Sphingosine-1-phosphate-d - ≥99% , CAS No.2260670-15-1

CAS: 2260670-15-1 Cat. No.: S1431659 PubChem CID: 136212727

GRADE & PURITY ≥99%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

Sphingosine-1-phosphate-d 7 is the deuterium labeled Sphingosine-1-phosphate. Sphingosine-1-phosphate (S1P) is an agonist of S1P1-5 receptors and a ligand of GPR3, GPR6 and GPR12. Sphingosine-1-phosphate is an intracellular second messenger and mobilizes Ca2+ as an extracellular ligand for G protein-coupled receptors. Sphingosine-1-phosphate is an important lipid mediator generated from Sphingomyelin or other membrane phospholipids.

Specifications

Spezifikationen & Reinheit

≥99%

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Reinheit

≥99%

Namen und Kennungen

Kanonisches Lächeln

CCCCCCCCCCCCCC=CC(C(COP(=O)(O)O)N)O

IUPAC Name

[(E,2S,3R)-2-amino-16,16,17,17,18,18,18-heptadeuterio-3-hydroxyoctadec-4-enyl] dihydrogen phosphate

InChIKey

DUYSYHSSBDVJSM-AVMMVCTPSA-N

INCHI

1S/C18H38NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h14-15,17-18,20H,2-13,16,19H2,1H3,(H2,21,22,23)/b15-14+/t17-,18+/m0/s1/i1D3,2D2,3D2

PubChem CID

136212727

Application Protocols

The following protocols are literature-based examples for deuterated sphingolipid standards and should be optimized per laboratory requirements. They are not item-specific validated methods.

• LC–MS/MS quantification of S1P (example workflow)

  1. Stock preparation: Dissolve at 5 mM in methanol containing 0.1% NH4OH. Aliquot into silanized glass vials; store at -20°C.
  2. Calibration: Prepare matrix-matched standards (e.g., stripped plasma) spanning 0.1–1,000 nM native S1P. Spike a fixed amount of S1P-d into all standards, QCs, and unknowns (e.g., 10 ng/mL final).
  3. Extraction: Precipitate proteins by adding 3–4 volumes cold MeOH. Vortex and incubate on ice 10 min; centrifuge 15,000 × g, 10 min, 4°C. Collect supernatant.
  4. Cleanup (optional): SPE on mixed-mode anion-exchange cartridges; elute with MeOH containing 1–2% NH4OH. Evaporate under N2 at room temp.
  5. Reconstitution: 100 µL of 70:30 MeOH:water with 5 mM ammonium formate, 0.1% formic acid.
  6. LC–MS/MS: Reverse-phase or HILIC; ESI positive or negative depending on method. Monitor MRM transitions for S1P and S1P-d with appropriate isotope mass shifts.

• Enzyme assay (S1P phosphatase) sketch

  • Incubate 1–10 µM S1P with enzyme in 50 mM HEPES, pH 7.4, 0.1% BSA, 2 mM MgCl2 at 37°C for 30 min. Quench with 4 volumes MeOH containing internal standard. Analyze products by LC–MS.

• Adsorption control

  • Pre-rinse plastics/glass with working solvent containing a small amount of BSA or base to reduce losses.

Biological Roles

This section summarizes established biology of sphingosine-1-phosphate (S1P) for scientific context; it does not describe item-specific specifications or make clinical claims.

• Biochemical pathway context (literature/general)

  • Biosynthesis: Sphingosine is phosphorylated by sphingosine kinases (SphK1/2) to form S1P.
  • Turnover: Dephosphorylated by S1P phosphatases or irreversibly cleaved by S1P lyase, linking to glycerophospholipid and fatty aldehyde metabolism.
  • Transport/carriage: Exported by specific transporters; circulates bound to albumin and ApoM/HDL.

• Molecular interactions

  • Extracellular signaling: Agonist of five GPCRs (S1PR1–S1PR5), regulating cytoskeletal dynamics and barrier functions (mechanistic/biochemical context only).
  • Intracellular roles: Reported to modulate calcium homeostasis and epigenetic enzymes in some systems (mechanistic literature).

• Relevance of deuterated analogs

  • Isotopic labeling preserves chemical connectivity and receptor interactions but shifts mass for MS discrimination; used to correct for ion suppression, extraction losses, and instrument variability.
  • Deuterium kinetic isotope effects on this class are negligible in typical analytical conditions; nonetheless, enzymatic studies should confirm that labeling does not alter processing in the specific assay.

Note: The above is general biochemical knowledge intended to inform experimental design; it is not a statement of the product’s grade or suitability for any clinical application.

Buffer Applications

This compound is not a buffering agent. However, preparing aqueous buffers that can carry amphipathic lipids is often necessary in assays.

• General guidance (literature)

  • Carriers: Include 0.1–0.5% fatty acid–free BSA to maintain S1P in solution and reduce surface adsorption.
  • pH/ionic strength: Mildly basic conditions (e.g., ≤0.1% NH4OH during stock dilution) improve dispersion before adjusting to final assay pH (typically pH 7.2–7.4).
  • Detergents: Low concentrations of nonionic surfactants (e.g., 0.01% Triton X-100, Tween-20) can aid solubilization if compatible with the assay and detection method.
  • Order of addition: Add the organic stock slowly to vortexed buffer to avoid local precipitation; brief sonication helps.

• Not typically applicable aspects

  • Classical buffer capacity data (pKa ranges, recipes) do not apply, as S1P-d is an analyte/standard rather than a buffering species. Focus on Solvent Selection and Application Protocols for practical handling.

Green Alternatives

While the compound itself is fixed, solvent systems used with sphingolipids can be optimized for greener chemistry without compromising analytical performance.

• Greener solvent choices (literature/general)

  • Replace chloroform with isopropanol or ethanol in extraction where feasible (e.g., IPA:MeOH:water protocols) to reduce halogenated solvent use.
  • Favor ethanol over acetonitrile when compatible with LC–MS separation and response (note: ACN often gives sharper peaks; evaluate tradeoffs).
  • Use aqueous ammonium formate/acetate buffers (volatile, MS-friendly) rather than non-volatile salts.

• Comparison (general)

  • Traditional Bligh–Dyer (CHCl3:MeOH:water): Excellent phase separation; uses chlorinated solvent; disposal burden high.
  • MTBE-based extraction: Less dense organic phase; reduced chlorinated waste; flammable; good recovery for phospholipids.
  • IPA:MeOH:water (single-phase): Halogen-free; safer; may co-extract more matrix—optimize cleanup (e.g., SPE).

• Practical guidance

  • Validate greener methods by comparing recovery, matrix effects, and precision versus legacy protocols using the same deuterated internal standard.
  • Consider energy savings by storing working solutions at -20°C rather than -80°C when stability data support it (verify for your item via CoA/SDS).

Pharmaceutical Uses

No therapeutic or clinical claims are made. The compound is supplied for research use only (from Product Data).

• Formulation and bioanalytical context (literature/general)

  • Internal standard: Used in regulated bioanalysis (e.g., LC–MS/MS) to quantify endogenous S1P in biological matrices for pharmacokinetic/pharmacodynamic research.
  • Reference material: Supports method validation parameters (linearity, accuracy, precision, selectivity, recovery, stability) per FDA/EMA bioanalytical method validation guidelines.
  • Matrix-matched calibrators: Applied to prepare calibration curves and QC samples in plasma/serum homogenates to account for matrix effects and recovery.

• Excipient status

  • Not recognized as a common pharmaceutical excipient. Any use in manufacturing would be restricted to analytical purposes, not as a formulation component.

• Documentation

  • Maintain the product CoA/SDS in study files to document isotopic enrichment, purity, and storage conditions, especially in GLP/GMP-adjacent environments.

Physical Properties

• Item-specific (from Product Data)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Storage Conditions: Store at -20°C.

• General/literature properties for sphingosine-1-phosphate (unlabeled; values provided for context only)

  • Physical form: Wax-like solid or amorphous powder; highly amphipathic.
  • Molecular formula (unlabeled S1P): C18H38NO5P (literature).
  • Molecular weight (unlabeled S1P): ~379.46 g/mol (literature); deuteration increases exact mass proportionally to D content.
  • Ionization/acid–base: Phosphate pKa1 ~1, pKa2 ~6.4–7.0; amine pKa ~8–9 → often zwitterionic around neutral pH (literature).
  • LogP/logD: High hydrophobic character (reported logP ~3–4; literature, method-dependent).
  • Solubility behavior: Poorly soluble in pure water; improved solubility as salts, with basic modifiers (e.g., NH4OH) or in polar organics (MeOH, EtOH, isopropanol, DMSO). Strongly adsorbs to plastics; use glass vials (literature best practice).
  • Phase transitions: Melting behavior often broad; no sharp BP under ambient pressure (thermally labile). Specific MP/BP not typically reported due to decomposition.
  • Hygroscopicity: Moderately moisture sensitive; phosphate headgroup can retain water.

Notes

• All numerical values above are literature/general for the non-deuterated analog and are NOT item-specific specifications. Consult the CoA/Spec Sheet for the exact isotopic composition, counterion, and any item-specific physical constants.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• What typically defines quality for isotopically labeled sphingolipids (general guidance)

  • Isotopic enrichment: Percent deuterium incorporation and labeling pattern (e.g., d3, d5, d7, d9). Higher and well-characterized enrichment improves quantitative LC–MS performance by minimizing isotopic overlap.
  • Chemical purity: Assessed by HPLC/UPLC (area %) and NMR; low levels of unlabeled analogs and structural isomers (e.g., chain length variants) are important.
  • Counterion and salt form: Free acid vs ammonium/sodium salt affects solubility and MS response; exact form should be stated on the CoA.
  • Residual solvents/water: Typically reported on CoA (e.g., Karl Fischer for water). Not specified for this item; refer to CoA/Spec Sheet.
  • Peroxide/UV/metal limits: Not generally applicable to this lipid class; if reported, consult CoA. Not specified for this item.

• Stabilizers/additives

  • No stabilizer information is provided for this item. Some vendors add small amounts of volatile base (e.g., NH4OH) to enhance solubility; verify any additives on the CoA.

• Practical note

  • For quantitative analysis, match the salt form and chain-unsaturation pattern of the internal standard to the analyte. Retain the CoA for documentation of isotopic enrichment and purity in regulated workflows.

Reaction and Applications

Given its stability and structure, Sphingosine-1-phosphate-d is not commonly used as a synthetic reagent; instead, it is primarily employed as an analytical internal standard and tracer.

• Analytical and research applications (literature/general)

  • LC–MS/MS internal standard: Deuterated S1P co-elutes closely with the native analyte, enabling accurate quantification in plasma, serum, cells, and tissues. Used in calibration curves, quality control samples, and recovery studies.
  • Metabolic tracing: Tracks sphingolipid metabolism, including dephosphorylation to sphingosine and onward conversion to ceramides/glycosphingolipids under controlled experiments.
  • Enzyme assays: Substrate/standard for sphingosine-1-phosphate phosphatases and lyase; supports determination of kinetic parameters when paired with orthogonal detection.
  • Lipidomics method development: Optimizes extraction efficiency, matrix effect correction, and instrument response factors during method validation.

• Practical tips (general best practice)

  • Minimize adsorption: Use silanized glass vials and low-bind tips; pre-rinse with solvent containing 0.1% NH4OH.
  • Co-solvent strategy: Prepare concentrated stocks (1–10 mM) in MeOH or DMSO; for aqueous assays, dilute into buffer with BSA or cyclodextrins.
  • Matrix effects: Match internal standard addition early in the workflow (pre-extraction) to correct for losses.
  • Salt form consistency: Match counterion between calibrators, QCs, and samples to reduce variability.

Note: No manufacturer application text was provided; the use-cases above are established literature practices for deuterated sphingolipid standards.

Reaction Conditions

Conventional organic reaction conditions are generally not relevant. Below are literature-based conditions for analytical and enzymatic uses.

• LC–MS sample preparation (general)

  • Stock solutions: 1–10 mM in methanol or DMSO; may include 0.05–0.1% NH4OH to accelerate dissolution.
  • Spiking: Add internal standard to biological samples prior to extraction (typ. 5–100 ng per 100 µL plasma) to correct for losses and matrix effects.
  • Extraction: Protein precipitation with MeOH or ACN:MeOH (1:1), or lipidomics extraction with IPA:MeOH:water or MTBE-based protocols. Keep samples cold.
  • Reconstitution: 50–80% aqueous methanol with 5–10 mM ammonium formate/acetate, pH ~4–6 for reversed-phase or HILIC separations.

• Enzymatic assays (general)

  • Buffer: 25–50 mM HEPES or Tris, pH 7.2–7.5, with 0.1% BSA to maintain solubility; Mg2+ as required by enzyme.
  • Temperature/time: 25–37°C; 10–120 min typical depending on enzyme activity. Quench with organic solvent containing internal standard for LC–MS readout.

• Stability considerations

  • Avoid prolonged exposure to strong acid/base and elevated temperatures. Protect from light and air; minimize adsorption by using glassware and low-bind plastics.

All values above are general literature guidance to assist experimental planning and are not item-specific specifications.

Safety and Handling

• Item-specific hazard data

  • Signal Word, H-Statements, GHS Classification, Pictograms: Not specified for this item; refer to SDS.
  • Shipping: Ice chest + ice pads (from Product Data).
  • Storage: Store at -20°C (from Product Data).

• General laboratory safety (literature/best practice for amphipathic lipids)

  • PPE: Lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Handle powders in a fume hood to avoid inhalation of fine particulates.
  • Incompatibilities: Avoid strong oxidizers and prolonged exposure to strong acids/bases that may hydrolyze the phosphate; avoid high temperatures. Prevent contact with reactive acylating/phosphorylating agents.
  • Handling notes: Compound may adsorb to plastics and glass; pre-rinse containers with solvent or use silanized glass to minimize loss. Use low-bind tips if plastics are unavoidable.
  • First aid (overview; consult SDS for details): If inhaled, move to fresh air. In case of skin/eye contact, rinse with water for at least 15 minutes. If ingested, rinse mouth and seek medical attention. Provide SDS to healthcare personnel.
  • Spills and disposal: Absorb small spills with inert material. Collect for disposal according to institutional and local regulations for organic laboratory waste. Avoid release to drains.
  • Stability considerations: Protect from light and moisture; repeated freeze–thaw can promote degradation or adsorption losses. Store aliquoted at -20°C or below.

Always consult the product-specific SDS for authoritative hazard classifications and response measures.

Solvent Selection

This compound is an amphipathic lipid phosphate with poor water solubility but improved solubility in select polar organics and basic aqueous media.

• Polarity/miscibility profile (literature/general)

  • Water: Limited solubility; dispersion improves with basic modifiers (e.g., 0.05–0.5% NH4OH) or carrier proteins (fatty acid–free BSA) and sonication.
  • Alcohols: Methanol, ethanol, isopropanol dissolve S1P efficiently, especially with a trace of base or acid (method-dependent). Suitable for LC–MS sample prep.
  • Aprotic solvents: DMSO aids stock preparation; DMF less preferred due to MS background.
  • Biphasic extraction: Often co-extracted with chloroform/methanol or isopropanol-based systems, then reconstituted in aqueous-organic LC mobile phase.

• Practical selection guidance

  • For LC–MS stocks: Methanol or methanol:water (80:20) with 0.05–0.1% NH4OH; alternatively DMSO. Filter through PTFE or use glass to reduce adsorption losses.
  • For biological buffers: Pre-dissolve in MeOH or DMSO, then dilute into buffer containing 0.1–0.5% fatty acid–free BSA; maintain final organic <2% to avoid perturbing systems.
  • Avoid high ionic strength or divalent cations when solubilizing free acid; use matching salt forms when possible.

• Quick comparison (literature/general)

  • Methanol: Excellent solubilizer; LC–MS compatible; may need slight base for rapid dissolution.
  • DMSO: High solvency; useful for small aliquots; watch for adsorption on plastics.
  • Water + NH4OH: Enables aqueous handling; adjust pH promptly to target after dilution.
  • PBS without carriers: Often poor due to aggregation; add BSA or organic cosolvent.

Storage and Reconstitution

• Item-specific storage and shipping (from Product Data)

  • Storage Conditions: Store at -20°C.
  • Shipped In: Ice chest + Ice pads.

• Item-specific appearance/reconstitution: Not specified for this item; refer to CoA/Spec Sheet.

• General handling and stability (literature/best practice for deuterated S1P)

  • Protection: Store under inert atmosphere if possible, protected from light and moisture. Use amber, silanized glass vials with PTFE-lined caps.
  • Aliquoting: Prepare small single-use aliquots to avoid repeated freeze–thaw and adsorption losses.
  • Stock solutions: 1–10 mM in methanol or DMSO; inclusion of 0.05–0.1% NH4OH can speed dissolution. For aqueous work, dilute organic stocks into buffer containing 0.1–0.5% fatty acid–free BSA with vigorous mixing.
  • Working stability: Organic stocks are typically stable for weeks at -20°C and days at 4°C; aqueous BSA-containing solutions are best prepared fresh or stored short-term (≤24–48 h) at 4°C. Verify stability for your item.
  • Container considerations: Strong adsorption to plastics and untreated glass can cause apparent loss; pre-condition containers with solvent or use low-bind consumables.

• Documentation

  • Because grade, isotopic enrichment, and exact counterion are not specified here, consult the CoA/Spec Sheet for definitive reconstitution guidance and any item-specific stability or concentration limits.

Structure and Identity

Brief description: Sphingosine-1-phosphate-d is an isotopically labeled sphingolipid headgroup derivative used primarily as an internal standard and tracer in sphingolipid analytics.

• Item-specific (from Product Data)

  • SKU: S1431659
  • Product Name: Sphingosine-1-phosphate-d
  • CAS: 2260670-15-1
  • PubChem CID: 136212727
  • InChIKey: 73554 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (general/literature description of the sphingosine-1-phosphate motif)

  • Core scaffold: A C18 long-chain amino alcohol (sphingosine) bearing a trans-Δ4 double bond, a 2-amino group, a 3-hydroxyl, and a terminal primary hydroxyl at C1 that is phosphorylated (1-phosphate).
  • Functional groups: Primary phosphate monoester (–O–PO3H−), secondary alcohol, primary amine (typically protonated near neutral pH), internal alkene, long hydrophobic aliphatic chain.
  • Charge state: Frequently exists as a zwitterion near physiological pH (protonated amine; deprotonated phosphate).
  • Isotopic label: The suffix “-d” indicates deuterium labeling; exact labeling pattern and enrichment are not specified for this item (consult CoA for positions and %D). This does not alter connectivity but slightly increases exact mass.

• 2D structure in words (literature/general): A linear C18 chain with one internal trans double bond; C2 bears –NH2, C3 bears –OH, and the C1 terminal –CH2–OH is converted to –CH2–O–PO3H−. The isotopic variant contains one or more D atoms at defined positions depending on specification.

Synthetic Utility

This item is not typically a building block for organic synthesis. Nevertheless, it has niche utility in biochemical and analytical method development.

• Limited chemical transformation use (literature/general)

  • Enzymology: Serves as a substrate/standard in assays of S1P phosphatases and lyase; isotopic labeling enables mass-differentiated product tracking (e.g., formation of labeled sphingosine upon dephosphorylation).
  • Derivatization for analytics: Under some workflows, phosphate derivatization (e.g., methylation) can enhance chromatographic behavior; the deuterated label maintains mass separation from analyte.

• Retrosynthetic value

  • Minimal; the molecule’s complex amphipathic nature and defined stereochemistry make it more a target than a synthon. When needed, total synthesis or semi-synthesis introduces deuterium at defined positions; however, such routes are specialized and outside routine lab practice.

If your objective is organic synthesis, consider simpler sphingoid bases or protected intermediates. For quantitation and tracing, this deuterated standard is the appropriate choice.

Target Specificity

Not applicable. This product is a small-molecule lipid standard, not an antibody or affinity reagent.

• No antigen, epitope, clone, isotype, or species-reactivity information applies.
• For receptor-binding studies involving S1PR1–5, consult primary literature; this listing provides no target-binding specifications.

Häufig gestellte Fragen

What is the purity of this product?

This product is supplied at ≥99% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

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 2260670-15-1. InChIKey DUYSYHSSBDVJSM-AVMMVCTPSA-N.

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.