15(S)-HEPE-d , CAS No.S1449656

CAS: S1449656 Cat. No.: S1449656 Formula: C₂₀H₂₅D₅O₃ Peso molecolare: 323.48

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

15(S)-HEPE-d 5 is the deuterium labeled 15(S)-HEPE.

Specifiche

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

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Nomi e identificatori

Peso molecolare

323.48

Application Protocols

Tested/validated application details are not specified for this item; refer to CoA/Spec Sheet.

General note: For isotope-dilution LC–MS/MS workflows with oxylipins, laboratories commonly spike deuterated standards into samples prior to extraction, use MTBE or ethyl acetate LLE or SPE (silica/HLB), and quantify by MRM in negative-ion ESI. Optimize instrument parameters empirically for your system and verify the mass shift and retention matching to the unlabeled analyte.

Biological Roles

General/literature context (biochemistry; not medical claims)

• Origin: 15(S)-HEPE is formed by 15‑lipoxygenase (15‑LOX) oxygenation of eicosapentaenoic acid (EPA, 20:5 n‑3), generating a chiral 15(S) hydroxy substituent and a conjugated diene system.
• Chemical family: ω‑3 oxylipin; monohydroxy eicosanoid analogous to 15‑HETE from arachidonic acid but derived from EPA.
• Fate and transformations: Can undergo further enzymatic oxidation/reduction (e.g., to keto derivatives) or nonenzymatic peroxidation and isomerization. Conjugation to glycerolipids or esterification to cholesteryl esters may occur in complex lipid pools (literature).
• Signaling context: Oxylipins often interact with nuclear receptors (e.g., PPARs) and can modulate enzyme activities and gene expression in vitro; specific receptor interactions for 15(S)-HEPE are reported in literature but are context- and concentration-dependent.
• Analytical relevance: Because endogenous levels can be low and matrix-sensitive, stable-isotope–labeled 15(S)-HEPE-d is valued for accurate quantitation in biological samples by isotope-dilution LC–MS/MS.

Note on isotope effects

• Deuteration minimally perturbs bulk physicochemical behavior but provides a mass shift for MS. If deuteriums reside on exchangeable positions (allylic/benzylic or hydroxyl), limited D/H exchange can occur under protic/acidic/basic conditions; labeling maps in the CoA guide method design.

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare biological buffers. For experimental work, dissolve in compatible organic solvents (e.g., methanol, ethanol, acetonitrile, isopropanol, or DMSO) and, if needed, dilute into buffered aqueous systems with appropriate co-solvent and mild acid (e.g., 0.01–0.1% formic or acetic acid) to maintain solubility and minimize adsorption.

Green Alternatives

Context: 15(S)-HEPE-d is an analyte/standard rather than a solvent or reagent used in bulk. Greenness pertains mainly to handling and sample preparation choices.

Greener handling strategies (general)

• Prefer alcohols over chlorinated solvents for stock solutions and LC mobile phases when method performance allows (e.g., MeOH/EtOH vs CHCl3/DCM).
• Use MTBE or ethyl acetate instead of hexane/DCM for lipid extractions in LLE workflows (literature: Matyash MTBE method improves phase separation and reduces chlorinated solvent use).
• Minimize solvent volumes by micro-extraction and 96‑well plate SPE formats; adopt UHPLC to reduce mobile phase consumption.
• Employ amber glass microvials with low-dead-volume inserts to cut waste and exposure.

Trade-offs (balanced view)

• Alcohol-rich eluents may slightly reduce retention of very nonpolar lipids; method re-optimization may be needed.
• DMSO offers superior solubility but is less volatile and can linger in LC systems; alcohol stocks are greener but may have lower solubility limits.

Comparison snapshot (general; not item-specific)

• Methanol/Water (0.01–0.1% formic acid): LC‑MS compatible, greener, supports negative-ion ESI.
• Isopropanol/Acetonitrile: Strong elution for lipids with manageable toxicity; higher viscosity may affect backpressure.
• Avoid: Routine use of chloroform or dichloromethane unless extraction efficacy demands it.

Pharmaceutical Uses

No pharmacopeial or excipient designation is provided for this item.

Appropriate use domain (general)

• Analytical reference standard: Deuterated 15(S)-HEPE is suited for isotope-dilution LC–MS/MS methods supporting research and QC of ω‑3–containing materials (e.g., to monitor oxylipin profiles during formulation stress testing).
• Process and stability studies: Useful as a marker in oxidative stress assays of EPA-rich matrices (oils, emulsions) to understand formation of specific oxylipins (research settings).

Item-specific details

• Grade/purity, residual solvents, isotopic enrichment, and stabilizers: Not specified for this item; refer to CoA/Spec Sheet.

Compliance note

• For research use only (RUO). Not for use in humans or for diagnostic procedures. No clinical or therapeutic claims are made or implied.

Physical Properties

Item-specific specifications (this product)

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Purity/grade: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight, formula, stereochemical purity, isotopic enrichment: Not specified for this item; refer to CoA/Spec Sheet.

General/literature properties for 15(S)-HEPE and deuterated analogs (for context; not product specifications)

• Physical state: viscous oil to waxy solid, depending on temperature and solvent (literature, typical for long-chain oxylipins).
• Solubility: low in water; soluble in polar organic solvents (methanol, ethanol, acetonitrile, isopropanol) and in DMSO; highly soluble in nonpolar/medium polarity organics (ethyl acetate, MTBE, hexane mixtures) when esterified; free acid shows better solubility in alcohols (literature).
• pKa (carboxylic acid): ~4.5–5.0 (literature, fatty acids).
• logP (neutral acid): typically high (≈5–7 for C20 oxylipins; literature), decreases upon ionization at basic pH.
• UV absorbance: conjugated diene/triene features can lead to λmax in the 230–235 nm region; exact spectrum depends on double-bond geometry (literature).
• Optical activity: single stereocenter at C15 (S); sign/magnitude of [α] depends on solvent and concentration (literature).

Handling behavior (general)

• Susceptible to autoxidation/isomerization; protect from light, heat, and air. Work cold, minimize exposure to bases and strong acids that can promote isomerization.

Quality and Grades

Item-specific quality

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Isotopic enrichment: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizer/additives (e.g., BHT, acidified solvent): Not specified for this item; refer to CoA/Spec Sheet.

How to interpret typical quality attributes for deuterated oxylipin standards (general guidance)

• Chemical purity: Expressed as % area by HPLC/UPLC or GC; high purity minimizes matrix interferences in quantitative assays.
• Isotopic purity (D-content): Reported as atom % D or as exact d‑label (e.g., d4, d5, d8). Sufficient mass shift is critical to avoid overlap with natural isotope envelopes of endogenous analytes.
• Positional labeling: Location of deuterium affects fragmentation pathways and potential D/H exchange; Positional map is often provided in CoA.
• Stereochemical purity: 15(S) configuration should be verified (e.g., chiral LC) to match biosynthetic analyte; racemization reduces quantitative fidelity in enantioselective assays.
• Residual solvents/water/peroxides/metal limits/UV cutoffs: Not specified for this item; refer to CoA/Spec Sheet for any applicable controls.

Fit-for-purpose recommendations

• For LC–MS/MS quantitation in lipidomics, prioritize lots with high isotopic enrichment, documented stereochemistry (15S), and low peroxide value. Confirm absence/presence of stabilizers if compatibility with downstream assays (e.g., derivatization) is critical.

Reaction and Applications

Primary use domain: analytical internal standard for quantitative lipidomics and oxylipin profiling, and as a reference material in enzymology of eicosanoid biosynthesis (general/literature context).

Analytical applications

• LC–MS/MS internal standard: Deuterium label provides a defined mass offset vs endogenous 15(S)-HEPE, enabling correction for extraction, ionization, and matrix effects. Use negative-ion ESI (m/z [M–H]−) for free acids; optimize collision energies for diagnostic fragments (literature).
• GC–MS workflows: Derivatize to pentafluorobenzyl (PFB) esters to enhance negative-ion chemical ionization; the D-label supports isotope-dilution quantitation (literature).
• Stability checks: Monitor for peroxide formation and geometric isomerization; periodic QC by UPLC–MS and UV at ~235 nm can flag degradation.

Biochemical applications

• Enzyme studies: Substrate/standard in assays involving 15‑lipoxygenase and downstream metabolic transformations; deuterium kinetic isotope effects can be probed when D is positioned near reactive sites (literature, label-position dependent).

Synthetic/derivatization utilities

• Temporary protection of the 15‑hydroxyl (e.g., as TMS or acetate) to control chromatographic behavior; reversible under mild conditions (literature).
• Esterification (Me/Et esters) to tailor volatility/solubility for GC or SFC; hydrolyze back to free acid as needed.

Practical tips

• Work on ice, under N2/Ar, in amber glass. Prepare fresh dilutions daily for high-sensitivity assays. Validate absence of D/H back-exchange under your conditions.

Reaction Conditions

General, literature-based conditions relevant to handling/derivatization of 15(S)-HEPE and analogs (not product specifications):

• Esterification (methyl ester for GC)

  • Reagents: 1–5% HCl in MeOH, or BF3·MeOH.
  • Conditions: 0–25°C, 10–60 min; exclude air/light. Quench with saturated NaHCO3 and extract with hexane/MTBE. Expected conversion: high for free acids; monitor to avoid overreaction of allylic alcohol.

• Alcohol protection (TMS ether)

  • Reagents: TMSCl (1.2–1.5 equiv), imidazole or pyridine, anhydrous CH2Cl2.
  • Conditions: 0–25°C, 15–60 min under N2/Ar. Workup with aqueous NH4Cl; avoid acidic silica to prevent isomerization.

• Oxidation to 15‑keto derivative

  • Reagent: Dess–Martin periodinane (1.1–1.5 equiv) in dry CH2Cl2.
  • Conditions: 0–10°C, 15–45 min; quench with aqueous Na2S2O3/NaHCO3. Yields: often good to excellent when oxygen and heat are minimized.

• LC–MS sample preparation

  • Stocks: 0.1–1 mg/mL in MeOH or EtOH, stored cold and under N2/Ar in amber vials.
  • Working dilutions: prepare freshly in MeOH/H2O (e.g., 70:30 with 0.01–0.1% acetic acid). Inject promptly to reduce on‑column oxidation.

Cautions

• Deuterium integrity: Avoid strong protic or basic media at elevated temperature to limit D/H exchange, particularly if labeling is at positions susceptible to exchange (consult CoA labeling map).

Safety and Handling

Authoritative safety data must be taken from the product SDS.

Item-specific hazard information

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

General safety guidance for oxylipins and deuterated lipid standards

• Likely hazards: May cause skin/eye irritation; avoid inhalation of aerosols and ingestion. Not volatile but can form fine droplets.
• PPE: Use lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Handle solutions in a fume hood to limit aerosol exposure.
• Incompatibilities: Avoid strong oxidizers, strong bases/acids (can induce isomerization/esterification), and prolonged exposure to light/air.
• Stability considerations: Polyunsaturated chains are prone to peroxidation. Work under inert gas (N2 or Ar), use amber vials, and keep cold.
• First aid (overview; defer to SDS):
  • Skin: Wash with soap and water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
  • Inhalation: Move to fresh air. Seek medical attention if symptoms persist.
  • Ingestion: Rinse mouth. Do not induce vomiting; seek medical advice.
• Spill response: Absorb with inert material (silica, vermiculite), place in chemical waste. Decontaminate surfaces with suitable organic solvent, then detergent.
• Waste disposal: Collect as organic hazardous waste according to institutional and regulatory requirements.

Logistics

• Storage conditions (item-specific): Store at -20°C.
• Shipping (item-specific): Shipped in ice chest with ice pads to maintain cold chain.

Solvent Selection

Compound class context: amphiphilic long-chain polyunsaturated fatty acid (free acid) with a secondary alcohol; low aqueous solubility; better solubility in polar organics and mixed solvent systems.

General solvent guidance (literature; not item-specific specs)

• Stock solutions: Commonly prepared at 0.1–10 mg/mL in ethanol, methanol, isopropanol, acetonitrile, or DMSO. Alcohols (MeOH/EtOH) balance solubility and LC‑MS compatibility.
• Aqueous media: Use co-solvent systems (e.g., 50–80% MeOH/H2O or MeOH/Water with 0.01–0.1% acetic or formic acid) to keep the free acid in solution and suppress adsorption.
• Nonpolar solvents: Ethyl acetate, MTBE, or hexane mixtures are useful for liquid–liquid extraction; however, the free acid favors more polar organics compared to its methyl/ethyl esters.
• Adsorption mitigation: Add small amounts of BSA-free carrier (0.1 mg/mL fatty-acid–free BSA for biological buffers) or 0.1% organic acid in LC eluents to reduce losses; pre-rinse plastics with solvent or use silanized glass.

Comparison to alternatives (selection rationale)

• vs DMSO: Highest solvating power but can complicate negative-ion ESI; alcohols are often preferred for lipidomics injections.
• vs chlorinated solvents (DCM/CHCl3): Strong solvents for lipids but less green and less LC-compatible; reserve for extraction or synthetic work.
• pH control: Keep solutions slightly acidic for stability and consistent ionization; avoid strong base that induces isomerization and saponification.

Storage and Reconstitution

Item-specific storage and shipping

• Storage: Store at -20°C.
• Shipping: Ice chest with ice pads (maintains cold chain).

General best practices for this compound class (not product specifications)

• Light/oxygen protection: Use amber vials; blanket headspace with N2/Ar. Minimize freeze–thaw cycles by aliquoting upon first thaw.
• Recommended solvents for reconstitution: Methanol or ethanol are commonly used for primary stocks; DMSO or acetonitrile are alternatives where higher solubility is required. Aim for 0.1–10 mg/mL depending on use.
• Working solutions: Prepare fresh daily or keep at 0–4°C protected from light for short periods. Acidify lightly (e.g., 0.01–0.1% acetic/formic acid) to improve stability and reduce adsorption.
• Container considerations: Prefer silanized glass or high-quality polypropylene; pre-rinse containers and LC vials with the chosen solvent to reduce adsorption.
• Stability notes: Polyunsaturated oxylipins are susceptible to peroxidation and isomerization; avoid basic pH and elevated temperatures. Periodically check integrity by LC–MS or UV at ~235 nm.

Reconstitution amount, exact concentration, and any stabilizers for this item: Not specified for this item; refer to CoA/Spec Sheet.

Use restriction: For research use only.

Structure and Identity

Brief overview: 15(S)-HEPE-d is a deuterium-labeled analog of 15(S)-hydroxyeicosapentaenoic acid (15(S)-HEPE), an ω-3 oxylipin derived from EPA. The “-d” denotes stable-isotope labeling (number and positions of D atoms not specified for this item).

• Item-specific identifiers

  • SKU: S1449656
  • Product name: 15(S)-HEPE-d
  • CAS: S1449656 (catalog placeholder)
  • 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)

  • Core scaffold: C20 polyunsaturated fatty acid with a terminal carboxylic acid and a single secondary alcohol at C15 with S absolute configuration.
  • Unsaturation pattern: derived from eicosapentaenoic acid (20:5; ω-3) with five cis double bonds; exact double-bond geometry/positions per 15-LOX pathway (literature) but may vary by isomeric specification; confirm via CoA.
  • Functional groups: one carboxylic acid (–CO2H), one secondary alcohol (–CHOH–), multiple alkenes.
  • Isotope label: one or more hydrogens replaced with deuterium to provide a mass shift for LC–MS quantitation; labeling positions and D-number not specified for this item.

• 2D description in words (general)

  • A 20‑carbon chain terminating in a carboxylate headgroup (C1) with five isolated/cumulated cis alkenes along the chain and a chiral secondary hydroxyl at C15 with S configuration; the ω-3 tail carries deuterium label(s) providing a defined mass offset relative to unlabeled 15(S)-HEPE.

Synthetic Utility

Although 15(S)-HEPE-d is primarily an analytical standard, its functional groups provide useful handles for derivatization and method development (general literature guidance):

• Carboxylic acid chemistry

  • Esterification to methyl/ethyl esters using acid catalysts (e.g., HCl/MeOH, BF3/MeOH) to enhance GC volatility or adjust chromatographic behavior; saponification returns the free acid.
  • Amide coupling (e.g., EDC/HOBt, HATU) to immobilize on solid supports for affinity studies or to generate reporter conjugates.

• Secondary alcohol transformations

  • Protection as silyl ethers (TMS/TBDMS) or acetates to suppress polarity during separations; deprotection under mild conditions preserves double-bond geometry.
  • Oxidation to the corresponding 15‑keto‑EPE using Dess–Martin periodinane or Swern conditions (low temperature to limit isomerization).

• Double-bond considerations

  • Polyunsaturation is sensitive to acid/base and heat; use low temperatures, antioxidants, and inert atmosphere. Avoid strong protic acids over extended times to prevent double-bond migration/cis–trans isomerization.

• Isotope label stewardship

  • Maintain conditions that minimize D/H exchange (avoid prolonged exposure to strong acids/bases and high temperatures). Confirm mass shift and isotopic purity by HRMS after derivatization.

Target Specificity

Not applicable. This product is a small-molecule lipid standard, not an antibody or affinity reagent. No antigen, epitope, or species reactivity information applies.