1-Docosanol-d , CAS No.D1423198

CAS: D1423198 Cat. No.: D1423198 Formula: C₂₂HD₄₅O Peso molecolare: 371.88

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

1-Docosanol-d 45 is the deuterium labeled 1-Docosanol. 1-Docosanol is a saturated fatty alcohol used traditionally as an emollient, emulsifier, and thickener in cosmetics, and nutritional supplement. 1-Docosanol is an inhibitor of lipid-enveloped viruses including herpes simplex.

Specifications

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

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Tipo di azione

INHIBITOR

Nomi e identificatori

• Peso molecolare: 371.88

Application Protocols

Item-specific tested applications and dilutions: Not specified for this item; refer to CoA/Spec Sheet.

General protocols for common uses of 1‑Docosanol‑d:

A. LC‑MS/GC‑MS internal standard preparation

• Stock solution: Dissolve at 1–10 mg/mL in isopropanol, ethanol, or hexane. Warm (40–50 °C) to expedite dissolution. Store aliquots at −20 °C.
• Working solution: Dilute into mobile phase (e.g., MeOH/IPA/H2O with 0.1% formic acid or ammonium acetate for LC‑MS) or into isooctane/toluene for GC‑MS.
• Spiking: Add a fixed amount to samples prior to extraction to correct for recovery and ionization variability. Verify absence of isotopic overlap with analyte fragments.

B. Enzymatic or chemical esterification (to generate labeled esters)

• Combine acid (1.1 eq), 1‑Docosanol‑d (1.0 eq), catalytic DMAP (5 mol%) with EDCI (1.2 eq) in 2‑MeTHF or toluene. Stir at rt–50 °C, 4–16 h. Work up and purify by silica gel (hexane/EtOAc).

C. Aqueous dispersion for biophysical studies

• Prepare a 50 mg/mL stock in warm ethanol. Add dropwise (1:20–1:50 v/v) to pre‑warmed buffer containing 0.05–0.2% nonionic surfactant under vigorous stirring or probe sonication. Validate dispersion by DLS.

Isotopic caution:

• If O–D labeled, minimize exposure to aqueous/protic conditions to limit H/D exchange. For C–D labels, standard handling is acceptable.

Always tailor conditions to your instrumentation and method SOPs.

Biological Roles

General biochemical context (parent 1‑docosanol and long‑chain fatty alcohols; literature):

• Membrane interactions: Long saturated alcohols intercalate into lipid bilayers and can influence bilayer order, phase behavior, and permeability. Their high hydrophobicity favors partitioning into lipid phases.
• Metabolic pathways: Primary fatty alcohols are oxidized by alcohol dehydrogenases to long‑chain aldehydes and further by aldehyde dehydrogenases to the corresponding fatty acids (e.g., docosanoic acid). These can enter elongation/desaturation pathways and beta‑oxidation.
• Lipid remodeling: Long‑chain alcohols serve as substrates for wax ester synthases and acyltransferases, forming wax esters and ether lipids (e.g., 1‑O‑alkyl glycerol intermediates) in certain organisms.
• Self‑assembly & surfactancy: C22 alcohols can form monolayers, mixed micelles with surfactants, and stabilize emulsions; used to probe interfacial phenomena.

Use of deuterated analogues:

• Tracing and quantification: Deuterium labels enable tracking incorporation/turnover by MS without altering carbon count or gross physicochemical behavior. They frequently serve as internal standards in lipidomics, allowing accurate quantitation of endogenous long‑chain alcohols or derivatives.
• Isotopic considerations: If the label resides on exchangeable sites (O–D), isotopic content can change in aqueous/protic media. C–D labels are generally stable under physiological conditions used in in vitro studies.

Note: These are general/literature roles. This product is intended strictly for research use; no clinical or therapeutic claims are made.

Buffer Applications

Not a buffering reagent. 1‑Docosanol‑d is a highly hydrophobic, long‑chain alcohol with negligible water solubility, so it is not used to set or maintain pH.

Practical guidance when incorporating into aqueous buffers for research workflows:

• Solubilization: Prepare a concentrated stock in warm ethanol or isopropanol (e.g., 10–100 mg/mL at 40–60 °C). Add slowly to the aqueous buffer under vigorous stirring to avoid precipitation.
• Use of carriers: Nonionic surfactants (e.g., polysorbates, Cremophor, Triton X‑100 alternatives) or cyclodextrins can help disperse the alcohol in aqueous media. Optimize surfactant concentration to stay above CMC.
• pH effects: The neutral primary alcohol does not contribute to buffering capacity. Maintain pH with standard buffers (phosphate, Tris, HEPES) as dictated by your biological system.
• Isotopic integrity: If the deuterium is at the hydroxyl (O–D), prolonged exposure to aqueous buffers, especially acidic or basic, will promote H/D exchange, diminishing deuterium content at that site. Keep contact time short if exchange is a concern.

For experiments where robust aqueous dispersion is essential, consider forming nanoemulsions or liposomal systems using phospholipids and co‑surfactants; characterize particle size and stability by DLS or microscopy.

Green Alternatives

Context: The analyte is a deuterated long‑chain fatty alcohol; substitution is often not feasible when isotopic labeling is required. Greener choices can, however, be made for solvents, reagents, and processes used with it.

Greener solvent and process options (literature/general):

• Dissolution and handling:
  • Prefer bio‑based ethanol or isopropanol (heated) over chlorinated solvents when possible.
  • Use heptane or cyclopentyl methyl ether (CPME) instead of hexane or DCM for nonpolar dissolution, considering performance and safety tradeoffs.
• Transformations (esterification/activation):
  • Employ EDCI/HOBt alternatives with catalytic DMAP in greener solvents (2‑MeTHF, CPME) rather than DCM/DCC. Enzymatic esterification (lipases) in green solvents or solvent‑free melts is often effective for long‑chain alcohols.
• Workup:
  • Minimize chlorinated waste; use aqueous ethanol and heptane partitions. Implement short‑path distillation or crystallization from green solvents.

Small comparison (illustrative):

• DCM/chloroform: Excellent solvency; high VOC impact and toxicity; halogenated waste.
• 2‑MeTHF/CPME: Good solvency, lower peroxide tendency than ethers like THF, partially bio‑sourced; still flammable—monitor peroxides over time.
• Ethanol/isopropanol: Green, readily available; may require heating due to high mp of C22 alcohols.

Notes:

• Isotopic integrity: If the deuterium is at the hydroxyl, avoid aqueous acidic/basic processes that induce H/D exchange; enzyme‑catalyzed esterifications often preserve C–D labels while proceeding under milder conditions.

Pharmaceutical Uses

No therapeutic claims are made. The following describes nonclinical/formulation contexts from general literature for long‑chain fatty alcohols and isotopologues:

• Excipient roles (general): Long‑chain saturated alcohols such as behenyl alcohol are widely used as rheology modifiers, consistency agents, and co‑emulsifiers in semisolid dosage forms (creams, ointments) and as matrix formers in solid dispersions. Deuterated analogues may be used as analytical internal standards for excipient or API quantification in formulation development by LC‑MS/GC‑MS.
• Manufacturing development: Isotopically labeled excipient analogues enable tracer studies of process robustness (e.g., mixing, phase inversion) and recovery during cleaning validation or extractables/leachables investigations.
• Quality control: Stable‑isotope standards improve accuracy in stability‑indicating assays, allowing separation of analyte signals from matrix background.

Regulatory and compendial notes:

• Pharmacopeial monographs may exist for behenyl alcohol (parent), but not necessarily for deuterated analogues. This item’s specific grade/purity and compliance status are Not specified for this item; refer to CoA/Spec Sheet.

Formulation handling tips:

• Melt incorporation at 70–80 °C into oil phases is typical. Verify isotopic integrity if the label is at the hydroxyl (risk of exchange in aqueous phases). For analytical uses, store separate labeled standards and avoid contact with reactive excipients (strong oxidants).

Physical Properties

Item-specific values (from Product Data):

• 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 the unlabeled parent (1‑docosanol; deuteration typically causes negligible changes in bulk properties):

• Physical form: Waxy solid or flakes at ambient temperature (literature).
• Melting point: ~74–78 °C (literature, parent compound).
• Boiling point: Very high; decomposes before boiling at 1 atm; reported bp >300 °C under reduced pressure often used (literature, parent compound).
• Density: ~0.80–0.82 g/mL near melt (literature, parent compound; temperature dependent).
• Solubility: Practically insoluble in water; soluble in nonpolar/aprotic organics (hexane, heptane, toluene), chlorinated solvents, and hot lower alcohols (ethanol, isopropanol) (literature, parent compound).
• LogP (parent): Very high hydrophobicity; logP >> 5 (literature trend for C22 primary alcohols).
• Refractive index: Not commonly reported for solid; measure in melt if needed (literature guidance).

Practical notes:

• Due to high mp, solutions are often prepared warm (40–60 °C) in suitable organic solvents.
• For mass spectrometry, confirm exact mass shift(s) from deuteration by HRMS (isotopic pattern). If deuterium is at the hydroxyl (O–D), isotopic exchange can occur in protic media, affecting apparent labeling.

All numerical values above are literature/general for the non‑deuterated parent and provided as guidance only. For this specific deuterated item, consult the CoA for definitive specifications.

Quality and Grades

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

Guidance on quality for isotopically labeled fatty alcohols:

• Isotopic enrichment: For quantitative MS applications, the critical quality attribute is %D incorporation at defined positions. Confirm by 1H/2H NMR and HRMS. The CoA typically reports nominal enrichment (e.g., ≥98 atom % D) and labeling site(s). Absent from the current Product Data—verify before quantitative use.
• Chemical purity vs. isotopic purity: Both matter. Chemical purity affects baseline and fragmentation background; isotopic purity affects accuracy in isotope‑dilution assays. Review GC/LC purity traces when available.
• Residual solvents and volatiles: Long‑chain alcohols may retain entrained solvent; drying under high vacuum at 40–50 °C minimizes this. Specifications, if controlled, will appear on the CoA.
• Water and peroxide content: Not specified for this item; refer to CoA/Spec Sheet. Long‑chain saturated alcohols are generally resistant to peroxidation compared to ethers, but limits may still be provided by QC.
• Stabilizers: Typically none required for saturated fatty alcohols; any stabilizer or antioxidant would be listed on the CoA if present.

Sourcing rationale:

• For lipidomics and tracer studies, choose lots with documented labeling site and enrichment, plus low background signals in the analytical method of interest (GC‑MS, LC‑MS). Request targeted impurity profiles (e.g., shorter/longer homologues) if your method is sensitive to chain‑length isomers.

Reaction and Applications

Applications (deuterated analogue):

• Analytical internal standard: Used in lipidomics and materials analysis to normalize recovery/ionization of long‑chain alcohols and derived esters by LC‑MS or GC‑MS. Confirm exact labeling site and enrichment for isotope‑dilution quantitation.
• Tracer studies: Follows uptake, oxidation (to aldehyde/acid), or incorporation into wax esters/ethers. Deuterium tracking by MS elucidates metabolic or processing pathways.

Reactivity of the primary alcohol (parent compound; literature):

• Esterification: Formation of deuterated behenate esters with carboxylic acids (DCC/DMAP, EDCI, acid chlorides) to create labeled lipids/surfactants.
• Oxidation: Conversion to 1‑docosanal (Dess–Martin, Swern) or docosanoic acid (TEMPO/bleach, Jones) for chain‑length‑matched labeled aldehydes/acids.
• Activation to leaving groups: Tosylation/mesylation (TsCl/MsCl + base) followed by substitution to access labeled docosyl derivatives (halides, azides, thiols, ethers).
• Etherification: Williamson synthesis after alkoxide generation (NaH, KH) in THF or toluene to afford long‑chain alkyl ethers.

Practical tips:

• Melting/solubility: Warm the reaction mixture to ensure homogeneous phase. Use vigorous stirring in biphasic systems.
• Dry conditions: Water suppresses esterification and activation reactions; dry solvents and glassware are recommended.
• Isotopic integrity: If O–D labeled, avoid acidic/basic aqueous workups that accelerate H/D exchange at the hydroxyl. For C–D labels, maintain moderate temperatures to limit any isotopic scrambling under strongly acidic conditions.

Quality control:

• Track reaction progress and labeling integrity by GC‑FID/GC‑MS or LC‑MS with exact‑mass monitoring of expected isotopologues.

Reaction Conditions

General literature conditions for transformations of long‑chain primary alcohols (applicable to parent compound; ensure preservation of deuterium label):

• Esterification (Steglich): Carboxylic acid (1.0–1.2 eq), DCC (1.2–1.5 eq), catalytic DMAP (5–10 mol%) in DCM or toluene, 0 °C to rt, 2–18 h. Filter DCU, concentrate, purify. Alternative: EDCI/HOBt or EDCI/DMAP in 2‑MeTHF.
• Acid chloride route: Acid chloride (1.1–1.5 eq) with pyridine or Et3N (2–3 eq) in DCM, 0 °C to rt, 1–6 h. Good for sterically unhindered C22 alcohols.
• Enzymatic esterification: Lipase (e.g., Candida antarctica, Novozym 435), neat melt or in green solvents (2‑MeTHF, t‑amyl alcohol), 40–70 °C, remove water by molecular sieves or reduced pressure; high selectivity, gentle on isotopic labels.
• Tosylation: TsCl (1.2–1.5 eq), pyridine (solvent/base) with catalytic DMAP at 0 °C to rt, 2–6 h. Follow with SN2 in polar aprotic solvent (DMF, DMSO, acetone) at 25–60 °C.
• Williamson ether: Generate alkoxide with NaH (1.1–1.5 eq) in dry THF or toluene, 0 °C to rt, then add primary alkyl halide (1.1–1.5 eq); 25–60 °C, 2–16 h.
• Oxidation to aldehyde: Dess–Martin (1.3 eq) in DCM, 0 °C to rt, 1–3 h; or Swern (oxalyl chloride/DMSO, −78 °C, then Et3N). To acid: TEMPO/NaOCl/NaBr, pH ~9–10, 0–5 °C to rt.

Notes for deuterated substrates:

• Avoid strong protic/acidic aqueous media if the label is at the hydroxyl (O–D) to minimize H/D exchange. C–D labels are generally robust; nonetheless, limit exposure to superacidic media and high temperatures.
• Monitor isotope integrity and position by HRMS and 2H NMR after each step.

Expected outcomes: Long‑chain alcohol reactions typically give high yields (70–95%) when mass transfer is managed (homogeneous phase, adequate temperature).

Safety and Handling

GHS and hazard information (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 safety guidance for long‑chain fatty alcohols and their deuterated analogues (literature/practice):

• Hazard profile: Typically low acute toxicity; may cause skin/eye irritation. Combustible as an organic solid; avoid dust formation and ignition sources.
• Personal protective equipment (PPE): Laboratory coat, safety glasses or goggles, and suitable gloves (e.g., nitrile). Use in a fume hood when heating, dissolving, or weighing fine powders.
• Handling: Melt/solution prep should be done with controlled heating. Prevent aerosolization of powdered/flake material. For isotopically labeled material intended for analytical use, minimize cross‑contamination and moisture exposure.
• Incompatibilities: Strong oxidizers (risk of exothermic reaction). For labeled material with O–D at the hydroxyl, avoid prolonged contact with protic solvents, aqueous buffers, acids/bases that catalyze H/D exchange.
• First aid (overview; defer to SDS):
  • Skin: Wash with soap and water.
  • Eyes: Rinse cautiously with water for several minutes; remove contacts if easy.
  • Ingestion: Rinse mouth; seek medical advice.
  • Inhalation: Move to fresh air; seek medical advice if symptoms occur.
• Fire response: Use CO2, dry chemical, or foam. Combustion may produce CO/CO2.

Always consult the item’s SDS for authoritative hazard, exposure limits, and emergency procedures.

Solvent Selection

Polarity and miscibility (general for long‑chain fatty alcohols):

• Polarity class: Nonpolar to weakly polar (single terminal –OH).
• Water: Practically insoluble; forms turbid dispersions unless emulsified.
• Organic solvents: Readily soluble in nonpolar and medium‑polarity organic solvents (hexane, heptane, cyclohexane, toluene, chloroform, dichloromethane). Solubility in lower alcohols (ethanol, isopropanol) improves markedly upon heating.

Selection guidance by application:

• MS internal standard/tracer: Use high‑purity solvents (LC‑MS grade). For ESI LC‑MS, dissolve in isopropanol, acetonitrile/isopropanol (1:1), or methanol/isopropanol with gentle warming. For GC‑MS, use hexane, isooctane, or toluene.
• Synthetic transformations (esterification, tosylation): Employ dry chlorinated solvents (DCM, chloroform) or toluene with catalytic DMAP or base. For Appel or halide formation, DCM/THF mixtures are common.
• Formulation/dispersion studies: Create stock in warm ethanol/isopropanol, then dilute into surfactant‑containing aqueous media (e.g., polysorbates) to avoid precipitation.

Comparisons:

• Hexane/heptane: Maximize solubility with minimal polarity; excellent for GC and nonpolar workup.
• Isopropanol/ethanol: Convenient and greener, but may be poor at room temperature; heat to 40–60 °C.
• DCM/chloroform: Strong solvents for rapid dissolution; less green and require fume hood handling.

Isotopic considerations:

• If the label is at the hydroxyl (O–D), avoid extended residence in protic solvents/water to minimize H/D back‑exchange. For C–D labels, exchange in common solvents is negligible.

Storage and Reconstitution

Item-specific storage and shipping (from Product Data):

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

General guidance for this class of materials:

• Container: Keep in tightly closed, inert containers (amber glass recommended) to prevent contamination and adsorption onto plastics. For analytical standards, aliquot to minimize freeze–thaw and headspace.
• Atmosphere: Typically stable in air; for long‑term storage, a dry, inert headspace (argon or nitrogen) helps limit adventitious oxidation of the primary alcohol.
• Moisture/light: Protect from moisture. Light sensitivity is minimal for saturated alcohols, but amber storage minimizes any photochemical risk.

Reconstitution and handling:

• Solubility: Warm gently (40–60 °C) to aid dissolution in isopropanol, ethanol, toluene, or hexane. Avoid overheating and prolonged exposure above the melting point without need.
• Isotopic integrity: If deuteration is at the hydroxyl (O–D), avoid prolonged contact with protic solvents and aqueous buffers to minimize H/D exchange. If C–D labeled, exchange is negligible under normal storage/handling.
• Stability: Long‑chain saturated alcohols are chemically robust; nonetheless, confirm integrity by MS before critical quantitative assays, especially after extended storage.

Disposal: Dispose of unused material and contaminated containers as organic chemical waste per institutional and regulatory guidelines.

All unspecified item‑level parameters (e.g., exact %D labeling, MW, appearance) are Not specified for this item; refer to CoA/Spec Sheet.

Structure and Identity

Short description: 1‑Docosanol‑d is an isotopically labeled analogue of 1‑docosanol (behenyl alcohol), a linear C22 primary fatty alcohol. The precise site(s) and degree of deuterium incorporation are not specified for this item; refer to CoA/Spec Sheet.

• Item-specific identifiers from Product Data:

  • SKU: D1423198
  • CAS: D1423198 (catalog placeholder; not a standard CAS)
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • 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 for the unlabeled parent, 1‑docosanol):

  • Linear, saturated aliphatic chain with 22 carbons (behenyl skeleton).
  • Terminal primary alcohol (–CH2OH) at C1; no rings, no unsaturation, no heteroatoms beyond the hydroxyl oxygen.
  • Typical parent molecular formula: C22H46O (literature, for non‑deuterated analogue). Deuteration replaces one or more hydrogens with deuterium (2H), minimally perturbing structure but shifting exact mass.

• 2D structure in words (parent compound, literature):

  • A straight, unbranched alkyl chain (C1–C22) with a hydroxymethyl group at carbon 1: HO–CH2–(CH2)20–CH3.

Notes on isotopic labeling:

• “‑d” denotes deuterated isotopologue(s). Without an explicit specification (e.g., –d1 at OH, –d2, –d47), the labeling position/number cannot be inferred for this specific item. Confirm by CoA, NMR, or HRMS prior to quantitative use.

Synthetic Utility

Functional group and reactivity (parent primary alcohol; literature):

• Nucleophilicity via alkoxide: Deprotonation (NaH, KH) enables Williamson ether syntheses with primary halides/sulfonates, generating long‑chain alkyl ethers and surfactants.
• Esterification: Forms fatty esters (wax esters, glycerides) via DCC/DMAP, EDCI/DMAP, acid chlorides (oxalyl chloride‑derived acyl chlorides), or enzymatic routes (lipase‑catalyzed), useful for materials and lipid standards.
• Activation as leaving group: Tosylate/mesylate formation (TsCl/MsCl with pyridine or Et3N, catalytic DMAP) followed by SN2 substitutions (azide, cyanide, thiolate) to access diverse C22 derivatives.
• Oxidation/derivatization: Swern or Dess–Martin to aldehyde; TEMPO/bleach to acid; Pinnick oxidation of aldehyde to acid.

Isotopic labeling value:

• Using 1‑Docosanol‑d as a building block transfers the deuterium tag into downstream derivatives (esters, ethers, aldehydes, acids), enabling labeled standards across a C22 lipid series. Choose conditions that preserve C–D bonds; avoid strong acid‑catalyzed rearrangements or high‑temperature processes that could induce H/D scrambling.

Practical considerations:

• Phase behavior: Conduct reactions above the melting point or in solvents that dissolve the substrate to ensure homogeneous kinetics.
• Workup/purification: Nonpolar products often crystallize on cooling; otherwise, apply normal‑phase chromatography (hexane/EtOAc gradients). Monitor isotopic integrity by HRMS and 2H NMR.

Applications:

• Preparation of deuterated wax esters, surfactants, and calibration standards for GC‑MS/LC‑MS; synthesis of labeled docosyl halides, azides (for click chemistry after reduction), and thiols for surface functionalization.

Target Specificity

This product is a small‑molecule chemical (a deuterated fatty alcohol), not an antibody, enzyme, or receptor ligand with defined biological target specificity.

• Item-specific target/epitope/isotype data: Not applicable.
• Species reactivity: Not applicable.

For analytical applications, “specificity” refers to isotopic fidelity and chromatographic/mass‑spectrometric distinguishability from endogenous 1‑docosanol and related lipids. Confirm by retention time matching and characteristic mass shift(s).