on small scale.
Supercritical CO2 requires specialized equipment but offers residue-free processing.
Adopt appropriate waste segregation for lipid-rich streams to facilitate recovery and minimize COD loadings.
Pharmaceutical Uses
No therapeutic claims are made. In pharmaceutical and biopharmaceutical research contexts, oleyl linoleate can serve as an excipient-like hydrophobic component for formulation development and process studies (research use only):
Oil phase in emulsions and microemulsions: used to explore droplet size control, interfacial stabilization, and drug partitioning in preformulation screenings.
Lipid nanoparticle (LNP) and nanoemulsion research: a fluid long-chain ester that can modulate viscosity and hydrophobic core properties when blended with surfactants and co-solvents.
Permeation studies (in vitro): model lipophilic matrix to evaluate solute diffusion in nonpolar phases or across artificial membranes (e.g., Franz cell set-ups), strictly for lab research.
Process compatibility: amenable to sterile filtration when warmed (reduced viscosity) and pre-diluted in suitable solvents; stability benefits from oxygen/light control to minimize peroxidation during storage and processing.
Regulatory context: not described here with a pharmacopeial monograph; any use in regulated products requires independent qualification and supplier/lot-specific documentation.
All uses above are confined to laboratory research and development. For any application beyond research, consult applicable regulations and conduct full compatibility and stability assessments with the specific lot (CoA/SDS required).
Physical Properties
Item-specific physicochemical specifications are not provided in the Product Data for this SKU. Consult the CoA/Spec Sheet for definitive release values.
Appearance (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (for general guidance only; not item specifications):
Approximate molecular weight: ~530.9 g/mol (calculated from formula)
Physical state: oily liquid at ambient temperature (typical for long-chain polyunsaturated esters)
Density: typically ~0.86–0.90 g/mL at 20–25 °C (literature, fatty esters of similar chain length)
Boiling behavior: very high; subject to thermal decomposition before true boiling under ambient pressure; distillable under high vacuum (literature, fatty ester class)
Melting point/pour point: typically well below room temperature due to three cis double bonds (literature)
Refractive index (nD 20): often in the range 1.46–1.48 for C36 polyunsaturated esters (literature)
Solubility: insoluble in water; soluble in nonpolar and moderately polar organic solvents (e.g., hexanes, toluene, dichloromethane, ethyl acetate, THF) (literature)
Partitioning: very hydrophobic; expected logP >> 6 (estimated from fragment constants)
Note: Actual values for this item may differ; always rely on the item’s CoA/SDS for precise property and safety information.
Quality and Grades
Grade/Purity (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret quality for this material (general guidance):
For lipidic esters like oleyl linoleate, typical quality attributes include:
Assay by GC/FID or HPLC (area %), with defined limits for related esters and free oleyl alcohol/linoleic acid.
Isomer composition: proportion of cis (Z) vs trans (E) double bonds; peroxide value and anisidine value (markers of oxidation) when applicable.
Residual solvents and moisture (Karl Fischer) where relevant to application.
Acid value/saponification value to quantify free acid and average molecular characteristics.
Relevance to applications:
Analytical/biochemical work benefits from low peroxide value and minimal isomerization.
Formulation studies often require tight control of color, odor, and oxidative markers for reproducibility.
Documentation:
Certificate of Analysis (CoA) should list assay, impurity profile, and any stabilizers or antioxidants if present.
A Specification Sheet (Spec) defines acceptable ranges; lot CoA provides actual measured values.
Note: In absence of item-specific grade statements, contact Aladdin Scientific for current lot CoA and quality attributes to ensure suitability for your intended research use.
Reaction and Applications
Oleyl linoleate is a versatile unsaturated fatty ester used across lipid chemistry, catalysis studies, and materials/formulation research.
Representative applications (literature/general):
Oxidation studies: model substrate for autoxidation, photooxidation, and antioxidant screening due to three isolated cis double bonds. Quantify peroxide/anisidine values or monitor conjugated diene formation by UV (λ ≈ 234 nm).
Epoxidation and dihydroxylation: double bonds enable Prilezhaev epoxidation (e.g., peracids or H2O2/formic acid systems) followed by ring opening; regioselectivity and over-oxidation can be tuned with catalysts.
Hydrogenation: selective partial hydrogenation to modulate degree of unsaturation (e.g., Pd/C, Pt/C, Ni catalysts); conditions tailored to avoid over-saturation or isomerization.
Ozonolysis/oxidative cleavage: affords long-chain aldehydes/acids/esters; useful for structural elucidation and value-added intermediates.
Transesterification/interestification: base- or enzyme-catalyzed exchange with alcohols (e.g., methanol, glycerol) for bioderivatives or structured lipids; lipases (e.g., Novozym 435) offer selectivity and mild conditions.
Polymer and materials: plasticizer or hydrophobe in coatings; reactive diluent in UV-curable systems after functionalization (e.g., acrylation of hydroxyl-bearing derivatives).
Formulation science: emollient/oil phase in nanoemulsions and lipid nanoparticles (research context), often blended with surfactants to tune droplet size and stability.
Practical tips:
Control oxygen/light during reactions to prevent adventitious autoxidation.
Use inhibitors (e.g., BHT in solvents) for analytical sample prep.
For catalytic hydrogenation, pre-degas solutions and monitor iodine value to target specific unsaturation levels.
Reaction Conditions
General literature guidance for transformations of unsaturated long-chain esters like oleyl linoleate (illustrative; not item-specific specifications):
Selective hydrogenation:
Catalyst: 5 wt% Pd/C (0.5–2 mol% Pd relative to C=C); Solvent: heptane or ethanol.
Conditions: H2 1–5 bar, 20–40 °C; monitor iodine value or GC. Lower pressure and temperature favor selectivity, reducing isomerization.
Epoxidation (Prilezhaev):
Reagent: mCPBA (1.0–1.2 equiv per C=C) in DCM at 0–25 °C with buffering (NaHCO3) to limit epoxide opening.
Alternative green system: H2O2 (30%) with formic acid or acetic acid in EtOAc or solvent-free, 30–60 °C; catalytic tungstate or Ti-silicate (TS-1) can enhance selectivity.
Hydroboration–oxidation:
9-BBN (1.0 equiv per targeted C=C) in THF, 0–25 °C; then H2O2/NaOH to furnish alcohols at terminal-like positions (regioselectivity varies across internal alkenes).
Ozonolysis:
Solvent: CH2Cl2 or MeOH at −78 to −20 °C; quench with Me2S or PPh3. Provides cleavage to long-chain aldehydes/acids/esters.
Base-catalyzed transesterification:
Catalyst: 0.1–1 mol% NaOMe or K2CO3; Solvent: MeOH (or neat with excess alcohol), 25–60 °C, 1–6 h. For selective processes, immobilized lipase (Novozym 435) at 40–60 °C under reduced water activity.
Analytical derivatization:
For GC, convert to methyl esters (FAME) after saponification to profile the acyl chain; or analyze the intact ester by high-temp GC with on-column injection.
Notes:
Remove dissolved oxygen (sparge with N2/Ar) for reactions sensitive to radical pathways.
Control light exposure to suppress photooxidation.
Scale-up: ensure efficient mixing due to high viscosity at lower temperatures; mild warming (30–40 °C) reduces viscosity.
Safety and Handling
Item-specific hazard classification is not provided in the Product Data. Always consult the SDS for authoritative information.
GHS 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 guidance for long-chain fatty acid esters (literature/good practice):
Expected hazards: typically low acute toxicity; may cause skin/eye irritation on contact. Slippery spill hazard. Combustible at elevated temperatures.
PPE: wear safety glasses with side shields, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). Avoid prolonged skin contact.
Handling: minimize exposure to air, heat, and light to limit autoxidation of unsaturated bonds. Work under inert atmosphere for oxidation-sensitive experiments.
Incompatibilities: strong oxidizing agents; radical initiators; prolonged exposure to UV/air promotes peroxidation. Avoid finely divided metal catalysts unless reaction-intended.
First aid (general):
Eye: rinse cautiously with water for several minutes; remove contact lenses if present and easy.
Skin: wash with soap and water; remove contaminated clothing.
Inhalation: move to fresh air; seek medical attention if symptoms occur (mists/aerosols are unlikely under normal handling).
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Fire safety: use CO2, dry chemical, or foam. Heated vapors/mists may ignite. Thermal decomposition can release irritating fumes.
Always defer to the official SDS for this SKU for definitive hazard, exposure controls, and emergency measures.
Solvent Selection
This item is a hydrophobic substrate/building block rather than a general-purpose solvent. Solvent considerations focus on dissolving and processing this ester efficiently.
Polarity/miscibility (literature):
Highly nonpolar; immiscible with water.
Readily soluble in hexanes, heptane, cyclohexane, toluene, chloroform, dichloromethane, MTBE, diethyl ether, ethyl acetate, THF. Limited solubility in acetonitrile and alcohols increases with temperature.
Dielectric/interaction profile: dominated by dispersion forces; solvation favored in low- to medium-polarity organic solvents. Hydrogen bonding is negligible.
Choosing a solvent by task:
Analytics (GC/FID, GC–MS): dissolve at low mg/mL in isooctane, hexane, or dichloromethane; consider addition of BHT in the diluent to suppress autoxidation during runs (general practice).
Preparative work and reactions (hydrogenation, epoxidation, transesterification): use toluene, heptane, tert-butanol, or solvent-free (neat) conditions as compatible with the catalyst/reagent system.
Lipid formulation and film casting: chloroform:methanol (2:1) is classical for thin film preparation; remove solvent under reduced pressure, then hydrate for vesicle work (if used as an additive in model membranes).
Comparison notes (literature):
Hexanes/heptane: excellent solubility, low polarity; minimal co-solvation of polar reagents.
Toluene: higher bp, good for thermal reactions and catalytic hydrogenation.
Ethyl acetate/MTBE: greener profiles than chlorinated solvents; moderate solvency for this ester.
Ensure solvent dryness and oxygen control when studying oxidation-sensitive transformations.
Shipped in (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
General handling and stability guidance for unsaturated fatty esters (literature/good practice; not item-specific specifications):
Protect from light, heat, and air to minimize autoxidation. Store in tightly sealed, preferably amber glass containers.
For long-term storage, consider inert gas blanketing (N2/Ar) and keep headspace minimal. Refrigeration (2–8 °C) can further slow oxidation but is not required per Product Data.
Avoid repeated warming/cooling cycles that may introduce condensation; if refrigerated, allow to equilibrate to room temperature before opening to prevent moisture ingress.
If supplied as a viscous liquid, warm gently (25–40 °C) to reduce viscosity before aliquoting. Do not overheat.
Reconstitution: not applicable (neat liquid). For solution preparation, use dry, oxygen-poor solvents. Document concentration and solvent in labeling, and note any stabilizers used in the diluent.
Quality monitoring: periodically check for increased peroxide value, color change, or odor indicative of oxidation if stored for extended periods.
Always refer to the product’s SDS and lot-specific CoA for definitive guidance on storage limits, container compatibility, and stability testing.
Structure and Identity
Oleyl linoleate is a long-chain unsaturated fatty ester formed from oleyl alcohol (C18:1, ω-9) and linoleic acid (C18:2, ω-6). It is a neutral lipid frequently used as a hydrophobic matrix or model substrate in lipid chemistry.
Product identifiers (from Product Data)
CAS: 17673-59-5
SKU: O991509
Product name: Oleyl Linoleate
Category: Life Science (research use only)
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature identity details (for reference; not item-specific specifications)
Common description: Mixed C36 monoester of a C18:1 alcohol with a C18:2 fatty acid
Expected molecular formula (literature): C36H66O2 (neutral ester formed with loss of H2O)
Approximate molecular weight (calculated from C36H66O2): ~530.9 g/mol
Structural features (descriptive)
Functional groups: one fatty acid ester (–CO2–) linking two C18 aliphatic chains.
Unsaturation: three isolated cis double bonds in total (one in the oleyl “alkoxy” chain; two in the linoleyl acyl chain, typically Δ9Z and Δ12Z for linoleate).
Topology: highly flexible, linear aliphatic chains; no rings; no heteroatoms beyond two oxygens of the ester.
Stereochemistry: geometric (E/Z) about the C=C bonds; naturally occurring precursors are commonly cis (Z), yielding a predominately Z-configuration at the three sites.
2D structural description (verbal)
An ester carbonyl flanked by: (a) a long ω-9-mono-unsaturated C18 chain bound via oxygen (oleyl moiety), and (b) a long ω-6-di-unsaturated C18 acyl chain (linoleate) bearing two non-conjugated double bonds.
Synthetic Utility
From a synthetic perspective, oleyl linoleate is a multifunctional platform featuring:
Three unactivated alkene sites enabling:
Selective hydrogenation (tuning saturation level, avoiding isomerization) with Pd/C, Pt/C, Ni, or homogeneous catalysts.
Electrophilic additions and functionalizations: epoxidation (peracids, H2O2/TS-1), hydroboration–oxidation (on less hindered double bonds), halogenation under controlled conditions.
Radical additions (e.g., thiol–ene) under photoinitiation to install thioether functionality.
Ester functionality enabling:
Transesterification with short alcohols (MeOH, EtOH) to generate fatty acid methyl/ethyl esters for analytics or derivatization (base- or enzyme-catalyzed).
Hydrolysis (acidic or basic) to access linoleic acid and oleyl alcohol for further conversion.
Amidation via activation (e.g., formation of acid from hydrolysis then coupling) for surfactant precursors.
Oxidative cleavage of alkenes (ozonolysis, Lemieux–Johnson) to yield long-chain carbonyl compounds and dicarboxyl derivatives.
Polymer/materials transformations:
Epoxidized derivatives serve as reactive plasticizers or precursors to polyols (ring-opening with diols/amines).
Acrylation or maleation of hydroxyl-bearing derivatives derived from this ester affords UV-curable resins.
Strategic considerations:
Exploit differential reactivity of the three alkenes by steric environment and solvent choice; kinetic selectivity is achievable.
Protect against autoxidation during multistep synthesis (oxygen exclusion, antioxidants, amber glassware).
Target Specificity
Not applicable. This product is a small-molecule lipid ester, not an antibody, enzyme, or affinity reagent. No target/epitope, species reactivity, clone, or isotype information applies.
Foire aux questions
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 room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 17673-59-5, the molecular formula is C36H66O2, and the molecular weight is 530.900 g/mol. InChIKey HCWKYEAMGMQHRV-RQOIEFAZSA-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.
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