C90-Dolichol , CAS No.26113-10-0

CAS: 26113-10-0 Cat. No.: C1439373 Fórmula: C₉₀H₁₄₈O Peso molecular: 1246.14

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Visão geral

C90-Dolichol (Dolichol-18) is an ester product.

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: 1246.14

Application Protocols

No item-specific, validated protocols are provided for this catalog entry. The following literature-style workflows are commonly used with dolichol and related lipids; optimize to your system.

• Stock solution preparation:

  • Dissolve at 1–10 mg/mL in CHCl3 or CHCl3:MeOH (2:1) in an amber vial. Flush with N2/Ar, cap tightly, and store at −20°C.

• Thin-film hydration (for liposomes/proteoliposomes):

  • Deposit required moles of dolichol (±other lipids) in a round-bottom flask; rotary evaporate to a uniform film; desiccate ≥1 h; hydrate with warm buffer while vortexing; optional sonication/extrusion.

• Detergent-mediated reconstitution (for OST assays):

  • Dry dolichol as a film in a microtube; add buffer containing mild detergent (e.g., DDM); vortex to clarify; add membrane proteins; gradually remove detergent (dialysis/biobeads) to form proteoliposomes.

• Analytical QC (suggested):

  • Assess by 1H NMR (allylic/olefinic regions), HRMS for mass profile, and TLC/HPLC to check homologue distribution and oxidation.

All conditions above are general literature guidance. For item-specific recommendations and acceptance criteria, consult the CoA and SDS.

Biological Roles

Dolichols are ubiquitous polyisoprenoid alcohols found in the endoplasmic reticulum (ER) membranes of eukaryotes. Their phosphorylated forms are central to protein glycosylation and glycolipid assembly.

Key functions (literature):

• Carrier lipid in N-glycosylation: Dolichyl phosphate (Dol-P) anchors the lipid-linked oligosaccharide (LLO) used by oligosaccharyltransferase (OST) to transfer a preassembled glycan to nascent polypeptides in the ER lumen.
• Sugar donor intermediates: Dolichyl-P-mannose (Dol-P-Man) and Dolichyl-P-glucose (Dol-P-Glc) act as donors in N-glycan and GPI-anchor biosynthesis.
• Membrane modulation: Due to its long, flexible isoprenoid chain, dolichol influences membrane fluidity, thickness, and protein mobility in ER-like bilayers.
• Turnover and metabolism: Generated via the mevalonate pathway from isopentenyl pyrophosphate (IPP) and farnesyl pyrophosphate (FPP) by cis-prenyltransferases, followed by saturation of the α-isoprene and dephosphorylation to the free alcohol.

Research implications:

• Exogenous C90-dolichol is used to reconstitute Dol-P pools in proteoliposomes or microsomal fractions, enabling mechanistic studies of OST and glycosyltransferases.
• Chain length affects enzyme specificity and membrane partitioning; C90 (≈dolichol-18) is commonly studied as a representative long-chain eukaryotic form.

No medical or clinical claims are made. This product is for research use only.

Buffer Applications

C90-Dolichol is a neutral, highly hydrophobic lipid and does not serve as a buffering agent. It has no intrinsic buffering capacity and is not used to set or maintain pH.

Practical guidance for use in buffered systems (literature):

• To introduce dolichol into aqueous buffers, first dissolve in an organic solvent (e.g., CHCl3, ethanol) and then incorporate into detergent micelles or liposomes before dilution into buffer.
• Common biological buffers (HEPES, Tris, phosphate) are compatible as aqueous phases once dolichol is properly formulated into a colloidal carrier; avoid high levels of residual organic solvent that may perturb proteins.

For researchers seeking buffer recipes or pH ranges: refer instead to the protocols for lipid film hydration, detergent-mediated reconstitution, or proteoliposome preparation, which are the relevant workflows for this compound.

Green Alternatives

While C90-Dolichol itself is the required analyte/substrate for many studies and has no direct “green replacement,” greener choices primarily concern the solvent system and handling.

Greener solvent considerations (literature-based):

• Prefer bio-derived or safer solvents where feasible (e.g., ethanol, isopropanol, 2-methyltetrahydrofuran) over chlorinated solvents.
• For thin-film lipid preparation, replace chloroform with cyclohexane/ethanol blends or heptane/IPA where solubility allows; verify film homogeneity and rehydration behavior.
• Use miniaturized workflows (microscale solvent volumes) and closed systems to reduce VOC emissions.

Comparison (illustrative):

• Chloroform vs Ethanol
  • Solubility: Excellent vs Moderate (may require warming/co-solvent)
  • Health/eco: Hazardous halogenated vs Safer, bio-based
  • Volatility: High vs High
• Dichloromethane vs 2-MeTHF
  • Solubility: Excellent vs Good-to-moderate
  • Health/eco: Halogenated vs Bio-based, better EHS profile

Operational green tips:

• Recover/reuse solvents via rotovap and proper segregation.
• Employ amber, gas-tight vials to extend solution life and reduce waste from oxidation.
• Plan co-formulation with other lipids to minimize repeated dissolution/drying cycles.

Note: Solvent substitution must be verified experimentally to ensure that dolichol dissolves fully and that downstream enzymatic or biophysical assays remain unaffected.

Pharmaceutical Uses

This product is supplied for research use only. No therapeutic or clinical claims are made.

Contextual information (non-clinical, literature):

• Excipient status: Dolichol is not a common pharmacopeial excipient. Its extreme hydrophobicity and susceptibility to autoxidation limit routine formulation use.
• Formulation research: In pre-formulation and biophysical studies, polyisoprenoid alcohols may be included in model membranes or liposomal systems to modulate bilayer properties and study protein–lipid interactions. Such applications are experimental and assay-driven.
• Manufacturing relevance: None specified. There is no item-specific compliance (USP/EP/JP) or GMP status provided for C90-Dolichol.

For any contemplated use beyond laboratory research, verify regulatory status independently and consult the lot-specific documentation. All specifications not explicitly provided here are: Not specified for this item; refer to CoA/Spec Sheet.

Physical Properties

Item-specific numerical specifications are not provided for this catalog entry; consult the CoA/Spec Sheet for definitive values.

General/literature characteristics for long-chain dolichols (~C90):

• Appearance: Typically a viscous, wax-like, hydrophobic oil/solid at room temperature; colorless to pale yellow.
• Melting/softening: Broad softening range rather than a sharp mp (literature observation for polydisperse polyisoprenoids).
• Boiling point: Not practical to define (thermal decomposition precedes boiling under ambient pressure).
• Density: Expected slightly less than water; exact value not specified for this item.
• Solubility:
  • Insoluble in water; forms no true aqueous solution.
  • Soluble in nonpolar and moderately polar organic solvents (literature): chloroform, dichloromethane, toluene, hexane, cyclohexane, ether, THF. Often soluble in ethanol/isopropanol upon gentle warming or with small co-solvent amounts.
  • Stock preparation commonly uses CHCl3:MeOH (2:1, v/v) or CHCl3 only (literature practice for lipids).
• LogP: Very high (qualitatively >10; literature expectation for C90 isoprenoids). No item-specific value.
• pKa: Not applicable (neutral primary alcohol; no acid/base behavior in water).
• UV-Vis: Weak end-absorption only (no conjugated chromophore beyond isolated C=C); no item-specific cutoff data.
• Peroxide formation: Not typical for polyisoprenoid alcohols (contrast with ethers), but autoxidation of double bonds can occur.

All quantitative parameters not explicitly listed above are: Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

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

Context for dolichol materials (general, for professional users):

• Homolog distribution: Commercial dolichol often comprises a narrow homolog mixture centered around the target chain length (here ~C90). CoA typically details the chain-length distribution (e.g., C85–C95) and any cis/trans characteristics.
• Analytical characterization: Common identity/quality controls include HRMS (to confirm average MW), 1H/13C NMR (allylic/olefinic region; terminal CH2OH), and HPLC or LC–MS profiles for homologue distribution. For oxidation state, iodine value or peroxide value may be reported; not specified for this item.
• Stabilizers/antioxidants: If present, these are explicitly stated on the CoA. For this item: Not specified for this item; refer to CoA/Spec Sheet.
• Residual solvents and water: For hydrophobic lipids, Karl Fischer water and residual solvent limits may be controlled; Not specified for this item.
• What the grade means (general):
  • Research/Lipidomics grade: Emphasis on low oxidation, narrow homolog distribution, and rigorous inert handling/packaging (amber, under N2). Suitable for enzymology reconstitutions or standards.
  • Analytical standard grade: Traceable purity and homologue quantitation for LC–MS response factors.

Always verify the exact grade, purity, and analytical acceptance criteria on the lot-specific CoA for C90-Dolichol (SKU C1439373).

Reaction and Applications

Research applications (literature):

• Glycoconjugate biosynthesis studies: Dolichol serves as the lipid precursor to dolichyl phosphate (Dol-P) and dolichyl-P-mannose/glucose, the carrier lipids in N-linked glycosylation pathways. Used to reconstitute oligosaccharyltransferase (OST) and related ER-membrane glycosylation systems in vitro.
• Lipidomics and standards: Employed as an internal standard or response calibrant in LC–MS workflows targeting polyisoprenoids and their phosphates.
• Membrane biophysics: Incorporated into model membranes or proteoliposomes to probe ER-like membrane properties and protein–lipid interactions.

Chemical transformations (synthetic applications):

• Phosphorylation to Dol-P: Conversion of the terminal alcohol to mono-phosphate using phosphoramidite or POCl3-derived methods under anhydrous, inert conditions, enabling downstream coupling to sugar phosphates.
• Acylation/Carbonate formation: Protection or functionalization of the primary alcohol for multistep syntheses.
• Hydrogenation/Isomer management: Selective hydrogenation (e.g., Pd/C, H2) to alter unsaturation if required; typically avoided when native geometry is desired.

Practical tips:

• Handle solutions under N2/Ar; add 0.01–0.05% BHT only if compatible with your assay (literature practice; not part of this item unless stated on CoA).
• For enzymatic assays, deposit dolichol as a thin film, dry thoroughly, then solubilize with detergent micelles before protein addition.
• Quantify by evaporative/light-scattering detection or HRMS; UV is weak due to limited chromophores.

All item-specific application validations are not provided; optimize conditions for your system.

Reaction Conditions

Typical conditions reported in the literature for transforming dolichol (general guidance; optimize per substrate and scale):

• Phosphoramidite phosphorylation (Dol → Dol-P precursor):

  • Solvent: Anhydrous DCM or DCM/MeCN.
  • Reagents: Dialkyl or bis(2-cyanoethyl) phosphoramidite; activator (e.g., 1H-tetrazole or ETT).
  • Temperature: 0–25°C; strictly dry, inert atmosphere.
  • Oxidation: mCPBA or tBuOOH at 0–25°C; workup under minimal air exposure.
  • Notes: Minimize acid exposure to prevent allylic cation rearrangements.

• POCl3 route to phosphate:

  • Solvent: Dry DCM/DMF; base: pyridine or triethylamine.
  • Temperature: 0–5°C for activation; then 0–25°C for quench/coupling.
  • Caution: Control exotherm; exclude moisture.

• Hydrogenation (if tuning unsaturation):

  • Catalyst: Pd/C (5–10 wt% relative to substrate).
  • Solvent: Ethyl acetate, ethanol, or hexane/EtOAc.
  • Conditions: 1–3 atm H2, 20–30°C, 2–24 h.
  • Monitor to avoid over-reduction if E-geometry is required elsewhere.

• Film preparation / liposome incorporation:

  • Dissolve in CHCl3 (or CHCl3:MeOH 2:1); evaporate to thin film; desiccate ≥1 h; hydrate with buffer above lipid Tm while vortexing; optional sonication or extrusion.

Yields are highly method- and scale-dependent and are not specified for this item. Always validate purity and oxidation state by NMR and HRMS after transformations.

Safety and Handling

Authoritative safety information must be taken from the product SDS. Item-specific hazard classification is not provided here.

• GHS classification / Pictograms / H-Statements: Not specified for this item; refer to SDS.
• Primary hazards (literature/chemical reasoning):
  • Combustible hydrophobic material; treat as an organic lipid. Low volatility but combustible if heated.
  • Autoxidation risk due to multiple C=C bonds; peroxidation and rancid odor may develop upon prolonged exposure to air/light.
• Personal protective equipment (PPE): Lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Work in a fume hood when handling organic solutions.
• Handling tips (lipid best practices):
  • Minimize exposure to air, heat, and light. Use amber vials, keep solutions under inert gas (N2/Ar).
  • Prepare aliquots to avoid repeated warm/cold and air exposure.
  • Use clean, dry glassware; avoid strong oxidants and radical initiators.
• Incompatibilities: Strong oxidizing agents; halogenating reagents; ozone; peracids. Avoid prolonged contact with powdered metals and catalytic surfaces in air (may promote autoxidation).
• First aid (general):
  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing. Seek medical attention if irritation persists.
  • Inhalation: Unlikely due to low volatility; move to fresh air if solvent vapors from solutions cause irritation.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Storage conditions for this item are provided under Storage & Reconstitution.

Solvent Selection

C90-Dolichol is an extremely hydrophobic, lipophilic polyisoprenoid alcohol. Solvent choice is key for dissolution, handling, and deposition on membranes.

Polarity/miscibility profile (literature):

• Water: Insoluble.
• Nonpolar / low-polarity solvents (preferred): Hexane, cyclohexane, toluene, chloroform, dichloromethane, diethyl ether, MTBE, THF.
• Polar protic (use with warming or co-solvent): Ethanol, isopropanol, n-propanol.
• Polar aprotic: DMSO and DMF can dissolve many lipids; test at small scale for compatibility with downstream biology.

Typical choices by application:

• Lipid film preparation: CHCl3 or CHCl3:MeOH (2:1, v/v) to co-dissolve dolichol with other lipids; rotary-evaporate to a thin film, then hydrate.
• Enzyme reconstitution (e.g., OST assays): Stock in CHCl3 or CHCl3:MeOH; dry under N2, then reconstitute with detergent micelles (e.g., DDM, Triton X-100) or proteoliposomes.
• Direct addition to aqueous systems: Pre-dissolve in EtOH/iPrOH or DMSO, then add slowly with vigorous mixing; keep final organic ≤1–2% (v/v) if sensitive proteins are present.

Quick comparison (literature-based):

• CHCl3: Excellent solubility; volatile; toxic; commonly used for thin-film prep.
• Hexane: Nonpolar; good solubility; limited miscibility with polar cosolvents; greener than chlorinated.
• Ethanol: Safer; may require warming and higher volumes; compatible with many bioassays.

Always filter solutions if particulate is observed and confirm solvent compatibility with your assay.

Storage and Reconstitution

• Storage (supplier data): Store at −20°C.
• Shipping: Ice chest + ice pads (cold chain).
• Research use only.

Best practices for dolichol (literature-based):

• Protect from light and air: Use amber, gas-tight vials; blanket headspace with nitrogen or argon.
• Aliquot upon receipt: Prepare small single-use aliquots to minimize freeze–thaw and headspace oxygen exposure.
• Solid/oil handling: If semi-solid, allow to warm to room temperature briefly in the dark before opening to avoid condensation.

Reconstitution guidance (general):

• For stock solutions, dissolve in chloroform or CHCl3:MeOH (2:1, v/v) to 1–10 mg/mL. Mix gently until clear. If using alcohols (EtOH/iPrOH), gentle warming may aid dissolution.
• For aqueous applications, deposit as a thin film and rehydrate with buffer containing a compatible detergent or co-lipids.
• After preparing solutions, flush with N2/Ar, cap tightly, and return to −20°C storage. Avoid repeated freeze–thaw cycles; discard if signs of oxidation (odor, discoloration, new peaks in NMR/LC–MS) are detected.

Item-specific stabilizers, exact solubilities, and concentration limits: Not specified for this item; refer to CoA/Spec Sheet.

Structure and Identity

C90-Dolichol is a long-chain polyisoprenoid primary alcohol; “C90” denotes an average carbon count of ~90, corresponding typically to an 18-isoprene-unit dolichol (dolichol-18) in literature.

• SKU: C1439373
• CAS: 26113-10-0
• Synonyms (literature): Dolichol-18; polyisoprenoid alcohol; long-chain isoprenoid alcohol
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (Literature for C90 dolichol often approximates C90H148O, noting microheterogeneity.)
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet. (Dolichols are mixtures; a single canonical SMILES is not typically representative.)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general, literature):

• Backbone: Linear head-to-tail polyisoprenoid with predominantly trans (E) double bonds and a saturated α-terminal isoprene unit (defining “dolichol” vs polyprenol).
• Functional group: One primary alcohol (–CH2–OH) at the ω-terminus; no other heteroatoms.
• Stereochemistry: Multiple E-configured C=C bonds along the chain; minor cis content may be present depending on source/synthesis.
• 2D description in words: A long zig-zag hydrocarbon chain composed of repeating isoprenoid units with isolated double bonds, capped at one end by CH3 and at the other by CH2OH.

Notes:

• Commercial dolichol materials are often homolog mixtures centered around a target chain length (here ~C90). Exact microheterogeneity, isomer distribution, and polydispersity are item-specific and should be verified on the CoA.

Synthetic Utility

As a long-chain primary alcohol with multiple isolated C=C bonds, C90-Dolichol is a versatile scaffold in glycoconjugate and membrane-mimetic synthesis.

Key functional handles (literature):

• Primary alcohol: Amenable to phosphorylation (→ Dol-P), esterification, carbonate/urethane formation, and etherification. Protecting groups (e.g., TBDPS, TBS, benzyl) can be applied when selective elaboration is needed.
• Isoprenoid double bonds: Sites for selective epoxidation, hydroboration–oxidation, or hydrogenation; care is needed to preserve the native E-geometry.

Representative transformations:

• Phosphoramidite phosphorylation: Activation with a phosphoramidite reagent under tetrazole catalysis in dry DCM/MeCN, followed by oxidation (e.g., mCPBA or tBuOOH) to the phosphate; deprotection yields dolichyl phosphate.
• POCl3 or CDI-based phosphorylation: Formation of a phosphate monoester under inert, anhydrous conditions, often in DCM/DMF with tertiary base.
• Glycolipid assembly: Coupling Dol-P to sugar-1-phosphates or pyrophosphate donors to build LLO analogs.

Retrosynthetic value:

• Provides a defined chain-length polyisoprenoid backbone that emulates native ER carrier lipids, enabling systematic studies of chain-length effects on enzyme recognition and membrane behavior.

Handling for synthesis:

• Maintain oxygen-free conditions to limit side reactions (allylic oxidation/polymerization).
• Use amberware and low-temperature storage for intermediates and final products.

Target Specificity

Not applicable. C90-Dolichol is a small-molecule lipid, not an antibody or affinity reagent. There are no antigens, epitopes, species reactivity, clones, or isotypes associated with this product.