This compound belongs to the class of organic compounds known as fatty acid methyl esters. These are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group.
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
No item-specific tested application protocols are provided for this product. General guidance for common uses:
GC-FAME standard preparation (general): Dissolve an accurately weighed amount in iso-octane or hexane to prepare stock standards (e.g., 1–10 mg/mL). Warm gently to ensure complete dissolution; verify by GC-FID.
Lipid sample spike-in (general): Prepare concentrated solution in chloroform:methanol (2:1) or isopropanol:hexane. Add defined aliquots to samples prior to extraction/derivatization to serve as an internal standard. Mix thoroughly.
Refer to your laboratory’s validated methods and the SDS before use.
Biological Roles
General biochemical context (literature):
Methyl hexacosanoate is a derivatized form (FAME) of cerotic acid (hexacosanoic acid, C26:0), a very long-chain saturated fatty acid present in plant cuticular waxes, beeswax, and some microbial lipids.
In vivo, fatty acids occur as free acids, acyl-CoA thioesters, glycerides, or complex sphingolipids; methyl esters are primarily analytical derivatives and are not central metabolic intermediates.
Metabolic relevance (indirect):
Hydrolysis (enzymatic or chemical) would yield hexacosanoic acid, which can enter peroxisomal beta-oxidation pathways in organisms capable of processing very long-chain fatty acids.
The extreme hydrophobicity and chain length influence membrane packing and barrier properties when incorporated into waxy matrices.
Research utility:
Serves as a standard to study chain-length–dependent behavior in lipid crystallization, melting transitions, and chromatographic retention.
Model substrate for evaluating ester hydrolysis kinetics in nonaqueous media or heterogeneous systems.
Note: This product is supplied for research use only. No medical or clinical claims are made or implied.
Buffer Applications
This compound is a nonpolar fatty acid methyl ester and is not used to prepare aqueous buffer systems. It is practically insoluble in water and has no significant acid/base buffering capacity in aqueous media. For laboratory use, see Solvent Selection for guidance on dissolving in suitable organic solvents prior to any partitioning or extraction steps.
Green Alternatives
Greener handling and solvent choices (general):
Prefer heptane or iso-octane over hexane where feasible to reduce n-hexane exposure hazards.
For dissolving and transfers, consider bio-based solvents such as 2-methyltetrahydrofuran (2-MeTHF) or Cyrene for certain operations; verify solubility (often limited in greener polar aprotics for very long-chain esters) and compatibility with your method.
For lipid extractions, adopt greener biphasic systems (e.g., isopropanol:heptane) instead of chloroform:methanol where method performance allows.
Sustainable sourcing (contextual):
Long-chain FAMEs can be produced from renewable fatty acid feedstocks via transesterification. When lifecycle impacts matter, request documentation of bio-based origin.
Process considerations:
Employ energy-efficient melting/dissolving (water bath at controlled temperatures) rather than prolonged hot-plate heating.
Minimize halogenated solvent use in analytics by validating hydrocarbon-based GC diluents and rinses.
Tradeoffs:
Highly hydrophobic analytes like methyl hexacosanoate may require nonpolar hydrocarbons for adequate solubility. While greener polar media are attractive, insufficient solubility can compromise accuracy in analytical standards.
Pharmaceutical Uses
Context (general, non-clinical):
Long-chain fatty esters are sometimes used as excipients or components in topical, cosmetic, and materials formulations due to their emollient and film-forming properties. Methyl hexacosanoate can serve as a hydrophobic structurant or reference material in formulation research.
Analytical role:
Useful as a reference standard in quality control labs performing GC analysis of FAME profiles in excipient oils and waxes.
Regulatory note:
No pharmacopeial status is stated for this specific item. Any use in regulated products would require appropriate qualification.
Manufacturing R&D considerations:
Evaluate melting behavior and compatibility with wax matrices (e.g., beeswax, carnauba) for texture tuning.
Due to extremely low volatility, it can reduce evaporative losses during thermal processing compared with shorter-chain esters.
No therapeutic or clinical claims are made; this product is intended for research and development use only.
Physical Properties
Note: No item-specific specifications were provided. Values below are literature/general expectations for long-chain saturated fatty acid methyl esters and should be used as guidance only, not as product specifications.
Phase/appearance (literature): Waxy solid or high-melting semi-solid at ambient temperature; becomes clear, low-viscosity liquid upon gentle warming above its melting range.
Melting point (literature): Typically in the ~60–70 °C range for C26 saturated FAMEs; exact value can vary with purity and polymorph. Not specified for this item; refer to CoA/Spec Sheet.
Boiling point (literature): Very high at ambient pressure (>350 °C); usually distilled under high vacuum (e.g., 0.1–1 mbar) at substantially lower temperatures. Not specified for this item; refer to CoA/Spec Sheet.
Density (literature): On the order of ~0.86–0.88 g/mL near melt; increases slightly upon cooling. Not specified for this item; refer to CoA/Spec Sheet.
Solubility (literature):
Water: Practically insoluble.
Organic: Readily soluble in nonpolar and moderately polar organics (hexanes, heptane, toluene, chloroform, dichloromethane, diethyl ether); limited solubility in acetonitrile and alcohols at room temperature but improves on warming.
LogP (literature): Very high (>>6), reflecting strong hydrophobicity.
Refractive index (literature): Typical of long-chain esters (nD ~1.44–1.46 near melt). Not specified for this item; refer to CoA/Spec Sheet.
Vapor pressure (literature): Extremely low at room temperature.
Always consult the product’s CoA/Spec Sheet for any item-specific values and the SDS for handling at elevated temperatures.
Quality & Grades
Item-specific quality information
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting typical grades for this compound class (general guidance):
GC/HPLC grade: Emphasizes low non-volatile residue and low UV background; suitable for chromatographic standards and quantitative lipidomics.
Analytical/reference standard grade: Tight assay specification and impurity profiling (isomeric/chain-length homogeneity), enabling calibration in FAME profiling.
Technical grade: Suitable for bulk synthesis or materials applications where trace impurities are less critical.
Stabilizers/antioxidants:
Long-chain saturated FAMEs are relatively oxidation-resistant compared to unsaturated analogs and generally do not require antioxidants. If any stabilizers are present, they will be declared on the CoA; none are specified here.
What to check on receipt (best practice):
Confirm melting behavior (sharpness of melt) and chromatographic purity (single major peak at the expected retention time by GC-FID).
Review residual solvent, moisture, and identity data (e.g., GC-MS, 1H/13C NMR) on the CoA if provided.
Always consult the item’s CoA/Spec Sheet for definitive specifications and acceptance criteria.
Reaction & Applications
Analytical/lipidomics applications (general):
Used as a calibration/retention-time standard in GC-FID/GC-MS profiling of fatty acid methyl esters (FAMEs), covering the long-chain saturated end (C26:0). Useful for evaluating column resolution and detector linearity at high carbon numbers.
Serves as an internal standard in quantifying very long-chain fatty acids after derivatization.
Materials and formulation roles (general):
Hydrophobic component in waxes and coatings; model compound for studying crystallization and polymorphism of long-chain esters.
Synthetic transformations (general examples):
Hydrolysis/saponification to hexacosanoic acid (cerotic acid) under acidic or basic conditions.
Reduction to the corresponding long-chain alcohol (hexacosanol) using LiAlH4 or borane reagents.
Transesterification to other alkyl esters (e.g., ethyl/benzyl hexacosanoate) with alcohol and acid/base catalysis.
Amidation (via acid after hydrolysis) to long-chain amides, surfactants, or lipid conjugates.
Practical tips:
Ensure complete dissolution or fine suspension before initiating reactions; mass transfer can limit rates for waxy substrates.
For GC work, verify absence of shorter/longer FAME impurities that can shift baselines at high retention times.
Use high-vacuum techniques for purification if needed; Kugelrohr or short-path distillation minimizes thermal residence time.
Reaction Conditions
The following are literature/general conditions for typical transformations of long-chain methyl esters; they are provided as guidance and should be optimized per application.
Hydrolysis (saponification to acid):
Base: KOH or NaOH in methanol or ethanol (0.5–2.0 M). Heat 40–70 °C for 1–4 h. Work up by dilution with water, acidify to pH <2, extract into hexanes/EtOAc, wash, and dry.
Acidic: HCl or H2SO4 (aqueous or in dioxane) under reflux; longer times due to low solubility.
Reduction to alcohol:
LiAlH4 in dry THF or diethyl ether, 0 °C to reflux, 2–16 h; quench carefully then work up. Alternatively BH3·THF can reduce esters under milder conditions.
Transesterification:
Acid-catalyzed: Catalytic H2SO4 or p-TsOH in the target alcohol (e.g., ethanol or benzyl alcohol), Dean–Stark water removal if necessary, 60–110 °C, several hours.
Base-catalyzed: Sodium alkoxide (e.g., NaOMe) 0.5–5 mol% in corresponding alcohol, 25–60 °C, 1–6 h.
Enzymatic exchange:
Lipase-catalyzed transesterification in solvent-free or organic media (e.g., tert-butanol, heptane), 30–60 °C, with molecular sieves to sequester water; useful for selectivity.
Purification/analysis:
GC-FID/GC-MS with nonpolar columns (e.g., DB-5, 30 m; temperature programming up to 350 °C) for retention time/identity; for very long chains, on-column or PTV injection reduces discrimination.
Note: Expect slower kinetics due to mass transfer limits; warming and efficient mixing are important. Always confirm conditions are compatible with long-chain waxy substrates.
Safety & Handling
Item-specific hazard data
GHS classification: Not specified for this item; refer to SDS.
Signal word / H-statements / Pictograms: Not specified for this item; refer to SDS.
General safety profile (literature/general):
Long-chain saturated fatty acid methyl esters are generally of low acute toxicity and low volatility. Nonetheless, handle as a laboratory chemical.
Primary hazards: Slippery material when spilled; may cause mild skin/eye irritation; combustible at elevated temperature. Heated liquid can cause thermal burns.
Personal protective equipment (PPE):
Safety glasses or chemical splash goggles; lab coat; disposable nitrile gloves. Use heat-resistant gloves if handling above the melting point.
Handling practices:
Work in a well-ventilated area; avoid aerosol generation when preparing standards.
When heating to liquefy, use a controlled warm water bath or heat block; avoid open flames.
Prevent contamination with strong oxidizers; avoid prolonged exposure to strong bases/acids unless intentionally performing hydrolysis.
Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical advice if irritation persists.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention per institutional protocols.
Inhalation: Unlikely due to low volatility; move to fresh air if mist/vapor inhalation occurs.
Always defer to the product SDS for authoritative and current safety information.
Solvent Selection
This product is a hydrophobic solid/liquid (near its melting range), not a solvent. Solvent selection here refers to dissolving/handling methyl hexacosanoate in analytical or synthetic workflows.
Polarity and miscibility (general):
Highly nonpolar; practically insoluble in water.
Freely soluble in hydrocarbons (hexanes, heptane, isooctane), aromatic solvents (toluene), and halogenated solvents (chloroform, dichloromethane). Moderately soluble in ethyl acetate and diethyl ether; limited in short alcohols at room temperature.
Typical use scenarios:
GC-FAME analysis: Prepare standards/solutions in iso-octane, hexane, or heptane to match common GC methods.
LC-MS or sample prep: Dissolve in isopropanol:hexane (e.g., 2:1) or chloroform:methanol mixtures for lipid sample handling; dilute further with mobile phase as needed.
Synthetic operations: Use toluene, hexanes, or THF/ether systems depending on reaction (e.g., transesterification, reductions following dissolution or suspension).
Practical tips:
Warm gently (40–60 °C) to aid dissolution; ultrasonication helps in nonpolar media.
Avoid high-water content mixtures; use co-solvents (e.g., isopropanol) if interfacing with aqueous systems.
Comparison (general):
Versus shorter-chain FAMEs (e.g., methyl palmitate): Lower volatility, higher melting point; requires warmer conditions to fully dissolve but affords improved stability and reduced evaporation losses.
Saturated long-chain methyl esters are relatively resistant to oxidation; nonetheless, protect from excessive heat and prolonged air exposure. Store tightly sealed under inert gas if extended storage is anticipated.
Avoid repeated heating/cooling cycles; if solidifies, warm gently to liquefy before dispensing.
Reconstitution/dissolution (general guidance):
To prepare solutions, allow the container to equilibrate to room temperature to avoid moisture condensation, then warm to ~40–60 °C if needed.
Suitable solvents: hexane, heptane, iso-octane, toluene, chloroform, dichloromethane, diethyl ether; limited solubility in short-chain alcohols at ambient but improves upon warming.
Recommended stock concentrations: 1–100 mg/mL depending on solvent and application (ensure complete dissolution and method compatibility).
Packaging/handling tips:
If supplied as a solid/wax, use a pre-warmed spatula or syringe when liquefied for accurate weighing/dispensing.
After opening, purge headspace with nitrogen/argon and recap promptly.
For any item-specific stability, impurity, or solution shelf-life data: Not specified for this item; refer to CoA/Spec Sheet.
Structure & Identity
Brief description: Methyl hexacosanoate is the methyl ester of hexacosanoic acid (cerotic acid), a linear, fully saturated C26 fatty acid. It is a long-chain aliphatic ester used widely as a FAME standard and hydrophobic building block.
Item-specific identifiers (from Product Data)
SKU: M298958
Product name: Methyl hexacosanoate
CAS: 5802-82-4
Storage: Store at 2–8°C; shipped on wet ice
Research use: For research use only
InChIKey (as provided): 379433 (note: not a standard InChIKey format; see literature identifiers below if needed)
Structure and general identifiers (literature/general chemistry)
Molecular formula (literature): C27H54O2
Molecular weight (literature): ~410.73 g/mol
Preferred IUPAC name (literature): Methyl hexacosanoate
SMILES (literature): COC(=O)CCCCCCCCCCCCCCCCCCCCCCCCC (linear, no unsaturation; count of carbons corresponds to C26 acyl chain + methyl ester)
InChIKey (literature): Not specified here; consult a structure database (e.g., PubChem CID 22048)
Structural features (general description)
Functional groups: One terminal methyl ester (–CO2Me); otherwise a saturated, linear alkyl chain (no rings, no heteroatoms beyond ester O).
Stereochemistry: Achiral; no stereocenters.
2D depiction in words: A methyl ester head group (MeO–C(=O)–) attached to a straight, unbranched C25 alkyl chain terminating in –CH3 (overall C26 in the acyl chain). Highly hydrophobic, with a single polar ester moiety at one end.
Synthetic Utility
Functional group leverage:
Terminal methyl ester enables interconversion to diverse derivatives:
Hydrolysis to hexacosanoic acid (acidic or basic conditions).
Reduction to hexacosanol (LiAlH4, BH3·THF), enabling subsequent etherification, esterification, or surfactant synthesis.
Transesterification to introduce specialized alcohols (e.g., benzyl, neopentyl) under acid/base catalysis.
The long, saturated alkyl chain imparts hydrophobicity and crystallinity, enabling use as a building block for waxes, phase-change materials, and hydrophobic anchors in conjugates.
Retrosynthetic value:
Serves as a protected acid equivalent in multistep routes where late-stage hydrolysis liberates the carboxylic acid without handling poorly soluble long-chain acids early on.
Amidation via acid chloride (after hydrolysis then SOCl2/oxalyl chloride activation) to produce long-chain amides.
Enzymatic transesterification using lipases (Novozym, Candida antarctica lipase B) in organic solvents for mild, selective exchange of the methyl group.
Crosslinking/materials: blending with diacids/diols (after suitable conversion) to access semicrystalline polyesters with high melting points.
Practical notes:
Ensure homogeneous phase by warming and vigorous stirring; heterogeneous reactions are diffusion-limited.
Purify by crystallization from ethanol/acetone blends or by high-vacuum short-path distillation if thermal stability permits.
Target Specificity
Not applicable. This product is a small-molecule fatty acid methyl ester, not a biological affinity reagent. No antigen/epitope or species reactivity applies. No item-specific data provided.
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