Arachidic acid-d - ≥99% , CAS No.1219803-69-6

CAS: 1219803-69-6 Cat. No.: A1440491 Formula: C₂₀H₄₀O₂ Molecular Weight: 316.6 PubChem CID: 131869358

GRADE & PURITY ≥99%

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Arachidic acid-d 4 is the deuterium labeled Arachidic acid. Arachidonic acid (Icosanoic acid), a long-chain fatty acid, is present in all mammalian cells, typically esterified to membrane phospholipids , and is one of the most abundant polyunsaturated fatty acids present in human tissue.

Specifications

Specifications & Purity

≥99%

Storage

Store at 2-8°C

Shipped In

Wet ice

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

Purity

≥99%

Names and Identifiers

Canonical Smiles

CCCCCCCCCCCCCCCCCCCC(=O)O

IUPAC Name

17,17,18,18-tetradeuterioicosanoic acid

InChIKey

VKOBVWXKNCXXDE-KHORGVISSA-N

INCHI

1S/C20H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-19H2,1H3,(H,21,22)/i3D2,4D2

PubChem CID

131869358

Molecular Weight

316.6

Application Protocols

No item-specific validated protocols are provided for this SKU; refer to CoA/Spec Sheet. General examples for deuterated fatty acid standards:

• LC‑MS lipidomics internal standard (general):

  • Prepare a 1–5 mg/mL stock in CHCl3:MeOH (2:1) or IPA:MeOH (1:1). Store aliquots at 2–8 °C under inert gas. Spike an appropriate fixed amount into samples prior to extraction (e.g., Bligh–Dyer or MTBE methods) to correct for recovery and ionization. Adjust spike level to bracket expected endogenous C20:0 concentrations.

• GC‑MS FAME analysis (general):

  • Convert a small portion to the methyl ester using acid-catalyzed methanolysis (e.g., 1–2% H2SO4 in MeOH, 60–70 °C, 1 h). Extract into hexane, wash with brine, dry, and analyze by GC‑MS. Use the mass shift for selective ion monitoring.

• Surface/monolayer preparation (general):

  • Dissolve in warm toluene or heptane (1–5 mg/mL). Immerse cleaned substrate (e.g., metal oxide nanoparticles) in solution for several hours at ambient to 60 °C, rinse with solvent, and dry under nitrogen. Characterize with IR (C–D stretch) or neutron reflectometry.

Always validate concentrations, matrix compatibility, and instrument response with your specific method. For research use only.

Biological Roles

Context (general/literature for arachidic acid, C20:0; no medical claims):

• Arachidic acid is a saturated very-long-chain fatty acid (VLCFA) found at low levels in plant waxes, seed oils (e.g., peanut), and certain biomembranes as part of complex lipids (triacylglycerols, phospholipids, sphingolipids).
• Metabolism: Incorporated via acyl-CoA synthetases to arachidoyl‑CoA; undergoes β‑oxidation in peroxisomes/mitochondria. Can be elongated/desaturated into related VLCFAs under specific conditions.
• Physicochemical role: Increases membrane order and melting transitions when incorporated into phospholipids due to long, saturated chains.

Deuterated analog utility (general):

• Tracer: Non-exchangeable deuterium along the hydrocarbon chain provides mass contrast, enabling flux studies of esterification into glycerolipids or degradation via β‑oxidation without perturbing hydrophobicity substantially.
• Internal standards: Serve as co-eluting mass-shifted standards for absolute quantitation of C20:0 species in complex matrices by LC‑MS/GC‑MS.
• Spectroscopy: Deuterium shifts IR/C–D stretching and enhances contrast in neutron scattering for studying lipid organization and phase behavior.

Note: Exact isotopic enrichment and labeling pattern determine the mass shift and must be confirmed by CoA prior to quantitative biological or analytical work. This product is for research use only.

Buffer Applications

This product is a highly hydrophobic fatty acid and is not typically used to prepare aqueous buffer systems.

Practical notes (general):

• In aqueous media, the free acid has extremely low solubility; forming salts (e.g., sodium arachidate) increases dispersibility and can generate micelles or vesicles at sufficient concentration.
• For biochemical assays, complexation with fatty-acid–free bovine serum albumin (BSA) is a common strategy to deliver defined amounts of long-chain fatty acids; however, this is application-specific and requires careful stoichiometric control and pH adjustment.

For routine buffering needs, use established buffer components (e.g., phosphate, HEPES, Tris). Refer to other sections for solvent selection and analytical/synthetic applications more relevant to this compound.

Green Alternatives

While the molecule itself is a saturated fatty acid (readily biodegradable), greenness considerations focus on solvent and reagent choices in handling and derivatization.

Greener solvent substitutions (general guidance):

• Replace chlorinated solvents:
  • Instead of chloroform/DCM, use ethyl acetate, isopropanol, 2‑MeTHF, CPME, or heptane/toluene where solubility/performance allow.
• Extraction and stock solutions:
  • IPA:MeOH and EA:heptane systems can substitute for CHCl3:MeOH lipid workflows with method re-optimization.

Comparison (general, qualitative):

• Chloroform: excellent solvency; high toxicity; poor EHS profile.
• Ethyl acetate: good solvency when warm; low toxicity; readily biodegradable.
• 2‑MeTHF/CPME: greener ethers with good nonpolar solvation; lower peroxide tendency than THF/Et2O; check method compatibility.
• Heptane/toluene: low polarity; good for crystallizations; lower hazard than chlorinated solvents but VOCs nonetheless.

Greener reagents for derivatization (general):

• Use catalytic acid (e.g., p‑TsOH) or solid acid resins for esterification instead of strong mineral acids where feasible.
• Employ EDC·HCl/DMAP in greener solvents (EtOAc, MeCN) rather than DCC in DCM; avoid HOBt where possible due to energetic hazards.
• Enzymatic routes: lipase-catalyzed esterification or amidation in solvent-free or green media at mild temperatures.

Waste minimization:

• Prepare concentrated stocks to reduce solvent volumes; recover and recycle heptane/EtOAc when possible. Validate any substitutions for your analytical platform.

Pharmaceutical Uses

No therapeutic claims are made. Context below addresses formulation and analytical roles (general):

• Excipient/vehicle context: Saturated long-chain fatty acids can be components of lipid excipient systems (e.g., in wax matrices, lipid nanoparticles, or as pro-moieties in lipophilic conjugates). The deuterated analog is not typically used as an excipient but rather as an analytical tool.
• Analytical standard: Deuterated arachidic acid is well-suited as an internal standard for quantitative assays of saturated C20:0 in raw materials, process streams, or stability samples by LC‑MS or GC‑MS.
• Process development: Can assist in mass-balance and extraction recovery studies due to the mass offset, without altering partition behavior substantially compared to the protiated species.

Regulatory and compendial status:

• Grade/purity and pharmacopeial monograph applicability: Not specified for this item; refer to CoA/Spec Sheet. Deuterated analogs generally do not have direct pharmacopeial monographs; they are used as reference standards under method validation.

Handling for GMP environments requires internal qualification of reference standards, stability protocols, and isotopic enrichment verification by validated methods.

Physical Properties

Only limited item-specific physico-chemical data are provided for this product.

• Item-specific values:

  • Appearance: 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 arachidic acid (C20:0) for context only:

  • Melting point: typically ~75–77 °C (literature). Deuteration can shift Tm slightly upward.
  • Boiling/decomposition: long-chain fatty acids char/decompose on heating; distillation is uncommon; high bp under reduced pressure (literature, qualitative).
  • Solubility: insoluble in water; soluble in nonpolar and moderately polar organic solvents (e.g., chloroform, dichloromethane, toluene, hot ethanol, ethyl acetate). Solubility improves on gentle warming.
  • pKa (carboxylic acid): ~4.8–5.0 (literature, in water/MeOH systems).
  • LogP: very high (strongly hydrophobic; literature qualitative for long-chain saturated fatty acids).

• Practical notes (general):

  • Deuterated analogs share phase behavior with protiated fatty acids; slight isotope effects can modify melting transitions but not order-of-magnitude solubility.
  • For solution preparation, warm solvent (30–50 °C) and brief sonication often aid dissolution.

For exact item-specific parameters (isotopic enrichment, formula, MW, appearance), consult the CoA/Spec Sheet.

Quality & Grades

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

Guidance on interpreting grade for deuterated fatty acids (general):

• Isotopic enrichment: For “-d” products, the critical specification is the deuterium incorporation (atom % D and labeling pattern, e.g., number of deuteriums retained at non-exchangeable sites). Verify via CoA (often supported by 1H/2H NMR and HRMS). Higher enrichment provides stronger mass shifts and cleaner internal standard behavior in MS.
• Chemical purity: Typically assessed by GC-FID/GC–MS or HPLC and NMR. Long-chain fatty acids should show minimal shorter/longer chain homologs and minimal unsaturated impurities.
• Residual solvents and water: Not specified for this item; refer to CoA/Spec Sheet. Drying under high vacuum at mild temperature can reduce volatiles, but observe CoA limits.
• Stabilizers: None typically required for saturated acids; unsaturated analogs may include antioxidants. For this saturated chain, prevent contamination rather than requiring stabilizers.
• What the grade implies (examples, general):
  • Analytical standard grade: tight assay and isotopic enrichment control; low background in GC/LC-MS.
  • Research grade: suitable for synthesis and general analytical calibration; verify enrichment before quantitative MS use.

Always rely on the product’s CoA for the definitive purity and enrichment figures for SKU A1440491.

Reaction & Applications

This deuterated saturated C20 fatty acid is primarily used as:

• Internal standard and tracer (general, literature):

  • LC-MS/GC-MS lipidomics: mass-shifted reference for quantitation of saturated C20:0 species; minimizes matrix effects by co-extraction and co-elution with endogenous analytes.
  • Metabolic studies: non-exchangeable deuterium along the alkyl chain enables tracing of incorporation into complex lipids or β-oxidation products without significant isotope scrambling.

• Representative transformations (general chemistry of fatty acids):

  • Esterification: Fischer esterification (ROH/H+), Steglich (DCC/DMAP), or acid chloride routes to give alkyl esters (e.g., methyl arachidate-d) useful for GC analysis or materials.
  • Amidation: EDC/HOBt or HATU couplings to give long-chain amides, surfactants, or probes; deuterium label is retained on non-exchangeable sites.
  • Activation: SOCl2 or oxalyl chloride to acyl chlorides for subsequent acylation of alcohols/amines (anhydrous conditions).
  • Salt formation: conversion to sodium/potassium carboxylates for micelle/vesicle studies or surface modification.

• Materials/surface uses (general):

  • Self-assembled monolayers on metal oxides or nanoparticles via carboxylate binding; deuteration facilitates neutron scattering or vibrational spectroscopy contrast.

Notes:

• Maintain anhydrous, neutral conditions to avoid unnecessary isotopic exchange at the acid proton; deuterium on the alkyl chain is non-exchangeable under standard conditions.
• Verify isotopic enrichment by MS prior to quantitative use.

Reaction Conditions

Typical conditions for transformations of long-chain fatty acids (general literature guidance; optimize for your system):

• Fischer esterification (to FAMEs):

  • Reagents: anhydrous MeOH or EtOH, catalytic H2SO4 or p‑TsOH (0.5–2 mol%).
  • Conditions: reflux 2–6 h; Dean–Stark not needed in methanol; remove solvent and neutralize carefully. For isotopic integrity, avoid prolonged high-temperature exposure if unnecessary.

• Steglich esterification:

  • Reagents: DCC (1.1 eq) and DMAP (0.1 eq) in dry DCM or EtOAc with ROH (1.5–2 eq).
  • Conditions: 0 °C to rt, 2–16 h; filter DCU; wash and purify. EDC·HCl can replace DCC in MeCN/EtOAc as a greener alternative.

• Acid chloride formation and acylation:

  • Reagents: SOCl2 (2–3 eq) with catalytic DMF; solvent: toluene or neat.
  • Conditions: 60–80 °C, 1–3 h; remove volatiles under reduced pressure; proceed immediately to acylation with alcohol/amine + base (pyridine/NEt3) at 0–25 °C.

• Amide coupling (carbodiimide/uronium):

  • Reagents: EDC·HCl (1.2 eq) + HOBt/HOAt or HATU (1.1 eq) with base (DIPEA) in DMF/MeCN/EtOAc.
  • Conditions: 0–25 °C, 2–16 h; monitor by TLC/LC-MS.

• Saponification/neutralization:

  • Convert to sodium/potassium salts with NaOH/KOH in alcohol/water at 0–25 °C; avoid excess base if preserving free acid.

Yields vary with scale and purification; long chains often crystallize well, aiding isolation. Confirm label retention by MS.

Safety & Handling

• GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to SDS for authoritative safety data.

General safety guidance for long-chain fatty acids and their deuterated analogs (literature/practice):

• Hazards: Typically low acute toxicity; may cause skin/eye irritation. Combustible organic solid; dust may present combustion risk in bulk processing.
• PPE: Use lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Avoid generating dust/aerosols. Use in a well-ventilated area or fume hood when weighing/dissolving.
• Handling: Avoid strong oxidizers. When heating to aid dissolution, use controlled temperature baths and closed containers to prevent splashing.
• Incompatibilities: Strong oxidizing agents; strong bases will form soaps (carboxylate salts) and alter handling properties (foaming/emulsification).
• First aid (overview, defer to SDS):
  • Skin/eyes: Rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; seek medical advice if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire-fighting: Use CO2, dry chemical, or foam. Combustion may produce CO/CO2.

Storage and shipping (item-specific):

• Storage: Store at 2–8 °C (per Product Data). Keep container tightly closed, in a dry place.
• Shipping: Shipped on wet ice (per Product Data).

Always consult the product SDS for definitive hazard and handling information.

Solvent Selection

Arachidic acid-d is a highly hydrophobic saturated long-chain fatty acid; solvent choice is driven by dissolution and compatibility with downstream methods.

• Polarity and miscibility (general):

  • Strongly nonpolar amphiphile with a single carboxylic acid group; negligible water solubility.
  • Readily soluble in nonpolar and moderately polar organic solvents: chloroform, dichloromethane, toluene, hexanes/heptane (often with warming), ethyl acetate, acetone (limited, improves when warm), hot ethanol/isopropanol, and in CHCl3:MeOH mixtures.
  • Forms soaps in basic aqueous media (carboxylate salts), increasing apparent solubility/emulsification.

• Practical selection by application (general):

  • GC or derivatization workflows: dissolve in nonpolar solvents (hexane, isooctane) or convert to methyl ester first (then use hexane/iso-octane).
  • LC-MS lipidomics internal standard: CHCl3:MeOH or IPA:MeOH with 0.1% formic acid/ammonium formate to aid injection; avoid prolonged aqueous exposure to minimize adsorption losses.
  • Synthetic transformations: use toluene, THF, DCM, or ethyl acetate depending on coupling chemistry; ensure anhydrous conditions for acid chloride formation or carbodiimide couplings.

• Small comparison (general):

  • Chloroform: excellent solvency for fatty acids; less green.
  • Ethyl acetate/IPA: greener, adequate with mild heating.
  • Heptane/toluene: good for high-temperature operations and crystallizations.

Warm solutions (30–50 °C) and brief sonication improve dissolution for weighing and stock preparation.

Storage & Reconstitution

• Storage conditions (item-specific): Store at 2–8 °C (per Product Data). Keep tightly closed in a dry environment. Minimize headspace and consider flushing with inert gas for long-term stability of prepared solutions.
• Shipping: Shipped on wet ice (per Product Data).

Reconstitution and solution handling (general):

• Solvents: CHCl3, DCM, toluene, heptane, ethyl acetate, or alcohols (ethanol/IPA; often warm) are suitable. CHCl3:MeOH or IPA:MeOH mixtures improve handling for LC‑MS stocks.
• Technique: Warm gently (30–50 °C) and sonicate briefly to aid dissolution. Prepare concentrated stocks (e.g., 1–10 mg/mL) and aliquot to reduce repeated warming cycles.
• Aqueous work: The free acid has negligible water solubility; for dispersions, adjust pH to form carboxylate salts or complex with fatty-acid–free BSA as appropriate for biochemical applications.
• Stability: Saturated long-chain fatty acids are generally stable; protect from moisture and prolonged exposure to strong light/heat. For deuterated materials, avoid unnecessary exposure to protic media if retention of any acid-proton deuterium is desired; non-exchangeable chain deuterium is robust.

Labels and specs:

• Molecular weight, formula, isotopic enrichment, and appearance are Not specified for this item; refer to CoA/Spec Sheet for lot-specific details.

Structure & Identity

Arachidic acid-d is a deuterium-labeled analog of arachidic acid (eicosanoic acid), a saturated C20 fatty acid used as a lipidomics standard and chemical building block.

• Item-specific identifiers (from Product Data):

  • CAS: 1219803-69-6
  • InChIKey: 381416 (as provided)
  • SMILES: 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.

• Structural features (general/literature description):

  • Backbone: A linear, saturated 20‑carbon aliphatic chain terminating in a carboxylic acid (–CO2H).
  • Functional groups: One carboxylic acid; otherwise fully saturated methylene chain.
  • Isotopic labeling: Non-exchangeable hydrogens along the alkyl chain are substituted with deuterium in the “-d” variant; labeling pattern/count depends on the specific lot/specification (consult CoA). The carboxyl proton is typically exchangeable and may not be deuterated.
  • Stereochemistry: None (no stereocenters in a fully saturated n-alkyl chain acid).

• 2D description (general):

  • HO–C(=O)–(CH2)n–CH3 with total carbon count = 20 (eicosanoic framework); deuterated analog bears –(CD2)– units along the chain depending on labeling pattern.

Note: Exact labeling extent and elemental analysis are item-specific; verify with the product’s CoA for precise isotopic enrichment and formula.

Synthetic Utility

Arachidic acid-d serves as a labeled acyl donor and hydrophobic scaffold for synthesis and materials studies.

Key reactivity (general):

• Carboxylic acid function enables formation of:
  • Esters via Fischer (ROH/H+, reflux), Steglich (DCC/DMAP), or acid chloride routes.
  • Amides via EDC/HOAt, HATU, or mixed anhydrides with mild bases.
  • Acid chlorides (SOCl2, oxalyl chloride) for subsequent acylations.
  • Carboxylate salts for surfactant-like behavior and surface modification.

Applications:

• Preparation of labeled methyl/ethyl esters for GC quantitation (FAME derivatives) where the mass shift affords selective detection.
• Synthesis of deuterated N‑acylethanolamides or other amide lipids as standards for endocannabinoid/lipid mediator assays (no medical use implied).
• Fabrication of deuterated monolayers on nanoparticles or planar surfaces; C–D vibrations and neutron contrast assist in interfacial characterization.

Isotope integrity:

• Deuterium along the saturated chain is non-exchangeable under typical conditions; avoid harsh hydrogenolysis or radical H/D exchange if preserving label is critical.
• The carboxyl proton (if deuterated) can exchange in protic media; prepare derivatives promptly if that specific label must be retained.

Always confirm isotopic enrichment of the final product by HRMS/NMR before use as a calibration standard.

Target Specificity

Not applicable. This product is a small-molecule fatty acid standard and does not possess biological target/antigen specificity, clone, isotype, or species reactivity. For intended analytical targets (e.g., C20:0 lipid species), see Reaction & Applications and Application Protocols for general guidance.

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥99% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at 2–8 °C. Refrigerated storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships chilled on wet ice. 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 1219803-69-6, the molecular formula is C20H40O2, and the molecular weight is 316.6 g/mol. InChIKey VKOBVWXKNCXXDE-KHORGVISSA-N.

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.