24:0 Lyso PC-d , CAS No.2483831-13-4

CAS: 2483831-13-4 Cat. No.: L1445826 Fórmula: C₃₂H₆₂D₄NO₇P Peso molecular: 611.87

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

24:0 Lyso PC-d 4 4 is the deuterium labeled 24:0 Lyso PC. 24:0 Lyso PC is a lysophospholipid (LyP). 24:0 Lyso PC could be used for mRNA drug delivery.

Specifications

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

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Nombres e identificadores

Peso molecular

611.87

Application Protocols

No manufacturer-tested application protocols are provided in the product data for this SKU.

General usage examples (literature; adapt to your method):

• LC–MS internal standard preparation
  • Prepare a 1 mg/mL stock in MeOH or IPA under inert gas. Aliquot to amber glass vials; store at −20°C.
  • Working solution: dilute to 1–10 µg/mL in MeOH:water (80:20) with 5 mM ammonium formate. Spike biological extracts at a fixed concentration prior to extraction or pre-injection depending on your quantitation strategy.
• Thin-film hydration for biophysical assays
  • Dissolve required amount in CHCl3:MeOH (2:1). Evaporate to a thin film under nitrogen, then under high vacuum (≥1 h).
  • Hydrate with warm buffer (e.g., 37–50°C depending on chain length) and sonicate to form micelles or dispersions.
• Enzymatic reacylation assay
  • Combine LPC with a chosen acyl-CoA and LPLAT enzyme in buffered aqueous media (pH 7.4–8.0) containing mild detergent or mixed micelles. Monitor conversion by LC–MS.

Always verify concentration by gravimetry or quantitative NMR where possible, and confirm isotopic integrity from the CoA prior to quantitative work.

Biological Roles

Contextual information on lysophosphatidylcholines (LPCs) with long saturated chains (literature; not product specifications):

• Structural class: LPCs are monoacyl glycerophosphocholines formed by partial hydrolysis of phosphatidylcholines or by de novo remodeling pathways.
• Membrane and colloid behavior: with a single acyl chain, LPCs act as detergent-like zwitterions that promote positive membrane curvature, solubilize proteins/lipids, and form micelles or mixed micelles.
• Metabolic pathways: LPCs arise via phospholipase A2 (PLA2) activity and can be reacylated to phosphatidylcholines by acyl-CoA:lysophospholipid acyltransferases (Lands cycle). LPCs may also be converted to lysophosphatidic acid (LPA) by autotaxin (lysophospholipase D).
• Chain-length effects: longer saturated chains (e.g., C24:0) increase hydrophobicity, raise phase transition temperatures, and alter micelle–bilayer equilibria compared with medium-chain LPCs. Such differences can influence protein–lipid interactions and enzyme kinetics in vitro.
• Analytical role: defined LPC species are routinely quantified as part of lipidomic profiling in cells, tissues, and biofluids; deuterated analogs are used as internal standards to correct for extraction and ionization variability.

Note: Any physiological or clinical interpretations depend on biological context and are outside the scope of this product description. This product is for research use only.

Buffer Applications

This compound is not a buffer component and does not serve as an acid–base buffering agent.

Practical notes (general/literature):

• Aqueous handling focuses on dispersion rather than buffering. Hydrate lipid films in your pre-selected buffer (e.g., phosphate, HEPES, or ammonium acetate for MS) and use sonication or brief warming to disperse the LPC.
• For mass spectrometry, volatile buffers (ammonium formate/acetate, low millimolar) in MeOH/ACN/IPA mixtures are commonly used to maintain spray stability and ion formation without interfering with the zwitterionic headgroup.

For optimized buffer composition in your specific assay, follow method-specific literature or instrument application notes.

Green Alternatives

While the molecule itself is the analyte of interest and not substitutable for its analytical role, greener choices can be made in handling and method design.

Greener solvent considerations (literature-based):

• Replace chloroform with less hazardous options when feasible. IPA and MeOH are preferred for many lipidomics workflows; methyl tert-butyl ether (MTBE) biphasic extraction can substitute for CHCl3-based Folch/Bligh–Dyer protocols.

Comparison (general guidance):

• Chloroform:methanol (2:1): excellent solubility; halogenated, toxic, and ozone-depleting risks.
• Isopropanol or methanol: good solubility for LPC; lower toxicity; fully miscible with water; MS-compatible.
• MTBE: effective for lipid extraction with reduced density hazards; less chlorinated waste; requires ventilation and fire precautions.

Operational improvements:

• Use microscale preparations and pre-aliquoted single-use vials to reduce solvent usage and waste.
• Opt for LC–MS mobile phases that are fully alcohol-based (e.g., ACN/IPA/Water) with volatile salts instead of halogenated solvents.
• Implement closed solvent delivery and waste capture to minimize emissions.

Trade-offs:

• Some highly saturated long-chain LPCs dissolve more readily in CHCl3:MeOH; switching to greener systems may require gentle heating, longer sonication, or small co-solvent fractions to achieve homogeneity.

Pharmaceutical Uses

No item-specific pharmacopeial status or excipient grade is provided for this product.

General research/formulation context (literature; not a clinical claim):

• LPCs are used in formulation research as membrane-active amphiphiles and as components of mixed micelles or liposomal systems to modulate permeability, particle stability, or drug release. Long saturated LPCs can influence bilayer rigidity and transition temperatures when blended with diacyl lipids.
• Deuterated LPCs are primarily analytical tools rather than excipients; they serve as internal standards for bioanalytical method validation supporting pharmacokinetic and stability studies of lipid species.
• Regulatory status: any use in human or veterinary products would require appropriate grade, specifications, and regulatory qualification. This catalog entry is for research use only.

If excipient use is contemplated in pre-formulation research, confirm material specifications (purity, residual solvents, isotopic content) and stability from the CoA, and establish compatibility with actives and other excipients under ICH-relevant conditions.

Physical Properties

Item-specific physicochemical constants are not provided for this catalog entry.

• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES, InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General/literature characteristics for long-chain LPCs (contextual information, not item specifications):

• Physical state: typically waxy solid or glass at room temperature for long saturated chains (e.g., ≥ C20), forming gels/lamellae in water.
• Amphiphilicity: zwitterionic headgroup with a single hydrophobic tail; forms micelles, mixed micelles, or lamellar phases depending on concentration and temperature.
• Solubility: freely soluble in chloroform:methanol mixtures (e.g., 2:1 v/v) and methanol; dispersible in aqueous buffers with sonication or with small cosolvent fractions; critical micelle concentration (CMC) decreases with chain length. Reported LPC CMC values range from low mM (short chains) to low–mid µM (long chains) at ambient temperature (literature, chain-dependent).
• Phase behavior: saturation and chain length raise gel–fluid transition temperatures; C24:0 LPC typically exhibits higher Tm than C16:0 LPC (literature trend).
• LogP/pKa: not meaningful in a simple sense due to zwitterionic nature; headgroup remains permanently charged (quaternary ammonium), phosphate diester anionic across physiological pH.
• UV/Vis: lacks strong chromophores; typically monitored by ELSD/CAD or MS rather than UV (literature practice).

For quantitative values applicable to this SKU (including any deuterium content), consult the CoA/Spec Sheet.

Quality and Grades

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Context and expectations for lysophospholipid standards (general guidance):

• Research grade lipids for analytical use are commonly provided at high chemical purity and known isotopic enrichment patterns when deuterated. For LC–MS lipidomics, residual solvents, salts, and isobaric impurities are critical; CoA typically lists purity by HPLC or TLC and isotopic enrichment (%D) and pattern (uniform vs positional).
• Deuterated internal standards: the value of “-d” materials lies in a defined mass shift and matched chromatographic behavior relative to endogenous analytes. The CoA should specify deuterium count and labeling position; absence of this information inhibits quantitative method validation.
• Stabilizers/antioxidants: Some lipid products include trace BHT or similar antioxidants; none are specified here. If present, the CoA will disclose type and level. Absence of a stabilizer may necessitate stricter oxygen/light control during storage and handling.
• Trace metals, water, and peroxide limits: Not specified for this item; refer to CoA/Spec Sheet.

Recommendation: Prior to regulated analyses, document lot-specific purity, isotopic pattern, and residual solvent content from the CoA and qualify the lot in your workflow (retention time, response factors, and recovery in matrix).

Reaction and Applications

Manufacturer applications: Not specified in product data. The following summarizes common research uses of deuterated long-chain LPCs (literature/general guidance):

Analytical/internal standard applications

• Quantitative lipidomics: serves as an internal standard for endogenous 24:0 LPC (and related LPCs by response factor) in LC–MS/MS. Deuterium labeling provides a defined mass shift without significantly altering chromatographic behavior.
• Method development: calibration curves, matrix spike–recovery, and ionization efficiency assessment in plasma, tissue extracts, or cell lysates.

Biochemical and biophysical applications

• Membrane/protein interactions: probe effects of long saturated LPC on membrane curvature, micellization, and protein reconstitution; modulate membrane-active enzymes and transporters in reconstituted systems.
• Enzymology: substrate/product standard in phospholipase A2/LysoPLD pathways; reference compound for reacylation (Lands cycle) studies with acyl-CoA:lysophospholipid acyltransferases.

Chemical applications

• Precursor in semi-synthesis of defined phosphatidylcholines by acylation of LPC (chemical or enzymatic). Deuterium label can track acyl migration or remodeling by MS.

Practical tips

• Minimize hydrolysis and oxidation: prepare stocks in dry MeOH or CHCl3:MeOH under inert gas; aliquot into amber vials.
• Avoid multiple freeze–thaw cycles; thaw quickly at room temperature, then keep on ice during use.
• For LC–MS, verify isotopic purity and mass shift from the CoA; optimize MRM transitions for the labeled species.

Reaction Conditions

Typical literature conditions relevant to transforming LPC into other lipids (general guidance; optimize per system):

Chemical reacylation to PC

• Solvent: dry chloroform, dichloromethane, or toluene with catalytic DMAP and base (e.g., triethylamine) when using activated esters or acid chlorides of the desired fatty acid.
• Temperature: 0–25°C; low temperatures help suppress acyl migration.
• Time: 0.5–6 h depending on reagent and sterics.
• Notes: protect from moisture; quench and purify rapidly (silica gel pretreated to reduce adsorption of zwitterions; use MeOH gradients or NH4OAc-modified eluents).

Enzymatic acylation

• Reagents: acyl-CoA donor, acyl-CoA:lysophospholipid acyltransferase (LPLAT) or lipase with transesterification capability.
• Solvent/buffer: aqueous buffer (pH 7–8) with detergent or mixed micelles; temperature 25–37°C.
• Advantages: regioselectivity and mild conditions; compatible with sensitive isotopic labels.

Analytical LC–MS setup for standards (for use, not synthesis)

• Stocks: 0.5–5 mg/mL in MeOH or IPA; store at −20°C in aliquots.
• Mobile phases: water/ACN/IPA with 5–10 mM ammonium formate or acetate and 0.1% FA as required.
• Ionization: positive ESI [M+H]+ and [M+Na]+ common; monitor diagnostic fragment of phosphocholine headgroup (m/z 184 in positive mode) while accounting for deuterium shift.

These conditions are illustrative; confirm compatibility with your deuterium labeling pattern and consult primary literature.

Safety and Handling

Item-specific hazard classification is not provided in the product data.

• GHS classification: Not specified for this item; refer to SDS.
• Signal word, H-statements, pictograms: Not specified for this item; refer to SDS.

General laboratory safety guidance for lysophospholipids (informational; defer to SDS/CoA):

• Potential hazards: amphiphilic lipids may cause skin/eye irritation and are harmful if ingested or inhaled as dust/aerosol. Handle solutions to avoid aerosol formation.
• PPE: lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Use a chemical fume hood for weighing, solvent handling, and solution preparation.
• Incompatibilities: avoid strong oxidizers and strong acids/bases that can hydrolyze the ester or cleave the phosphate. Avoid prolonged exposure to elevated temperature, light, and moisture, which accelerate oxidation/hydrolysis.
• Special risks: lipid oxidation is facilitated by adventitious peroxides in solvents and by air exposure; even saturated chains benefit from oxygen- and light-minimized handling. Use amber vials, dry oxygen-free solvents, and inert gas blankets when feasible.
• First aid (overview; consult SDS): on skin/eye contact, rinse with water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If swallowed, rinse mouth and seek medical attention. Provide SDS to responders.
• Waste: collect organic solutions and contaminated disposables as halogen-free organic waste unless local regulations dictate otherwise.

Always consult the product’s SDS for authoritative, item-specific safety information.

Solvent Selection

This compound is an amphiphilic lysophospholipid; solvent choice determines aggregation state and handling practicality.

General/literature guidance (not item specifications):

• Lipid stock preparation
  • Excellent: chloroform:methanol (2:1 to 1:1 v/v), methanol, isopropanol. These dissolve LPCs well and are compatible with lipid film preparation and LC–MS injection after dilution.
  • Good: ethanol, acetonitrile (often with water ≤20%).
  • Aqueous buffers: LPCs disperse with sonication; small cosolvent fractions (5–20% MeOH/IPA) aid clarity. Above CMC, micelles/mixed micelles form.
• Polarity/behavior: zwitterionic headgroup with single hydrophobic chain favors micelle formation over bilayers; long-chain saturated LPCs can form gels/lamellae at lower temperatures and aggregate above certain concentrations.
• Practical choices by application
  • LC–MS lipidomics: prepare standards in MeOH or IPA (sometimes MeOH:CHCl3 for primary stock), dilute into MeOH:water or IPA:ACN:water with 0.1% formic acid or 5 mM ammonium formate as method dictates.
  • Biophysical assays: dissolve in organic solvent, form a thin film, dry thoroughly, then hydrate in buffer with controlled temperature and sonication to achieve desired aggregates.

Mini-comparison (literature-based):

• Methanol: miscible with water; MS-friendly; modest lipid solubility.
• Isopropanol: higher lipid solubility; good for shotgun lipidomics.
• Chloroform:methanol: strongest for initial dissolution; less green; typically evaporated prior to aqueous work.

Use inhibitor-free, peroxide-tested solvents to minimize lipid degradation.

Storage and Reconstitution

Item-specific storage/shipping

• Storage conditions: Store at −20°C (per product data).
• Shipped in: Ice chest + Ice pads (per product data).

Additional best practices (general guidance; not product specifications):

• Protect from light and air. Store in amber glass vials with PTFE-lined caps under inert gas (argon or nitrogen) to minimize oxidation and isotopic exchange.
• Avoid moisture ingress; keep desiccated. Repeated freeze–thaw cycles can degrade lipids—prepare single-use aliquots.

Reconstitution/stock preparation (typical for LPCs)

• Dissolve the material in dry methanol or chloroform:methanol (2:1) to prepare a concentrated stock (e.g., 1–5 mg/mL). Swirl gently; avoid vigorous vortexing that entrains air.
• For aqueous applications, form a thin film by evaporating solvent under nitrogen, then apply high vacuum to remove residuals. Hydrate with prewarmed buffer, and sonicate to obtain clear dispersions.
• For LC–MS internal standard use, dilute stock into MeOH or IPA and store aliquots at −20°C. Bring vials to room temperature before opening to prevent condensation.

Shelf-life

• Exact retest/expiry dating is lot-specific. Inspect by LC–MS or HPLC for degradation (lyso-to-GPC hydrolysis, oxidation) at defined intervals. Refer to the CoA for any lot-specific stability statements.

Research Use Note: For research use only.

Structure and Identity

This item is a deuterium-labeled lysophosphatidylcholine bearing a saturated C24:0 (lignoceroyl) fatty acyl chain. Exact deuterium placement/count is not specified for this catalog entry.

• Product name: 24:0 Lyso PC-d (deuterated lysophosphatidylcholine)
• CAS: 2483831-13-4
• 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.

Structural features (general/literature):

• Lysophosphatidylcholines (LPCs) are monoacyl glycerophosphocholines with a glycerol backbone esterified by a single fatty acyl group (here, C24:0) and bearing a phosphocholine headgroup via a phosphodiester at sn-3.
• The monoacyl substitution can be at sn-1 or sn-2; the specific regioisomer for this item is not specified.
• Functional groups: phosphate diester, quaternary ammonium (choline), ester linkage, long aliphatic chain; amphiphilic zwitterion.
• 2D description: a long saturated alkyl chain (24 carbons) attached through an ester to a glycerol scaffold; the terminal glycerol carbon carries a phosphocholine moiety (–O–PO3–O–CH2–CH2–N+(CH3)3). Deuteriums substitute for some hydrogens in one or more moieties (pattern not specified).

Identity notes:

• Deuterium labeling facilitates mass spectrometric discrimination from endogenous LPC and improves use as an internal standard. Exact isotopic enrichment and labeling position determine the mass shift (consult CoA).

Synthetic Utility

Although typically used as a reference standard or biochemical tool, a long-chain LPC can serve as a versatile intermediate in lipid chemistry (general/literature guidance):

• Reacylation to phosphatidylcholines (PC): starting from LPC, selective acylation at the free hydroxyl (sn-2 or sn-1 depending on regioisomer) affords defined diacyl PCs. This underpins semi-synthetic access to asymmetric PCs with controlled chain lengths/saturation.
• Isotopic tracing: deuterium labels enable tracking of acyl migration (sn-2→sn-1) and remodeling in vitro by MS, aiding mechanistic studies of the Lands cycle and lipase specificity.
• Headgroup chemistry: the phosphocholine unit can be retained while modifying the acyl chain or, less commonly, transformed after protection of the phosphate diester for constructing tailored zwitterionic amphiphiles.
• Enzymatic transformations: acyltransferases (LPLATs) use LPC + acyl-CoA to form PC with high regioselectivity under mild conditions, offering biocatalytic routes that preserve sensitive labels.
• Conjugation strategies: activation of fatty acids (NHS esters, acid chlorides) enables coupling to LPC; conversely, controlled hydrolysis can yield glycerophosphocholine (GPC) as a scaffold.

Caveats:

• Maintain low water activity and exclude acids/bases to prevent ester hydrolysis.
• Control temperature and time to minimize acyl migration; employ rapid workups and, if needed, acyl-migration inhibitors or low-temperature conditions.

Target Specificity

This product is a chemical standard, not a biological affinity reagent. No target, epitope, clone, or species reactivity applies.

• Item-specific immunological/biological target data: Not applicable.
• Any specificity discussed for this product pertains to molecular composition (chain length and isotopic label) rather than binding to a biological target.

Preguntas frecuentes

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 2483831-13-4, the molecular formula is C32H62D4NO7P, and the molecular weight is 611.87 g/mol.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.