Hexacosanoic acid-d , CAS No.2692624-17-0

CAS: 2692624-17-0 Cat. No.: H1438255 Fórmula: C₂₆H₄₉D₃O₂ Peso molecular: 399.71

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Visão geral

Hexacosanoic acid-d 3 is deuterium labeled Hexacosanoic acid. Hexacosanoic acid is a long-chain fatty acid related to various diseases such as adrenoleukodystrophy (ALD), adrenomyeloneuropathy (AMN) and atherosclerosis.

Specifications

Condições de armazenamento de armazenamento

Store at -20°C

Enviado em

Ice chest + Ice pads

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Nomes e identificadores

Peso molecular

399.71

Application Protocols

Item-specific, tested application protocols are not provided. The following general protocols are commonly used for deuterated fatty acid standards in analytical workflows; adjust to your method and consult the CoA for labeling details.

• LC-MS/MS internal standard stock
  • Dissolve at 1–5 mg/mL in isopropanol or methanol (or CHCl3:MeOH 2:1), warming gently to 40–50 °C to aid dissolution. Store aliquots at −20 °C in amber vials. Spike 10–100 ng per sample depending on matrix and sensitivity.
• Lipid extraction spiking
  • Add the internal standard prior to extraction (e.g., Bligh–Dyer or MTBE protocol) to correct for recovery. Maintain organic:aqueous ratios to avoid precipitation.
• GC-MS of FAMEs
  • Convert to methyl ester using acid-catalyzed methanolysis (e.g., 1–2% H2SO4 in MeOH, 60–70 °C, 1 h). Extract into hexane, wash, and analyze on a nonpolar column (e.g., DB-5ms). Monitor the diagnostic mass shift corresponding to the deuterium content.
• NMR reference materials
  • For 1H NMR, deuterated chains reduce signal intensity; use 13C NMR or MS to confirm incorporation. Choose CDCl3 or C6D6 to minimize exchange at –COOD if present.

Note: Exact dilutions, detector transitions, and collision energies are method-specific and should be optimized in-house.

Biological Roles

General background on the unlabeled parent (hexacosanoic acid; cerotic acid, C26:0):

• Biochemical classification
  • Very-long-chain saturated fatty acid (VLCFA). Predominantly found in plant cuticular waxes, suberin, and certain wax esters. Minor component in some animal lipids.
• Metabolism
  • Biosynthesized via fatty acid elongation (ELOVL enzymes) from long-chain acyl-CoAs.
  • Catabolized primarily by peroxisomal β-oxidation, yielding shorter acyl-CoAs for further mitochondrial oxidation. Activation to cerotyl-CoA by acyl-CoA synthetases precedes metabolism.
• Functional roles
  • Contributes to hydrophobic barriers (plant cuticle), mechanical protection, and water repellency when incorporated into wax esters and polymers.
  • Serves as a precursor to long-chain alcohols (hexacosanol) and wax esters via acyltransferases and reductases.
• Isotopic applications
  • Deuterated hexacosanoic acid is used to track incorporation into complex lipids and to quantify endogenous C26:0 by mass spectrometry using isotope-dilution strategies.

Note: The above describes general biochemical context and analytical utility. No medical or clinical claims are made. For this specific product, the exact deuterium labeling sites are not specified and should be confirmed on the CoA for proper interpretation of metabolic fate and exchange behavior.

Buffer Applications

Hexacosanoic acid-d is a highly hydrophobic, long-chain fatty acid and is not used as a buffering agent. It has negligible aqueous solubility and lacks a useful pKa in the physiological pH range for buffer capacity in water. For aqueous work, prepare organic stock solutions (e.g., in isopropanol, methanol, or CHCl3) and spike into samples as required. Refer to Solvent Selection and Application Protocols for practical handling guidance.

Green Alternatives

Because Hexacosanoic acid-d is a labeled analytical standard rather than a process solvent or bulk reagent, “green alternatives” focus on solvent choices and workflow design rather than replacing the analyte itself.

• Greener solvent choices for preparation and chromatography (general)
  • Prefer ethyl acetate or isopropanol over chlorinated solvents when feasible for sample preparation; however, solubility of C26 acids is often superior in CHCl3/DCM.
  • For LC-MS mobile phases, ethanol or isopropanol can substitute for methanol or acetonitrile in some methods, reducing toxicity and supply risks.
• Sample economy and waste reduction
  • Use high-concentration stock solutions and microliter aliquots to minimize solvent waste and repeated thawing.
  • Employ on-column focusing and short gradients to lower solvent consumption.
• Sourcing considerations
  • When feasible for unlabeled method development, use the non-deuterated parent (hexacosanoic acid) to optimize procedures before switching to the labeled standard, conserving the isotopically enriched material.

Comparison (general tendencies)

• CHCl3: excellent solubility; higher toxicity, halogenated waste.
• Isopropanol/ethanol: safer profile; may require warming for complete dissolution; compatible with LC-MS.
• Heptane/iso-octane: low toxicity/volatility; good for GC calibration mixes; limited polarity for mixture compatibility.

Pharmaceutical Uses

• Role in pharmaceutical/biotech labs (general)
  • Utilized as a deuterated analytical standard in bioanalytical assays (e.g., LC-MS/MS quantitation of VLCFAs) for method validation, calibration curve preparation, and internal standardization in complex matrices.
  • May serve in metabolism studies to assess chain-elongation or β-oxidation pathways in preclinical research models.
• Excipients/status
  • No pharmacopeial excipient role is typical for hexacosanoic acid, especially in deuterated form. This product is intended for research and analytical use only (Product Data: Research Use Only).
• Formulation notes
  • For analytical spiking into biological samples, prepare concentrated stocks in isopropanol or methanol; ensure compatibility with the extraction protocol (e.g., Folch, Bligh–Dyer, or MTBE-based lipid extraction). Avoid buffers that could cause precipitation when mixing aqueous and organic phases.

No therapeutic or clinical claims are made. Always follow internal validation procedures when deploying isotopically labeled standards in regulated workflows.

Physical Properties

Item-specific specifications are not provided in the Product Data. Values below are literature/typical for the non-deuterated parent (hexacosanoic acid, cerotic acid) and are offered for context only; the exact properties of the deuterated isotopologue may differ slightly.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet. (Parent is a white, waxy solid.)
• Melting point (literature, parent): typically in the mid–80 °C range (commonly reported ~86 °C). Long-chain even-numbered saturated fatty acids show increasing Tm with chain length.
• Boiling point: not commonly used operationally; long-chain fatty acids tend to decompose before distillation at ambient pressure. Vacuum sublimation or high vacuum distillation may be feasible if needed.
• Density (literature, parent): on the order of ~0.85–0.90 g/mL near the melting range; strongly temperature dependent. Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (literature, parent):
  • Water: negligible.
  • Organic: soluble in nonpolar and moderately polar organics (chloroform, dichloromethane, toluene, hexane) and in hot alcohols; dissolves readily when warmed above its Tm.
• Partitioning (literature, parent): very hydrophobic with high logP (commonly reported >8 for C26:0). Exact value for this item not specified.
• Refractive index, UV cutoff, residual metals/impurities: Not specified for this item; refer to CoA/Spec Sheet.

Practical handling note (general): prepare solutions by warming with gentle heat (40–60 °C) in a compatible solvent to ensure complete dissolution; avoid overheating to prevent thermal degradation or isotopic scrambling at labile sites.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Implications for deuterated standards (general guidance)
  • Isotopic enrichment and labeling pattern are critical quality attributes for quantitative MS/NMR applications. Review the CoA for:
    • Deuterium incorporation (% D overall, site-specific if available).
    • Residual unlabeled hexacosanoic acid content.
    • Water and residual solvent content.
    • GC/LC purity and presence of shorter/longer chain homologs.
  • For trace-analytical workflows (lipidomics), low background and clean baselines are essential; materials intended as analytical/internal standards often undergo additional purification and testing for lot consistency.
• Stabilizers/additives
  • No stabilizer information is provided for this item. If a –COOD group is present, no stabilizers are typically required, but exposure to protic solvents will exchange the carboxyl deuterium; this does not affect non-exchangeable C–D sites.
• Documentation recommendations
  • Request CoA/Spec Sheet for: detailed isotopic labeling description, chromatographic purity, and any method suitability statements (e.g., GC-MS/LC-MS compatibility).

Reaction and Applications

• Analytical and tracer applications (manufacturer context expanded; general)
  • Deuterated very-long-chain fatty acids are widely used as internal standards for quantitative lipidomics by GC-MS or LC-MS/MS, providing retention-time matching and mass offsets that correct for matrix and ionization effects.
  • Stable-isotope tracing: incorporation studies into wax esters, glycerolipids, or amide conjugates in plant or microbial systems; assess elongation/β-oxidation fluxes. Verify labeling pattern (non-exchangeable vs –COOD) to interpret scrambling.
  • Derivatization: conversion to methyl esters (FAME) for GC analysis is routine; the C–D content at non-exchangeable sites is retained through typical Fischer or BF3–MeOH protocols, while a –COOD proton/deuteron will exchange.
• Synthetic/manufacturing uses (general)
  • Serves as a labeled building block for preparing deuterated wax esters, amides, and long-chain alcohols (via reduction). Useful in calibrating yields and monitoring losses in workup by isotope dilution.
• Practical tips
  • Calibrate concentrations gravimetrically; prepare solutions in CHCl3 or isooctane. For LC-MS, include an antioxidant (e.g., 50–100 ppm BHT) if samples will be stored long-term to mitigate slow auto-oxidation at the carboxyl end and any adventitious peroxides in solvents.
  • For GC-MS: derivatize to FAME or TMS derivatives to improve volatility and peak shape. Validate that derivatization reagents do not induce H/D exchange (avoid strong protic acids at elevated temperature if preserving –COOD D).
  • Store aliquots to avoid repeated thaw/heat cycles that may change concentration due to adsorption to glassware.

Reaction Conditions

General literature guidance for transforming long-chain fatty acids; adjust conditions based on the desired derivative and verify compatibility with deuterium labeling:

• Methyl ester (FAME) preparation
  • Fischer esterification: MeOH, catalytic H2SO4 (1–5% v/v), reflux 1–3 h. Retains non-exchangeable C–D; any –COOD exchanges rapidly. Work up by neutralization and extraction.
  • Alternative: BF3–MeOH or HCl–MeOH reagents (shorter times, 60–90 °C). Validate absence of unwanted H/D exchange at elevated temperatures.
• Steglich esterification (mild)
  • ROH, DCC (1.1–1.5 equiv), catalytic DMAP in CH2Cl2 or THF, 0 °C to rt, 2–18 h; good for thermally sensitive isotopic materials.
• Amide formation
  • EDCI/HOBt or HATU with amine nucleophiles in DMF or CH2Cl2, rt to 40 °C, 2–12 h. Include base (DIPEA) to neutralize HCl byproducts.
• Acid chloride formation
  • SOCl2 (2–5 equiv), catalytic DMF, reflux 1–2 h; distill off excess under reduced pressure. Follow by coupling with alcohols/amines in pyridine or Et3N.
• Reduction
  • LiAlH4 in dry THF, 0 °C to reflux, 1–4 h to yield hexacosanol. Quench carefully to avoid emulsions.
• Purification and analysis
  • Silica gel chromatography with hexane/EtOAc or hexane/DCM gradients; tailing can be minimized with 0.1–0.5% acetic acid. For GC, convert to FAME/TMS derivatives to improve volatility and peak shape.

These conditions are general literature values; specific parameters for this item are not provided in the Product Data.

Safety and Handling

• GHS/Classification (item-specific)
  • Signal word: Not specified for this item; refer to SDS.
  • H-statements: Not specified for this item; refer to SDS.
  • GHS classification and pictograms: Not specified for this item; refer to SDS.
• General hazards (chemistry knowledge for long-chain fatty acids)
  • Low volatility; minimal inhalation hazard under normal handling of solids. Dust may cause mechanical irritation. Can cause skin/eye irritation upon contact.
  • Combustible organic solid; may burn if heated strongly. Avoid ignition sources when handling hot melts.
• PPE and engineering controls
  • Wear appropriate lab PPE: lab coat, safety glasses, and chemically resistant gloves (e.g., nitrile). Use local exhaust when weighing fine powders or during hot dissolution.
• Storage incompatibilities and conditions
  • Store at −20 °C (Product Data). Keep tightly closed, protected from moisture and light. Allow to equilibrate to room temperature in a sealed container before opening to minimize condensation.
  • Incompatible with strong oxidizers and strong bases/acids when hot (can promote saponification or decomposition). For deuterated materials, avoid prolonged exposure to protic media if –COOD labeling is present (rapid H/D exchange).
• First-aid overview (consult SDS for details)
  • Skin/eyes: rinse with water for at least 15 minutes; remove contaminated clothing.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
  • Inhalation of dust: move to fresh air; seek medical attention if symptoms persist.
• Spill/fire response (general)
  • Solid spills: sweep up gently to avoid dust, place in compatible container for disposal.
  • Fire: use CO2, dry chemical, or foam. Thermal decomposition may produce irritating fumes.

Solvent Selection

Hexacosanoic acid-d is a very hydrophobic, high-melting fatty acid analog. Solvent choice is governed by its long alkyl chain and the need to preserve isotopic integrity.

• Polarity and miscibility (general)
  • Polarity class: nonpolar to weakly polar solute with a single polar headgroup.
  • Miscible/soluble in: chloroform, dichloromethane, toluene, xylene, hexane/heptane, cyclohexane; soluble in hot alcohols (methanol, ethanol, isopropanol). Good solubility in DMSO and DMF when warmed.
  • Insoluble in water at room temperature.
• Practical recommendations
  • For stock solutions for MS: chloroform, chloroform/methanol (2:1), or isooctane are common for fatty acid standards. For LC-MS in RP solvents, prepare concentrated stocks in isopropanol or methanol with 0.1% formic acid, then dilute into mobile phase; note that any –COOD label will exchange in protic modifiers.
  • Warm gently (40–60 °C) to dissolve; sonication can assist. Filter through PTFE if particulate remains.
• When to choose alternatives
  • If using normal-phase silica, use hexane/dichloromethane with small acid modifiers to suppress tailing; for RP separations, use acetonitrile/isopropanol blends.
  • For NMR of deuterated standards, avoid protic deuterated solvents if you must preserve exchangeable deuterium at the carboxyl; choose CDCl3 or C6D6 rather than CD3OD/D2O.
• Compatibility notes
  • Avoid strong base in alcohols (saponification). Minimize prolonged heating in protic media to prevent any unintended H/D exchange at labile positions.

Storage and Reconstitution

• Storage conditions (item-specific)
  • Store at −20 °C (Product Data). Shipments are on ice in an ice chest with ice pads (Product Data). Keep container tightly closed and protected from light and moisture.
• Stability
  • In the solid state at −20 °C, long-chain fatty acids are generally stable for extended periods. Avoid repeated warming/cooling cycles that can introduce condensation and adsorption losses.
  • If the carboxyl group is deuterated (–COOD), deuterium at this site will exchange rapidly in protic media; this does not affect non-exchangeable C–D along the alkyl chain.
• Reconstitution
  • To prepare stock solutions, add a suitable solvent (e.g., chloroform, dichloromethane, toluene, isopropanol, methanol, or DMSO) and warm gently to 40–60 °C with vortexing or brief sonication until fully dissolved. Cool to room temperature before use.
  • Typical analytical stocks: 1–10 mg/mL in CHCl3:MeOH (2:1), isopropanol, or iso-octane. Use amber glass vials with PTFE-lined caps. Filter through PTFE if needed.
• Aliquoting and shelf life
  • Dispense into single-use aliquots to minimize headspace and freeze–thaw cycles. For solution storage, keep at −20 °C; bring to room temperature before opening to prevent moisture ingress. Monitor concentration by gravimetry or UV (if derivatized) as appropriate over time.
• Specifications not provided
  • Exact solubility limits, water content, and assay/purity for this item are not specified; refer to the CoA/Spec Sheet.

Structure and Identity

• Item-specific identifiers
  • CAS: 2692624-17-0 (Product Data)
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• Naming and scope
  • Product name: Hexacosanoic acid-d (Product Data). The “-d” denotes a deuterium-labeled isotopologue; the exact labeling pattern and number of deuterium atoms are not specified for this item.
• Structural features (general/literature description of the non-labeled parent, hexacosanoic acid, also known as cerotic acid)
  • A straight-chain, saturated C26 fatty acid with a terminal carboxylic acid (–CO2H) and a linear C25 alkyl tail (no rings, no unsaturation, no stereocenters).
  • Functional groups: one carboxylic acid; remaining framework is aliphatic sp3 C–C and C–H (or C–D in the labeled material).
  • 2D description: HOOC–(CH2)24–CH3 (parent structure). In the deuterated material, some or all hydrogens may be replaced by deuterium; if the carboxyl hydrogen is deuterium (–COOD), that position is exchangeable.
• Isotopic considerations (general)
  • Non-exchangeable deuterium at aliphatic carbon positions is typically stable under neutral conditions.
  • Exchangeable deuterium at –COOD will readily exchange with protic media (H2O, MeOH, acids/bases). Verify labeling pattern on the CoA before isotopic quantitation work.

Synthetic Utility

From a synthesis perspective (general to fatty acids and deuterated analogs):

• Functional handles
  • Carboxylic acid enables classical derivatizations: esterification (Fischer, Steglich), amidation (carbodiimide/HOBt or EDCI/DMAP), and activation to acid chloride (SOCl2, oxalyl chloride) for coupling.
  • Reduction to the corresponding alcohol (hexacosanol-d) using LiAlH4 or BH3·THF; further conversion to halides or tosylates allows access to labeled long-chain building blocks.
• Value in deuterium labeling
  • Provides a mass offset that survives most transformations at non-exchangeable positions (C–D along the chain). Avoid conditions that could scramble deuterium if alpha-activation or exchange is possible; the carboxyl –OD label (if present) is exchangeable.
• Materials chemistry
  • Esterification with fatty alcohols furnishes deuterated wax esters useful for studying crystallinity, phase behavior, and surface properties of waxy materials.
• Retrosynthetic utility
  • Serves as a terminal building block to append a long hydrophobic segment to amphiphiles, surfactants, and solid supports via amide/ester linkages, enabling construction of deuterated standards for complex lipids (e.g., cerotamides, glycerolipids) and model membranes.

Note: For applications requiring strict retention of isotopic labels, consult the CoA for labeling sites and plan protective strategies (e.g., avoid strong acids/bases in protic solvents at elevated temperature).

Target Specificity

Not applicable. This product is a small-molecule, deuterated fatty acid standard and does not possess “target specificity” attributes such as antigen/epitope recognition, clone, or isotype. No item-specific data are provided for this section.