Stearic acid-d7 - ≥98%,≥98 atom% D , CAS No.951209-59-9

CAS: 951209-59-9 Cat. No.: S1440121 Formule: C₁₈H₂₉D₇O₂ Poids moléculaire: 291.52

QUALITÉ & PURETÉ ≥98%,≥98 atom% D

Synonyms

Octadecanoic-16,16,17,17,18,18,18-d7 Acid

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Vue d’ensemble

Stearic acid-d 7 is the deuterium labeled Stearic acid. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

Spécifications

Synonymes

Octadecanoic-16,16,17,17,18,18,18-d7 Acid

Spécifications et pureté

≥98%,≥98 atom% D

Conditions de stockage de stockage

Protected from light,Store at -20°C,Argon charged

Expédié en

Ice chest + Ice pads

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Pureté

≥98%,≥98 atom% D

Noms et identifiants

CAS alternatif

57-11-4（unlabeled）

Poids moléculaire

291.52

Propriétés chimiques et physiques

• Sensibilité: light sensitive；heat sensitive

Application Protocols

No item-specific tested protocols are provided for this listing. The following general practices are commonly used for deuterated fatty acids in analytical workflows (informational; adjust to your method and instrumentation):

• LC–MS lipidomics internal standard

  • Prepare a 1–5 mM stock in CHCl3:MeOH (2:1). Store at −20 °C under argon in amber vials.
  • Spike a fixed amount into samples before extraction (e.g., Bligh–Dyer or MTBE methods) to correct for recovery and ionization variability.
  • Monitor M+7 precursor and appropriate product ions; verify retention time near unlabeled analyte.

• BSA-complexed fatty acid for cell studies

  • Dissolve stearic acid-d7 in a small volume of warm 0.1–0.2 M NaOH to form sodium stearate.
  • Add dropwise to warm (37 °C) fatty acid–free BSA solution (e.g., 5–10% w/v) under stirring to achieve target FA:BSA molar ratio (commonly 2–6:1). Filter-sterilize if needed.

• Surface monolayer preparation

  • Dissolve in chloroform (1–5 mg/mL). Deposit on aqueous subphase or solid substrate; allow solvent evaporation to form monolayer; characterize by ellipsometry or neutron reflectometry.

Always verify compatibility with your cells/instrumentation and consult the SDS.

Biological Roles

Stearic acid is a major saturated fatty acid in animals and plants; the d7 label enables precise tracking without altering core biochemical behavior.

• Endogenous context (general biochemistry)

  • Incorporated into membrane phospholipids, sphingolipids, triacylglycerols, and cholesteryl esters, influencing membrane order and lipid raft formation.
  • Metabolic pathways include activation to stearoyl-CoA, mitochondrial β-oxidation, peroxisomal oxidation, and desaturation by stearoyl-CoA desaturase to oleoyl-CoA.
  • Transported in plasma bound to albumin; intracellular trafficking via FABPs.

• Uses of the deuterated analog

  • Isotopic tracing of uptake, acylation, remodeling (Lands’ cycle), and oxidation using MS-based isotopologue analysis.
  • Internal standard in lipid extraction efficiency assessments and quantitation of stearate-containing lipid species.
  • Studies of monolayer/film mechanics where deuteration facilitates neutron and IR spectroscopic contrast.

• Notes

  • Deuterium substitution on carbon yields non-exchangeable labels under physiological conditions, maintaining label integrity during typical experiments.
  • Avoid clinical or diagnostic use; this product is for research use only.

Buffer Applications

Not typically used as a buffer component due to very low aqueous solubility and lack of buffering capacity near physiological pH. For aqueous applications involving stearic acid-d7:

• Practical approaches (general)

  • Prepare fatty acid–BSA complexes: dissolve stearic acid-d7 in ethanol or a small volume of warm NaOH to form sodium stearate, then slowly add to pre-warmed fatty acid–free BSA in buffer (e.g., PBS) while stirring to achieve clear solutions.
  • Alternatively, generate sodium/potassium stearate in carbonate/bicarbonate buffer (pH ≥ 8) for micelle/vesicle studies; titrate to target pH after dispersion.

• Buffer compatibility

  • Avoid strong oxidizing buffers; maintain inert atmosphere if solutions are stored. Use amber containers to limit photodegradation.

• Reference

  • For precise recipes (FA:BSA molar ratios, temperature profiles), consult lipid handling literature and adapt to experimental scale.

Green Alternatives

As a substance, stearic acid-d7 itself is not replaced by a “greener” chemical when isotopic labeling is required. However, greener choices can be made in handling, solvents, and synthesis.

• Greener solvent choices for dissolution/processing (general)

  • Prefer bio-based ethanol or isopropanol (with gentle heating) over chlorinated solvents when compatible with the workflow.
  • Consider 2-MeTHF or CPME instead of THF or DCM for coupling/activation steps, provided reagents remain efficient.
  • For extractions, heptane/ethyl acetate systems may replace hexane/DCM where solubility permits.

• Oxidation control without excess hazards

  • Use inert gas headspace and amber containers rather than adding stabilizers.
  • Store at −20 °C to slow degradation, reducing waste.

• Small comparison (general)

  • Chlorinated solvents (DCM/CHCl3): excellent solubility, MS-friendly; higher environmental/health burden.
  • Alcohols (EtOH/iPrOH): safer, renewable options; may require heat and have limited solubility at room temperature.
  • Ethers (2-MeTHF): greener profile vs THF; good for coupling but may not dissolve highly crystalline solids at RT.

• Sourcing considerations

  • Where possible, select lots made from sustainably sourced starting materials and with minimized waste solvents (supplier documentation).

Pharmaceutical Uses

This product is for research use only and is not intended for human or veterinary use. In a general formulation context (informational):

• Excipients related to stearic acid (general)

  • Stearic acid and its salts/derivatives (e.g., magnesium stearate) are widely used as lubricants, emulsifiers, and matrix components in solid dosage forms and cosmetics. These roles leverage hydrophobicity and lubricity.

• Relevance of the deuterated analog

  • Deuterated stearic acid can serve as a process tracer or analytical internal standard during development work to evaluate extraction recovery, matrix effects, or to validate analytical methods for stearate-containing excipients or APIs.

• Regulatory note

  • No pharmacopeial monograph applies to the deuterated analog per se. Any GMP or clinical use would require separate qualification; this catalog item is not supplied for such use.

Physical Properties

Item-specific physicochemical specifications for this catalog entry are not provided.

• Item-specific values

  • 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.

• Typical properties for stearic acid and deuterated analogs (literature/estimated; for method development only, not product specifications)

  • Melting point: ~69–70 °C (stearic acid, literature). Deuteration generally shifts MP minimally.
  • Boiling point: ~383 °C at 760 mmHg with decomposition (stearic acid, literature).
  • Density (solid, 20–25 °C): ~0.84–0.85 g/cm3 (stearic acid, literature).
  • pKa (carboxyl): ~4.7–5.0 in water (fatty acids, literature).
  • logP (octanol/water): ~8 (stearic acid, literature) indicating strong hydrophobicity.
  • Solubility: Insoluble in water; soluble in nonpolar and moderately polar organics (e.g., chloroform, dichloromethane, toluene, hot ethanol/methanol, acetone) and in basic aqueous media as stearate (literature).
  • Critical micelle/monolayer behavior: readily forms monolayers and self-assembled films at air–water and solid–liquid interfaces (literature).

• Practical notes (general)

  • Warm gently (40–60 °C) to aid dissolution in organic solvents.
  • For aqueous work, dissolve as stearate salt or complex with fatty acid–free BSA. Avoid prolonged heating with air exposure to minimize oxidation.

Quality and Grades

• Item-specific grade/purity

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

• Considerations for isotopically labeled fatty acids (general guidance)

  • Isotopic enrichment: For quantitative MS workflows, knowledge of deuterium enrichment (%D) and labeling pattern is crucial to ensure consistent mass shift and chromatography. Verify enrichment on the CoA.
  • Chemical purity: Residual unlabeled stearic acid can influence quantitation; look for high chemical purity and low related fatty acid impurities (e.g., palmitic/oleic acids) on the CoA.
  • Oxidative stability: Deuterated fatty acids can oxidize similarly to protiated analogs. Suppliers may recommend inert gas backfill (argon) and light protection, as specified for this item.
  • Solvent residues/UV specs: Not specified for this item; refer to CoA/Spec Sheet.

• What the listed storage/shipping implies for this item

  • Argon charged and protected from light, stored at −20 °C, shipped cold: indicates preservation of chemical and isotopic integrity by limiting oxidation and photodegradation. Upon receipt, promptly return to −20 °C under inert atmosphere.

• Documentation

  • Request the lot-specific Certificate of Analysis for detailed purity, isotopic enrichment, residual solvent, and analytical method data prior to critical quantitation work.

Reaction and Applications

This deuterium-labeled fatty acid is primarily used as an internal standard and tracer, but it also participates in typical carboxylic acid transformations.

• Analytical applications (general best practices)

  • LC–MS/MS internal standard for quantitative lipidomics: spiking into extracts for absolute/relative quantitation of stearate and related lipid species. The +7 Da mass shift enables clear separation of precursor/product ion channels.
  • Metabolic tracing: monitor uptake, β-oxidation, elongation, and desaturation pathways in cells or model systems using MS isotopologue distributions.
  • Surface science: formation of deuterium-labeled monolayers on metals/oxides for neutron reflectometry or vibrational spectroscopy.

• Synthetic/derivatization applications

  • Esterification: Fischer (acid-catalyzed, alcohol solvent) or DCC/DMAP to give labeled alkyl stearates for standards.
  • Amide coupling: EDC/HOBt, HATU, or mixed anhydride routes to labeled amides (e.g., N-acylated lipids, surfactants).
  • Acyl chloride formation: SOCl2 or (COCl)2 with catalytic DMF to access reactive intermediates for further transformation.
  • Salt formation: sodium/potassium stearate (saponification) for aqueous dispersions and micelle studies.

• Practical tips

  • Maintain inert atmosphere and minimize light to preserve isotope-verified composition.
  • For MS work, match the solvent system and injection matrix to sample composition to avoid differential ionization of labeled vs unlabeled analytes.
  • Validate retention time parity and fragmentation behavior relative to unlabeled analytes; deuterium can cause slight isotopologue-dependent retention shifts (isotope effect), typically small for C–D in long chains.

Reaction Conditions

General literature guidance for transforming long-chain fatty acids; adjust to your substrate and scale. These are not item specifications.

• Acid chloride formation

  • Reagents: SOCl2 (2–5 eq) or oxalyl chloride (2–3 eq) with catalytic DMF.
  • Solvent: dry DCM or toluene; 0–80 °C; 1–4 h until gas evolution ceases. Inert atmosphere.

• Steglich esterification

  • Conditions: alcohol (1.2–3 eq), DCC (1.2–1.5 eq), catalytic DMAP in dry DCM/THF; 0 °C to rt, 2–16 h. Filter dicyclohexylurea.

• Fischer esterification

  • Conditions: refluxing alcohol (MeOH/EtOH/iPrOH) with catalytic H2SO4 or TsOH; Dean–Stark if using higher alcohols; 3–24 h.

• Amide coupling

  • EDCI/HOBt or HATU with base (DIPEA) in DMF/DCM; 0 °C to rt or 40 °C; 2–16 h. Minimize adventitious water.

• Saponification / salt formation

  • Dissolve in minimal ethanol/THF; add stoichiometric NaOH or KOH in water/EtOH; 0–25 °C; complete within 0.5–2 h. Neutralize/exchange as needed.

• Notes on isotope preservation

  • C–D bonds in the alkyl chain are robust under these conditions. Avoid metal-catalyzed H/D exchange (e.g., Pd/C hydrogenation) or radical chain-transfer conditions if label position must remain fixed.

• Expected outcomes (literature)

  • Typical isolated yields: 70–95% for well-optimized ester/amide couplings with long-chain fatty acids; ensure adequate mixing and solubility (warm solvents).

Safety and Handling

Follow good laboratory hygiene and consult the SDS for authoritative guidance. This product is supplied for research use only.

• Item-specific hazard data

  • Signal word: Not specified for this item; refer to SDS.
  • Hazard statements (H-codes): Not specified for this item; refer to SDS.
  • GHS classification/pictograms: Not specified for this item; refer to SDS.

• General safety considerations for long-chain fatty acids (informational)

  • Typically regarded as low acute toxicity; may cause skin or eye irritation upon contact. Dusts or aerosols may cause respiratory irritation.
  • Combustible organic solid; avoid ignition sources and dust accumulation.
  • Peroxide formation is not a concern for saturated fatty acids; however, autoxidation of the carboxylate tail can occur on prolonged air/heat/light exposure producing peroxides and aldehydes—minimize oxygen and light.

• Handling practices

  • Use in a fume hood or well-ventilated area. Wear lab coat, safety glasses, and appropriate gloves (e.g., nitrile).
  • Prevent contamination with strong oxidizers and bases/acids during storage.
  • For isotopic integrity, avoid excessive heating and acidic/basic conditions that might promote isotope exchange at the carboxyl OH (if deuterated there; this product carries deuterium on carbon positions, which are non-exchangeable under typical conditions).

• First-aid overview (general)

  • Skin/eye contact: rinse with water for several minutes; remove contaminated clothing. Seek medical attention if irritation persists.
  • Inhalation: move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: rinse mouth; seek medical advice.

Solvent Selection

Stearic acid-d7 is highly hydrophobic; solvent choice governs handling, stock solutions, and derivatization.

• Polarity/miscibility profile (literature)

  • Water: essentially insoluble at ambient conditions.
  • Miscible/soluble: chloroform, dichloromethane, toluene, hexanes (warm), ethyl acetate (warm), acetone (warm), ethanol/methanol (hot), isopropanol (hot). Soluble in aqueous base as stearate.
  • Dielectric context: prefers low- to medium-polarity organic media; forms micelles/vesicles only with surfactants or as salts.

• Practical recommendations

  • For LC–MS lipidomics stocks: chloroform, methanol, or CHCl3:MeOH (2:1 or 1:1) are common. Keep solutions anoxic, amberized, and cold.
  • For derivatization (ester/amide formation): use dry DCM, THF, or toluene. Include base/scavengers as appropriate; exclude moisture.
  • For aqueous biological assays: pre-complex with fatty acid–free BSA or prepare sodium/potassium stearate in buffered saline (pH > 8), then dilute.

• Comparison (general)

  • Versus shorter saturated acids (e.g., lauric, palmitic): stearic requires warmer/less polar solvents to dissolve; longer chain increases hydrophobicity.
  • Versus unsaturated analogs (e.g., oleic): stearic is more crystalline with higher MP; dissolution may require gentle heating.

• Note

  • Avoid prolonged storage of solutions in alcoholic solvents with air exposure; oxidized byproducts can accumulate and confound MS quantitation.

Storage and Reconstitution

• Item-specific storage and shipping

  • Storage: Protected from light; Store at −20 °C; Argon charged (as provided).
  • Shipping: Ice chest + ice pads (as provided). Upon receipt, minimize time at ambient temperature and return to −20 °C under inert atmosphere.

• Handling best practices

  • Allow container to warm in a desiccator to room temperature before opening to prevent moisture condensation.
  • Reseal promptly; purge headspace with argon or nitrogen. Use amber vials to limit light exposure.
  • Aliquot on first opening to avoid repeated freeze–thaw and to protect isotopic integrity.

• Reconstitution guidance (general)

  • Organic stocks: dissolve at 10–100 mM in CHCl3, DCM, toluene, or CHCl3:MeOH (2:1). For alcohols, gentle heating (40–50 °C) may be needed. Use dry, oxygen-free solvents for long-term stocks.
  • Aqueous use: prepare sodium/potassium stearate by neutralization with equimolar base, or pre-complex with fatty acid–free BSA at 37 °C.
  • Working solutions: keep cold and protected from air/light; discard if oxidation (odor/color change, broadened MS baseline) is detected.

• Stability note

  • Long-chain fatty acids can slowly oxidize; storing cold, dark, and under inert gas significantly extends shelf life. For quantitative MS, periodically verify concentration and integrity by LC–MS against fresh standards.

Structure and Identity

Stearic acid-d7 is an isotopically labeled saturated C18 fatty acid in which seven hydrogen atoms along the aliphatic chain are replaced by deuterium (2H). It retains the carboxylic acid headgroup and an unbranched, fully saturated hydrocarbon tail. No stereocenters are present; the molecule is achiral.

• Item-specific identifiers

  • CAS: 951209-59-9 (provided)
  • 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.

• Structural features (general chemistry/literature)

  • Core scaffold: octadecanoic acid (stearic acid) backbone with seven non-exchangeable C–D bonds distributed along the methylene chain.
  • Functional groups: one terminal carboxylic acid (–CO2H); remainder sp3 aliphatic carbons.
  • 2D description: HO–C(=O)–(CH2)n–CH3 linear chain (n total carbons in chain = 16 methylenes plus terminal methyl; seven positions deuterated). The carboxyl terminus confers weak acidity; the long chain drives hydrophobicity and self-assembly.

• Isotopic note (general)

  • Deuteration provides +7 Da mass shift versus unlabeled stearic acid, enabling mass spectrometric discrimination while preserving chemical behavior closely matching the protiated analog.

Synthetic Utility

As a labeled C18 carboxylic acid, stearic acid-d7 is a versatile acyl donor in synthesis of isotopically defined lipids and surfactants.

• Transformations (general)

  • Activation: convert to the acid chloride (SOCl2, (COCl)2) or mixed anhydrides for subsequent coupling; retain C–D integrity under typical conditions.
  • Ester formation: Fischer esterification or Steglich (DCC/DMAP) to prepare labeled alkyl or glycerol esters; useful for standardizing GC derivatization (e.g., FAMEs) with known mass shift.
  • Amide coupling: EDCI/HOBt, HATU, or carbodiimide-mediated coupling to amines (fatty amides, lipopeptides).
  • Salt/surfactant formation: neutralization with NaOH/KOH/amine bases for micellar systems.

• Retrosynthetic value

  • Serves as a building block for deuterated phospholipids, sphingolipids, wax esters, and polymerizable derivatives (e.g., acrylates via ω-functionalization followed by acylation).

• Isotope integrity considerations

  • Avoid conditions that induce exchange or scrambling at labeled carbons (severe hydrogenolysis, radical H/D exchange). Standard acyl transfer and condensation chemistries preserve the C–D bonds.

• Analytics

  • NMR: 2H NMR enables direct observation of labeled sites; 13C/1H spectra show reduced protonated signals at labeled positions.
  • MS: predictable +7 Da shift across common ionization/fragmentation modes; confirm fragments retaining the labeled chain.

Target Specificity

Not applicable to this product type. Stearic acid-d7 is a small-molecule fatty acid standard/tracer and does not possess antibody or probe target specificity. For relevant information, see Reaction & Applications and Biological Roles.

Foire aux questions

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). This product is isotopically enriched to ≥98 atom% deuterium. Isotopic enrichment is a separate specification from chemical purity — a labelled compound has both. Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C, protected from light, under argon. It is supplied under an argon blanket; reseal under inert gas after each use.

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 951209-59-9, the molecular formula is C18H29D7O2, and the molecular weight is 291.52 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.