1-Hydroxyoctadecane-d , CAS No.86369-69-9

CAS: 86369-69-9 Cat. No.: H1432100 Formule: C₁₈H₃₆D₂O Poids moléculaire: 272.51

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Vue d’ensemble

1-Hydroxyoctadecane-d 2 is the deuterium labeled 1-Hydroxyoctadecane. 1-Hydroxyoctadecane is an endogenous metabolite.

Specifications

Conditions de stockage de stockage

Store at -20°C

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.

Noms et identifiants

Poids moléculaire

272.51

Application Protocols

No item-specific, validated protocols are provided for this product. The following general procedures are commonly used with deuterated long-chain alcohols in research and analytical settings:

• Preparation of stock solutions

  • Weigh accurately at room temperature; warm gently (40–60 °C water bath) if needed to soften. Dissolve at 1–10 mg/mL in chloroform, toluene, or warm ethanol/isopropanol. Vortex/sonicate to aid dissolution. Aliquot and store at −20 °C.

• GC–MS internal standard (illustrative)

  • Spike samples (lipid extracts) with a known amount of the deuterated alcohol prior to derivatization (e.g., trimethylsilylation with BSTFA + 1% TMCS, 60–70 °C, 30–60 min). Analyze by GC–MS in EI/SIM mode monitoring characteristic m/z of the deuterated vs native analyte. Construct calibration curves using matrix‑matched standards.

• LC–MS workflows

  • Dissolve in isopropanol or methanol; if needed, include a small fraction of nonpolar cosolvent to fully solubilize before dilution with aqueous mobile phase. Use MRM/SIM transitions separated by the deuterium mass shift. Avoid glass adsorption by conditioning vials with organic solvent.

• Surface deposition

  • Prepare 0.1–1.0 mg/mL in toluene or hexane; deposit on substrate by drop‑casting or dip‑coating; allow solvent to evaporate under clean, dust‑free conditions.

Validate and optimize for your instrument and matrix; confirm isotopic integrity post‑processing.

Biological Roles

General context for the non-deuterated parent (1‑octadecanol) and the utility of its deuterated analogue:

• Fatty alcohol biology (literature)

  • Long-chain fatty alcohols are biosynthesized from fatty acyl‑CoAs via fatty acyl‑CoA reductases and serve as precursors to wax esters and ether lipids. They participate in cuticular wax formation in plants and are components in certain marine waxes.
  • Metabolic interconversion with corresponding aldehydes and acids occurs via alcohol dehydrogenases and fatty alcohol oxidases.

• Use of deuterated analogues

  • Isotopically labeled fatty alcohols enable tracking of uptake, esterification to wax esters, or oxidation to acids in cell-free systems and organismal studies using MS-based isotopologue analysis.
  • Deuterium labeling enhances contrast in neutron scattering and certain vibrational spectroscopies, facilitating studies of chain packing, membrane interactions, and monolayer behavior.

• Notes

  • Exact metabolic behavior of the labeled compound closely mirrors the unlabeled analogue; kinetic isotope effects are generally small for processes not involving C–D bond cleavage at the labeled positions.
  • Item-specific biological testing or characterization is not provided for this product; use is restricted to research applications as indicated (For research use only).

Buffer Applications

This product is a hydrophobic, long‑chain alcohol and is not typically used to prepare aqueous buffer systems or to control pH. It has negligible water solubility and no buffering capacity near physiological pH.

• Practical note
  • For work requiring aqueous dispersions (e.g., model membranes), dissolve first in a water‑miscible cosolvent (ethanol, isopropanol) or an organic phase, then emulsify with surfactants or lipids. Alternatively, deposit from organic solvent onto substrates prior to introducing aqueous media.

For buffer reagents and pH control, consider dedicated buffering systems (phosphate, Tris, HEPES, MOPS) instead.

Green Alternatives

As a labeled substrate/standard, the compound itself is typically irreplaceable in isotopic workflows. However, greener choices can be made in solvents and processing routes.

• Greener solvent options (general guidance)

  • Prefer bio-based ethanol or isopropanol for stock solutions where compatible with the analytical platform; warm slightly to aid dissolution.
  • Replace chlorinated solvents (chloroform, DCM) with toluene, heptane, or cyclopentyl methyl ether (CPME) for dissolution/deposition tasks when feasible.
  • For esterifications, use solvent-free melt conditions or green solvents (2-MeTHF, CPME) with catalytic methods (e.g., enzymes or catalytic acid resins) when appropriate.

• Comparison (illustrative)

  • Chloroform/DCM: Excellent solubility, but higher environmental and health concerns.
  • Toluene/heptane: Good solubility, lower toxicity; higher boiling points may increase energy for removal.
  • Alcohols (EtOH, i-PrOH): Renewable sources available; may require heating and offer slower dissolution.

• Sourcing considerations

  • Where possible, select deuterated materials produced with greener deuterium sources and energy‑efficient syntheses; request supplier sustainability statements.

• Waste minimization

  • Prepare concentrated stock solutions and aliquot to reduce solvent use and repeated thaw/dissolve cycles.
  • Employ microscale sample prep in MS workflows to cut solvent volumes.

Pharmaceutical Uses

No item-specific pharmacopeial status or excipient grade is provided for this deuterated material.

General context (non-clinical; formulation/manufacturing perspective):

• The non-deuterated parent, stearyl alcohol, is widely employed as a waxy excipient and rheology modifier in ointments, creams, and suppositories, providing consistency, occlusivity, and controlled release characteristics.
• Deuterated analogues are rarely used in commercial formulations, but may serve as tracers during process development, release testing method development (e.g., LC/GC internal standards), or to study excipient–API interactions in research settings.
• If an excipient application is intended, verify compliance with relevant compendial monographs (e.g., NF/Ph. Eur. for stearyl alcohol) and confirm that the deuterated variant meets required impurity and isotopic specifications; this product is offered for research use only.

Note: Avoid medical or therapeutic claims; this material is not supplied for clinical use.

Physical Properties

Item-specific physico-chemical specifications are not provided for this deuterated material; consult the CoA/Spec Sheet for exact values.

General/literature values for the non-deuterated parent (1‑octadecanol, stearyl alcohol) are provided for context only:

• Physical state: Waxy solid; forms needles or flakes (literature, parent compound).
• Melting point: Typically ~58–60 °C (literature, parent compound).
• Boiling point: High; often distilled under vacuum (e.g., ~210–220 °C at reduced pressure; literature, parent compound).
• Density: Approx. 0.81–0.85 g/mL at 20–25 °C (literature, parent compound).
• Solubility: Practically insoluble in water; soluble in nonpolar and mid‑polarity organics (hexanes, toluene, chloroform, dichloromethane) and in hot alcohols (ethanol, isopropanol) (literature, parent compound).
• LogP: High (hydrophobic; literature, parent compound).
• pKa: Alcohol O–H ~16 in water; ~29–30 in DMSO (literature, general alcohol values).
• Refractive index: Not typically reported for solids; molten values available in literature for the parent.

Notes

• Deuteration causes only minor shifts in bulk properties relative to the protio analogue; exact melting range and isotopic enrichment-dependent values should be verified on the item’s CoA.

Quality and Grades

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

• Isotopic quality considerations (general for deuterated fatty alcohols)

  • Isotopic enrichment: The fraction of deuterium incorporation and labeling pattern (e.g., terminal, chain-wide, or specific positions) strongly influence mass spectral behavior and tracer fidelity. Verify %D and labeling sites on the CoA.
  • Chemical purity: For quantitative applications (lipidomics/internal standard use), residual protio analogue, peroxides, or shorter/longer homologs should be minimized. Request GC/FID or GC–MS purity traces where applicable.
  • Water/volatile content: Moisture can affect accurate weighing and derivatization. Karl Fischer and residual solvent data, if available, support quantitative work.
  • Oxidative stability: Long-chain alcohols are generally stable, but trace oxidation to aldehyde/acid can occur upon prolonged exposure to air and heat. CoA may include related substances by GC.

• What the grade implies (general guidance)

  • Research-grade deuterated standards typically target high chemical purity and defined isotopic enrichment; low UV background is not usually relevant. For analytical-grade/isotopic-standard grade, expect certification of isotopic distribution and impurity profile suitable for MS quantitation.

Reaction and Applications

Applications leverage the long, saturated C18 chain and the deuterium label for tracing and quantitation.

• Analytical and tracing

  • Internal standard in lipidomics or surfactant analyses by GC–MS/LC–MS. The deuterium label provides mass separation from endogenous 1‑octadecanol while retaining nearly identical chromatographic behavior.
  • Metabolic fate studies of fatty alcohols/waxes: follow incorporation into esters, ethers, or oxidation to aldehydes/acids using MS isotopologue profiles.

• Surface and materials science

  • Formation of hydrophobic films/monolayers on graphite, gold (via thiol linkers after derivatization), or oxide surfaces (after silanization of substrates). Useful for probing chain packing using IR and neutron scattering (benefits from deuterium contrast).

• Synthetic/derivatization uses (general)

  • Esterification to labeled stearyl esters (Fischer esterification, Steglich conditions) to create deuterated wax esters.
  • Oxidation to stearaldehyde or stearic acid (Swern, Dess–Martin, TEMPO–bleach, or Jones — choose conditions to avoid H/D scrambling at nonexchangeable sites).
  • Conversion to alkyl halides (Appel; PBr3) or sulfonates (tosylate/mesylate) for subsequent SN2 to introduce functional handles while retaining the isotopic label.

• Practical tips

  • Dry conditions are generally not critical for the alcohol itself, but are important for moisture‑sensitive coupling reagents.
  • Avoid prolonged strong-acid or base at elevated temperature to minimize any risk of H/D exchange beyond the inherently exchangeable hydroxyl proton.

Reaction Conditions

General literature guidance for the parent stearyl alcohol and its derivatives; adapt to preserve deuterium labeling and confirm on small scale.

• Esterification

  • Fischer: Carboxylic acid (1.2–2.0 eq), catalytic H2SO4 or p‑TsOH, toluene or solvent‑free melt, 80–120 °C with Dean–Stark where applicable; 4–24 h. Steglich: DCC/EDC (1.1–1.5 eq), DMAP (0.1 eq), DCM/toluene, 0–25 °C to RT, 2–16 h.

• Oxidation

  • Swern: (COCl)2/DMSO, −78 °C; then Et3N, −78→0 °C to give aldehyde. Dess–Martin: DMP (1.3 eq), DCM, 0–25 °C. TEMPO/bleach: pH ~9, 0–25 °C to acid via aldehyde. Avoid strongly acidic aqueous media at elevated T that could risk H/D scrambling at exchangeable sites.

• Activation and substitution

  • Tosylation: TsCl (1.2–1.5 eq), pyridine or NEt3, 0–25 °C; 2–6 h. Appel: PPh3/CBr4 (or CCl4), DCM, 0–25 °C; 1–3 h to give alkyl halide. Subsequent SN2 in polar aprotic solvents (DMF/DMSO) at 60–100 °C.

• Ether formation

  • Williamson: NaH (1.1 eq) or KHMDS, THF/toluene, 0–25 °C to form alkoxide; then add primary alkyl halide, 25–80 °C.

• Workup/purification

  • Nonpolar to mid‑polarity solvents; silica gel with gradients from hexanes to EtOAc. High-melting products may require warming to load.

• Expected yields

  • Many of the above proceed in good to excellent yields (60–90%) for long-chain substrates in literature; verify on your substrate and scale.

Always verify isotopic integrity by MS/NMR after each step.

Safety and Handling

• GHS/Regulatory (item-specific)

  • 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 alcohols; literature guidance)

  • Hazards: Low acute toxicity; may cause skin or eye irritation. Combustible as a hydrocarbon-derived organic solid. Molten material can cause thermal burns.
  • PPE: Laboratory coat, safety glasses or goggles, and suitable gloves (e.g., nitrile). Avoid prolonged skin contact with molten material.
  • Handling: Minimize dust/flake generation. For preparing solutions, warm gently in a water bath to aid dissolution—do not overheat. Use local exhaust when weighing or dissolving in volatile solvents.
  • Incompatibilities: Strong oxidizers (risk of exotherm), strong reducing agents for oxidized forms, and strong acids/bases that can catalyze side reactions at elevated temperatures.
  • Fire safety: Keep away from ignition sources. In case of fire, alcohol-resistant foam, dry chemical, or CO2 are appropriate; cool containers with water spray.
  • First aid (overview): Skin/eye contact—rinse with water for several minutes; remove contaminated clothing. Inhalation of solvent vapors from solutions—move to fresh air. Ingestion—rinse mouth; seek medical advice. Always follow the SDS for authoritative instructions.

• Environmental: Avoid release to the environment; collect waste in appropriate organic waste streams.

Solvent Selection

This compound is a hydrophobic, long-chain primary alcohol. Solvent choice is driven by the need to dissolve a waxy, high‑melting solid and to maintain stability of the deuterium label.

• Polarity and miscibility (literature, parent compound)

  • Water: Practically insoluble.
  • Alcohols: Soluble when hot (ethanol, isopropanol); moderate solubility in higher alcohols at ambient.
  • Nonpolar/medium-polar: Good solubility in hexanes, heptane, toluene, chloroform, and dichloromethane.
  • Polar aprotic: Limited solubility in acetonitrile and acetone unless warmed.

• Practical recommendations

  • For analytical standards: Prepare stock solutions at 1–10 mg/mL in chloroform, toluene, or warm ethanol/isopropanol. For LC–MS workflows using reverse-phase, isopropanol or methanol with a small fraction of chloroform/toluene (where instrument-compatible) can aid dissolution before dilution.
  • For surface/self-assembly studies: Use toluene or hexane to deposit monolayers or films on hydrophobic substrates; gentle heating may be required.
  • Avoid highly protic/acidic media if preserving labile protecting groups or avoiding H/D exchange at the hydroxyl proton (exchangeable by nature).

• Comparison (general)

  • Versus shorter alcohols (e.g., dodecanol): Lower volatility and higher hydrophobicity; requires stronger nonpolar solvents.
  • Versus fatty acids: Alcohol avoids acid-catalyzed corrosion and is less polar; different solubility in polar solvents.

Storage and Reconstitution

• Item-specific storage and shipping

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

• General storage guidance

  • Keep container tightly closed under an inert atmosphere (e.g., nitrogen or argon) when feasible to limit slow oxidative processes during long-term storage.
  • Protect from prolonged heat and light. Avoid repeated warm–cool cycles; the material is a waxy solid with a melting range near that of the parent compound.
  • For analytical use, prepare concentrated stock solutions, aliquot into amber vials, and store at −20 °C. Minimize headspace to reduce solvent evaporation and oxidation.

• Reconstitution/solubilization

  • Warm gently (40–60 °C water bath) to soften or melt before weighing. Dissolve in suitable organic solvents such as chloroform, toluene, hexane, or warmed ethanol/isopropanol. Sonication can assist dissolution.
  • For aqueous applications, pre-dissolve in a miscible organic solvent before dilution; consider surfactants or lipid carriers for stable dispersions.

• Stability notes

  • The hydroxyl proton is exchangeable; deuteration at the O–D position will exchange in protic media. Nonexchangeable C–D labels are generally robust but verify isotopic integrity periodically by MS/NMR, especially after reactions or extended storage.

Always refer to the product CoA/SDS for item-specific stability and handling details.

Structure and Identity

A deuterium-labeled, long-chain saturated primary alcohol corresponding to 1-octadecanol (stearyl alcohol) with one or more hydrogens replaced by deuterium. Useful as an isotopic tracer or internal standard in lipid and surfactant studies.

• Item-specific identifiers
  • CAS: 86369-69-9
  • 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/literature description)
  • Backbone: C18 saturated n-alkyl chain (octadecyl) bearing a terminal primary alcohol (–CH2OH) functionality.
  • Isotopic label: One or more D (2H) atoms incorporated; exact labeling pattern/enrichment not specified for this item.
  • Functional groups: Primary alcohol; long hydrophobic alkyl chain.
  • Stereochemistry: None (acyclic, no stereocenters anticipated in parent 1-octadecanol).
• 2D description (general)
  • A linear chain of eighteen carbons with a hydroxymethyl end (–CH2OH) and a methyl tail (–CH3) at the opposite end; deuterium substitution(s) occur in place of protium at unspecified position(s).

Synthetic Utility

As a saturated C18 primary alcohol bearing a deuterium label, this compound is a versatile building block and tracer for synthetic and mechanistic studies.

• Transformations retaining the C18 backbone

  • Esterification: Formation of labeled stearyl esters (Fischer, Steglich) for waxes and pro‑materials. Enzymatic esterifications (lipases) enable mild conditions.
  • Oxidation: To stearaldehyde (e.g., Swern, Dess–Martin) or stearic acid (TEMPO/bleach, Jones). Choose conditions that avoid isotope scrambling.
  • Activation: Tosylation/mesylation to generate excellent leaving groups for subsequent SN2 substitution; Appel or PBr3/PCl3 for alkyl halides.
  • Ether formation: Williamson ether synthesis via octadecyl alkoxide with alkyl halides bearing desired functionality.

• Uses of the deuterium label

  • Isotopic tracing to dissect reaction pathways, measure isotope effects, or quantify product distributions by MS.
  • Creation of isotopically defined standards for GC–MS/LC–MS quantitation of long-chain alcohols and derived esters.

• Retrosynthetic value

  • Serves as a terminal handle for elongation/functionalization at the alcohol end while preserving a hydrophobic tail that imparts phase behavior useful in separations and self-assembly.

Note: Exact labeling pattern/enrichment is not specified for this item; plan syntheses to maintain deuterium at nonexchangeable positions and limit exposure to conditions promoting H/D exchange.

Target Specificity

Not applicable. This product is a small-molecule, deuterated fatty alcohol and does not have antigen/epitope specificity, clone, isotype, or species reactivity. For analytical targets, see Reaction & Applications and Application Protocols for guidance on use as an internal standard.

Foire aux questions

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

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 86369-69-9, the molecular formula is C18H36D2O, and the molecular weight is 272.51 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.