Methyl pentadecanoate-d , CAS No.68060-02-6

CAS: 68060-02-6 Cat. No.: M1450715 Formula: C₁₆H₃D₂₉O₂ Molecular Weight: 285.60

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Methyl pentadecanoate-d 29 is the deuterium labeled Methyl pentadecanoate.

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: 285.60

Application Protocols

No vendor-validated bioassay protocols are provided for this small-molecule reagent. Common laboratory uses include:
• Preparation of GC–MS calibration curves: spike known amounts into n-hexane or iso-octane, analyze by SIM using D-shifted ions; construct response factors versus a protio analogue.
• LC–MS lipidomics internal standard: add to samples prior to extraction (e.g., Folch or MTBE methods) and carry through the workflow to correct for recovery and ionization variability.
• NMR verification: acquire 1H NMR in CDCl3 to confirm low protio content at labeled positions (attenuated or missing signals) and 2H NMR to observe the deuterium resonance(s).

For detailed, application-specific protocols, consult relevant peer-reviewed methods and adapt to your instrumentation and regulatory environment.

Biological Roles

Item-specific biological roles: not applicable; this is a deuterium-labeled analytical/synthetic reagent.

Context (literature/general):
• Pentadecanoic acid (C15:0) is an odd-chain saturated fatty acid occurring at low levels in ruminant fats and certain microorganisms; it is sometimes used as a marker in dietary and microbial studies.
• The methyl ester form is not a natural metabolite but is routinely generated during derivatization (e.g., BF3–MeOH or HCl–MeOH) to convert complex lipids to FAMEs for GC analysis.
• Deuterated methyl pentadecanoate serves as an internal standard or tracer to support quantitation or to study ester hydrolysis/transesterification mechanisms.

No medical or clinical claims are made; for laboratory research and analytical method development only.

Buffer Applications

This product is a highly hydrophobic fatty acid methyl ester and is not used to prepare aqueous buffers or common biochemical buffer systems.

Practical note: when spiking into biological samples or aqueous buffers for analytical purposes, pre-dissolve in a suitable organic carrier (e.g., isopropanol, acetonitrile/isopropanol, or a small volume of heptane) and add with vigorous mixing or via solvent-partition protocols to avoid precipitation and adsorption losses.

Green Alternatives

Considerations relate primarily to solvents and process choices, since the analyte itself is the target molecule.

Greener handling/analysis choices (literature/general):
• Replace chlorinated solvents (CH2Cl2, CHCl3) with hydrocarbons (heptane, iso-octane) or ethers with better EHS profiles (CPME, 2-MeTHF) where compatible with your method.
• For GC sample prep, n-hexane can be replaced by heptane or iso-octane to reduce neurotoxicity concerns, maintaining similar volatility and performance.
• For extractions, consider bio-based ethyl acetate/heptane systems versus halogenated solvents.
• Minimize solvent volumes using microextraction or SPME approaches in analytical workflows.
• Energy: take advantage of low-temperature solubility to crystallize/enrich where applicable, rather than using high-temperature distillations.

Trade-offs:
• Hydrocarbons are less polar than chlorinated solvents; ensure adequate solubility and injection reproducibility.
• CPME/2-MeTHF absorb some moisture; for water-intolerant steps (e.g., precise isotopic work), ensure proper drying.
• Switching solvents may slightly shift retention and ionization in LC–MS; revalidate calibration and response factors.

Summary table (general):
• CH2Cl2 → CPME/heptane: lower toxicity/halogen footprint, similar solvency for FAMEs.
• Hexane → Heptane/iso-octane: safer alternative with comparable GC behavior.

Pharmaceutical Uses

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

General context (non-clinical):
• Deuterated fatty acid methyl esters are primarily used as analytical reference materials and internal standards in pharmaceutical QC (e.g., monitoring extractables/leachables or residual solvents in lipid-based formulations, and characterizing excipient FAME profiles).
• They may aid in validating sample preparation recoveries for lipid-containing drug products by stable-isotope dilution mass spectrometry (SID-MS).
• Not intended for therapeutic or diagnostic use.

Physical Properties

Item-specific properties:
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general values (for unlabeled methyl pentadecanoate; provided for context only):
• Typical physical state: hydrophobic liquid or low-melting wax near ambient, depending on sample history (literature).
• Typical density: on the order of ~0.85–0.87 g/mL at 20–25 °C (literature for saturated C15–C16 FAMEs).
• Solubility: essentially insoluble in water; miscible with nonpolar and moderately polar organic solvents such as hexanes, toluene, diethyl ether, dichloromethane, and chloroform (literature).
• Refractive index: typical nD25 around 1.43–1.45 for long-chain FAMEs (literature).
• LogP: high (>>3), consistent with long-chain fatty acid methyl esters (literature).
• Boiling behavior: distills under reduced pressure; at atmospheric pressure may thermally degrade before clean distillation (literature).

Notes on deuteration:
• Deuteration increases exact mass and subtly shifts vibrational spectra; 1H NMR signals are reduced/absent at labeled positions, while 2H NMR can be used for label verification.
• Bulk thermophysical properties of a deuterated analogue are typically very similar to the protio compound (literature).

Quality & Grades

• Grade/Purity for this catalog item: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and guidance:
• For deuterated internal standards, analytical performance often depends more on isotopic enrichment, labeling position, and low background contaminants than on classical purity alone. In absence of a stated isotopic enrichment, verify via CoA, 1H/2H NMR, and HRMS.
• If intended for GC/LC–MS quantitation (lipidomics, metabolomics), review CoA for:

• Isotopic enrichment and distribution (e.g., percent D and positional information).
• Residual protio content and potential isobaric interferences.
• Volatile/semivolatile impurities that can affect baselines (solvent residues, low boilers).
  • If a stabilizer is used: Not specified for this item; refer to CoA/Spec Sheet.
  • Trace specifications (water, peroxides, metals, UV cutoff): Not specified for this item; refer to CoA/Spec Sheet.

Best practices:
• For quantitative work, confirm purity/isotopic pattern by GC–MS or LC–HRMS against the CoA.
• Store and handle under conditions that preserve isotopic integrity (minimize proton–deuteron exchange by avoiding strong acids/bases, protic media, and prolonged heating).

Reaction & Applications

Use domains (deuterated fatty acid methyl ester):
• Stable-isotope internal standard: widely used in lipidomics and environmental analysis to correct for extraction, injection, and ionization variability in GC–MS or LC–MS workflows. Deuteration yields predictable mass shifts and minimal chromatographic perturbation relative to the protio analyte.
• Calibration/response factor determination in GC of FAMEs; retention-index alignment across instruments and columns.
• Tracer studies: track dilution or exchange processes; confirm ester hydrolysis/transesterification pathways by monitoring D-label in products (requires known labeling pattern; verify via CoA).

Synthetic/transformational uses (general):
• Hydrolysis (saponification) to pentadecanoic acid-d for downstream coupling (amide formation, activation to acid chloride/anhydride).
• Transesterification to other alkyl esters (e.g., Et, iPr) under acid or base catalysis.
• Reduction to the corresponding alcohol (pentadecanol-d) via LiAlH4, DIBAL, or borohydride systems with activators; retention of deuterium depends on label position and conditions.

Practical tips:
• For quantitative MS use, keep solutions anhydrous and avoid strong acids/bases to minimize H/D exchange on labile positions (e.g., if label resides at the methoxy or alpha positions).
• Prepare fresh dilute standards in hydrocarbon or IPA/ACN solvent; store working solutions cold and protected from light.
• Degas mobile phases and use glassware free of residual detergents that can cause background in GC–MS total ion chromatograms.

Reaction Conditions

General literature guidance for transformations of fatty acid methyl esters (FAMEs):
• Basic hydrolysis (saponification): KOH or NaOH in MeOH/H2O (typically 0.5–2 M base) at RT to 60 °C for 0.5–4 h; work up by acidification and extraction to give pentadecanoic acid-d (yields commonly high, >80%, literature).
• Acidic hydrolysis: aqueous HCl or H2SO4 with co-solvent (THF/dioxane) under reflux; slower than base-catalyzed routes (literature).
• Transesterification: catalytic base (NaOMe in MeOH or tBuOK in corresponding alcohol) at 0–40 °C for 0.5–2 h; for acid-catalyzed, H2SO4 (1–5 mol%) in ROH, reflux, 1–4 h (literature).
• Reduction to alcohol: LiAlH4 in dry ether/THF at 0–25 °C, 1–3 h; quench cautiously; or DIBAL-H in toluene/hexane at −78 to 0 °C to stop at the aldehyde (literature yields vary, often 70–95%).
• Formation of acid chloride (after hydrolysis): SOCl2 or oxalyl chloride with catalytic DMF in DCM or toluene, 0–25 °C, 1–3 h; immediate use recommended (literature).

Notes for deuterated substrates:
• Prefer aprotic, anhydrous media and mild temperatures to minimize H/D exchange.
• Verify isotopic integrity post-reaction by HRMS and 2H NMR.
• When using metal hydrides, avoid protic quench until the hydride is fully consumed; perform cold, staged quenches to limit exchange (literature best practice).

Safety & Handling

Authoritative safety data must be taken from the product SDS. Item-specific GHS classification, pictograms, and H-statements: Not specified for this item; refer to SDS.

General handling guidance for fatty acid methyl esters and their deuterated analogues (literature/standard practice):
• Hazards: typically combustible liquids; may cause mild skin/eye irritation. Avoid inhalation of vapors/aerosols and prolonged skin contact.
• PPE: wear lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to control vapors and prevent aerosol formation.
• Incompatibilities: strong oxidizers; strong bases and acids can catalyze transesterification or hydrolysis. Avoid prolonged exposure to air and light if ultra-trace oxidation could impact analytical use.
• Peroxide formation: not a typical concern for saturated esters (unlike ethers), but routine periodic inspection is good practice for all organics.
• First aid (overview; defer to SDS):

• Skin: wash with soap and water; remove contaminated clothing.
• Eyes: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
• Ingestion: rinse mouth; seek medical advice.
• Inhalation: move to fresh air; seek medical attention if symptoms occur.
  • Fire-fighting: use CO2, dry chemical, or foam; cool containers with water spray.
  • Waste: collect organic waste in labeled flammable-organics container; follow institutional and local regulations.

Research Use: For research use only.

Solvent Selection

Polarity and miscibility (literature/general):
• Class: nonpolar to weakly polar ester; long-chain hydrophobe.
• Water: negligible solubility.
• Organic solvents: readily soluble in hydrocarbons (n-hexane, heptane, iso-octane), chlorinated solvents (CH2Cl2, CHCl3), aromatics (toluene), and ethers (MTBE, diethyl ether, THF). Limited solubility in highly polar aprotic solvents (acetonitrile) and alcohols; solubility improves with warming.

Selection guidance by application:
• GC methods: dissolve in n-hexane or iso-octane for FAME analysis; these give sharp peaks and minimal column bleed.
• LC–MS: use isopropanol/acetonitrile (with minimal water) or methanol/IPA mixtures commonly used for lipidomics; avoid high-water mobile phases to prevent phase separation.
• Synthetic manipulations (hydrolysis, transesterification): methanol or ethanol with catalytic base/acid; product workups benefit from nonpolar extraction solvents.
• NMR: CDCl3 is preferred; toluene-d8 or acetone-d6 are alternatives if solubility or temperature constraints arise.

Comparison notes:
• Versus shorter FAMEs, long-chain FAMEs have lower polarity and higher hydrophobicity, so choose stronger nonpolar eluents for chromatography.
• For green chemistry, prefer heptane or cyclopentyl methyl ether (CPME) over chlorinated solvents when feasible (see Green Alternatives).

Storage & Reconstitution

Item-specific storage:
• Storage conditions: Store at −20 °C (per Product Data).
• Shipped in: Ice chest + ice pads (per Product Data).

General handling and stability guidance:
• Upon receipt, allow any condensation to dissipate before opening. If the material appears solid or viscous at low temperature, warm gently to ambient to ensure homogeneity before aliquoting.
• To minimize freeze–thaw cycles, prepare small, single-use aliquots in amber glass vials; purge headspace with inert gas (N2 or Ar) for high-sensitivity MS applications.
• Keep tightly closed, protected from light and moisture. Avoid prolonged exposure to strong acids/bases and protic solvents to prevent hydrolysis or H/D exchange.
• Short-term bench handling at room temperature is generally acceptable for weighing and solution prep; return promptly to −20 °C after use.

Reconstitution/stock solutions:
• Solvents: heptane, iso-octane, toluene, CH2Cl2, or LC–MS-grade IPA/ACN mixtures, depending on the intended method. Use anhydrous solvents for isotopic integrity.
• Typical stock concentrations for analytical use are method-dependent; Not specified for this item—consult your method and instrument linearity.
• Label vials with preparation date, solvent, and concentration; verify periodically by GC/LC–MS for long-term studies.

Structure & Identity

• Item name: Methyl pentadecanoate-d (deuterium-labeled methyl pentadecanoate; exact labeling pattern/degree not specified).
• CAS: 68060-02-6
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general description):
• Core scaffold: a straight-chain C15 saturated fatty acyl moiety present as its methyl ester (i.e., methyl ester of pentadecanoic acid, an odd-chain fatty acid).
• Functional group: a terminal methyl ester (–COOCH3).
• Saturation: fully saturated alkyl chain (no C=C or aromatic units).
• Isotopic label: contains one or more deuterium atoms (D) incorporated at unspecified position(s); deuteration does not change valency or gross connectivity but increases mass and shifts NMR/isotopic patterns.
• Stereochemistry: none (acyclic, saturated).

2D structure in words (general): a linear C15 alkyl chain terminating in a carboxylate methyl ester; the opposite end bears a methyl group. Deuterium label(s) replace one or more hydrogens either on the methoxy group and/or along the alkyl chain (pattern not provided).

Synthetic Utility

Functional group and reactivity:
• Terminal methyl ester enables classical transformations:

• Hydrolysis (acidic or basic) to pentadecanoic acid-d.
• Transesterification to alternative esters (Et, iPr, benzyl).
• Reduction to alcohol (pentadecanol-d) or to aldehyde (via partial reduction, e.g., DIBAL at low temperature).
• Conversion to amides via acid activation after hydrolysis (SOCl2/oxalyl chloride then amine; or coupling reagents after forming the acid).
  • The long alkyl chain provides a hydrophobic handle for surfactant/lipid-mimetic constructs and for phase-behavior studies where deuterium labeling facilitates contrast in NMR or neutron scattering.

Isotopic considerations:
• Preserve D-label by avoiding conditions that promote H/D exchange (strong protic acids/bases, metal hydride reductions in protic media, prolonged reflux in alcohols).
• When label position is on the methoxy group, transesterification or hydrolysis in protic media can scramble or remove the isotopic tag; confirm label location from the CoA.

Analytical leverage:
• Use as a co-eluting or near-co-eluting internal standard for GC–MS quantitation of saturated C15 FAMEs; select ion monitoring at the D-shifted m/z improves selectivity.
• HRMS enables verification of isotopic pattern and detection of minor protio content that could bias quantitation at low levels.

Target Specificity

Not applicable. This product is a small-molecule chemical standard/reagent and does not possess biological target specificity (no antigen, epitope, clone, or isotype).