Store liposomes at 4°C under N2 for short-term use.
LC–MS internal standard use (outline):
Prepare a concentrated stock in CHCl3:MeOH under inert gas.
Spike extraction solvents or sample prior to extraction at known pmol/ng amounts.
Analyze by LC–MS/MS in negative ESI, monitoring class-specific fragments and acyl anions; construct calibration curves across the expected range.
Note
Optimize conditions (temperatures, concentrations, injection solvents) to your instrument and co-lipid composition. Always consult the item’s CoA for any product-specific recommendations.
Biological Roles
General biology (literature; no clinical claims)
Phosphatidylglycerol (PG) is an anionic glycerophospholipid present in bacterial membranes and in eukaryotic organelles (notably mitochondrial inner membranes) and serves as a biosynthetic precursor to cardiolipin.
Mixed-chain PGs with polyunsaturated acyls (e.g., 22:4) influence membrane packing, surface charge density, and curvature stress, which can modulate membrane protein function in reconstitution studies.
The presence of a PUFA chain increases susceptibility to lipid peroxidation, making PG species potential substrates in studies of oxidative stress and lipid oxidation pathways.
In biophysical assays, PG’s negative charge impacts electrostatics at the bilayer interface, protein binding (e.g., cationic peptides), and ion transport models.
Item-specific note
No biological role data specific to SKU P1443620 are provided. If the “d” indicates deuteration, such labeling is commonly used for tracer studies and internal standards in lipidomics, but the exact labeling pattern and intended role for this item are not specified—consult the CoA/Spec Sheet.
Buffer Applications
Not typically applicable.
17:0-22:4 PG-d is a hydrophobic phospholipid, not a buffering agent. It does not establish defined pH ranges in aqueous systems.
Practical guidance
For membrane reconstitution, hydrate dry lipid films with a suitable buffer (e.g., 10–50 mM HEPES, Tris, or phosphate, 100–150 mM NaCl, pH 7.2–7.5) as dictated by your protein/assay.
Maintain neutral pH to minimize ester hydrolysis and prevent headgroup ionization changes beyond the typical anionic state of PG at physiological pH.
Green Alternatives
Context
The primary environmental burden when working with PG lipids is typically from chlorinated solvents (e.g., chloroform, dichloromethane) used for dissolution and extraction.
Greener solvent strategies (literature/practice)
Replace chloroform where feasible with isopropanol (IPA), ethanol, or IPA/ACN/H2O mixtures for LC–MS sample handling.
For film formation, tert-butanol/water co-solvent with lyophilization can produce dry, fluffy cakes that rehydrate well—reducing chlorinated solvent use.
Use microscale SPE-based lipid cleanup to cut solvent volumes.
Safety/Environment: High toxicity; chlorinated waste.
Isopropanol/ethanol
Performance: Good for stocks and LC–MS-compatible dilutions; may require mild warming/sonication for complete dissolution.
Safety/Environment: Lower toxicity; simpler waste handling.
ACN/IPA/H2O (LC–MS)
Performance: Robust for ESI with ammonium acetate/formate.
Safety/Environment: Non-chlorinated, but ACN requires proper handling.
Trade-offs
Expect slightly longer dissolution times and potential need for agitation or brief warming when eliminating chlorinated solvents. Validate recovery and response factors for quantitative workflows after changing solvent systems.
Pharmaceutical Uses
General formulation context (no therapeutic claims)
Phospholipids, including PGs, are used as excipients in research-scale liposomal and nanoparticle formulations to modulate surface charge (anionic), membrane rigidity, and encapsulation behavior.
Mixed-chain PGs with PUFA tails can alter membrane fluidity; however, oxidative stability must be carefully managed during formulation development (antioxidants, inert gas blanketing, low-temperature processing).
PG can serve as a helper lipid to adjust zeta potential and promote interactions with cationic components in complex delivery systems.
Item-specific note
No pharmacopeial status, GMP grade, or excipient designation is provided for this item. It is labeled For research use only and should not be used in human or veterinary applications. Verify regulatory status and specifications on the CoA/Spec Sheet if exploring pre-formulation studies.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
General/literature characteristics for phosphatidylglycerols of similar composition
Physical state: Non-volatile, waxy solid or glassy film at ambient; PUFAs lower Tm relative to fully saturated PGs (literature).
Phase behavior: Mixed-chain PGs with one saturated and one polyunsaturated acyl chain typically exhibit low gel–fluid transition temperatures (Tm often well below 0–10°C), enhancing membrane fluidity (literature).
Solubility: Insoluble in water as monomers; forms vesicles/micelles with appropriate methods. Freely soluble in chloroform, chloroform:methanol (2:1 or 1:1 v/v), dichloromethane; moderately soluble in methanol, ethanol, isopropanol; soluble in tert-butanol/water during lyophilization protocols (literature).
Partitioning: Strongly lipophilic; high logP expected for long-chain glycerophospholipids (literature; item-specific value not specified).
Stability: Susceptible to autoxidation due to the 22:4 acyl chain; protect from air, light, and heat (literature guidance).
Measured numeric values (this item)
Density, BP, MP/Tm, refractive index, pKa, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades for lipid standards (general)
Research/lipidomics grade: Typically indicates high purity by HPLC/LC–MS and low levels of oxidized species; suitable for quantitative lipidomics and biophysical studies. If this item is intended as an isotopically labeled standard (the “d” suffix), documentation should include labeling pattern and isotopic enrichment.
Salt form and residual solvents: CoA should indicate counterion (free acid vs ammonium vs sodium salt) and residual solvent content. These affect mass spec response and hydration behavior.
Oxidation controls: High-quality PUFA-containing lipids are often packed under inert gas in amber vials; peroxide/anisidine values may be reported for some suppliers. For this item, any such specifications are not provided here—refer to CoA/SDS.
What to verify upon receipt (practical tips)
Inspect vial integrity and check for inert gas headspace or desiccant.
Review CoA for: purity assay, labeling pattern (if deuterated), salt form, residual solvents, and recommended reconstitution solvents.
For quantitative work, confirm identity and purity by LC–MS/MS using characteristic PG headgroup fragments and fatty acyl anions.
Reaction and Applications
Item-specific manufacturer applications
Not provided in Product Data. The following are common research uses for phosphatidylglycerols with mixed saturated/PUFA chains (literature/practice):
Applications (general, research use only)
Lipidomics/internal standards: Deuterated PGs (if applicable to this item) are commonly used as internal standards for quantitative LC–MS/MS of endogenous PG species, aiding correction for extraction and ionization variability.
Model membranes and biophysics: Reconstitution into large/small unilamellar vesicles (LUVs/SUVs) to probe anionic lipid effects on membrane protein activity, curvature, and phase behavior.
Surfactant and mitochondrial mimetics: PG contributes to bacterial and mitochondrial inner membrane models; mixed-chain PGs modulate bilayer elasticity and packing.
Analytical method development: Retention time markers for normal-phase and HILIC separations of glycerophospholipids.
Practical tips
Minimize oxidation of the 22:4 chain: prepare fresh solutions, purge with N2/Ar, use amber vials, and keep cold.
Avoid base/acid hydrolysis: neutral pH buffers for hydration; limit exposure to strong nucleophiles and prolonged high temperatures.
Film hydration: Form a thin film in a round-bottom vial (rotary evaporation), then hydrate with buffer above Tm with gentle vortexing/sonication; optional freeze–thaw cycles improve lamellarity.
Mass spectrometry: In negative ESI, PGs yield [M–H]− and characteristic headgroup (m/z 153) and fatty acyl anion fragments (literature).
Reaction Conditions
Not conventional organic reaction chemistry.
This lipid is used under assembly/processing conditions rather than as a reagent in named organic reactions.
General processing conditions for PG lipids (literature/practice)
Thin-film hydration: Dissolve in CHCl3:MeOH (2:1), evaporate to a thin film under reduced pressure, dry under high vacuum ≥1 h, hydrate with buffer warmed slightly above Tm (often room temperature suffices for mixed-chain PGs), vortex, and apply 3–10 freeze–thaw cycles. Optional extrusion (50–200 nm) yields LUVs.
Sonication: Brief bath sonication can help dissolve dry films in alcohol-rich mixtures; avoid prolonged probe sonication to limit oxidation/heating.
LC–MS prep: Prepare 1–10 mM stocks in CHCl3:MeOH; dilute to µM levels in IPA/ACN/H2O with 5–10 mM ammonium acetate or formate immediately before analysis. Maintain samples on ice and minimize air exposure.
Antioxidation: Work under N2/Ar, use amber glassware, keep ≤4°C during prep. Analyze freshly prepared solutions to limit peroxidation artifacts.
Expected outcomes (literature)
Stable, homogeneous liposomes and reproducible MS response when handled under inert, low-temperature conditions. Yields for assemblies are generally quantitative relative to input mass.
Safety and Handling
Item-specific (from Product Data)
Storage conditions: Store at −20°C.
Shipping: Ice chest + ice pads.
GHS classification, signal word, hazard statements, pictograms: Not specified for this item; refer to SDS.
General safety considerations for phospholipids (literature/practice)
Expected hazards: Phosphatidylglycerols are generally regarded as low acute toxicity research chemicals; main risks are solvent-related (e.g., chloroform, methanol) and peroxide/oxidation byproducts of polyunsaturated chains.
Oxidation sensitivity: The 22:4 chain is prone to peroxidation. Work under inert atmosphere (nitrogen/argon), minimize exposure to light, and keep solutions cold. Use amber vials and consider adding a trace antioxidant to working solutions if compatible with your application (verify with your protocol and analytical method).
Incompatibilities: Strong oxidizers, strong bases/acids (hydrolysis), and elevated temperatures.
PPE: Lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Handle organic solvents in a fume hood.
First aid (overview; defer to SDS): If inhaled (solvent vapors), move to fresh air. Skin/eye contact—rinse with water for at least 15 minutes, remove contaminated clothing, seek medical advice. If ingested, rinse mouth and seek medical attention. Provide SDS to responders.
Waste: Collect phospholipid solutions and halogenated/non-halogenated solvents in designated containers per institutional and local regulations.
SDS: Consult the product-specific SDS for authoritative hazard, exposure, and spill response information.
Solvent Selection
Item-specific (from Product Data)
No item-specific solvent recommendations provided; follow your application protocol and CoA guidance.
General solvent guidance for PG lipids (literature/practice)
Primary dissolution: Chloroform or chloroform:methanol (2:1 or 1:1 v/v) provides rapid dissolution and good vial wetting. Dichloromethane can be an alternative. Keep solutions cold and under inert gas.
Alcohols: Methanol, ethanol, and isopropanol can dissolve PGs at moderate concentrations; higher alcohol content assists in LC–MS mobile phases.
Aqueous systems: PGs do not dissolve as monomers; form vesicles/liposomes upon hydration of a thin lipid film or via detergent-assisted methods. Inclusion of a small amount of ethanol/tert-butanol can aid reconstitution before buffer addition.
LC–MS workflows: Typical mobile phases include ACN/IPA/H2O with ammonium formate/acetate; sample stocks are often in CHCl3:MeOH and diluted into IPA-rich mixtures immediately before injection to avoid phase separation.
Comparison (general)
Chloroform:methanol
Pros: Best solubilization; classic Bligh–Dyer/Folch extraction compatibility.
Cons: Toxicity and environmental burden.
Isopropanol/ACN mixtures
Pros: MS-friendly, lower toxicity than chloroform; compatible with direct infusion/LC.
Cons: Slower dissolution from dry films; may require sonication/heating (≤30–40°C, inert atmosphere).
Storage and Reconstitution
Item-specific (from Product Data)
Storage: Store at −20°C.
Shipping: Ice chest + ice pads.
General best practices for PG lipids with PUFA chains (literature/practice)
Long-term storage: Keep solid material or concentrated solutions at −20°C or below, protected from light, preferably under inert gas (N2/Ar). For very long-term storage, −80°C is common.
Aliquoting: Prepare single-use aliquots to avoid repeated freeze–thaw and headspace oxygen exposure. Use amber vials with PTFE-lined caps.
Reconstitution: Dissolve in CHCl3 or CHCl3:MeOH (2:1 or 1:1). For LC–MS, dilute into IPA/ACN/H2O immediately before analysis. For liposome formation, evaporate solvent to a thin film, then hydrate with buffer at or slightly above the lipid’s Tm (typically near or below room temperature for mixed-chain PGs; exact Tm for this item is not specified).
Stability after reconstitution: Use organic solutions within days; store at ≤−20°C under inert gas if longer storage is necessary. Aqueous dispersions are best used within 24–72 h at 4°C under N2.
Inspection: Discard if noticeable odor of rancidity, discoloration, or abnormal MS background suggests oxidation.
Specifications not provided for this item
Exact stabilizers, salt form, concentration limits, and shelf-life: Not specified for this item; refer to CoA/Spec Sheet.
Structure and Identity
Item-specific (from Product Data)
Product name: 17:0-22:4 PG-d (SKU: P1443620)
CAS: 2342575-46-4
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.
General structural description (literature)
Compound type: Glycerophospholipid of the phosphatidylglycerol (PG) class.
Backbone: sn-glycerol-3-phosphate bearing a glycerol headgroup (phosphatidylglycerol) and two esterified fatty acyl chains at sn-1 and sn-2.
Acyl chains: One saturated C17:0 (heptadecanoyl) and one polyunsaturated C22:4 (all-cis docosatetraenoyl; typical double-bond positions in PG literature include Δ7,10,13,16 or related isomers, but exact geometry/positions for this catalog item are not specified).
Stereochemistry: Naturally occurring PGs are typically sn-1/sn-2 stereodefined at the glycerol backbone; precise stereochemical assignment for this item is not specified.
Ionization: The phosphate group confers anionic character (net −1 at neutral pH for PG). PGs are commonly handled as free acids or as ammonium/sodium salts; exact counterion for this item is not specified.
“d” suffix: Often denotes an isotopically labeled (deuterated) variant in lipidomics; the precise labeling pattern and deuterium count are not specified for this item and should be verified in the CoA/Spec Sheet.
2D structure in words (literature)
A central glycerol bears two ester carbonyls linking C17:0 (linear alkyl) and C22:4 (cis-alkenyl) chains; the third position connects via phosphate to a second glycerol headgroup.
Synthetic Utility
Context
As a complex lipid, 17:0-22:4 PG-d is typically a target compound rather than a reagent for general organic synthesis.
Utility in chemical biology/materials (literature/practice)
Membrane scaffolding: Serves as a defined anionic lipid component for assembling bilayers, liposomes, and supported lipid membranes used to study protein–lipid interactions and ion channels.
Isotopic tracing: If deuterated (implied by “d”), can be used as an internal standard for quantitative lipidomics, enabling absolute/relative quantitation of endogenous PG species by LC–MS/MS.
Reactive handles: While PG lacks easily addressable functional groups under mild conditions, its ester linkages can participate in controlled hydrolysis/transesterification for analytical derivatization (e.g., fatty acyl profiling by methanolysis) in method development.
Limitations
Susceptible to oxidation and hydrolysis; not suitable as a base-stable substrate.
Limited participation in canonical small-molecule reactions; handling is dominated by supramolecular assembly rather than covalent modification.
Target Specificity
Not applicable.
This product is a small-molecule lipid standard, not an antibody or affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies to this item.
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