1-Stearoyl-sn-glycero-3-phosphocholine: Key Facts & FAQs
1-Stearoyl-sn-glycero-3-phosphocholine: Key Facts & FAQs
1-Stearoyl-sn-glycero-3-phosphocholine is a saturated lyso-phosphatidylcholine (LPC 18:0) composed of a stearic acid (C18:0) acyl chain esterified at the sn-1 position of the glycerophosphocholine backbone, widely used as a biochemical reference standard and membrane-lipid research tool.
- Chemical Name
- 1-Stearoyl-sn-glycero-3-phosphocholine
- Common Abbreviation
- LPC 18:0 / 1-Stearoyl LPC
- Lipid Class
- Lysophosphatidylcholine (lyso-PC)
- Acyl Chain
- Stearic acid, C18:0 (saturated), esterified at sn-1
- Aladdin SKU
- S757518
- Recommended Storage
- -20 °C under inert atmosphere, away from light and moisture (verify with CoA)
- Typical Application
- Membrane biophysics, lipidomics standards, cell signaling studies
What Is 1-Stearoyl-sn-glycero-3-phosphocholine?
1-Stearoyl-sn-glycero-3-phosphocholine (LPC 18:0) is a naturally occurring lysophospholipid generated primarily through the action of phospholipase A2 (PLA2) on diacyl phosphatidylcholine species containing a stearoyl chain at the sn-1 position. Unlike its diacyl counterpart, it carries a single fatty acid chain, giving it a cone-shaped molecular geometry that significantly influences membrane curvature and bilayer integrity.
Structurally, the molecule consists of three key domains: (1) a choline head group that confers zwitterionic character at physiological pH, (2) a glycerol-3-phosphate linker, and (3) a fully saturated C18:0 stearoyl chain at the sn-1 hydroxyl. The absence of unsaturation in the acyl chain makes LPC 18:0 particularly useful as a chemically stable reference compound for lipidomics workflows and for mechanistic studies in which oxidative lability must be minimized.
In biological systems, lysophosphatidylcholines including LPC 18:0 act as bioactive lipid mediators with roles in inflammation, immune-cell recruitment, and membrane remodeling. Circulating LPC species are major components of oxidized low-density lipoprotein (oxLDL) and have been studied in the context of cardiovascular disease, metabolic syndrome, and host-pathogen interactions.
Purity, Grade, and Quality Specifications
For lipid biochemistry and lipidomics applications, reagent purity is critical because trace impurities—including related lyso-PC species, free fatty acids, or oxidation products—can confound quantitative mass spectrometry data and cell-based assays. Researchers should always consult the Certificate of Analysis (CoA) supplied with each lot of Aladdin S757518 for lot-specific purity data, including HPLC purity percentage and water content.
Key quality parameters to verify before use include:
- HPLC purity: Typical research-grade lyso-PC reagents are supplied at ≥98% purity by HPLC; confirm with the CoA for the specific lot.
- Identity confirmation: ESI-MS or NMR data confirming the expected molecular weight (MW ≈ 523.7 g/mol for LPC 18:0) and characteristic fragmentation pattern (m/z 184 phosphocholine head-group fragment in positive-ion mode).
- Absence of lyso-PC isomers: Verify that sn-2 isomer (1-lyso-2-stearoyl-sn-glycero-3-phosphocholine) content is below reportable threshold, as isomers can migrate and interconvert under acidic or basic conditions.
- Water content: Hygroscopic lipid powders may absorb moisture; Karl Fischer titration values should be noted when preparing gravimetric solutions.
Review flag: specific purity values are not confirmed in the source material and must be verified against the product CoA before citing in publications.
Solubility, Reconstitution, and Storage Guidelines
Proper handling of LPC 18:0 is essential to maintain chemical integrity and experimental reproducibility. As a single-chain amphiphile, LPC 18:0 forms micelles rather than bilayers above its critical micelle concentration (CMC) in aqueous media; researchers should be aware of concentration-dependent self-assembly behavior when designing aqueous stock solutions.
Recommended solvents for reconstitution:
- Chloroform or chloroform/methanol (e.g., 2:1, v/v): Preferred for preparing concentrated lipid stocks; store under nitrogen or argon to prevent oxidation and hydrolysis.
- Ethanol or methanol: Acceptable for preparing dilute working solutions; avoid prolonged storage in protic solvents.
- Aqueous buffers: LPC 18:0 is poorly soluble in pure water; use sonication or vortexing to disperse at low concentrations (below CMC) for biological assays. Note that the CMC of saturated LPC species is chain-length dependent; consult primary literature for precise CMC values for LPC 18:0.
Storage: Store at -20 °C in a sealed vial under inert gas (nitrogen or argon). Aliquot upon first opening to minimize freeze-thaw cycles. Protect from light and moisture. Verify expiry date on CoA. Reconstituted solutions in organic solvent may be stored at -20 °C for short-term use; consult CoA for specific stability data.
Review flag: CMC value for LPC 18:0 is not provided in the source material; a literature value should be cited. Specific stability timepoints not confirmed in source material.
Research Applications of LPC 18:0
1-Stearoyl-sn-glycero-3-phosphocholine is employed across a broad range of research disciplines owing to its structural simplicity and biological relevance:
1. Lipidomics and Mass Spectrometry Standards: LPC 18:0 serves as an internal or external reference standard in LC-MS/MS-based lipidomics workflows. Its well-characterized fragmentation pattern (precursor ion [M+H]⁺ ≈ 524.4; diagnostic fragment m/z 184 for the phosphocholine head group in positive-ion mode ESI-MS) enables accurate quantification of LPC species in complex biological matrices such as plasma, cerebrospinal fluid, and cell lysates.
2. Membrane Biophysics: As a lysophospholipid, LPC 18:0 is incorporated into model membrane systems (liposomes, supported bilayers) to study lipid packing, membrane curvature, and lateral phase behavior. The saturated acyl chain increases gel-to-liquid-crystalline phase transition temperature compared to unsaturated LPC analogs, making LPC 18:0 a valuable tool for controlled phase studies.
3. Cell Signaling and Inflammation Research: LPC species are known to activate G protein-coupled receptors (including GPR4, TDAG8/GPR65, and OGR1/GPR68) and have been shown to influence macrophage activation, T-cell chemotaxis, and endothelial function. LPC 18:0 is used to probe these pathways in vitro at defined concentrations.
4. Drug Delivery and Formulation Research: Lysophospholipids are used as membrane-permeabilization enhancers and solubilization agents in pharmaceutical formulation studies; LPC 18:0 provides a saturated, chemically stable model compound for such investigations.
Review flag: specific receptor binding affinities, EC50 values, or GPR activation data for LPC 18:0 specifically are not confirmed in source material and should be cited from primary literature.
Ordering, Pricing, and Customer Support
1-Stearoyl-sn-glycero-3-phosphocholine is available from Aladdin Scientific under SKU S757518. To obtain current pricing, available pack sizes, and stock status, visit the product page on the Aladdin website or contact your regional Aladdin sales representative.
Ordering options:
- Online ordering through the Aladdin Scientific web store with registered account
- Purchase order (PO) submission for institutional procurement
- Bulk or custom quantities: contact Aladdin technical sales for quotation
Shipping and storage on receipt: Lipid reagents are typically shipped on dry ice or with cold-pack insulation depending on quantity and destination. Upon receipt, immediately transfer to -20 °C storage. Inspect packaging integrity and confirm the lot number matches the CoA provided.
Returns and quality concerns: If the product does not meet the specifications listed on the CoA, contact Aladdin customer service within the return window specified in Aladdin's return policy. Provide the lot number, CoA, and a description of the quality concern to expedite resolution.
Technical support: For application-specific questions regarding solubilization protocols, assay design, or analytical characterization of LPC 18:0, contact Aladdin's technical support team via the website inquiry form or email.
Frequently asked questions
What is the molecular weight of 1-Stearoyl-sn-glycero-3-phosphocholine (LPC 18:0)?
The molecular weight of 1-Stearoyl-sn-glycero-3-phosphocholine (LPC 18:0) is approximately 523.7 g/mol. In positive-ion ESI-MS, the protonated molecule [M+H]⁺ appears at approximately m/z 524.4, with a diagnostic phosphocholine head-group fragment at m/z 184. Always verify against the CoA for the specific lot.
How should I dissolve LPC 18:0 for cell-based assays?
For cell-based assays, prepare a concentrated stock solution of LPC 18:0 in a water-miscible organic solvent such as ethanol or DMSO, then dilute into aqueous cell culture medium to the desired working concentration while keeping the organic solvent volume below cytotoxic thresholds (typically ≤0.1% v/v). Alternatively, LPC 18:0 can be dispersed in fatty-acid-free BSA-containing buffer to deliver the lipid in a biologically relevant carrier format. Avoid concentrations above the CMC if monomeric delivery is required, and always include a vehicle-only control.
What is the difference between sn-1 and sn-2 lyso-PC isomers, and does it matter for my assay?
In sn-1 lyso-PC (such as LPC 18:0, Aladdin S757518), the acyl chain is esterified at the sn-1 position of the glycerol backbone, leaving the sn-2 hydroxyl free. In the sn-2 isomer, the acyl chain is at the sn-2 position. These positional isomers have different physical properties, enzymatic susceptibility, and potentially different biological activities. Critically, under mildly acidic or basic conditions or during prolonged storage, acyl migration between sn-1 and sn-2 positions can occur, generating isomeric mixtures. For rigorous quantitative or signaling studies, it is important to use a well-characterized, high-purity lot and to minimize conditions that promote acyl migration.
Can LPC 18:0 be used as an internal standard for lipidomics mass spectrometry?
Yes, LPC 18:0 is commonly used as a reference or surrogate standard in LC-MS/MS lipidomics experiments, particularly for quantifying LPC species in biological samples, because it is a naturally occurring but relatively minor LPC species in many matrices, allowing spike-in at concentrations above endogenous levels. For absolute quantification, a stable-isotope-labeled version (deuterium- or 13C-labeled LPC 18:0) is preferred to correct for matrix effects and ionization variability; check Aladdin's catalog for isotope-labeled analogs. Verify endogenous LPC 18:0 levels in your specific biological matrix before use as an internal standard.
What are the key stability risks for LPC 18:0 during storage and handling?
The primary stability risks for LPC 18:0 are: (1) hydrolysis of the ester bond at the sn-1 position, liberating stearic acid and glycerophosphocholine, accelerated by moisture, heat, and extreme pH; (2) acyl migration to generate the sn-2 isomer under mildly acidic or basic conditions; and (3) oxidation, although less prevalent for a fully saturated acyl chain compared to polyunsaturated analogs. To minimize these risks, store under inert gas at -20 °C in a tightly sealed vial, use dry solvents for reconstitution, and avoid repeated freeze-thaw cycles by working with single-use aliquots.
References
- Fahy E, Subramaniam S, Murphy RC, et al. Update of the LIPID MAPS comprehensive classification system for lipids. J Lipid Res. 2009;50(Suppl):S9-S14. doi:10.1194/jlr.R800095-JLR200
- Croset M, Brossard N, Polette A, Lagarde M. Characterization of plasma unsaturated lysophosphatidylcholines in human and rat. Biochem J. 2000;345(1):61-67. doi:10.1042/bj3450061
- Ryser MF, Ugarte F, Thieme S, Bornhauser M, Roesen-Wolff A, Brenner S. S1P(1) overexpression stimulates S1P-dependent chemotaxis but simultaneously induces autologous desensitization of S1P responses. Biochem Biophys Res Commun. 2008. [Placeholder — replace with primary reference for LPC receptor pharmacology]
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