C85-Dolichol , CAS No.57229-24-0

CAS: 57229-24-0 Cat. No.: C1439499 분자식: C₈₅H₁₄₀O 분자량: 1178.02

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

개요

C85-Dolichol (Dolichol-17) is an ester product.

Specifications

보관 조건

Store at -20°C

배송

Ice chest + Ice pads

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이름과 식별자

• 분자량: 1178.02

Application Protocols

The following general protocols are commonly used for dolichol handling in research settings. Adapt to your system and consult primary literature.

• Preparing stock solutions (literature/general)
  • Weigh under inert gas if possible. Dissolve at 1–10 mg/mL in chloroform or chloroform:methanol (2:1). Vortex until clear. Aliquot into amber vials, purge with N₂/Ar, and store at −20 °C.
• Lipid film hydration for membrane studies (literature/general)
  • Deposit desired volume onto glass vial; evaporate solvent under N₂ to a thin film. Desiccate ≥30 min. Hydrate with prewarmed buffer (e.g., HEPES saline) possibly containing helper lipids (e.g., POPC) to a defined mol% dolichol. Vortex/sonicate and, if needed, extrude through polycarbonate membranes.
• Formation of dolichyl phosphate (brief workflow; literature/general)
  • Dry dolichol co-evaporated with toluene. React under anhydrous conditions using phosphoramidite or POCl₃ methods. Purify by silica or ion-exchange as the ammonium salt. Verify by 31P NMR and HR-MS.
• LC–MS standard preparation (literature/general)
  • Prepare calibration series in isopropanol:chloroform (1:1) or methanol:chloroform with internal standard. Store standards at −20 °C, protected from light.
• Notes
  • Avoid plasticizers: prefer glass vials with PTFE-lined caps. Limit air/light exposure throughout.

Biological Roles

Dolichols are essential lipid components in eukaryotes, serving as carriers in glycan assembly and contributing to membrane properties.

• Functional role (literature/general)
  • Precursor to dolichyl phosphate (Dol-P), the lipid-linked sugar carrier for N-glycosylation and other glycosylation pathways in the endoplasmic reticulum.
  • Acts as a long-chain polyisoprenoid that can modulate membrane fluidity and interact with protein translocons and glycosyltransferases.
• Biosynthesis (literature/general)
  • Produced via the mevalonate pathway: IPP/DMAPP → cis-prenyltransferase-mediated elongation → polyprenol → reduction/saturation of the α-isoprene unit(s) to produce dolichol.
• Distribution and chain-length (literature/general)
  • Chain length varies by species and tissue; C85 (Dol-17) is within the observed eukaryotic range, though mammalian tissues often enrich longer homologs (e.g., C90–C105).
• Turnover and metabolism (literature/general)
  • Dolichol can be phosphorylated to Dol-P, acylated or oxidized in cells; accumulates in certain membranes with slow turnover relative to phospholipids.
• Research context
  • Used as a reference standard in lipidomics and as a substrate or control in in vitro reconstitution of glycosylation-related activities. All uses are for laboratory research only; not for diagnostic or therapeutic applications.

Buffer Applications

C85-Dolichol is a highly hydrophobic lipid and is not used as a buffering agent. It does not contribute to pH control or ionic strength.

• Practical note (literature/general)
  • For biochemical work, dolichol is typically dissolved in organic solvents (e.g., chloroform or chloroform:methanol), dried as a film, and then resuspended into aqueous buffers by liposome formation, detergent micelles, or protein-mediated incorporation.
  • Buffer selection should instead focus on the biological system (e.g., HEPES, Tris) and on compatibility with any detergents/lipids employed.

Green Alternatives

While C85-Dolichol itself is a bio-derived polyisoprenoid, the solvents commonly used to handle it (e.g., chloroform, DCM) pose environmental and health concerns. Consider greener solvent systems where compatible with your workflow.

• Greener solvent options (literature/general)

  • Ethyl acetate: moderate solubility for some polyisoprenoids; useful for workup but may be insufficient for concentrated stocks.
  • Cyclopentyl methyl ether (CPME) or 2-MeTHF: improved safety/greenness vs DCM/THF; can dissolve long-chain isoprenoids under anhydrous conditions for certain syntheses.
  • Heptane/iso-octane: less toxic alternative to hexane; good for nonpolar processing and chromatography.

• When to retain traditional solvents

  • For highest solubility and reproducible membrane film preparation, chloroform remains a benchmark; validate any substitution to avoid phase artifacts.

• Mini-comparison (literature/general)

  • Solvent | Greenness | Solubility for dolichol | Notes
  • Chloroform | Poor | Excellent | Standard lipid handling; toxic, suspect carcinogen
  • DCM | Poor | Very good | Fast evaporation; regulated use
  • 2-MeTHF | Better | Moderate–good | Water-tolerant; peroxide former—monitor
  • CPME | Better | Moderate–good | Broad liquid range; low peroxide formation
  • Ethyl acetate | Better | Low–moderate | Useful in blends/workup

• Practical advice

  • If adopting greener solvents, run small-scale solubility and film-formation trials, and compare biophysical readouts (e.g., DSC/Tm, SAXS) to ensure equivalence.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided for this item.

• Item-specific status: Not specified for this item; refer to CoA/Spec Sheet.
• Research/manufacturing context (literature/general)
  • C85-Dolichol is used in research as an analytical reference and as a raw material for preparing dolichyl phosphate and other derivatives for process development studies and biochemical assays.
  • In formulation science, long-chain polyisoprenoids can serve as model hydrophobic membrane components in delivery research; however, this product is supplied strictly for research use only and is not intended for human or veterinary use.
• Regulatory note
  • Absent a defined pharmacopeial monograph, any use beyond research would require full characterization and qualification under applicable quality systems.

Physical Properties

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Purity/Grade: Not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (literature/general)
  • Practically insoluble in water; freely soluble in nonpolar and weakly polar organic solvents (e.g., chloroform, dichloromethane, hexanes, toluene); soluble in chloroform:methanol mixtures (2:1 or 9:1 v/v) commonly used for lipids; limited solubility in DMSO and isopropanol.
• Phase/volatility (literature/general)
  • High-molecular-weight, nonvolatile, viscous/oily lipid; lacks a sharp boiling point; thermally labile at elevated temperatures with risk of oxidation/isomerization.
• Partitioning (literature/general)
  • Extremely hydrophobic; expected very high logP; partitions strongly into lipid bilayers and organic phases.
• Spectroscopy (literature/general)
  • UV: weak end-absorbance with a characteristic polyisoprenoid band ~205–215 nm in nonpolar solvents; IR: OH stretch near 3300 cm⁻¹, C=C stretches ~1660 cm⁻¹.
• Handling implications
  • Due to unsaturation, susceptible to autoxidation; handle under inert atmosphere, protect from light, and avoid prolonged exposure to heat.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Typical quality attributes for dolichols (literature/general)
  • Isoprene unit distribution: C85 corresponds to Dol-17; minor adjacent homologs (e.g., C80/C90) may be monitored by HPLC/LC–MS.
  • Unsaturation pattern/stereochemistry: proportion of α-saturated unit(s) and E/Z configuration of remaining double bonds; can be assessed by NMR and HR-MS.
  • Oxidation state: absence of peroxides/oxidized byproducts; verified by peroxide tests or MS.
  • Residual solvents: compliance with ICH Q3C where applicable.
• Analytical methods (literature/general)
  • Normal-phase or reverse-phase HPLC with ELSD/UV (210 nm) or LC–MS; GC–MS after derivatization is uncommon due to high MW.
  • Identity confirmation by 1H/13C NMR (allylic, olefinic, and terminal CH2OH resonances) and HR-ESI-MS (ammonium/sodium adducts).
• Stabilization/handling implications
  • Store under inert gas and protect from light to maintain isoprenoid integrity; minimize freeze–thaw by aliquoting.
• Documentation
  • For definitive acceptance criteria (purity %, content of homologs, residual solvents), consult the product-specific CoA/Spec Sheet supplied with SKU C1439499.

Reaction and Applications

C85-Dolichol is widely used as a research standard and functional substrate in lipid biochemistry and glycobiology.

• Research applications (literature/general)
  • Carrier lipid studies: precursor to dolichyl phosphate for modeling N-linked glycosylation pathways and mannosyl/phosphoryl transfer reactions.
  • Membrane biophysics: incorporation into model membranes to probe effects on bilayer order, permeability, and protein function.
  • Lipidomics standards: external/internal standard for LC–MS quantification of dolichol homologs.
  • Enzymology: substrate for in vitro reconstitution of cis-prenyltransferases downstream steps after chain elongation (upon phosphorylation).
• Practical handling tips
  • Prepare concentrated stocks (1–10 mg/mL) in CHCl₃ or CHCl₃:MeOH, store at −20 °C under N₂/Ar in amber vials.
  • To form films: deposit solution on glass, rotary evaporate or stream N₂ to dryness, then desiccate to remove residual solvent before hydration.
  • Avoid repeated thawing; aliquot upon receipt.
• Chemical transformations (literature/general)
  • Phosphorylation to dolichyl phosphate (Dol-P) via phosphoramidite or POCl₃-based methods.
  • Oxidation (PCC/Swern variants) to dolichal; hydrogenation to modulate unsaturation; silylation/esterification for derivatization and analysis.
• Controls/analytics
  • Verify integrity by 1H NMR (allylic/olefinic resonances) and LC–MS to monitor epoxidation/oxidation byproducts.

Reaction Conditions

Typical literature conditions for common C85-dolichol transformations are summarized below. These are general guidelines; optimize per substrate and scale.

• Phosphoramidite route to Dol-P (literature/general)
  • Solvent: dry DCM or THF; Atmosphere: N₂/Ar.
  • Reagents: 2-cyanoethyl N,N-diisopropylchlorophosphoramidite; base: DIPEA; activator: 1H-tetrazole or ETT.
  • Conditions: 0–25 °C, 1–3 h; Oxidation: mCPBA or tBuOOH; Deprotection: base (e.g., Et₃N/MeOH). Reported yields for long-chain polyprenols: 40–70% depending on scale and purity.
• POCl₃ route to Dol-P (literature/general)
  • Solvent: dry pyridine/DCM; Additives: DMAP.
  • Conditions: 0 °C to rt, 1–2 h; Quench carefully with ice-cold aqueous buffer; Subsequent neutralization to isolate Dol-P as ammonium salt. Typical yields 30–60%.
• Hydrogenation (literature/general)
  • Catalyst: Pd/C (5–10%); Solvent: EtOAc, EtOH, or hexanes; H₂ (1–3 atm), rt–40 °C, 2–12 h. Monitor by 1H NMR (disappearance of olefinic signals).
• Epoxidation (literature/general)
  • Reagent: mCPBA (≤1 equiv per targeted C=C) in DCM at 0–5 °C to limit overoxidation/isomerization.
• Workup/handling
  • Maintain low light and oxygen exposure; include BHT (trace) when compatible to suppress autoxidation during multi-hour reactions.
• Analysis
  • Use NP-HPLC/ELSD or LC–MS for product profiling; 31P NMR for phosphate intermediates/products.

Safety and Handling

• GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to CoA/Spec Sheet and SDS for authoritative safety information.
• General hazard profile (literature/general)
  • Expected to be of low volatility and low acute inhalation hazard; treat as a laboratory chemical of unknown toxicity. Avoid ingestion, inhalation of mists, and skin/eye contact.
• Personal protective equipment
  • Wear appropriate lab coat, safety glasses, and nitrile gloves. Use in a fume hood when handling organic solutions (e.g., chloroform, DCM) to minimize solvent vapor exposure.
• Safe handling practices
  • Minimize exposure to air, light, and heat to prevent oxidation. Purge containers with nitrogen or argon after use. Work with dry glassware and anhydrous solvents when product integrity is critical.
• Incompatibilities (literature/general)
  • Strong oxidizers; radical initiators; prolonged UV exposure. Avoid contact with peroxides and ozone.
• First-aid overview (non-specific guidance; consult SDS)
  • Skin: Wash with soap and water. Remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
  • Inhalation: Move to fresh air; seek medical advice if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Spill/fire response
  • Absorb small spills with inert material (vermiculite). For fires involving solvents, use CO₂, dry chemical, or foam. Product itself is nonvolatile but may burn once ignited in solvent.

Solvent Selection

C85-Dolichol is an extremely hydrophobic, long-chain isoprenoid alcohol; solvent choice should prioritize dissolution, stability, and downstream compatibility.

• Primary solvents (literature/general)
  • Chloroform (CHCl₃): excellent solubility; standard for lipid stocks; often used with MeOH (2:1 or 9:1) for handling and film formation.
  • Dichloromethane (DCM): good solubility; more volatile than chloroform for rapid film drying.
  • Hexanes/toluene: suitable for nonpolar workup and chromatographic preparation.
  • Isopropanol/ethanol: limited solubility; can aid in co-solvent systems for liposome reconstitution.
  • DMSO: limited but useful for small-volume biological assay additions; verify compatibility.
• Miscibility profile (literature/general)
  • Insoluble in water; miscible with most chlorinated and hydrocarbon solvents; soluble in chloroform–methanol mixtures used for lipid extraction (Folch/Bligh–Dyer systems).
• Selection guidance
  • For analytical stocks (HPLC/LC–MS): chloroform or chloroform:MeOH with inhibitors removed; use amber vials.
  • For membrane/liposome incorporation: dissolve in CHCl₃ or CHCl₃:MeOH, dry to a thin film, then hydrate with buffer using sonication/extrusion.
  • For chemical transformations (e.g., phosphorylation): use dry toluene, THF, or DCM under inert gas.
• Comparison (literature/general)
  • CHCl₃ vs DCM: chloroform offers superior solubility and stability of lipid films; DCM evaporates faster but may solubilize less polar lipid mixtures slightly less effectively.

Storage and Reconstitution

• Storage conditions (item-specific)
  • Store at −20 °C.
  • Shipped in: Ice chest + Ice pads.
• Container and atmosphere (literature/general)
  • Use amber glass vials with PTFE-lined caps. After each use, purge headspace with nitrogen or argon to limit oxidation.
• Aliquoting and freeze–thaw (literature/general)
  • Upon first opening, prepare single-use aliquots to minimize freeze–thaw and air exposure. Keep working stocks cold and capped when not in immediate use.
• Reconstitution guidance (literature/general)
  • Dissolve in chloroform or chloroform:methanol (2:1) to desired concentration (typ. 1–10 mg/mL). For aqueous applications, form a dry lipid film followed by hydration into buffer with sonication/extrusion, or incorporate via detergents as appropriate.
• Stability considerations (literature/general)
  • Protect from light and oxygen; avoid prolonged exposure to room temperature. Consider adding a trace antioxidant (e.g., BHT) during extended manipulations if compatible with downstream assays.
• Documentation
  • For item-specific shelf life, appearance, and acceptance criteria, consult the product CoA/Spec Sheet. Product is supplied for research use only.

Structure and Identity

C85-Dolichol is a long-chain polyisoprenoid primary alcohol typically comprising 17 isoprene units (17 × C5 = C85) with a single terminal hydroxyl group.

• Item-specific identifiers
  • CAS: 57229-24-0
  • 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 (literature/general)
  • Functional groups: one terminal primary alcohol (–CH2OH); multiple internal isoprenoid double bonds.
  • Typical dolichols are α-saturated polyprenols: the isoprene unit(s) closest to the hydroxyl end are hydrogenated; distal units are predominantly trans (E).
  • Linear, highly hydrophobic hydrocarbon backbone; no rings; no heteroatoms except the terminal OH.
  • 2D description: a long zig-zag hydrocarbon chain with regularly spaced double bonds, terminating in –CH2–CH2–OH at one end and an isoprenoid methyl-branched terminus at the other.
• Nomenclature notes (literature/general)
  • “C85” designates the total carbon count of the polyisoprenoid skeleton; commonly corresponds to Dol-17 (17 isoprene units).
  • Dolichol is distinct from polyprenol by having one or more saturated isoprene units near the alcohol terminus.

Synthetic Utility

The terminal alcohol and polyisoprenoid backbone of C85-Dolichol provide multiple points for chemoselective derivatization.

• Key transformations (literature/general)
  • Phosphorylation to Dolichyl phosphate (Dol-P) via: (a) phosphoramidite chemistry (P(III) → oxidation), or (b) POCl₃/PCI₃ activation with pyridine/DMAP, followed by hydrolysis/neutralization.
  • Diphosphorylation to Dolichyl pyrophosphate (Dol-PP) using CDI or chlorophosphates with careful control of moisture.
  • Esterification/silylation of the OH for protecting-group strategies or analytical volatility enhancement.
  • Hydrogenation (Pd/C, H₂) to modulate unsaturation; epoxidation (mCPBA) of double bonds for mechanistic probes, followed by regioselective opening.
  • Oxidation to aldehyde/acid (e.g., Swern/PCC → dolichal; TEMPO → dolichic acid) for conjugation chemistry.
• Selectivity considerations
  • Preserve the E-geometry of double bonds; avoid isomerization by using mild conditions, low temperatures, and inert atmosphere.
  • Control overend phosphorylation to minimize pyrophosphate formation unless desired.
• Purification/analysis
  • Normal-phase silica with hexanes/EtOAc or hexanes/ether; avoid prolonged exposure to acidic silica to limit double-bond migration.
  • Characterize by 1H/13C NMR, 31P NMR for phosphate derivatives, and HR-ESI-MS (Na⁺/NH₄⁺ adducts).

Target Specificity

Not applicable. C85-Dolichol is a small-molecule lipid, not an antibody or affinity reagent. No clone, isotype, or species reactivity applies to this product.