17:0-18:1 PG-d , CAS No.2342575-59-9

CAS: 2342575-59-9 Cat. No.: P1450263 分子式: C₄₁H₇₃D₅NaO₁₀P 分子量: 790.05 EC番号: 998-969-6

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

概要

17:0-18:1 PG-d 5 is deuterium labeled 17:0-18:1 PG.

Specifications

保管条件

Store at -20°C

入荷

Ice chest + Ice pads

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名前と識別子

• 分子量: 790.05

Application Protocols

Item-specific, validated protocols are not provided for this SKU. The following are general, literature-based procedures tailored to phosphatidylglycerol standards; adapt as needed.

• LC–MS internal standard usage (literature):

  1. Prepare a 0.5–1.0 mg/mL stock in isopropanol or chloroform:methanol (2:1). Aliquot and store at −20°C under inert gas.
  2. Spike a fixed amount (e.g., 50–500 pmol per sample) into biological matrices prior to extraction.
  3. Extract lipids (Bligh–Dyer, Folch, or MTBE methods). Analyze by LC–MS/MS in negative ESI with PG-targeted MRM/PRM transitions set according to the deuterated mass of this standard (verify exact m/z from CoA).

• Liposome preparation (literature):

  1. Dissolve lipids, cast thin film, dry thoroughly.
  2. Hydrate with buffer at temperature above Tm; apply 5–10 freeze–thaw cycles.
  3. Extrude through polycarbonate membranes (e.g., 100 nm) to obtain LUVs. Store at 4°C and use within days; add 0.01% antioxidant only if compatible with your assay.

• Enzyme assay substrate presentation (literature):

  1. Prepare SUVs (pure PG or mixed with PC/PE).
  2. Incubate with enzyme in appropriate buffer (pH 7–8, 25–37°C).
  3. Quench and analyze by LC–MS to quantify products.

Always confirm isotopic labeling details (site and degree) on the CoA to define masses and transitions.

Biological Roles

General/literature context for phosphatidylglycerol (PG):

• Cellular distribution: PG is a major anionic phospholipid in bacterial membranes and present in eukaryotes at lower abundance, notably as a precursor to cardiolipin in mitochondria.
• Functional properties: The anionic headgroup contributes to membrane surface charge, modulating interactions with cationic peptides, peripheral proteins, and divalent cations (Ca2+, Mg2+). The presence of one unsaturated acyl chain (18:1) reduces bilayer packing, influencing fluidity and curvature stress.
• Biosynthesis: In bacteria and mitochondria, PG is formed from phosphatidic acid via CDP-diacylglycerol and phosphatidylglycerophosphate pathways (literature). Chain remodeling by acyltransferases introduces diverse acyl patterns.
• Protein interactions: PG can activate or stabilize certain membrane enzymes and channels; it affects insertion and function of antimicrobial peptides and is implicated in protein translocation processes (literature).
• Analytical use: Deuterated PG analogs serve as biological surrogates/internal standards to trace extraction and ionization, enabling accurate quantification of endogenous PG species without perturbing cellular metabolism when used as spike-in standards.

No medical or clinical claims are made. All uses are for research and laboratory studies on membrane composition, dynamics, protein–lipid interactions, and lipidomics workflows.

Buffer Applications

This product is a hydrophobic/amphiphilic lipid rather than a classical buffering agent; it is not used to set or maintain solution pH. Accordingly, typical buffer recipes (e.g., phosphate, Tris, HEPES) do not apply.

Relevant laboratory context (literature):

• Hydration media for vesicle preparation commonly use physiological buffers (e.g., 10–50 mM HEPES, 100–150 mM NaCl, pH 7.0–7.4). The anionic PG headgroup remains deprotonated in this range, contributing negative surface charge to vesicles.
• Inclusion of chelators (e.g., 0.1–1 mM EDTA) can suppress divalent cation–induced aggregation. Conversely, adding Ca2+/Mg2+ can promote fusion/aggregation for specific studies.
• For enzymology, mixed micelles or vesicles are prepared in the assay buffer appropriate to the enzyme; detergent (e.g., 0.05–0.5% Triton X-100 or OG) may be used to ensure substrate availability.

If you require a true pH buffer component, select from standard buffering systems and then disperse the lipid into that buffer using film hydration, sonication, or extrusion as appropriate.

Green Alternatives

For this amphiphilic lipid, “green alternatives” are best considered in the context of solvent systems and handling practices rather than replacing the molecule itself.

Greener handling strategies (literature/guidance):

• Prefer alcohol-rich solvent mixtures (e.g., isopropanol:methanol:water) over chlorinated solvents when compatible with the application (e.g., LC–MS injection, stock preparation for short-term use). Note that initial dissolution may still require a stronger solvent such as chloroform.
• Minimize solvent volumes by preparing concentrated stocks and aliquoting to reduce waste and repeat freeze–thaw cycles.
• Use glassware compatibility to enable solvent recycling when appropriate and compliant with your facility’s policies.
• Apply inert atmosphere storage to extend shelf life and reduce waste due to oxidation.

Illustrative comparison (literature):

• Chloroform:methanol (2:1): Excellent solvency; higher toxicity and environmental burden.
• Isopropanol:methanol:water (2:1:1): LC–MS friendly and less hazardous; may require sonication/mild heating to fully dissolve; limited long-term stability of solutions.
• Ethyl acetate: Generally poor for PG due to headgroup polarity; may work only in mixed systems.

Trade-offs: Chlorinated solvents remain the most effective for rapid dissolution and film casting but carry health and environmental costs. Alcohol-rich systems are safer but can be slower and may not dissolve highly ordered phases without assistance.

Pharmaceutical Uses

Item-specific pharmacopeial status or excipient grade: Not specified for this item; refer to CoA/Spec Sheet. This product is designated for research use only.

General, non-clinical formulation context (literature):

• Phosphatidylglycerols are used in research formulations as anionic components of liposomes or lipid nanoparticles to adjust surface charge, protein adsorption, and colloidal stability. They can modulate encapsulation efficiency for cationic cargoes and influence in vitro release behavior.
• Deuterated variants are primarily analytical tools (e.g., in-process controls and stability-indicating assays by LC–MS) rather than functional excipients.
• Considerations for formulation work:
  • Purity and residual antioxidant content (if any) may affect oxidative stability and interaction with actives.
  • Chain composition (17:0/18:1) dictates bilayer Tm and fluidity; unsaturation introduces peroxidation liability under stress.
  • Regulatory use requires compliance with relevant pharmacopeial monographs and excipient standards; this research product is not intended for human or veterinary administration.

All discussion is for laboratory research and development contexts only; no therapeutic or clinical claims are made.

Physical Properties

Item-specific numeric properties (BP, MP/phase transition, density, UV cutoff, etc.): Not specified for this item; refer to CoA/Spec Sheet.

General/literature physical characteristics for phosphatidylglycerols similar to 17:0/18:1 PG:

• Physical state: non-volatile, waxy solid or semi-solid; forms thin films; highly amphiphilic.
• Solubility (literature):
  • Soluble in halogenated/organic lipid solvents such as chloroform, dichloromethane, and mixtures of chloroform:methanol (2:1, 1:1). Also soluble in methanol, ethanol, isopropanol to varying extents.
  • Essentially insoluble in pure water; dispersible as micelles or vesicles with the aid of sonication, extrusion, or detergents.
• Phase behavior (literature): Mixed-acyl PGs exhibit chain-melting transitions (Tm) typically below room temperature when containing an 18:1 chain; exact Tm depends on chain placement and unsaturation/isotope labeling and is not provided for this item.
• pKa (literature): PG headgroup carries one negative charge near neutral pH; apparent pKa values for the phosphate moiety are well below physiological pH, yielding an anionic lipid under typical buffer conditions.
• LogP/partitioning: Not commonly reported as a single value for amphiphiles; they self-assemble rather than follow simple octanol/water partitioning.

For precise quantitative values pertinent to this SKU (e.g., Tm, water content), consult the item’s CoA/Spec Sheet.

Quality and Grades

Item-specific grade, purity, stabilizer content, residual solvent or peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on quality for phospholipid standards and research lipids (general/literature):

• Research-grade/deuterated lipid standards are typically supplied at high chemical purity with well-defined acyl composition and isotopic labeling to support quantitative lipidomics. The exact isotopic enrichment and positional labeling (e.g., uniform dX on headgroup or acyl chains) should be confirmed on the CoA.
• Stabilizers: Antioxidants (e.g., BHT) may be included by some suppliers to mitigate autoxidation of unsaturated chains; presence/absence must be verified on the item CoA to avoid interference with sensitive analyses.
• QC characterization usually includes HPLC/UPLC purity, HRMS (m/z), and sometimes 31P NMR to confirm headgroup integrity and acyl composition. Acceptance criteria are supplier-specific; verify on the Spec Sheet.
• For chromatography-centric work (LC–MS/LC–MS/MS), very low levels of non-target isobars and minimal in-source fragmentation are important. If you require specific blanks/background levels, request the CoA and lot-specific MS traces.

If you need a defined grade (e.g., isotope-enriched internal standard grade vs. formulation grade), contact us with your application so we can match a suitable lot.

Reaction and Applications

Manufacturer-supplied application text: Not provided for this item.

General/literature applications relevant to 17:0-18:1 phosphatidylglycerol (including deuterated variants):

• Quantitative lipidomics: Deuterium-labeled PG species are widely used as internal standards to correct for extraction efficiency, ionization variability, and matrix effects in LC–MS/MS workflows. The non-native acyl composition (C17:0/C18:1) reduces endogenous background in mammalian matrices.
• Membrane biophysics and model membranes: PG-rich bilayers mimic bacterial inner membranes and anionic eukaryotic mitochondrial surfaces. Mixed with PE/PC to tune curvature and surface charge; used in vesicle leakage, binding, and protein reconstitution assays.
• Enzymology: Substrate/standard for phospholipases (PLA1/PLA2, PLD) and kinases/transferases in vitro; deuteration can facilitate kinetic isotope effect or MS readout discrimination (literature).
• Materials and delivery research: Component in anionic liposomes or lipid nanoparticles for nucleic acid complexation studies (non-clinical), where headgroup charge modulates colloidal stability and protein corona formation.
• TLC/UPLC method development: Chain-length and unsaturation provide characteristic retention and MS fragments (m/z of [M−H]−, diagnostic 153 Da PG headgroup fragment, literature), enabling calibration of instrument response.

For any quantitative use, confirm the isotopic enrichment pattern on the lot-specific CoA to set MRM/PRM transitions and isotope windows appropriately.

Reaction Conditions

There are no classical “reaction conditions” for using this lipid as a reagent in organic transformations. The following literature-based conditions pertain to common laboratory operations with PG lipids.

• Lipid film hydration and vesicle formation (literature):
  • Dissolve lipid in chloroform:methanol (2:1). Evaporate under nitrogen to a thin film. Desiccate under high vacuum (≥1 h). Hydrate with buffer (e.g., HEPES 10 mM, NaCl 150 mM, pH 7.4) above the lipid’s Tm with vortexing. Optional freeze–thaw cycles (5–10×). Size by extrusion (e.g., 50–200 nm membranes) or probe sonication to obtain SUVs.
• LC–MS sample prep (literature):
  • Prepare ~0.1–1 mg/mL stock in chloroform or IPA. Spike internal standard at fixed pmol amounts into samples prior to extraction (e.g., Bligh–Dyer or MTBE methods). Analyze by negative-ion ESI, monitoring [M−H]− and characteristic PG fragments (e.g., 153 Da headgroup).
• Enzymology (literature):
  • For PLA assays, present substrate in mixed micelles (e.g., Triton X-100) or SUVs. Typical buffers: pH 7.0–8.0, 25–37°C. Monitor product formation over minutes to hours by LC–MS.

All values above are general guidance only; optimize for your system and consult the CoA for any item-specific recommendations.

Safety and Handling

Item-specific GHS classification, signal word, hazard and precautionary statements, and pictograms: Not specified for this item; refer to the product SDS.

General safety guidance for glycerophospholipids:

• Expected hazards: Neutral to low acute toxicity; not volatile; dust not expected. Nevertheless, handle as a laboratory chemical. Avoid inhalation of powders/aerosols and prolonged skin contact. For solutions in organic solvents (e.g., chloroform/methanol), observe the solvent’s hazards (flammability, toxicity).
• PPE: Laboratory coat, safety glasses, and appropriate chemical-resistant gloves. Work in a fume hood when using volatile organic solvents.
• Incompatibilities: Strong oxidizers can degrade unsaturated lipids; acids/bases and lipases can hydrolyze ester linkages. Avoid prolonged exposure to light, air, and elevated temperature to limit oxidation of the 18:1 chain.
• First aid (overview; defer to SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel.
• Stability considerations: Minimize freeze–thaw cycles for solutions; store under inert gas when possible to reduce oxidative degradation. Always consult the official SDS for authoritative information.

Solvent Selection

Item-specific solvent recommendations are not provided; see CoA/Spec Sheet for any constraints. The following are general, literature-based guidelines for phosphatidylglycerols and deuterated analogs:

• Primary dissolution:
  • Chloroform or chloroform:methanol (2:1 or 1:1 v/v) are classic lipid solvents giving rapid dissolution at mg/mL levels.
  • Alternatives: Dichloromethane, methanol, ethanol, isopropanol. For stock solutions intended for LC–MS, use LC–MS grade solvents.
• Aqueous dispersion:
  • PGs do not dissolve in water; they form vesicles (SUV/LUV), micelles (with detergents), or mixed lipid assemblies. Hydration buffers commonly include NaCl (100–150 mM) and are adjusted to pH 7.0–7.4.
• Polarity/miscibility (literature): Amphiphilic; insoluble in nonpolar alkanes; freely miscible with polar organics mentioned above when dry.
• Choosing among options:
  • Use chloroform:methanol for film casting and thin-layer preparation.
  • Use isopropanol:methanol:water (e.g., 2:1:1) for LC–MS injection compatibility.
  • Avoid prolonged exposure to basic alcohols to limit transesterification.

Quick comparison (literature):

• Chloroform: Excellent solvency; toxic/regulated.
• DCM: Good solvency; more volatile; still hazardous.
• Methanol/IPA: Moderate solvency; LC–MS compatible; may need mild heat or sonication.
• Toluene/hexane: Poor solvency for PG headgroups.

Storage and Reconstitution

Item-specific storage conditions: Store at -20°C. Shipping conditions: Shipped in an ice chest with ice pads. Appearance, stabilizer, and reconstitution solvent recommendations: Not specified for this item; refer to CoA/Spec Sheet.

General/literature guidance for PG lipids and deuterated standards:

• Long-term storage: Keep as a dry film or powder at −20°C or below, protected from light and moisture. For extended storage, −80°C is preferred. Purge vials with inert gas (argon/nitrogen) after each use.
• Aliquoting: Prepare small, single-use aliquots to minimize freeze–thaw and headspace oxygen exposure. Use amber glass vials with PTFE-lined caps.
• Solution stability: Stocks in chloroform, methanol, or isopropanol are stable for weeks at −20°C when protected from air/light; inspect for signs of oxidation (odor/color) and confirm integrity by LC–MS as needed. Aqueous dispersions (liposomes) are typically stable for days at 4°C; avoid microbial growth and consider adding sterile filtration where compatible.
• Reconstitution (general): Dissolve initially in chloroform or chloroform:methanol (2:1). For LC–MS-compatible stocks, exchange to isopropanol or methanol by gentle evaporation under nitrogen and re-dilution. Ensure complete dissolution by brief sonication and warming above any phase transition temperature.

Always follow the lot-specific recommendations on the CoA/Spec Sheet for this SKU.

Structure and Identity

Item-specific identifiers provided: CAS 2342575-59-9. Other identifiers (SMILES, InChIKey, Molecular Formula, Molecular Weight): Not specified for this item; refer to CoA/Spec Sheet.

General/literature description of structure:

• 17:0-18:1 PG-d denotes a phosphatidylglycerol (PG) glycerophospholipid bearing two fatty acyl chains: a saturated C17:0 (heptadecanoyl) chain and a mono-unsaturated C18:1 chain (typically oleoyl, Δ9-cis, literature). The “PG” headgroup is sn-glycero-3-phospho-(1′-sn-glycerol), an anionic headgroup at physiological pH.
• The “-d” suffix is commonly used to indicate a deuterium-labeled analog in lipidomics standards (literature). Exact labeling pattern and degree of deuteration: Not specified for this item; refer to CoA/Spec Sheet.
• Core structural features (literature):
  • Glycerol backbone (sn-1, sn-2 esterified with fatty acids; sn-3 linked to phosphate).
  • Phosphate diester linking to a terminal glycerol headgroup (anionic phosphomonoester).
  • One saturated (C17) and one cis-mono-unsaturated (C18:1) acyl chain provide amphiphilicity and negative curvature tendencies.
• 2D description in words (literature): A three-carbon glycerol scaffold with two ester linkages to long aliphatic chains, and a phosphate group bridging to another glycerol moiety; overall a zwitterion-free, net negative lipid under neutral/basic conditions.

Synthetic Utility

As a complex lipid, 17:0-18:1 PG-d is not a general-purpose synthetic intermediate in classical organic synthesis. Its primary “synthetic” relevance is within lipid chemistry and analytical workflows.

General/literature utility:

• Standard/reference material: Employed as a mass-labeled internal standard for quantifying endogenous PGs by LC–MS/MS. Enables calibration curves, recovery correction, and instrument performance tracking.
• Enzymatic transformations: Substrate or probe for phospholipases (PLA1/PLA2/PLD) and transacylases in vitro; product distributions can be analyzed by MS to elucidate enzyme selectivity and kinetics.
• Chemical derivatization (analytical): PGs can be derivatized at the phosphate or headgroup (e.g., charge-tagging) to enhance ionization/sensitivity; the deuterated backbone assists in distinguishing derivative peaks from endogenous lipids (literature).
• Assembly chemistry: Serves as a component in constructing defined lipid mixtures, asymmetric bilayers, or tethered bilayers on surfaces for biophysical measurements (QCM-D, SPR, neutron reflectometry).

If your goal is small-molecule synthesis, this material is unlikely to be appropriate. For lipid chemistry, consult protocols specific to glycerophospholipids, and verify isotopic labeling details on the CoA to design MS transitions.

Target Specificity

Not applicable. This product is a small-molecule lipid standard, not an antibody or biologic. No antigen, epitope, species reactivity, clone, or isotype information is relevant.