15-Hydroxy Lubiprostone-d , CAS No.1217511-55-1

CAS: 1217511-55-1 Cat. No.: H1450744 Formula: C₂₀H₂₇D₇F₂O₅ Peso molecolare: 399.52

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

15-Hydroxy Lubiprostone-d 7 is the deuterium labeled 15-Hydroxy Lubiprostone.

Specifications

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Nomi e identificatori

Peso molecolare

399.52

Application Protocols

• Item-specific (Product Data)

  • No validated application protocols are provided for this item; refer to CoA/Spec Sheet.

• Literature/general example workflows (fit-for-purpose validation required)

  • LC–MS/MS internal standard use
    • Prepare a 1–5 mM stock in anhydrous DMSO. Aliquot and store at −20°C, protected from light.
    • Prepare working IS solution (e.g., 10–100 ng/mL) in 50:50 MeOH:water with 0.1% formic acid.
    • Spike a constant volume of IS into calibration standards, QCs, and study samples before extraction to correct for recovery and matrix effects.
    • Extract via protein precipitation (3–4 volumes cold MeOH/ACN), SPE (C18/HLB), or LLE (MTBE/EtOAc) as suited to your matrix. Dry under N2 at ≤30°C, reconstitute in initial mobile phase, and analyze by LC–MS/MS.
  • Stability check
    • Assess short-term bench-top and autosampler stability, freeze–thaw stability, and long-term frozen stability under your exact conditions. Monitor any H/D exchange by HRMS if labeling positions are at risk.
  • Co-elution/identity confirmation
    • Inject unlabeled analyte and deuterated standard separately and as a mixture. Verify consistent retention time and expected MS transitions with minimal cross-talk between channels.

• Note

  • The above are general templates. Optimize concentrations, volumes, and transitions for your instrument and assay.

Biological Roles

• Item-specific (Product Data)

  • No biological role claims are made for this catalog item. It is designated for research use only.

• Literature/general context for lubiprostone and hydroxylated analogs

  • Lubiprostone is a prostaglandin E1–like bicyclic fatty acid derivative. Hydroxylation at C15 is a known metabolic/structural variation within prostaglandin analog families.
  • Such molecules can engage lipid-signaling pathways in vitro and are of interest when studying metabolism, receptor engagement, and downstream signaling typical of prostaglandin-like compounds. Actual biological potency and selectivity of 15-hydroxy lubiprostone specifically must be experimentally determined and are not specified for this item.
  • Deuterated analogs are typically biologically isofunctional with minimal changes in receptor interactions when deuterium is placed at non-exchangeable, non-reactive positions; however, they are primarily used as analytical standards rather than as biological probes.

• Research relevance

  • Internal standards help quantify endogenous or xenobiotic levels of hydroxylated prostaglandin analogs in complex matrices (cell lysates, plasma, tissue homogenates) to support biochemical pathway elucidation, metabolism profiling, and stability testing.

• Important note

  • No medical or clinical claims are made. Any assessment of biological activity requires dedicated experimentation with appropriate controls. Consult the primary literature for receptor pharmacology and pathway mapping of the specific analog of interest.

Buffer Applications

• Applicability

  • This product is a lipophilic, polyoxygenated small molecule standard and is not a buffer component. Conventional buffer formulation guidance (pKa selection, ionic strength) is not typically applicable.

• Practical handling in buffered systems (literature/general)

  • If dilution into aqueous buffer is required (e.g., for bioassays), first prepare a concentrated stock in DMSO or ethanol, then add slowly to the buffer with vigorous mixing to avoid precipitation. Final cosolvent levels are commonly kept at ≤0.5–1% v/v for cell-based assays, if applicable to your study design.
  • To increase apparent solubility transiently, include carrier proteins (e.g., BSA) or cyclodextrins where methodologically appropriate; validate for nonspecific binding and background.
  • Avoid high-pH buffers unless necessary, as strong base can promote isomerization or hydrolysis of prostaglandin-like structures (general caution).

• Summary

  • Use this material as an analyte or internal standard within buffered workflows rather than as a buffer constituent. Optimize cosolvent content and mixing protocols to maintain homogeneity.

Green Alternatives

• Context

  • This item is a specialized deuterated, polyoxygenated lipid analog intended primarily as an analytical standard or research reference. Green alternatives are therefore considered at the level of solvent and workflow selection rather than replacing the analyte itself.

• Greener solvent strategies (literature/general)

  • Prefer MeOH or EtOH over chlorinated solvents for routine handling when feasible.
  • Replace acetonitrile with ethanol/isopropanol in some LC methods where selectivity permits, acknowledging changes in elution strength and viscosity.
  • Utilize 2-propanol or ethyl acetate for film dissolution instead of CH2Cl2/CHCl3 when compatible with downstream steps.

• Process considerations

  • Use microscale preparations and single-use aliquots to minimize solvent consumption and chemical waste.
  • Adopt aqueous-organic mobile phases with volatile modifiers (formic acid, ammonium formate/acetate) to simplify waste treatment in LC–MS.

• Trade-offs (general)

  • Chlorinated solvents offer superior solubility and recovery for hydrophobic lipids; greener replacements may reduce recovery or change chromatography and require method re-optimization.
  • Higher viscosity alcohol-rich mobile phases can increase backpressure and may decrease MS sensitivity compared to ACN.

• Summary

  • Maintain the analyte identity for metrological traceability; implement green chemistry by optimizing solvent systems, scaling down, and consolidating steps to cut waste generation without compromising analytical performance.

Pharmaceutical Uses

• Item-specific (Product Data)

  • No pharmacopeial grade or excipient status is specified for this item; refer to CoA/Spec Sheet. For research use only.

• Literature/general context

  • Deuterated hydroxylated analogs of lubiprostone are primarily research/analytical tools used for method development, stability studies, and quantitative bioanalysis (e.g., isotope-dilution LC–MS) of related substances in development or quality control settings.
  • As a deuterated reference, it can support impurity profiling, forced-degradation studies, and metabolite identification workflows by providing co-elution and MS response tracking relative to the non-deuterated target.

• Formulation/R&D roles (non-therapeutic)

  • Reference standard: calibration, system suitability, and recovery tracking in extraction and sample preparation.
  • Stability-indicating methods: monitor oxidative/hydroxylative transformation products in stress studies by spiking with isotopically labeled analogs.
  • Matrix-matched validation: assess ion suppression/enhancement and accuracy in biological or formulation matrices.

• Compliance note

  • This product is not produced or qualified to any pharmacopeial monograph based on the available information. It should not be used as an API, excipient, or in human/animal applications. Establish traceability via internal or third-party certified reference materials if required by your quality system.

Physical Properties

• Item-specific (Product Data)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Other specifications (bp, mp, density, UV cutoff, solubility parameters): Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general (for class context; not product specifications)

  • State/appearance: Many prostaglandin-like, polyhydroxylated fatty-acid derivatives are oils or low-melting amorphous solids that can be tacky and hygroscopic; they are often supplied as films or solutions.
  • Solubility profile: Typically soluble in polar aprotic organics (DMSO, DMF), moderately soluble in lower alcohols (MeOH, EtOH), miscible with chlorinated solvents (CH2Cl2, CHCl3), and poorly soluble in water at neutral pH due to lipophilicity and partial ionization of the carboxylate.
  • pKa (carboxylic acid, typical): approximately 4–5 (literature, generic for aliphatic carboxylic acids with proximal electron-withdrawing/oxygenated substituents).
  • LogP/logD: Prostaglandin analogs and lubiprostone derivatives are generally lipophilic (literature). Specific values depend on substitution and deuteration and must be confirmed experimentally for the item.
  • Optical rotation: Chiral lipids may display significant [α]D; actual values are compound- and lot-dependent and should be taken from the CoA where available.

• Practical notes

  • Prepare concentrated stocks in dry, oxygen-free solvent when possible and protect from light to minimize oxidative degradation and isomerization (general guidance for polyoxygenated lipids).

Quality and Grades

• Item-specific (Product Data)

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

• Interpreting grade for deuterated standards (literature/general)

  • Isotopic purity/enrichment: For deuterium-labeled standards, two independent quality attributes are common—chemical purity (by HPLC/GC/NMR) and isotopic enrichment (atom % D at specified positions), often supported by HRMS/isotopologue distribution. These parameters directly impact quantitative LC–MS accuracy.
  • Residual solvents and volatiles: Trace solvent content and water should be controlled because hygroscopic films can pick up moisture; review CoA for Karl Fischer and residual solvent data if provided.
  • Identity confirmation: 1H/13C NMR, 2H NMR (where applicable), HRMS, and sometimes IR/optical rotation are used to verify structure and stereochemistry for prostaglandin-class molecules.
  • Chromatographic purity: Reporting at a specific detection wavelength can underestimate impurities in chromophore-poor matrices; orthogonal detection (ELSD/CAD) is often used in addition to UV for lipids.

• Practical guidance

  • When using as an internal standard, match the matrix and extraction workflow used for the analyte. Lot-to-lot verification (retention time, MS transitions, response factors) is recommended. If grade is unspecified, assume research grade and validate fit-for-purpose in your method.

Reaction and Applications

• Item-specific (Product Data)

  • Manufacturer applications: Not specified for this item in the catalog entry beyond “For research use only.”

• Literature/general applications relevant to 15-hydroxy lubiprostone analogs and their deuterated forms

  • Analytical internal standard: Deuterium-labeled analogs are widely used as isotope-dilution internal standards for quantitative LC–MS/MS of the corresponding unlabeled analyte (e.g., 15-hydroxy lubiprostone) in biological or formulation matrices. The mass shift separates analyte and IS transitions while matching extraction and ionization behavior.
  • Metabolism studies: Useful in tracing oxidative/hydroxylation pathways of lubiprostone under microsomal or chemical oxidation conditions; deuterium can aid in kinetic isotope effect (KIE) probing when label is at reactive positions (labeling sites not specified here).
  • Method development: Employed to optimize chromatographic resolution, assess recovery in SPE/LLE, and correct for matrix effects.
  • Structural reference: Provides MS/MS fragmentation benchmarks for assigning product ions of the unlabeled metabolite.

• Practical tips (general)

  • Prepare calibration curves with a fixed IS concentration across standards and QCs. Verify absence of H/D back-exchange under sample preparation and LC–MS conditions (particularly if deuterium is on exchangeable positions—site not specified here; confirm via CoA/SDS or supplier note).
  • Avoid prolonged exposure to strong bases or elevated temperatures that could induce isomerization or hydrolysis of polyoxygenated lipid motifs.

Reaction Conditions

• Item-specific (Product Data)

  • No reaction condition data are specified for this item; refer to CoA/Spec Sheet.

• Literature/general guidance relevant to handling and analytical use

  • Stock solutions: 1–10 mM in anhydrous DMSO or MeOH, stored at −20°C in amber vials. Thaw on ice and minimize freeze–thaw cycles by aliquoting.
  • LC–MS/MS: Electrospray in negative-ion mode often provides strong signal for carboxylate-containing lipids; positive mode may be used with adduct formation (e.g., [M+NH4]+) depending on method. Optimize source temperature and declustering potentials to limit in-source fragmentation.
  • Chromatography: Reverse-phase C18 or phenyl-hexyl columns; gradients from aqueous 0.1% formic acid (or ammonium acetate) to ACN/MeOH. Column temps 30–45°C may improve peak shape for lipophilic acids. Guard columns recommended due to matrix fouling.
  • Derivatization (optional, literature): For GC–MS, convert the acid to a methyl/ethyl ester and protect polyols with silylating agents under mild conditions; confirm no H/D exchange during derivatization if deuterium is near exchangeable sites.
  • Stability: Avoid strong base (>pH 9) and prolonged heating. Work under subdued light and inert atmosphere when feasible to suppress oxidation/isomerization.

• Yields/kinetics

  • Not applicable; this product is supplied as a finished analytical standard. Any reported yields or rates would pertain to specific synthetic literature and are not item-specific.

Safety and Handling

• Item-specific (Product Data)

  • GHS classification: Not specified for this item; refer to SDS.
  • Signal word: Not specified for this item; refer to SDS.
  • Hazard (H) statements: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.
  • Storage conditions: Store at -20°C.
  • Shipping: Ice chest + ice pads.
  • Research use: For research use only.

• General safety guidance (literature/general; consult the SDS for authoritative instructions)

  • PPE: Use laboratory coat, safety glasses, and appropriate chemically resistant gloves. Handle inside a fume hood to avoid inhalation of aerosols/solvent vapors.
  • Handling: Polyunsaturated/oxygenated lipids may be sensitive to air, heat, and light. Work quickly with cold, dry solvents; minimize headspace oxygen. Use amber vials or foil wrap.
  • Incompatibilities: Strong oxidizers, strong bases (may cause saponification/epimerization), and strong acids (may catalyze dehydration/isomerization). Avoid prolonged exposure to elevated temperatures.
  • First-aid overview: In case of skin contact, wash with soap and water. If in eyes, rinse with water for several minutes and seek medical advice. If inhaled, move to fresh air. If ingested, rinse mouth and seek medical attention. Always follow site SOPs and SDS guidance.
  • Waste: Dispose of solutions and residues according to institutional hazardous waste procedures for organic chemicals; deuterated compounds are managed as standard organic chemical waste unless otherwise specified by local regulation.

Solvent Selection

• Item-specific (Product Data)

  • No solvent recommendations are specified for this item; refer to CoA/Spec Sheet.

• Literature/general solvent behavior for prostaglandin-like, polyoxygenated lipids

  • Polarity class: Amphiphilic, overall lipophilic with an acidic headgroup. Often handled as the free acid or occasionally as salts/esters in methods development.
  • Good solvents (typical): DMSO, DMF, methanol, ethanol, acetonitrile (moderate), dichloromethane, chloroform, ethyl acetate. Limited solubility in nonpolar hydrocarbons unless esterified.
  • Aqueous media: Poor water solubility at neutral pH as free acid; solubility increases above pH ~7 by forming the carboxylate, but base-sensitive functional groups may degrade. Use caution with high-pH buffers.
  • Sample prep for LC–MS: Prepare primary stocks at 1–10 mM in anhydrous DMSO or MeOH. For working standards, dilute into 50–80% aqueous MeOH/ACN containing 0.1% formic acid (to suppress adsorption) immediately prior to use.
  • Adsorptive losses: Minimize by using silanized glass, low-bind plastics, and adding small amounts of organic modifier (e.g., 0.1–1% DMSO) to working solutions.

• Comparison (general)

  • DMSO: maximal solvating power; good for long-term frozen aliquots.
  • MeOH/EtOH: convenient for daily working solutions and LC–MS compatibility.
  • CH2Cl2/CHCl3: excellent for film formation and recovery, but avoid for LC–MS injection without exchange.

Storage and Reconstitution

• Item-specific (Product Data)

  • Storage conditions: Store at -20°C.
  • Shipped in: Ice chest + ice pads.
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• General guidance for deuterated, polyoxygenated lipid standards (literature/general)

  • Protection: Store in airtight, amber containers to protect from moisture, oxygen, and light. If supplied as a film, purge headspace with inert gas (N2/Ar) after each use when feasible.
  • Aliquoting: Prepare single-use aliquots of concentrated stock solutions (e.g., 1–10 mM in anhydrous DMSO or MeOH) to minimize freeze–thaw cycles and adsorption losses.
  • Thawing: Warm to room temperature briefly or thaw on ice before opening to reduce condensation. Vortex and, if necessary, briefly sonicate to ensure homogeneity.
  • Reconstitution: For solid/film material, dissolve in a small volume of dry solvent (DMSO, MeOH, or CH2Cl2/MeOH mixture), then dilute to the desired concentration. Filter through a low-protein-binding 0.2 µm PTFE filter if particulate matter is observed.
  • Stability: Avoid repeated freeze–thaw cycles and prolonged exposure to basic conditions. Confirm stability under your specific storage and autosampler conditions; track by LC–MS peak area and purity profile.

• Documentation

  • Record preparation dates, solvent lot, concentration, and storage temperature for each aliquot. Refer to the product’s CoA/Spec Sheet for any lot-specific stability or handling notes.

Structure and Identity

• Item-specific (Product Data)

  • Product name: 15-Hydroxy Lubiprostone-d (SKU: H1450744)
  • CAS: 1217511-55-1
  • 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.
  • Isotopic label: “-d” denotes a deuterium-labeled analog (degree and positions of deuteration not specified).

• Literature/general description (for context; not item-specific specs)

  • 15-Hydroxy lubiprostone is described in the literature as a hydroxylated metabolite/analog of the prostaglandin E-type bicyclic fatty acid derivative lubiprostone. Structures in this class typically feature:
    • A polyoxygenated, 20-carbon chain framework with a constrained bicyclic core reminiscent of prostaglandins.
    • Multiple stereocenters (configurations vary by analog) and terminal carboxylic acid functionality.
    • Additional secondary hydroxyl at C15 relative to lubiprostone; the exact regiochemistry and stereochemistry should be confirmed from the CoA/SDS for this catalog item.
  • Deuterium incorporation is commonly used to create mass-differentiated internal standards for LC–MS/MS assays; the labeling pattern determines the exact formula and exact mass shift.

• 2D structural features (narrative; literature context)

  • Expected functional groups: carboxylic acid, several secondary/tertiary alcohols, aliphatic chain segments, possibly an internal cyclic ether/bicyclic ring system characteristic of lubiprostone analogs.
  • Stereochemistry: multiple chiral centers; absolute configurations and deuterium placement must be verified against the product’s CoA.

Synthetic Utility

• Applicability

  • As a deuterium-labeled, functionally elaborate molecule, 15-Hydroxy Lubiprostone-d is not a general-purpose building block. Its principal synthetic utility lies in serving as a labeled comparator in analytical and mechanistic studies.

• Literature/general utility

  • Isotopic tracing: When deuterium is positioned at mechanistically relevant sites, changes in reaction rates and product distributions can reveal oxidation pathways and potential kinetic isotope effects during in vitro metabolism or chemical transformations.
  • Reference in synthesis validation: Enables verification of synthetic routes to 15-hydroxy lubiprostone by co-injection and MS/MS matching, supporting assignment of stereochemistry and assessing isomerization.
  • Derivatization benchmarking: Prostaglandin-like acids are often derivatized (e.g., methyl/ethyl esters, silyl ethers) for GC–MS or stability; the deuterated analog provides a control for derivatization efficiency and artifact monitoring.

• Functional group considerations (general)

  • Carboxylic acid enables ester formation and amide coupling for prodrug or analytical derivatization studies.
  • Multiple alcohols allow selective protection (e.g., TBDMS/TBS, acetonide) and deprotection, though conditions should be mild to avoid rearrangement of the bicyclic core typical of lubiprostone analogs.

• Note

  • The exact deuteration pattern is critical for interpreting results; consult the CoA for labeling sites before designing mechanistic experiments.

Target Specificity

• Not applicable to this product type.
  • This item is a small-molecule, deuterated lipid analog and not an antibody, oligonucleotide, enzyme, or affinity reagent. There are no antigen/epitope, clone, isotype, or species-reactivity characteristics.
  • For studies of receptor interactions (e.g., prostaglandin-related receptors), target specificity must be determined experimentally for the specific unlabeled/labeled analog; no target data are provided for this item.