4'-trans-Hydroxy Cilostazol-d , CAS No.T1444697

CAS: T1444697 Cat. No.: T1444697 Fórmula: C₂₀H₂₂D₅N₅O₃ Peso molecular: 390.49

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

4'-trans-Hydroxy Cilostazol-d 5 is the deuterium labeled 4'-trans-Hydroxy Cilostazol.

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: 390.49

Application Protocols

No vendor-validated assay protocols are provided in the Product Data. The following general protocol outlines use as an LC–MS/MS internal standard; adjust to your laboratory’s method and regulatory guidance.

• Stock preparation: Dissolve accurately weighed material in DMSO, methanol, or acetonitrile to prepare a primary stock (e.g., 0.5–1.0 mg/mL). Actual solubility for this item is not specified; confirm visually.
• Aliquoting: Prepare single-use aliquots in low-bind vials; store at −20°C.
• Working solutions: Dilute the stock into 50:50 ACN:water or MeOH:water with 0.1% formic acid (or method-specific buffer) to prepare an internal standard working solution at the desired concentration.
• Sample spiking: Add a fixed volume of IS working solution to all calibrators, QCs, and unknowns before extraction (protein precipitation, LLE, or SPE). Maintain constant IS concentration across the batch.
• Chromatography (example framework): Reversed-phase C18 or phenyl-hexyl column; gradient from aqueous buffer (e.g., 5–10 mM ammonium formate, 0.1% formic acid) to organic (ACN or MeOH). Monitor MS/MS transitions for both analyte and IS.
• System suitability: Verify retention time match, peak symmetry, and consistent IS response. Evaluate carryover and matrix effects.
• Stability: Limit bench-top and autosampler times; re-inject QCs to monitor drift.

Note: These are general, literature-informed steps; exact conditions must be established and validated for your specific instrumentation and assay.

Biological Roles

Item-specific biological data are not provided in the Product Data. The following context reflects general, literature-based information about the parent compound and this metabolite class, intended solely to inform research use.

• Metabolic context (literature): 4′-Hydroxy metabolites of cilostazol arise from oxidative metabolism of the cyclohexyl ring (e.g., via hepatic cytochrome P450s). The “trans” descriptor indicates stereochemical configuration at the hydroxylated center on the cyclohexyl ring.
• Functional moieties: The molecule contains a tetrazole (acidic), a dihydroquinolinone (lactam), an aliphatic ether, and a secondary alcohol, enabling hydrogen bonding and affecting membrane interaction and protein binding (literature trends).
• Isotopic labeling role: Deuteration is used exclusively for analytical purposes, enabling mass spectrometric distinction from endogenous analyte while retaining near-identical physicochemical behavior (literature). Deuteration does not confer biological activity per se for research uses.
• Pathway studies: In vitro systems (human liver microsomes, hepatocytes, recombinant CYPs) commonly generate such hydroxylated metabolites; the labeled standard facilitates accurate quantitation in enzyme phenotyping, intrinsic clearance estimation, and metabolite profiling (literature).

Important: No medical or clinical claims are made. This product is intended strictly for laboratory research, bioanalytical method development, and related non-clinical investigations, as explicitly noted in the Research Use statement.

Buffer Applications

This compound is not a buffering reagent and is not typically used to prepare or control pH. Consequently, classic buffer system guidance (pKa selection, recipes) is not applicable.

Practical note (analytical use):

• When formulating LC–MS mobile phases or sample diluents, volatile buffers such as ammonium formate/acetate (pH ~3–6) are commonly employed to improve peak shape and ionization for tetrazole-containing analytes. Optimize ionic strength to balance sensitivity and chromatographic performance. This is general guidance; no item-specific buffer behavior is provided.

Green Alternatives

As an analytical standard, this compound itself is not readily substituted; however, greener choices can be made in the associated sample preparation and chromatography. The following considerations are general, literature-based recommendations:

• Mobile phase selection:
  • Prefer water/ethanol or water/methanol over water/acetonitrile when compatible with separation and detection. Ethanol is greener but may increase backpressure and change selectivity.
  • Use low concentrations of volatile buffers (ammonium formate/acetate) instead of non-volatile salts.
• Sample preparation:
  • Minimize organic solvent volumes by micro-scale protein precipitation or SPE with reduced elution volumes.
  • Explore aqueous-compatible SPE sorbents to reduce use of halogenated solvents.
• Solvent recycling: Employ solvent recovery systems for MeOH/ACN when feasible.
• Energy considerations: Store at −20°C as required (Product Data) but limit freeze–thaw cycles with aliquoting to reduce waste from degraded material.

Illustrative comparison (general guidance):

| Use case | Conventional choice | Greener alternative | Trade-offs | |---|---|---|---| | LC mobile phase organic | Acetonitrile | Ethanol or methanol | Viscosity increases; may alter selectivity/retention | | Protein precipitation | Acetonitrile | Ethanol | Slightly less efficient precipitation in some matrices | | Liquid–liquid extraction | MTBE/CH2Cl2 | Ethyl acetate | Potentially higher co-extraction of matrix components |

Note: Any change should be validated to maintain analyte/IS co-behavior and method performance.

Pharmaceutical Uses

No excipient or pharmacopeial status is provided in the Product Data. As a deuterated small-molecule standard, this material is used in pharmaceutical R&D and QC laboratories as follows (general, non-clinical context):

• Bioanalytical calibrator/internal standard: Supports quantitative LC–MS/MS assays in discovery, preclinical, and quality control settings for the corresponding unlabeled analyte/metabolite.
• Method validation: Serves in the establishment of linearity, accuracy, precision, recovery, matrix effects, and stability parameters according to regulatory guidance (e.g., FDA/EMA bioanalytical method validation). The product itself is for research use only and is not a drug substance or excipient.
• Reference for metabolism studies: Aids in metabolite identification and semi-quantitative assessments during in vitro ADME workflows (microsomes, S9, hepatocytes) and non-clinical studies.

Item-specific pharmacopeial listings, excipient uses, or GMP status: Not specified for this item; refer to CoA/Spec Sheet and contact Aladdin Scientific for regulatory support documentation if required.

Physical Properties

Item-specific physicochemical specifications are not provided in the 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.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point (MP): Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point (BP): Not applicable for a high-MW, multifunctional solid; decomposition is more likely (general statement).
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable to solids; Not specified for this item.
• UV-Vis characteristics: Not specified for this item; refer to CoA/Spec Sheet. Quinolinone chromophore typically shows UV absorbance in the 250–320 nm region (literature, for parent scaffold).
• LogP/logD: Not specified for this item; refer to CoA/Spec Sheet. Hydroxylation generally decreases lipophilicity vs. cilostazol (literature trend).
• pKa: Not specified for this item; refer to CoA/Spec Sheet. Tetrazoles often exhibit acidic pKa ~4–5 (literature, scaffold-level), while the lactam and alcohol functionalities can participate in H-bonding without strong basicity.
• Solubility (qualitative, literature guidance):
  • Likely low solubility in water; enhanced solubility in polar aprotic organic solvents (MeOH, ACN, DMSO). Actual solubility for this item is Not specified; confirm experimentally or refer to CoA.

Note: Deuteration minimally affects bulk physical properties; exact mass and isotopic pattern differ for MS applications (literature).

Quality and Grades

• Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Role of stable-isotope standards (general): Deuterated analogs are employed as internal standards in quantitative LC–MS/MS to correct for matrix effects, ionization variability, and sample preparation losses. Best practice requires known isotopic enrichment and defined labeling sites (information not provided here; see CoA/Spec Sheet).
• Characterization expectations (general):
  • Identity confirmation by HRMS (exact mass shift due to D-labels), NMR (residual proton patterns and deuterium incorporation), and HPLC purity by UV/MS.
  • Water content and residual solvents, if relevant, should be reported in the CoA for method validation. Not specified for this item.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Typically, no stabilizer is added to small-molecule standards unless noted.
• Batch-to-batch consistency: Critical for quantitative work. Use the lot-specific CoA for potency assignment (purity-corrected concentration calculations) and isotopic purity (%D at labeled positions), neither of which are provided in the Product Data.
• Documentation: For regulated studies, retain CoA, SDS, and any chromatograms provided with the lot. Verify that the labeled analog co-elutes with the analyte under your LC method or, alternatively, is chromatographically resolvable but shares extraction/ionization behavior.

Reaction and Applications

Primary utility is as a stable-isotope-labeled reference material for analytical chemistry rather than as a synthetic reagent. The following use cases reflect typical applications for deuterated small-molecule metabolites (literature/best practice):

• LC–MS/MS internal standard: Spike into calibration standards, QCs, and unknowns for robust quantitation of 4′-trans-hydroxy cilostazol in biological matrices (plasma, urine, tissue homogenates) or in in vitro samples (microsomes, hepatocytes). Choose concentration to bracket expected analyte levels and maintain a constant IS response.
• Metabolite identification/confirmation: Co-injection of the labeled standard assists in retention time matching and MS/MS spectral confirmation (diagnostic neutral losses, fragment ion mass shifts reflecting deuterium positions).
• Recovery and matrix-effect studies: Evaluate extraction efficiency (protein precipitation, LLE, SPE) and ion suppression/enhancement by comparing analyte/IS response across lots and matrices.
• Stability studies: Monitor analyte degradation under bench-top, autosampler, freeze–thaw, and long-term storage conditions using the IS-normalized response.
• Derivatization workflows (example, literature): Phenolic/secondary alcohol functionalities can be derivatized (e.g., dansylation) to boost detectability in LC–MS or fluorescence assays; if derivatized, ensure deuterium labels are not located at reactive/cleavable positions that could scramble during reaction.
• Not typically used in synthetic transformations: As a labeled standard, it is not a common building block or reagent for bond-forming reactions.

Note: The exact number and positions of deuterium atoms are not specified for this item; consult the CoA to ensure suitability for the intended MS method.

Reaction Conditions

No item-specific reaction conditions are provided, as this product is intended as an analytical standard rather than a reagent. The following general, literature-based notes may assist if derivatization or stability studies are planned:

• Typical solvents: Anhydrous acetonitrile, dichloromethane, DMF, or pyridine for acylation/sulfonylation of secondary alcohols. Methanol/ACN–water for analytical solution preparation.
• Temperatures: Many derivatizations proceed at 0–25°C; mild heating (30–50°C) may be used to drive sluggish reactions. Avoid prolonged high temperatures to preserve H/D labeling.
• Catalysts/bases: Tertiary amines (e.g., DIPEA, TEA) for acylations; DMAP for acyl transfer. Avoid strong bases/acids that could cause deuterium exchange or tetrazole degradation.
• Times: 0.5–4 h typical for acylations/sulfonylations; monitor by LC–MS. For analytical solutions, dissolve immediately before use and minimize bench-top exposure.
• Yields (derivatization, literature): Often high (70–95%) for acylations on unhindered secondary alcohols under optimized conditions; actual outcomes depend on substrate and conditions.
• Stability testing: Assess bench-top (2–6 h), autosampler (4–24 h at 4–10°C), freeze–thaw (≥3 cycles), and long-term (−20°C) stability with IS-normalized LC–MS response per bioanalytical guidance. These are general recommendations; validate for your method.

Note: Exact deuterium positions for this item are not specified; choose conditions that minimize any potential H/D exchange.

Safety and Handling

Always handle according to your institutional EHS procedures. Product Data do not include GHS classification for this item; consult the product SDS for authoritative information.

• GHS/CLP data: Not specified for this item; refer to SDS for signal word, hazard statements, and pictograms.
• General hazards (class-based, literature): Small-molecule organic standards may cause irritation to skin, eyes, and respiratory tract. Avoid ingestion and inhalation. Deuteration does not change toxicological class qualitatively.
• PPE: Use lab coat, nitrile gloves, and safety glasses; handle powders in a fume hood to prevent dust inhalation and contamination.
• Storage conditions (item-specific): Store at −20°C (Product Data). Protect from light and moisture. Keep container tightly closed.
• Shipping (item-specific): Shipped in ice chest with ice pads (Product Data) to maintain low temperature.
• Incompatibilities (general): Strong oxidizers, strong acids/bases may degrade tetrazole/ether linkages or induce hydrolysis/oxidation. Avoid prolonged exposure to elevated temperatures.
• Peroxide formation: Not applicable (no ether solvent use); compound contains an ether linkage but is a solid analyte, not a peroxide-forming solvent.
• First aid (overview; defer to SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with plenty of water for at least 15 minutes; remove contaminated clothing.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Waste: Dispose according to local regulations for organic laboratory chemicals. Avoid release to the environment.

Solvent Selection

This compound is a hydroxylated, deuterium-labeled derivative of a lipophilic quinolinone. Item-specific solubility data are not provided; the following guidance is based on literature behavior of the scaffold.

• Preferred analytical solvents (literature/good practice):
  • DMSO: strong solvency for polyfunctional, lipophilic analytes; useful for preparing high-concentration stocks.
  • Methanol (MeOH) or acetonitrile (ACN): common for LC–MS sample preparation and calibration standards; miscible with aqueous mobile phases.
  • Water: limited solubility expected; consider ≤5–20% organic co-solvent for working solutions.
• Polarity and miscibility (general): Moderately polar overall due to lactam, tetrazole, and alcohol functionalities, yet hydrophobic surface area remains substantial. Good compatibility with polar aprotic solvents; poor solubility in alkanes/ethers is typical.
• Acid/base modifiers (LC–MS): 0.1% formic acid or ammonium formate in water/ACN often improves peak shape and ionization for tetrazole-containing analytes (literature). Optimize to avoid deuterium–hydrogen exchange at labile sites (ensure labels are non-exchangeable; confirm via CoA).
• Comparison (general):
  • MeOH vs ACN: MeOH increases elution strength in reversed phase for hydrophobic analytes and can enhance ESI response for some compounds; ACN often yields sharper peaks and lower backpressure.
  • DMSO: excellent for stock solutions; dilute into MeOH/ACN:water prior to injection to avoid peak broadening.
• Practical tips: Filter mobile phases (0.2 µm), degas, and equilibrate columns thoroughly; verify absence of precipitation upon aqueous dilution by visual check or light scattering.

Storage and Reconstitution

• Storage (item-specific): Store at −20°C (Product Data). Protect from light and moisture. Keep container tightly sealed.
• Shipping (item-specific): Shipped in an ice chest with ice pads (Product Data) to maintain low temperature.
• Reconstitution solvent: Not specified for this item; refer to CoA/Spec Sheet. General practice is to dissolve small-molecule standards in DMSO, methanol, or acetonitrile based on solubility testing.
• Concentration assignment: Determine using accurate weighing (analytical balance) and purity-corrected calculations from the lot-specific CoA (if purity is provided). For gravimetric stocks, record temperature and balance calibration.
• Aliquoting: Prepare small, single-use aliquots to avoid repeated freeze–thaw. Use low-bind polypropylene or amber glass vials.
• Freeze–thaw guidance: Minimize cycles; thaw on ice or at room temperature briefly, mix gently, and promptly return unused material to −20°C. Avoid repeated needle punctures that can introduce moisture.
• Solution stability: Not specified for this item; establish bench-top, autosampler (4–10°C), and long-term (−20°C) stability experimentally under your method conditions.
• Aqueous dilutions: When diluting into aqueous buffers, include organic co-solvent (e.g., 5–50% MeOH or ACN) to prevent precipitation; verify clarity visually.
• Documentation: Retain preparation logs, CoA, and chromatograms for traceability in regulated studies.

Research Use Note: For research use only (Product Data).

Structure and Identity

Brief overview: This catalog item is a deuterium-labeled, hydroxylated derivative of cilostazol intended as an analytical/research standard. Item-specific identifiers are largely not provided in the Product Data.

• Product name: 4'-trans-Hydroxy Cilostazol-d (stable-isotope labeled standard)
• CAS: T1444697 (catalog placeholder; Not a validated CAS registry number in the Product Data)
• 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 context):

• Parent framework: cilostazol is a 3,4-dihydro-2(1H)-quinolinone scaffold bearing a butoxy tether to a cyclohexyl-tetrazolyl moiety (literature).
• Hydroxylation site: “4′-trans-hydroxy” refers to oxidation on the cyclohexyl ring, giving a secondary alcohol with trans relationship to the substituent (literature). The –d suffix denotes deuterium incorporation at one or more non-exchangeable positions for mass spectrometric discrimination (literature).
• Functional groups expected: secondary alcohol (phenolic/benzylic-type on cyclohexyl), ether linkage (butoxy), tetrazole ring, and a dihydroquinolinone (lactam) core (literature). No stereochemical assignment beyond the “trans” descriptor is provided in the Product Data.

2D structure description (general):

• A bicyclic quinolinone ring system tethered via an aliphatic ether chain to a cyclohexyl ring that bears a tetrazolyl substituent; the cyclohexyl ring also carries a hydroxyl in trans orientation relative to the chain substituent (literature). Deuterium labels do not alter connectivity but shift exact mass (literature).

Synthetic Utility

This material is primarily an analytical reference standard rather than a synthetic intermediate. Nevertheless, understanding functional group reactivity can inform any bespoke derivatization or conjugation work (general, literature-based):

• Functional groups and reactivity:
  • Secondary alcohol on cyclohexyl: amenable to esterification (acyl chlorides/anhydrides), carbamate formation, sulfonylation (e.g., tosylates), or oxidative transformations to ketone (e.g., Dess–Martin, TEMPO-based) if needed for reference purposes.
  • Tetrazole: acidic (N–H) site can engage in salt formation; nucleophilicity is weak. Avoid strong acids/bases that may cause ring opening under harsh conditions.
  • Ether linkage: generally stable; susceptible to cleavage only under strong acidic conditions.
  • Dihydroquinolinone (lactam): can participate in hydrogen bonding; relatively stable under neutral conditions.
• Stable-isotope integrity: Any synthetic modification risks H/D exchange if deuterium is placed at benzylic/allylic or heteroatom-adjacent positions. Without item-specific labeling map, avoid conditions that promote exchange (strong acids/bases, metal-catalyzed hydrogenation).
• Derivatization for analytics: Formation of chromophoric/fluorophoric derivatives (e.g., dansyl chloride for hydroxyls post-activation) may enhance detectability; ensure that derivatization does not shift retention away from the unlabeled analyte if co-elution is required.

Item-specific reactivity, yields, and conditions are not provided; consult the CoA/Spec Sheet or perform small-scale feasibility tests.

Target Specificity

Not applicable. This product is a small-molecule analytical standard and not a biological targeting reagent (e.g., antibody, inhibitor with defined target data). No target, epitope, species reactivity, clone, or isotype information is provided or relevant to this item.