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.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular
506.900 g/mol
XLogP3
15.300
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
31
Exact Mass
506.506 Da
Monoisotopic Mass
506.506 Da
Topological Polar Surface Area
26.300 Ų
Heavy Atom Count
36
Formal Charge
0
Complexity
442.000
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
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Application Protocols
No item-specific, validated application protocols are provided for this SKU. For general use:
Lipid analytics: Prepare ~1–5 mg/mL solutions in hexane, isooctane, or CHCl3 for GC/LC injections. For LC–MS, APCI(+) often affords stronger response for neutral wax esters.
Enzymatic assays: Disperse in isooctane or as emulsions with nonionic surfactants; quantify conversion by GC after suitable quench/extraction.
Materials/formulation: Incorporate into the oil phase; heat to 40–60 °C if needed to ensure homogeneity before emulsification.
Always optimize conditions to your instrumentation and objectives. Refer to the CoA/SDS for any product-specific constraints.
Biological Roles
General biochemistry (literature; not product-specific):
Wax esters like palmityl oleate are neutral lipids found in biological systems including plant cuticles, sebaceous secretions, and certain marine organisms (e.g., zooplankton, some fish), where they function as energy storage and protective hydrophobic barriers.
Metabolism: Hydrolyzed by specific wax-ester hydrolases (WEH) and carboxylesterases to yield fatty alcohols (cetyl alcohol) and fatty acids (oleic acid), which can enter β‑oxidation or be re-esterified. In bacteria such as Acinetobacter, wax ester synthase/acyl-CoA:fatty alcohol acyltransferase (WS/DGAT) catalyzes biosynthesis.
Physical biology: Due to high hydrophobicity and low polarity, wax esters assemble into oil droplets and can modulate membrane properties when incorporated into lipid phases; they have very low critical micelle tendencies and act primarily as dispersed oils in emulsions.
Analytical biology: Used as calibration/response standards in lipidomics to benchmark extraction recovery, chromatographic separation, and MS ionization (often APCI+). The internal cis-alkene allows structural confirmation via characteristic fragmentation or derivatization (e.g., epoxidation for double-bond localization).
Note: These roles are offered as general biochemical context only. This product is for research use only and is not intended for diagnostic or therapeutic applications.
Buffer Applications
Palmityl oleate is a highly hydrophobic neutral ester and is not used as a buffering agent. It has no meaningful acid/base buffering capacity in aqueous media.
Practical note: If introducing this lipid into aqueous buffer systems (e.g., for biocatalysis), employ emulsifiers/surfactants, liposomes, or biphasic solvent systems to disperse the substrate. Otherwise, refer to sections on Solvent Selection and Reaction & Applications for relevant handling guidance.
Green Alternatives
Although palmityl oleate is a reagent/material rather than a solvent, sustainability considerations often arise in its use and in the choice of processing media.
Feedstock perspective (general):
Palmityl oleate can be produced via esterification of bio-based oleic acid (from vegetable oils) and cetyl alcohol (from fatty alcohol production). When sourced from renewable lipids and certified supply chains, its bio-based content supports green chemistry Principle 7 (renewable feedstocks).
Tradeoff: reduced polarity may slow some reactions or solubilization of polar co-reagents.
Ethereal bio‑solvents (2‑MeTHF, CPME)
Pros: derived from biomass; good solvency for hydrophobes; lower peroxide formation than THF (CPME)
Cons: cost, odor, and sometimes water content management.
Reaction strategies:
Employ enzymatic catalysis (lipases) under mild conditions and in recyclable solvents or solvent‑free melt conditions to reduce energy and waste.
Use flow hydrogenation with reusable catalysts and H2 efficiency to minimize solvent volumes.
Note: If biodegradability or ecotoxicity is a key requirement, document the full formulation matrix; the ester itself is readily biodegradable in many systems, but additives/solvents dictate overall footprint.
Pharmaceutical Uses
General formulation context (literature; not product-specific and without clinical claims):
Role: Palmityl oleate (cetyl oleate) is used as a hydrophobic emollient, lubricity enhancer, and oil-phase component in topical formulations, transdermal systems, and cosmetic preparations. It can modulate spreadability and sensory feel and serve as a carrier for lipophilic actives in research formulations.
Function in dosage forms: Oil phase of emulsions (o/w, w/o), suspension vehicle, and potential penetration aid in experimental dermal systems. As a neutral ester, it often exhibits good oxidative stability relative to polyunsaturated oils but still benefits from antioxidants.
Regulatory/compendial: Specific pharmacopeial monographs for cetyl oleate may not be universally available; when compendial compliance is required, verify applicable standards (acid value, peroxide value, saponification value, identity) and document excipient grade. For this item, grade/purity are not specified; consult CoA.
Compatibility: Generally compatible with common emollients (isopropyl myristate, medium-chain triglycerides), waxes, and silicone fluids. Avoid strong acids/bases that catalyze hydrolysis in aqueous systems.
Note: This information supports research/formulation development only. No claims are made regarding safety or efficacy in humans or animals.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general values (typical for cetyl oleate; for reference only):
Physical state at ambient: colorless to pale-yellow oily liquid; very low volatility
Melting point: typically below room temperature (reported around −2 to +5 °C; literature)
Boiling point: very high; thermal decomposition likely before normal boiling under ambient pressure; distillable under high vacuum (literature)
Refractive index (n20 D): ~1.447–1.453 (literature)
Solubility: insoluble in water; miscible with nonpolar organics (hexanes, heptane, toluene); good solubility in chlorinated solvents (CH2Cl2, CHCl3) and ethers; limited in acetonitrile/alcohols (literature)
LogP/partitioning: very hydrophobic; estimated clogP >10 (literature)
Viscosity: low-to-moderate at 20–25 °C; decreases with gentle warming (literature)
Practical notes:
Warm gently (30–40 °C) to reduce viscosity for accurate volumetric transfer.
For analytics, GC with on-column or PTV injection and high-T columns (e.g., non-polar phases) are commonly used; derivatization not required for the ester, but epoxide/hydrogenated derivatives may aid specific studies.
Quality and Grades
Item-specific grade/purity/stabilizer: Not specified for this item; refer to CoA/Spec Sheet.
Context for professional users (general information):
Typical offerings for wax esters may include technical grade (formulation use), reagent grade (synthetic/analytical use), and high-purity grades for lipidomics. Higher grades emphasize low peroxide value, low acid value (minimal free oleic acid/cetyl alcohol), and narrow GC purity profiles.
UV/fluorescence background: Neutral lipids have low UV absorbance above ~220–230 nm but may show weak absorbance near 205 nm; “HPLC grade” where applicable emphasizes low non-volatile residue and low baseline drift for evaporative detectors.
Stabilizers/antioxidants: Some suppliers add trace antioxidants (e.g., BHT) to retard autoxidation of the C=C. Presence/absence of stabilizer can affect oxidative stability and bioassays. Always verify in the CoA if stabilizer-free material is required.
Trace parameters (acid value, peroxide value, water): Critical for reproducibility in catalytic and enzymatic work. If not specified, determine in-house (e.g., Karl Fischer for water, iodometric/peroxide value tests) when sensitivity to these parameters is expected.
Recommendation: For quantitative lipidomics or enzymology, request batch CoA with GC (>95–98% main component), acid value, and peroxide value.
Reaction and Applications
Common research uses of palmityl oleate (cetyl oleate) leverage its internal alkene and ester functionalities.
Applications (literature/general):
Lipid standards: as a representative wax ester for method development in GC-FID/MS, LC‑MS (APCI), and thin-layer chromatography.
Model substrate in biocatalysis: lipase-catalyzed hydrolysis/esterification and interesterification studies; kinetic profiling of wax-ester hydrolases.
Materials/formulation research: hydrophobe/emollient phase in emulsions, microcapsules, and as a carrier oil in dispersions.
Transformations and derivatizations:
Selective hydrogenation of the C=C to give cetyl stearate (Pd/C, 1–5 bar H2, hexane/toluene, rt–40 °C).
Epoxidation of the double bond (mCPBA in CH2Cl2, 0–25 °C) followed by ring opening to diols/halohydrins for structure–property studies.
Ozonolysis of the olefin to generate long-chain aldehydes/acids for surfactant building blocks.
Cross-metathesis/isomerization with Ru catalysts (Grubbs/Hoveyda) to tailor chain distribution.
Base- or acid-catalyzed transesterification to produce isotopically labeled analogs or alter alcohol/acid fragments.
Practical tips:
Dry, neutral conditions preserve the ester during non-hydrolytic reactions; avoid strong base or acid if ester integrity is required.
For clean hydrogenations, pre-wash Pd/C to remove traces of water/acid; monitor by GC.
Minimize oxygen/light during reactions at elevated temperature to limit autoxidation of the C=C.
Always adapt conditions to scale and equipment; the above are literature-style examples, not product specifications.
Reaction Conditions
General literature-style conditions for common transformations of palmityl oleate; adapt to your scale and equipment:
Hydrogenation (C=C saturation):
Catalyst: 5 wt% Pd/C (2–10 mol% Pd vs. C=C)
Solvent: hexane, heptane, or toluene; degassed
Conditions: 1–5 bar H2, 20–40 °C, 1–6 h; monitor by GC/1H NMR; product ~cetyl stearate
Epoxidation (alkene to oxirane):
Reagent: mCPBA (1.1–1.5 eq) with NaHCO3 buffer
Solvent: CH2Cl2, 0–25 °C, 1–4 h; quench, wash to remove acids; avoid excess acid to limit ester hydrolysis
Ozonolysis (cleavage):
O3 in O2 at −78 to 0 °C in CH2Cl2/MeOH, then reductive workup (Me2S, PPh3, or Zn/AcOH) or oxidative (H2O2) to furnish aldehydes/acids; handle oxidants with care
Transesterification (alcohol exchange):
Base-catalyzed: NaOMe (0.5–5 mol%), ROH (excess), 25–60 °C, hours; remove ROH under vacuum; neutralize
Enzymatic: CAL‑B (immobilized), 40–60 °C in isooctane or solvent-free melt; drives selectivity with minimal side reactions
Metathesis (double-bond remodeling):
Catalyst: Grubbs II/Hoveyda–Grubbs II (1–10 mol%)
Solvent: toluene or DCM, 30–60 °C, 2–12 h; remove ethylene under slight vacuum or N2 sweep if needed
These conditions are representative literature guidance only and not performance guarantees for this SKU.
Safety and Handling
Item-specific hazard data (GHS/CLP): Not specified for this item; refer to the product SDS for authoritative classification, pictograms, H-statements, and PPE guidance.
General laboratory safety for long-chain neutral lipids/wax esters (literature/typical):
Hazards: Generally considered of low acute toxicity; treat as a combustible liquid. Can form slippery films if spilled. Prolonged heating may lead to decomposition and smoke/irritant fumes.
PPE: Safety glasses, lab coat, and appropriate gloves (e.g., nitrile). Use in a well-ventilated area; a fume hood is prudent for heating, aerosol generation, or solvent handling.
Incompatibilities: Strong oxidizers (may promote exothermic reactions); strong acids/bases can catalyze hydrolysis, especially at elevated temperatures or in the presence of water.
Handling: Avoid aerosol formation; wipe up spills promptly with absorbent. When transferring viscous material, use warmed syringes or positive-displacement pipettes.
Fire safety: Keep away from ignition sources. Use CO2, dry chemical, or foam for extinguishing. Cool containers with water spray if exposed to fire.
First aid (overview): Skin/eye contact—wash with water and soap; remove contaminated clothing. Inhalation of mists—move to fresh air. Ingestion—rinse mouth; do not induce vomiting; seek medical advice. Always follow local institutional protocols.
Note: Consult the SDS for this SKU before first use; it supersedes general guidance.
Solvent Selection
Palmityl oleate is a highly hydrophobic, neutral wax ester.
Polarity/miscibility (literature/general):
Water: insoluble.
Hydrocarbons (hexane, heptane, isooctane, toluene): miscible; preferred for handling and extractions.
Chlorinated solvents (CH2Cl2, CHCl3): good solubility; useful for reactions and NMR.
Ethers (MTBE, diethyl ether, THF): good to moderate solubility.
Polar protic (MeOH, EtOH): limited solubility at RT; miscibility improves on warming or with cosolvents.
Polar aprotic (MeCN, DMF, DMSO): generally poor to moderate solubility; dissolution may require heating.
Practical tips:
Prepare stock solutions 0.05–1.0 M in hexanes, toluene, or CHCl3 depending on use (chromatography vs. reaction chemistry).
Gentle warming (30–40 °C) aids dissolution and pipetting.
For enzymatic transformations in aqueous systems, employ emulsifiers or biphasic setups with organic cosolvents (e.g., isooctane) to enhance substrate availability.
Comparison (when to choose alternatives):
For greener processing, prefer heptane/isoparaffins over chlorinated solvents.
For NMR, CDCl3 is conventional; C6D6 or toluene‑d8 can reduce ester exchange risks under basic conditions.
Note: Solvent choice should also consider downstream analytics (e.g., avoid high-boiling oils if GC analysis is planned).
Storage and Reconstitution
Item-specific storage from Product Data: Room temperature.
Shipping: Not specified for this item; refer to CoA/Spec Sheet.
General guidance for this class of compounds:
Store tightly closed under inert gas (nitrogen/argon) if possible to minimize slow autoxidation of the cis-alkene, especially for long-term storage.
Protect from prolonged exposure to heat, light, and air. Amber bottles and minimal headspace are recommended for archival samples.
Moisture considerations: While neutral esters are relatively stable, avoid strong acids/bases and aqueous conditions that promote hydrolysis over time.
Reconstitution/Preparation:
If material is viscous, warm gently (30–40 °C) to pour or pipette.
Prepare stock solutions in hexane, toluene, or CHCl3 at desired concentrations. For biological assays, consider isooctane or emulsified systems.
Filter solutions (PTFE, 0.45 μm) if particulate forms upon cooling.
Freeze–thaw: Not generally required; avoid freezing aqueous emulsions to prevent phase separation. For neat material, room temperature storage is typical.
Note: Where critical, determine peroxide/acid values periodically to track oxidative/hydrolytic stability during extended storage.
Structure and Identity
Palmityl oleate (also called cetyl oleate or hexadecyl (Z)-octadec-9-enoate) is a long-chain wax ester formed from oleic acid and cetyl (hexadecyl) alcohol.
Item-specific (from Product Data):
CAS: 22393-86-8
CID: 5377655
InChIKey: 173696
Literature/computed identifiers and features (for reference only; not product specifications):
Structural features: one long C18 monounsaturated acyl chain (oleate, cis-Δ9) esterified to a saturated C16 alkoxy chain; overall a neutral, nonpolar ester with an internal cis-alkene and an ester linkage.
2D description: a linear C18 chain bearing a single internal C=C (cis) terminates in a carboxylate carbonyl linked via –O– to a linear C16 alkyl chain; no ring systems or heteroatoms besides the ester oxygen atoms.
Notes: When using identifiers for informatics, confirm exact stereochemistry of the C=C (commonly Z-9-oleate) in the supplier’s CoA if critical to your application.
Synthetic Utility
From a synthetic standpoint, palmityl oleate presents two orthogonal handles: an internal cis-alkene and an ester linkage.
Functional group chemistry (literature):
Alkene: amenable to hydrogenation, epoxidation (mCPBA), dihydroxylation (OsO4 or Mn-catalyzed protocols), ozonolysis/oxidative cleavage, hydroboration–oxidation (gives secondary alcohols), thiol–ene additions, and Ru-catalyzed olefin metathesis.
Ester: participates in transesterification (base, acid, or enzymatic), aminolysis under forcing conditions, and saponification (base-promoted hydrolysis) to regenerate oleic acid and cetyl alcohol.
Strategic uses:
As a modular hydrophobe: transform the alkene to introduce polar headgroups post-functionalization (e.g., epoxide opening with nucleophiles) creating amphiphiles/surfactants with controlled tail length.
Isotopic labeling: exchange the alcohol or acid fragments via interesterification for tracer studies.
Materials chemistry: crosslink via thiol–ene or epoxide chemistries to prepare soft networks/coatings from renewable feedstocks.
Selectivity/control tips:
Protect the ester (neutral conditions) when targeting alkene modifications; minimize acid/base to avoid hydrolysis.
For metathesis, dry, degassed nonpolar solvents (toluene, DCM) and 1–5 mol% Ru catalysts at 30–60 °C are typical; internal alkenes may require higher catalyst loadings.
These considerations are general literature guidance and not specifications for this item.
Target Specificity
Not applicable. This product is a small-molecule wax ester and is not an antibody, probe, or biologic. No target-binding specificity data are associated with this item.
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