Myristoleyl arachidate , CAS No.2692623-59-7

CAS: 2692623-59-7 Cat. No.: M1439928 Formula: C₃₄H₆₆O₂ Molecular Weight: 506.89

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Myristoleyl arachidate is an ester product.

Specifications

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

Molecular Weight

506.89

Application Protocols

Item-specific tested applications are not provided; Not specified for this item—refer to CoA/Spec Sheet. Below are general, non-binding protocols commonly used for hydrophobic lipid esters.

1. Preparation of stock solutions

• Dissolve at 5–10 mg/mL in chloroform or toluene. Gentle warming (30–40 °C) and brief sonication can help. Store aliquots in amber vials, under nitrogen/argon, at −20 °C.

2. Lipid film formation (for rehydration or coating)

• Evaporate an organic solution on a clean glass vial or round-bottom flask under a stream of nitrogen. Desiccate under high vacuum 1–2 h to remove residual solvent. For mixed films, co-dissolve components to ensure homogeneity.

3. Langmuir monolayer setup

• Spread 20–100 µL of a ~0.1–1.0 mg/mL chloroform solution onto an aqueous subphase. Allow 5–10 min for solvent evaporation before compression. Record surface pressure–area isotherms at controlled temperature.

4. Hydrogenation screening (analytical scale)

• To a 10 mL vial add 10 mg ester in 2 mL EtOAc, 10% w/w Pd/C (1 mg). Stir under H2 balloon at rt; monitor by TLC (hexane/EtOAc 9:1) or 1H NMR until olefin signals disappear. Filter over celite, wash, evaporate.

Always adapt to your specific equipment and observe safety best practices.

Biological Roles

Item-specific biological data: Not specified for this item; refer to literature for general context.

General context for long-chain fatty esters:

• Storage/structural roles: In biology, fatty acids are often stored and transported as esters (e.g., triglycerides, wax esters). Myristoleyl arachidate is a mixed wax-ester-like molecule combining one unsaturation with a long saturated chain, offering a model for studying how unsaturation affects packing and melting behavior in lipid assemblies.
• Enzymatic processing: Lipases, esterases, and wax-ester hydrolases can act on long-chain esters; reaction rates depend on chain length, degree of unsaturation, and interfacial area. This compound can serve as a substrate in enzymology studies examining selectivity for unsaturated alcohol chains.
• Biophysical properties: The presence of a single cis double bond generally decreases crystallinity and lowers transition temperatures relative to fully saturated analogs, impacting membrane mimicry, permeability, and protein–lipid interactions in model systems.
• Analytical surrogates: Defined long-chain esters are sometimes used as hydrophobic internal standards or retention markers in lipidomics workflows to normalize extraction efficiency and chromatographic performance.

Note: This product is for research use only and is not intended for use in humans or animals.

Buffer Applications

This compound is an extremely hydrophobic, neutral long-chain ester and is not used to prepare aqueous buffer systems or to control pH. It has negligible water solubility and no acid/base functionality within the physiological pH range.

Practical guidance:

• For experiments requiring aqueous environments, dissolve in a suitable organic solvent (e.g., CHCl3, toluene, ethyl acetate) and deposit as thin films or deliver via solvent injection into buffer with vigorous mixing; include appropriate solvent controls.
• If interfacial studies are desired, prepare monolayers on buffered subphases using standard Langmuir trough techniques.

Refer instead to the Solvent Selection, Reaction & Applications, and Application Protocols sections for relevant handling guidance.

Green Alternatives

Greenness can be improved primarily through solvent and process choices; the core reagent is a high-molecular-weight lipid whose intrinsic hazards are relatively low but whose manufacture and handling can be optimized.

Greener solvent choices for handling and film casting (general guidance):

• Replace chloroform/dichloromethane with ethyl acetate, methyl tert-butyl ether (MTBE), or cyclopentyl methyl ether (CPME) when compatible with the application.
• Use heptane in place of hexane (reduced neurotoxicity profile) for chromatography or dissolution.
• Employ ethanol or isopropanol as minor co-solvents to aid spreading in LB troughs when feasible.

Comparison (literature-based, general):

• CHCl3: excellent solvency; poor EHS profile and ozone-depleting legacy. Disposal burdens are high.
• Ethyl acetate: biodegradable, low toxicity, adequate solvency with mild warming; faster evaporation than alcohols.
• CPME/2-MeTHF: good solvency and hydrophobicity; form fewer peroxides than ethers like THF; water-tolerant.

Process considerations:

• Conduct hydrogenations at ambient temperature/pressure where possible to reduce energy use.
• Favor biocatalytic transesterification/hydrolysis with immobilized lipases in green solvents or solvent-free systems.
• Minimize waste by preparing concentrated stock solutions and using microscale LB deposition.

Trade-offs:

• Greener solvents may dissolve the ester more slowly or require slightly elevated temperatures; verify film quality and purity (residual solvent) by IR/GC.

Pharmaceutical Uses

No item-specific pharmacopeial status or excipient grade is provided for this product; Not specified for this item—refer to CoA/Spec Sheet.

General, non-clinical context for long-chain fatty esters:

• Excipients: Long-chain wax esters and triglyceride analogs are sometimes used in formulation science as hydrophobic vehicles, matrix formers, or consistency modifiers in semi-solids. However, use requires well-defined grade controls (residual solvents, peroxide value, identity) and regulatory documentation not provided here.
• Preformulation tools: Defined esters can serve as model hydrophobic phases to screen solubilization strategies, assess partitioning, and study drug–lipid interactions for oral or topical dosage form research.
• Manufacturing aids: Hydrophobes may reduce dusting, serve as mold-release aids, or adjust melt rheology in hot-melt extrusion research.

Important: This listing is for research use only and is not intended for human or veterinary drug products or clinical applications.

Physical Properties

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

Literature/computed expectations for a C34 fatty ester with one double bond (informational, not product specifications):

• Physical state: waxy solid or highly viscous oil at ambient temperature (long-chain fatty esters often soften near room temperature; exact MP depends on isomeric purity and cis/trans geometry).
• Approximate molecular weight (computed from putative structure): ~506.9 g/mol.
• Solubility: essentially insoluble in water; soluble in nonpolar and moderately polar organic solvents (e.g., n-hexane, heptane, toluene, CH2Cl2, CHCl3, ethyl acetate). Limited solubility in alcohols; miscibility improves on gentle warming.
• LogP: expected to be very high (>10, literature expectation for C>30 monoesters), indicating strong hydrophobicity.
• Density: typically ~0.85–0.90 g/mL at 20–25°C for similar long-chain esters (literature range; actual may vary).
• Boiling behavior: very high boiling/decomposition; typically handled without distillation. Thermal analysis (DSC/TGA) is preferred over BP reporting for similar lipids.
• Refractive index: typically around nD 1.45–1.47 for related long-chain esters (literature).

Practical notes:

• Gentle warming (30–40°C) can aid dissolution and film formation.
• Due to the unsaturation, oxidative susceptibility is higher than the fully saturated analog (myristyl arachidate). Work under inert atmosphere when feasible.

Quality & Grades

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

General guidance for lipid ester quality considerations:

• Purity metrics: For long-chain esters, typical characterization includes NMR (1H/13C), IR (ester C=O ~1735–1750 cm−1), GC-FID/GC-MS for homogeneity and chain-length distribution, and HPLC for isomeric purity. For unsaturated species, cis/trans ratio and double-bond position verification (e.g., ozonolysis/derivatization GC) are often reported in CoA.
• Stabilizers/antioxidants: Not specified for this item; refer to CoA/Spec Sheet. In general, trace antioxidants (e.g., BHT) may be used for unsaturated lipids to limit peroxidation. If present, they should be declared on the CoA.
• Research Use Only: This product is designated for research use; not for human or veterinary use.
• What different grades imply (general):
  • Synthetic/Research grade: Suitable for most chemical and materials work; UV background and trace residues not tightly controlled.
  • HPLC/LC–MS grade (if offered): Tight control of nonvolatile residues and UV absorbance; beneficial when the ester will be used as an analytical standard.
  • BioReagent grade (if offered): Lower peroxide value and better control of trace metals/water for sensitive biophysical assays.
• Verification: For quantitative studies (e.g., monolayer phase behavior), verify peroxide value and unsaturation integrity upon receipt and after storage.

Reaction & Applications

This molecule is a defined mixed long-chain fatty ester (C20:0 acid × C14:1 alcohol). Typical research applications include:

Lipid/biophysical studies:

• Model hydrophobic matrix for studying membrane-mimetic environments, diffusion in lipid films, and phase behavior of mixed saturated/unsaturated chains.
• Langmuir and Langmuir–Blodgett (LB) monolayers: investigate effects of a single cis double bond on packing and compressibility compared to fully saturated analogs.
• Thin-film/coating studies: evaluate barrier properties, water vapor transmission, and crystallinity of long-chain esters.

Reactivity/chemistry:

• Controlled hydrogenation (Pd/C, H2, rt–40°C) to convert the C14:1 moiety to the saturated myristyl arachidate; monitor by 1H NMR (olefinic signals ~5.3 ppm) and iodine value.
• Epoxidation of the C=C (e.g., mCPBA, 0 °C to rt) to access oxirane derivatives for further functionalization (opening with nucleophiles, regioselective transformations).
• Transesterification studies: a substrate for lipase-catalyzed exchange with isotopically labeled alcohols/acids, probing enzyme selectivity for chain length and unsaturation.
• Hydrolysis kinetics: compare chemical (NaOH/MeOH, biphasic) vs. enzymatic (lipases) ester cleavage rates as a function of phase behavior.

Analytical uses:

• Retention-time/response standards for GC or LC of very hydrophobic esters; derivatization may be needed for GC due to high BP.

Practical tips:

• Work under inert gas and subdued light to preserve the unsaturated bond.
• For monolayer work, use freshly prepared CHCl3 solutions and verify peroxide levels.

Reaction Conditions

General literature guidance for typical transformations of long-chain unsaturated esters (informational; optimize per your setup):

• Esterification (synthesis):

  • DCC (1.1–1.5 eq), DMAP (0.05–0.1 eq), CH2Cl2, 0 °C to rt, 2–16 h; workup via urea filtration; yields commonly 70–90% for unhindered long-chain substrates.
  • Acid chloride route: Convert arachidic acid to acyl chloride (SOCl2, reflux 2–3 h, catalytic DMF), then couple with myristoleyl alcohol and pyridine at 0–25 °C; 70–90% yields typical.

• Hydrogenation of C=C:

  • Pd/C (5–10 wt%), H2 (1 atm), hexane/EtOAc or EtOAc/EtOH, rt–40 °C, 2–8 h; monitor disappearance of olefinic 1H NMR (~5.3 ppm). Avoid over-reduction of ester by keeping mild conditions.

• Epoxidation:

  • mCPBA (1.1–1.3 eq), CH2Cl2, 0 °C to rt, 1–4 h; quench with Na2SO3; isolate epoxide by silica gel (use hexane/Et2O). Unsaturated long-chain esters typically give good to excellent yields.

• Transesterification (biocatalytic):

  • Immobilized Candida antarctica lipase B (CALB), 40–60 °C, solvent-free or in MTBE/2-MeTHF, with 2–5 eq alcohol; reduced pressure to remove coproduct. Selectivity depends on chain length and unsaturation.

• Hydrolysis:

  • Base: KOH/MeOH–H2O (1–2 M), 20–40 °C, hours; gives arachidate salt + myristoleyl alcohol; extractively separate.
  • Enzyme: Lipase in buffered aqueous emulsion with surfactant; rate scales with interfacial area.

Note: Values are representative literature conditions for similar substrates and are not product specifications.

Safety & Handling

Item-specific hazard data: Not specified for this item; refer to SDS for authoritative information.

General safety profile for long-chain fatty esters (informational):

• GHS: Often not classified as acutely hazardous; however, treat as a combustible organic solid/oil. Avoid aerosol generation and prolonged skin contact.
• PPE: Safety glasses, lab coat, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood when handling powders, sprays, or organic solvent solutions.
• Incompatibilities: Strong oxidizers. Unsaturated bonds are susceptible to autoxidation; minimize exposure to air, heat, and light. Avoid alkali metal alkoxides or strong bases if ester stability is critical (can promote transesterification/saponification under harsh conditions).
• Thermal stability: High flash point; may decompose on strong heating. Do not distill to dryness.
• First aid (general):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin: Wash with soap and water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if easy to do.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
• Spill/cleanup: Absorb with inert material (vermiculite), collect for disposal. Degrease surfaces with suitable detergent/solvent.
• Always consult the product-specific SDS before use.

Solvent Selection

Polarity and miscibility (general for long-chain esters):

• Polarity: Very nonpolar; high logP. Insoluble in water; excellent solubility in nonpolar organics.
• Good solvents: chloroform, dichloromethane, toluene, xylene, n-hexane/heptane, cyclohexane, ethyl acetate (moderate). Solubility in lower alcohols (EtOH, iPrOH) is limited at room temperature but improves with mild heating or co-solvents.
• Poor solvents: Water; very polar aprotics (DMSO, DMF) can dissolve to some extent at elevated temperature but are rarely preferred for thin-film or monolayer work due to high boiling point and residues.

When to choose which solvent:

• Film casting/monolayers: CHCl3 or CH2Cl2 for rapid evaporation and clean films; add a small fraction of MeOH to aid spreading if needed.
• Preparative handling/purification: n-Hexane/EtOAc mixtures for flash chromatography; toluene or heptane for recrystallization of high-purity fractions (if crystalline).
• Stock solutions: 1–10 mg/mL in CHCl3 or toluene; store cold under inert gas.

Comparison (general):

• CHCl3 vs. Hexane: CHCl3 gives better solvation and film uniformity; hexane offers lower toxicity and easier waste handling but slower dissolution.
• Ethyl acetate: greener profile and reasonable solvency; may require warming for high concentrations.

Practical tips:

• Warm to 30–40°C and sonicate briefly to dissolve quickly.
• Filter through PTFE if particulate forms on storage (oxidation products or microcrystals).

Storage & Reconstitution

Item-specific instructions (from Product Data):

• Storage Conditions: Store at −20°C.
• Shipped In: Ice chest + Ice pads.

General handling and stability guidance for unsaturated long-chain esters:

• Protect from air, light, and moisture to limit autoxidation and hydrolysis. Store in amber, airtight containers. Consider inert gas blanket (N2/Ar), especially for opened containers.
• Avoid repeated freeze–thaw cycles; dispense into small, single-use aliquots upon first opening.
• If solidified, warm gently to room temperature or to 30–40 °C to liquefy before dispensing. Do not overheat.

Reconstitution/solution preparation:

• Prepare stock solutions in chloroform, toluene, or ethyl acetate at 1–10 mg/mL. Filter through a PTFE syringe filter if particulates are observed.
• For film preparation, evaporate solvent under a nitrogen stream and dry under high vacuum prior to use.

Quality checks on storage:

• Visual: note any cloudiness or precipitate formation in solutions; discard if significant.
• Analytical: for sensitive applications, periodically check by 1H NMR (loss of olefinic signals indicates hydrogenation; new aldehydic peaks suggest oxidation) or peroxide value assays.

Note: Follow local regulations and consult the SDS for stability, incompatibilities, and safe disposal.

Structure & Identity

Overview: Myristoleyl arachidate is a long-chain fatty acid ester composed of an unsaturated C14 alcohol moiety (myristoleyl, derived from myristoleic acid; one cis double bond) esterified with a saturated C20 fatty acid (arachidic acid, eicosanoate). The result is a neutral, highly hydrophobic waxy lipid.

Item-specific identifiers (from Product Data):

• CAS: 2692623-59-7
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: 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.

Literature/computed identity notes (for the nominal structure):

• Putative composition: an ester linking arachidic acid (C20:0) to myristoleyl alcohol (C14:1, Δ9 cis)
• Estimated formula (computed): C34H66O2
• Estimated molecular weight (computed): ~506.9 g/mol
• Key functional groups: one ester carbonyl; aliphatic chains (C34 total) containing one internal cis C=C.

2D/structural description (general):

• Linear C20 chain terminating in an ester carbonyl connected to a C14 chain that contains a single internal cis double bond (no rings, no heteroatoms beyond the ester oxygens). The molecule is non-ionic and lacks H-bond donors; it has one H-bond acceptor (the carbonyl oxygen).

Synthetic Utility

Functional elements and reactivity (general):

• Ester functionality: amenable to hydrolysis (acidic or basic), transesterification (acid/base or enzymatic), and reduction to the corresponding alcohol (e.g., DIBAL-H to aldehyde at low temperature; LiAlH4 to diols/higher alcohols).
• Olefin handle: single internal cis C=C on the C14 chain enables hydrogenation, epoxidation (mCPBA), dihydroxylation (OsO4 or KMnO4), hydroboration–oxidation (for terminal or near-terminal alkenes; regioselectivity depends on position), and radical additions under photochemical conditions.

Use-cases:

• Scaffold for preparing a suite of analogs (hydrogenated, epoxidized, deuterated) to dissect the role of unsaturation in film packing, melting, and permeability.
• Lipase selectivity probes: swap the alcohol or acid portion via transesterification to test enzyme preference for chain length and unsaturation.
• Radiolabel/isotope routing: assemble 13C/2H labels on one half (acid or alcohol) to track interfacial reactions and monolayer dynamics.

Retrosynthesis perspective:

• Accessible from arachidic acid (C20:0) and myristoleyl alcohol (C14:1) via standard esterification (DCC/DMAP or EDCI/DMAP in CH2Cl2) or via acid chloride formation (SOCl2, catalytic DMF) followed by coupling with the alcohol under non-basic conditions to preserve the cis geometry.

Handling tip: Maintain inert atmosphere and include antioxidant traces during transformations involving the C=C to suppress peroxidation.

Target Specificity

Not applicable. This product is a small-molecule lipid ester, not an antibody, protein, or targeted biological reagent. No antigen/epitope or species specificity is relevant to its use.

Frequently Asked Questions

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 2692623-59-7, the molecular formula is C34H66O2, and the molecular weight is 506.89 g/mol.

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.