Serotonin-dβ-D-glucuronide , CAS No.S1450301

CAS: S1450301 Cat. No.: S1450301 Formula: C₁₆H₁₆D₄N₂O₇ Molecular Weight: 356.36

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Serotonin-d 4 β-D-glucuronide is the deuterium labeled Serotonin β-D-glucuronide.

Specifications

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Molecular Weight: 356.36

Application Protocols

No item-specific, validated application protocols are provided for this listing. The following general workflows are commonly used with serotonin glucuronide standards in research labs (literature/general):

• Preparation of stock solutions:

  • Warm vial to room temperature in a desiccator. Dissolve in water or 50:50 MeOH/H2O to a convenient concentration (e.g., 0.1–10 mM per laboratory need). Vortex until fully dissolved. Filter only if necessary.
  • Aliquot and store at −20 °C. Avoid repeated freeze–thaw cycles.

• LC–MS/MS calibration curve (bioanalytical):

  • Prepare serial dilutions in surrogate matrix (e.g., 1% BSA in PBS) or extracted blank matrix to cover the expected range.
  • Process along with samples using protein precipitation (ACN or MeOH, 3–4× volume), centrifuge, and inject supernatant.
  • Monitor MRM transitions appropriate to your instrument and optimize collision energies for indole/glucuronate fragments.

• Enzymatic deconjugation control:

  • Spike known amounts into buffer with β-glucuronidase (pH ~4.5–5.0) and into heat-inactivated control.
  • Incubate at 37 °C; quench at set time points; quantify released serotonin vs. intact conjugate.

These are example practices only; validate and document conditions per your SOPs. Research use only.

Biological Roles

Literature/general context: Serotonin-dβ-D-glucuronide is a phase II conjugate of serotonin formed by UDP-glucuronosyltransferases (UGTs), most commonly via O-glucuronidation of the phenolic 5-hydroxyl.

• Biotransformation: Glucuronidation increases polarity and facilitates clearance via urine or bile. Enzymes implicated include hepatic and extrahepatic UGT isoforms (e.g., UGT1A/UGT2B families; literature), with formation observed in liver microsomes and hepatocytes.
• Charge state and transport: The glucuronate carboxylate imparts an anionic character at physiological pH, potentially interacting with organic anion transport processes (e.g., MRPs) during excretion (literature/general).
• Analytical biomarker role: Presence and levels can reflect serotonin metabolism and phase II capacity in in vitro systems (microsomes, S9, hepatocytes) or model organisms. It is often monitored alongside sulfate and parent amine to build metabolic balance.
• Enzymatic lability: The conjugate is a substrate for β-glucuronidase, which hydrolyzes the glycosidic bond to regenerate serotonin (literature). This property underpins deconjugation workflows in sample prep.

Note: The above describes biochemical context and should not be interpreted as medical or clinical guidance. This product is supplied strictly for research use only (per Product Data).

Buffer Applications

This compound is not a buffering agent and is not used to maintain pH in biochemical systems. However, it is commonly prepared and handled in buffers during analytical workflows.

Practical notes (general):

• Compatible buffers for dissolution and handling: low ionic strength phosphate or acetate (pH ~4–7) when UV detection is used; volatile buffers (ammonium formate/acetate, pH ~3–6) for LC–MS/MS.
• Avoid strong basic buffers (pH >8) and concentrated mineral acids, which can accelerate glucuronide hydrolysis.
• Ionic strength: keep minimal (1–10 mM) for MS sensitivity and to reduce ion suppression.

If your application requires controlled deconjugation, sodium acetate buffer (~pH 4.5–5.0) is often used for β-glucuronidase incubations (literature/general), but optimize conditions with your enzyme source and matrix.

Green Alternatives

This product is a metabolite standard, not a process solvent or bulk reagent, so “green alternatives” focus on method conditions and solvent systems used with it.

Greener handling and method choices (general):

• Prefer aqueous buffers and minimize organic solvent content for dissolution and chromatography where sensitivity allows.
• Use volatile, lower-toxicity mobile phase additives (ammonium acetate/formate) instead of non-volatile salts for LC–MS.
• Choose methanol (biobased availability, lower toxicity) over acetonitrile where chromatographic performance is acceptable.
• Miniaturize assays (microvolume LC vials, 96-well plates) to reduce solvent consumption and waste.

Illustrative comparison (general):

• ACN/H2O mobile phases: strong elution, excellent MS performance but higher environmental footprint.
• MeOH/H2O mobile phases: somewhat higher viscosity/backpressure but renewable sourcing potential and lower toxicity.
• 100% aqueous HILIC/ion-pair-free RP methods: maximal greenness but may require method redevelopment and can impact retention/peak shape for very polar analytes.

Waste and stability:

• Prepare only the quantity needed per batch to limit expired waste.
• Neutralize and dispose of aqueous-organic waste per local regulations; segregate halogenated solvents if used elsewhere in the workflow.

Pharmaceutical Uses

This material is not an excipient and has no therapeutic indication. In pharmaceutical and biopharma laboratories it can serve as a reference or system-suitability standard (research use only) in the following contexts (literature/general):

• Drug metabolism studies: Positive control/product standard for UGT-mediated conjugation of indole/phenol-containing drug candidates in microsomal/hepatocyte assays.
• Bioanalytical method development: Calibration/quality control standard for LC–MS/MS quantification of serotonin conjugates in preclinical matrices; supports validation parameters such as accuracy, precision, selectivity, carryover, and stability.
• Enzyme inhibition/phenotyping: Marker product to assess UGT activity and to evaluate potential inhibition by candidate compounds in vitro.

Regulatory note: Any use in regulated studies requires full characterization and traceability. Request batch-specific CoA including identity (NMR/HRMS), purity, and water/residual solvent if your SOPs require them. No pharmacopeial monograph is known for this specific conjugate (literature check recommended). All uses are for research/laboratory purposes only.

Physical Properties

Item-specific numerical specifications have not been provided for this catalog entry. Where useful, general/literature expectations are noted; confirm with the item’s CoA/Spec Sheet for definitive values.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not applicable (decomposes before boiling; literature expectation for glucuronides).
• Solubility (literature/general): expected to be highly soluble in water and aqueous buffers due to the glucuronate carboxylate and multiple hydroxyls; limited solubility in nonpolar organic solvents. Often soluble in methanol/water and acetonitrile/water mixtures used for LC–MS.
• pKa (literature/general trends): carboxylate of glucuronic acid ~3–3.5 (acidic); primary amine of serotonin side chain pKa ~9–10 (basic). The indole NH is very weakly acidic (pKa >15). Net charge is pH-dependent and can be zwitterionic around physiological pH.
• LogP/LogD (literature/general): strongly hydrophilic; expected low logP with logD markedly negative at neutral pH.
• Hygroscopicity: many sugar conjugates are hygroscopic; handle rapidly at ambient and store tightly sealed (general guidance).
• UV absorbance (literature/general): indole chromophore absorbs around 220–230 nm and ~275–280 nm; useful for HPLC-UV detection. Exact cutoff/extinction: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index/density: Not specified for this item; refer to CoA/Spec Sheet.

Quality & Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet. In the absence of a declared grade, Aladdin supplies research-use material suitable for analytical and laboratory applications.

Guidance on common grades (general information):

• Analytical/reference standard grade: intended for quantitative LC–MS/LC–UV assays; key attributes include tight assay, low residual solvents, and documented identity (NMR/HRMS). If your application is quantitative bioanalysis, request a CoA with purity by qNMR or HPLC and identity confirmation.
• Biochemical grade: emphasizes low bioburden and trace metal content for enzyme assays. For studies involving β-glucuronidase kinetics or transporters, low inorganic contamination is desirable.

Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet. Many glucuronide standards are supplied neat without stabilizers; if present, they will be listed on the label/CoA.

Batch-specific documentation: For traceability and method validation, obtain the batch CoA including assay method, chromatographic purity, residual solvent, and water content (if Karl Fischer is reported). Where isotopic/internal standardization is required, consider preparing gravimetrically with NIST-traceable balances and documenting solution concentration by mass.

Reaction & Applications

As a phase II metabolite standard, Serotonin-dβ-D-glucuronide is primarily used in analytical and biochemical contexts rather than as a general synthetic reagent.

Analytical/biochemical applications (literature/general):

• LC–MS/MS reference material for quantifying serotonin glucuronidation in biofluids, tissue homogenates, hepatocyte/UGT incubation samples, and transporter studies.
• Enzymology: substrate/product standard in β-glucuronidase hydrolysis assays; helps establish calibration curves and validate deconjugation efficiency.
• Metabolomics and profiling: panel member in targeted neurotransmitter conjugate analyses; facilitates method development, retention time locking, and MRM transition optimization.

Practical tips:

• Prepare gravimetric stock in water or aqueous MeOH at known concentration; store aliquots at −20 °C. Verify concentration by UV (indole chromophore) or qNMR if purity is known (literature/general).
• For LC–MS/MS, use low-pH volatile buffers (e.g., 2–10 mM ammonium formate with 0.1% formic acid) to enhance positive-mode response of the protonated amine; negative mode can monitor the glucuronate fragment depending on method.
• Avoid prolonged exposure to high pH (>8) and to elevated temperature; glucuronide linkages can hydrolyze chemically or enzymatically (literature), confounding quantitation.

Not typically used in classical organic reactions (e.g., cross-couplings, condensations); see Synthetic Utility for limited niche uses.

Reaction Conditions

This product is primarily employed in analytical/enzymatic experiments rather than classical organic reactions. Representative literature/general conditions relevant to its handling and study include:

• β-Glucuronidase hydrolysis (deconjugation):

  • Buffer: sodium acetate, pH 4.5–5.0.
  • Temperature: 37 °C.
  • Enzyme: β-glucuronidase (e.g., from Helix pomatia or recombinant sources); units and incubation time depend on matrix and target load; typical incubations 0.5–2 h (optimize empirically).
  • Endpoint: liberation of serotonin, monitored by LC–MS/MS.

• UGT-mediated formation (in vitro biosynthesis):

  • Matrix: human liver microsomes or recombinant UGTs.
  • Cofactor: UDP-glucuronic acid (UDPGA), Mg2+.
  • Buffer: Tris or phosphate, pH 7.4; include alamethicin preactivation for microsomes (literature practice).
  • Temperature: 37 °C, 15–60 min; quench with ice-cold organic solvent.

• LC–MS/MS method development (analytical):

  • Column: C18 or polar-embedded RP; HILIC is also used for very polar conjugates.
  • Mobile phase: water with 0.1% formic acid or 2–10 mM ammonium formate; organic phase ACN or MeOH.
  • Ionization: ESI positive and/or negative; monitor characteristic indole and glucuronate fragments.

All parameters above are general guidance from literature; adjust to your matrix, instrument, and performance requirements.

Safety & Handling

Hazard classification data have not been provided for this specific item. Always consult the SDS for authoritative guidance. General safe-handling practices for polar bioorganic metabolites apply.

• GHS/Signal word/H-statements/Pictograms: Not specified for this item; refer to SDS.
• Storage: Store at −20 °C (Product Data). Protect from moisture and light. Keep container tightly closed. Shipments are supplied in an ice chest with ice pads to maintain cold chain.
• Handling: Work in a clean, dry environment. Allow the vial to equilibrate to room temperature in a desiccator before opening to minimize moisture uptake. Avoid generating dust or aerosols.
• Incompatibilities (general): Strong oxidizers. Strong acids or bases can promote hydrolysis of the glucuronide linkage; avoid extended exposure during storage or handling. Avoid elevated temperatures in solution.
• PPE: Lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood when weighing powders or preparing solutions.
• First aid (general): If inhaled—move to fresh air; seek medical attention if symptoms occur. Skin contact—wash with soap and water. Eye contact—rinse cautiously with water for several minutes; remove contact lenses if present and easy to do. Ingestion—rinse mouth; seek medical advice. Provide SDS to healthcare personnel.
• Spills and disposal: Avoid release to the environment. Absorb small spills with inert material (e.g., vermiculite), collect for disposal. Dispose in accordance with institutional and local regulations.
• Stability concerns: Aqueous solutions may slowly hydrolyze (enzymatically or chemically) especially at extreme pH or elevated temperature (literature/general). Prepare fresh or store aliquots frozen.

Solvent Selection

This compound is a highly polar glucuronide metabolite; solvent choices should prioritize aqueous compatibility and analytical method needs.

• Polarity/miscibility (literature/general): Highly polar and hydrophilic; readily soluble in water and in common LC solvents when water is present (e.g., MeOH/H2O, ACN/H2O). Sparingly soluble in purely nonpolar media (e.g., hexanes, toluene).
• Recommended dissolution media: Water, physiologically relevant buffers (e.g., phosphate, acetate) in the pH 3–7 range; for LC–MS, use volatile buffers (ammonium formate/acetate, pH ~3–6) at low ionic strength to preserve ionization efficiency.
• pH considerations: Avoid prolonged exposure to strong acid/base which can hydrolyze the glucuronide linkage. For stock solutions, mildly acidic aqueous media (pH 3–5) often improve stability (literature/general practice).
• Co-solvents: If higher organic content is required, use 50:50 MeOH/H2O or ACN/H2O. Dimethyl sulfoxide (DMSO) can dissolve many polar metabolites, but small aqueous-organic mixtures are typically preferable for LC compatibility.

Comparison (general):

• Water/buffer: maximal solubility and biological relevance; potential hydrolysis at extreme pH.
• MeOH/H2O: good solubility; UV transparency above ~205 nm; compatible with LC–UV and LC–MS.
• ACN/H2O: strong elution strength in reversed-phase LC; excellent MS compatibility.

Tip: Filter stock solutions (0.2 µm PTFE or PVDF) only if necessary; excessive filtration can cause non-specific adsorption of zwitterionic analytes—pre-wet filters with matrix solvent.

Storage & Reconstitution

• Storage conditions (from Product Data): Store at −20 °C. Shipments are provided in an ice chest with ice pads.
• Light/moisture protection: Keep tightly capped in a desiccated environment; protect from light to preserve indole chromophore integrity (general practice for indolic compounds).
• Stability: Long-term stability depends on temperature, moisture control, and pH of solutions. Aqueous solutions are more prone to hydrolysis; prepare fresh or store aliquots frozen. Specific shelf-life: Not specified for this item; refer to CoA/Spec Sheet.

Reconstitution (general guidance):

• Solvents: Water or 50:50 MeOH/H2O; for LC–MS use volatile buffer systems if needed (e.g., 2–10 mM ammonium formate, pH ~3–6).
• Concentration: Choose to suit your assay; item-specific recommended concentration is not specified. Record gravimetric additions for accuracy.
• Filtration: If particulate is present, briefly centrifuge or filter through 0.2 µm PTFE/PVDF. Minimize adsorption by pre-wetting with matrix solvent.

Working solution handling:

• Maintain on ice during use; return unused portions to −20 °C promptly.
• Avoid repeated freeze–thaw by preparing single-use aliquots.
• Do not store in strongly acidic or basic media. For best stability, keep solutions mildly acidic and shielded from light (literature/general).

Research Use Note: For research use only.

Structure & Identity

Serotonin-dβ-D-glucuronide is a glucuronide conjugate of serotonin (5-hydroxytryptamine), typically represented as the β-D-glucuronide linked through the phenolic oxygen on the indole ring (5-O-glucuronide; literature). It combines an indole-ethylamine scaffold with a β-D-glucuronic acid moiety via an O-glycosidic bond.

• SKU: S1450301
• Product name: Serotonin-dβ-D-glucuronide
• CAS: S1450301 (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 (literature/general):

• Indole ring system (bicyclic, benzene fused to pyrrole) bearing a 2-carbon side chain terminating in a primary amine (–CH2–CH2–NH2).
• Phenolic position at C-5 of the indole typically forms an O-glycosidic bond to β-D-glucuronic acid (glucuronide). The glucuronic acid carboxylate confers an anionic character near neutral pH.
• Functional groups: indole NH (weakly acidic), primary aliphatic amine (basic), glycosidic ether linkage, uronic acid carboxylate (acidic).
• Stereochemistry: the sugar moiety is β-D configured (literature notation), introducing multiple defined stereocenters in the pyranose ring.

2D description in words (literature): indole core with a 5-O-linked β-D-glucuronopyranosyl group; the ethylamine extends from C-3 of the indole. Overall a zwitterionic/polar molecule with one negative charge (carboxylate) and one positive charge (protonated amine) depending on pH.

Synthetic Utility

As an isolated glucuronide metabolite, Serotonin-dβ-D-glucuronide is not a common starting material for multistep synthesis. Its primary value lies in analytical and biochemical applications. That said, niche synthetic/chemical biology uses exist (literature/general):

• Standard for method validation in chemical synthesis of serotonin O-glucuronides (e.g., to confirm regiochemistry and spectral data of synthetic targets).
• Chemical stability probe: used to benchmark glycosidic bond stability under various reaction conditions, informing protecting-group or deprotection strategy selection in carbohydrate or indole chemistry.
• Enzymatic synthesis studies: substrate/product reference in UGT-catalyzed in vitro glucuronidation using UDPGA, aiding optimization and kinetics interpretation.

Reactive moieties and considerations (general):

• Glycosidic ether linkage is acid/base labile—avoid strong acid catalysts or high-temperature base that can cleave the bond.
• Primary amine can participate in salt formation and can be derivatized (e.g., acylation, carbamate formation) under mild conditions, though this typically destroys the identity as the authentic metabolite.

For retrosynthesis or derivatization, it is usually preferable to prepare the conjugate from protected glucuronic acid donors and protected serotonin derivatives, then deprotect under carefully controlled conditions (outside the scope of this product’s intended use).

Target Specificity

Not applicable. This product is a small-molecule metabolite standard, not an antibody, probe, or biologic with defined target binding parameters. No antigen/epitope, species reactivity, clone, or isotype information applies.