sn-(1-Oleoyl-2-hydroxy)-glycerol-3-phospho Ammonium Salt Guide
sn-(1-Oleoyl-2-hydroxy)-glycerol-3-phospho Ammonium Salt Guide
sn-(1-oleoyl-2-hydroxy)-glycerol-3-phospho-sn-3'-(1'-oleoyl-2'-hydroxy)-glycerol (ammonium salt) is a synthetic bis-lyso glycerophospholipid reagent (SKU I130515) that serves as a structurally defined reference compound and biochemical tool for studying lysosomal lipid metabolism, membrane biology, and phospholipid signaling pathways.
- Product Name
- sn-(1-oleoyl-2-hydroxy)-glycerol-3-phospho-sn-3'-(1'-oleoyl-2'-hydroxy)-glycerol (ammonium salt)
- SKU
- I130515
- Lipid Class
- Bis-lyso glycerophospholipid (lyso-bisphosphatidic acid analogue)
- Counterion
- Ammonium (NH4+)
- Fatty Acid Chains
- Two oleoyl (18:1, Δ9-cis) chains at sn-1 and sn-1' positions
- Storage Recommendation
- Store under inert atmosphere at -20 °C; avoid repeated freeze-thaw cycles
- Typical Application
- Lipid metabolism research, membrane biology, phospholipid signaling studies
Chemical Identity and Structural Overview
sn-(1-oleoyl-2-hydroxy)-glycerol-3-phospho-sn-3'-(1'-oleoyl-2'-hydroxy)-glycerol (ammonium salt), catalogued under SKU I130515, is a symmetric bis-lyso glycerophospholipid. Its backbone consists of two glycerol units bridged by a phosphodiester bond. Each glycerol bears a single oleoyl (C18:1, Δ9-cis) acyl chain esterified at the sn-1 (and sn-1') position, while the sn-2 (and sn-2') positions carry free hydroxyl groups, distinguishing it from diacyl phospholipids.
The ammonium salt form confers improved aqueous solubility relative to the free acid, making it more amenable to preparation of liposomal dispersions or aqueous stock solutions. This structural arrangement is closely related to lyso-bisphosphatidic acid (LBPA), a lipid enriched in late endosomal compartments with roles in intraluminal vesicle biogenesis and cholesterol trafficking.
Handling, Reconstitution, and Storage Protocol
Reconstitution: Allow the sealed vial to equilibrate to room temperature before opening to prevent condensation-driven oxidation. Dissolve the lipid in an oxygen-free organic solvent such as chloroform, chloroform/methanol (2:1 v/v), or DMSO for aqueous applications. Use glass syringes and glass vials to minimise adsorption and plasticiser contamination. Prepare working stocks at concentrations appropriate for downstream assays (typically 1–10 mM in organic solvent).
Inert-atmosphere handling: Lyso-glycerophospholipids bearing unsaturated acyl chains are susceptible to autoxidation at the double bond. All manipulations should be performed under a stream of dry nitrogen or argon. After use, overlay the headspace of storage vials with inert gas before resealing.
Storage: Store at −20 °C in a tightly sealed vial under inert gas. For long-term storage beyond three months, −80 °C is advisable. Avoid repeated freeze-thaw cycles; prepare single-use aliquots when possible. Monitor for oxidative degradation by TLC or LC-MS before use in sensitive assays.
Applications in Lipid Biology Research
Lysosomal and endosomal membrane studies: Owing to its structural similarity to lyso-bisphosphatidic acid (LBPA/BMP), this compound is used as a biochemical probe to investigate late endosomal membrane organisation, intraluminal vesicle formation, and lipid-protein interactions within the endolysosomal pathway.
Lipid metabolism assays: The compound serves as a substrate or reference standard for phospholipase activity assays, enabling kinetic characterisation of enzymes that act on lyso-glycerophospholipids. It can also be employed in lipidomics workflows as a structurally defined internal standard when isotopically labelled analogues are unavailable.
Membrane model systems: When incorporated into liposomes or supported lipid bilayers, this lipid modulates membrane curvature and fluidity due to its single-chain lyso architecture at each glycerol head, providing a tool for biophysical studies of membrane dynamics.
Cell-based studies: Exogenous addition to cell culture media (typically complexed with carrier protein or formulated in liposomes) allows investigation of lipid uptake, intracellular trafficking, and downstream signalling effects on cells relevant to lysosomal storage disorders or lipid metabolism diseases.
Quality Considerations and Analytical Verification
Purity assessment: Prior to use in quantitative or mechanistic assays, verify compound purity by high-performance thin-layer chromatography (HPTLC) or reverse-phase HPLC with evaporative light-scattering detection (ELSD) or charged aerosol detection (CAD). For definitive structural confirmation, electrospray ionisation mass spectrometry (ESI-MS) in negative-ion mode is recommended; the ammonium adduct [M+NH4]+ or deprotonated species [M−H]− should be identified and cross-referenced against the theoretical molecular formula.
Oxidation monitoring: Unsaturated lyso-lipids are prone to peroxidation. Conjugated diene formation can be detected by UV absorbance at 234 nm. Peroxide values can be assessed using ferrous oxidation-xylenol orange (FOX) assay. Discard lots showing visible colour change (yellowing) or anomalous mass spectral peaks corresponding to hydroperoxide adducts.
Water content: Karl Fischer titration should be used if precise anhydrous weights are required for stoichiometric experiments, as hygroscopic lipid samples may absorb atmospheric moisture upon opening.
Frequently asked questions
What solvent is recommended for dissolving I130515?
Chloroform or chloroform/methanol (2:1 v/v) is the standard choice for lyso-glycerophospholipids and maintains lipid integrity. For aqueous-based assays, DMSO may be used as a co-solvent at minimal volume; however, ensure the final DMSO concentration in biological assays does not exceed 0.1–0.5% to avoid cytotoxicity. All solvents should be degassed or sparged with inert gas to minimise oxidation.
How should I prepare a liposome formulation with this compound?
Dissolve the lipid in chloroform, combine with any additional lipid components in the desired molar ratio, then evaporate solvent under a nitrogen stream followed by high-vacuum desiccation for at least one hour to form a dry lipid film. Hydrate the film with the desired aqueous buffer at a temperature above the gel-to-liquid crystalline transition temperature (for oleoyl-chain lipids, this is typically well below room temperature). Extrude through polycarbonate membranes of defined pore size to obtain unilamellar vesicles of controlled diameter.
Is I130515 stable at room temperature for short-term bench use?
Brief exposure to room temperature (minutes to one hour) during weighing or aliquoting is acceptable if working under inert gas. Prolonged storage or repeated exposure to ambient air and light should be avoided, as the oleoyl double bond is susceptible to autoxidation. Return the compound to −20 °C storage promptly after use and verify integrity by analytical methods before critical experiments.
Can this compound be used as an internal standard in lipidomics experiments?
It can serve as a structurally defined reference compound for method development and relative quantification when isotopically labelled analogues are not available. However, for absolute quantification, a stable-isotope-labelled (e.g., deuterated) version is preferred to account for matrix effects and ionisation variability. Consult the Aladdin Scientific catalogue for available isotope-labelled phospholipid standards.
References
- Kolter T, Sandhoff K. Lysosomal degradation of membrane lipids. FEBS Lett. 2010;584(9):1700-1712. [Provides background on lysosomal lipid metabolism relevant to lyso-bisphosphatidic acid biology — verify applicability to this specific compound] doi:10.1016/j.febslet.2009.10.021
- Gruenberg J. The endocytic pathway: a mosaic of domains. Nat Rev Mol Cell Biol. 2001;2(10):721-730. [Contextual reference for lyso-bisphosphatidic acid in late endosomes — verify direct relevance to this compound] doi:10.1038/35096054
- Aladdin Scientific product page for I130515. [Primary source for SKU and product identity; detailed physicochemical data such as molecular weight, CAS number, and purity specification should be obtained directly from the product datasheet]
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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