16α-Hydroxydehydroepiandrosterone-d , CAS No.97453-29-7

CAS: 97453-29-7 Cat. No.: H1440762 分子式: C₁₉H₂₂D₆O₃ 分子量: 310.46

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

概要

16α-Hydroxydehydroepiandrosterone-d 6 (16α-Hydroxy-DHEA-d 6 ) is the deuterium labeled 16α-Hydroxydehydroepiandrosterone.

Specifications

保管条件

Store at 2-8°C,Protected from light,Argon charged

入荷

Wet ice

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名前と識別子

分子量

310.46

Application Protocols

The following are example, literature-style workflows for using a deuterated steroid internal standard. They are general guidance and not validated for this specific lot. Adjust as needed.

LC–MS/MS (plasma/serum) example (literature/general):

• Stock: Dissolve in LC–MS–grade methanol at 1 mg/mL; store at 2–8 °C, protected from light, under inert gas. Working IS solution: 10–100 ng/mL in 50% MeOH/water.
• Sample prep: Spike 10–50 μL of IS into 200 μL sample; precipitate proteins with 600 μL cold ACN or MeOH; vortex 1 min; centrifuge 15,000 g, 10 min.
• Cleanup: SPE (optional) on C18/polymeric sorbent; condition (MeOH, then water), load, wash (5–10% MeOH in water), elute (MeOH or ACN).
• LC: C18, 0.3 mL/min; gradient 30–90% B (ACN or MeOH with 0.1% FA) over 8 min.
• MS: Optimize source and collision energies for both native analyte and deuterated IS. Monitor co-elution and consistent area ratios.

GC–MS (urine) with TMS derivatization (literature/general):

• Hydrolysis (if analyzing conjugates): Enzymatic β-glucuronidase/sulfatase as required; neutralize.
• Extract with ethyl acetate; dry; add BSTFA + 1% TMCS (100 μL) and heat 60 °C for 30 min.
• Inject 1 μL on HP-5MS column; monitor characteristic ions for analyte and deuterated IS.

Note: Validate linearity, accuracy (recovery 85–115%), precision, matrix effects, and stability per your regulatory framework.

Biological Roles

Background on the non-deuterated parent (literature; not item-specific):

• Dehydroepiandrosterone (DHEA) is an adrenal steroid precursor. 16α-hydroxylation yields 16α-hydroxy-DHEA, a phase I metabolite that can undergo further phase II conjugation (e.g., sulfation or glucuronidation) in liver and extrahepatic tissues.
• Enzymology: 16α-hydroxylation of C19 steroids has been associated with certain cytochrome P450 isoforms (e.g., CYP3A family) in hepatic microsomes (literature). Subsequent conjugation is commonly mediated by sulfotransferases (SULTs) and UDP-glucuronosyltransferases (UGTs).
• Physicochemical context: Addition of the 16α-hydroxyl lowers lipophilicity and can modulate receptor-binding profiles relative to DHEA, though detailed affinities are system-dependent (literature).

Relevance of the deuterated analog:

• The deuterated form serves as a mass spectrometric surrogate for the native metabolite, enabling accurate quantitation in complex matrices by compensating for ion suppression/enhancement and extraction variability.
• In tracer studies, non-exchangeable deuterium labels can assist in tracking metabolic transformations, isotopologue distributions, and kinetic isotope effects (when labeling positions are known). For this item, the exact labeling pattern is Not specified for this item; refer to CoA/Spec Sheet.

Research use only: No clinical/medical claims are made. Employ within biochemical and analytical research to study steroid metabolism and analytical method performance.

Buffer Applications

This material is a hydrophobic, deuterated steroidal analyte/standard and is not used as a buffer component.

• Typical aqueous buffering systems (e.g., phosphate, Tris, HEPES) are not applicable for preparing concentrated solutions of this compound due to low water solubility (literature). Instead, prepare stocks in compatible organic solvents (e.g., methanol, acetonitrile, or DMSO) and dilute into buffered mobile phases as needed for LC–MS.
• If incorporating into aqueous samples, use co-solvent strategies (≤1–2% DMSO or 5–20% organic modifier) to prevent precipitation and maintain homogeneity during analytical runs.

For buffer selection guidance related to chromatography (mobile-phase additives), see Solvent Selection.

Green Alternatives

Green chemistry considerations relate mainly to solvent and workflow choices, as the analyte is a specialized deuterated standard with no practical "substitute" for isotope-dilution quantitation.

Greener solvent choices (literature/best practice):

• Prefer LC–MS–grade methanol over acetonitrile when chromatographic performance allows; MeOH is generally considered more benign and is bio-derived in some supply chains.
• Use ethanol or 2-propanol for sample preparation when compatible, reducing reliance on halogenated solvents.
• Minimize DMSO content; though effective, it can persist in waste streams.

Comparison (general):

• Acetonitrile: Excellent peak shape, but petrochemical origin and toxicity concerns; shortages impact availability.
• Methanol: Greener profile, but can alter selectivity; may require higher pressures in high aqueous mobile phases.
• Supercritical CO2 (SFC): For chiral/normal-phase separations where applicable, SFC can reduce organic solvent usage significantly; validate ionization efficiency for MS interfaces.

Process-level improvements:

• Scale down assays (microflow LC–MS) to cut solvent use.
• Employ 96-well SPE or μSPE to reduce solvent volumes.
• Consolidate calibration curves across panels to minimize repeated preparations and waste.

Note: The unique role of deuterated internal standards has no direct green alternative; instead, optimize the analytical method to reduce solvent and energy footprints.

Pharmaceutical Uses

No therapeutic or clinical use is claimed for this product. It is intended strictly for research use as an analytical standard.

Relevant roles in pharmaceutical R&D/QC (general, literature):

• Analytical reference standard: Deuterated internal standards are widely employed in bioanalytical method development and validation (e.g., per FDA/EMA bioanalytical method validation guidance) to support pharmacokinetic and metabolite profiling studies of steroidal compounds.
• Matrix calibration: Used to construct calibration curves and quality controls in biological matrices (plasma, serum, urine) for quantitation of 16α-hydroxy-DHEA.
• Process controls: Applied as a spike-in to monitor extraction efficiency, derivatization yield (for GC–MS), and instrument performance in regulated laboratory workflows.

Excipient status and pharmacopeia:

• Not an excipient; no pharmacopeial monograph is implied or provided for this deuterated analog.

Note: For any regulated application, always verify CoA details (purity, isotopic enrichment, stability) and maintain full traceability and documentation as required by your quality system.

Physical Properties

Item-specific physico-chemical specifications are not provided in the product data.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight and formula: Not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties for closely related compounds (for method planning only; not item specifications):

• Parent (non-deuterated) 16α-hydroxy-DHEA is a neutral, non-volatile steroidal solid with high crystallinity and low aqueous solubility.
• Typical solubility behavior (steroids, literature): sparingly soluble in water; soluble in polar aprotic and protic organic solvents such as methanol, ethanol, acetonitrile, acetone, and DMSO; enhanced solubility upon gentle warming or sonication.
• LogP: Steroidal hydroxy-ketones often exhibit logP in the 2–3.5 range (literature, varies by substitution). The additional 16α-OH reduces lipophilicity compared to DHEA.
• pKa: Phenomenological pKa for secondary/tertiary alcohols in steroids is typically >14 (non-ionizing in neutral water); the 17-ketone is non-ionizable under neutral conditions (literature).
• Thermal behavior: Many steroidal solids melt between ~150–220 °C depending on crystallinity and hydration (literature ranges only).

Practical notes (general):

• For quantitative work (e.g., LC–MS), prepare stock solutions in LC–MS–grade methanol or acetonitrile; filter if particulates remain. Validate solubility and stability empirically for your platform.

Quality and Grades

Item-specific grade/purity information is not provided in the product data and should be verified on the CoA/Spec Sheet.

Context and expectations for this class of material (general):

• Isotopically labeled steroids are commonly supplied at high chemical purity for use as internal standards in LC–MS/GC–MS. Typical documentation includes chemical purity (%), isotopic enrichment (atom % D at labeled positions), and residual solvent limits (literature/good practice). None of these parameters are specified here for this item; please consult the CoA.
• Stabilization: No stabilizer is noted in the product data. The item is shipped on wet ice and recommended to be stored at 2–8 °C, protected from light, under argon—measures consistent with minimizing oxidative/isomerization pathways for conjugated steroidal enones.
• Grade terminology: If labeled as “analytical standard” or “LC–MS grade” on the CoA, this generally implies low levels of UV-absorbing impurities and well-characterized isotopic distribution suitable for quantitative isotope-dilution workflows. Absent such a designation here, users should verify suitability for their method by small-scale validation.

Recommendations:

• Review CoA for: chemical purity, isotopic labeling map, isotopic enrichment, residual solvents, and water content. If UV/fluorescence background or specific metal limits are critical for your method, confirm explicitly—Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

Primary value: an isotopically labeled internal standard and tracer for analytical quantitation and metabolism studies of 16α-hydroxy-DHEA.

Analytical applications (literature/general):

• LC–MS/MS internal standard for targeted steroid panels, improving accuracy via isotope-dilution quantification. The deuterated analog co-elutes closely with the native analyte while being mass-resolved by MRM transitions.
• GC–MS with derivatization (e.g., TMS ethers) to enhance volatility; the deuterated standard corrects for matrix effects, extraction recovery, and derivatization efficiency.
• Metabolic profiling: Use as a spike-in standard for enzyme assays involving hydroxylation, sulfonation, or glucuronidation of DHEA metabolites.

Reaction chemistry (general, steroid class):

• Functional handles include secondary alcohols at C3β and C16α (esterification, silylation, oxidation to ketones) and a 17-ketone (oxime/hydrazone formation, reductive transformations). The Δ5 double bond participates in selective epoxidation/hydroxylation under mild conditions (literature).

Practical tips:

• Prepare fresh working solutions; minimize freeze–thaw and light exposure (per product guidance). Validate MRM transitions to avoid H/D back-exchange regions if labeling is on exchangeable sites (label pattern for this item is not specified—verify on CoA).
• For solid-phase extraction (SPE), C18 or polymeric reversed-phase sorbents with aqueous loading and organic elution are commonly effective for hydroxy-steroids.

Reaction Conditions

Guidance below is general for hydroxy-keto steroids and analytical workflows; it is not item-specific.

• Derivatization for GC–MS (literature):

  • Reagents: BSTFA + 1% TMCS or MSTFA for trimethylsilyl (TMS) ether formation at 3β- and 16α-OH.
  • Solvent: Anhydrous acetonitrile or pyridine; avoid water.
  • Conditions: 60–70 °C, 20–60 min; monitor by GC–MS for complete derivatization.

• LC–MS/MS (reverse phase) of underivatized analyte (literature):

  • Column: C18, 2.1 × 50–100 mm, sub-2–3 μm.
  • Mobile phase: Water (A) with 0.1% formic acid or 5–10 mM ammonium formate; MeOH or ACN (B) with same additive.
  • Gradient: 30–90% B over 5–10 min; adjust for resolution from isobaric steroids.
  • Detection: ESI in positive or negative mode depending on response; many hydroxy-keto steroids ionize in ESI(+) as [M+H]+ or in ESI(−) as [M−H]−.
  • Typical MRM: Transitions depend on instrument and derivatization; optimize empirically. Ensure mass shift matches deuteration pattern (not specified for this item; consult CoA).

• Stability considerations:

  • Protect from light and oxygen; use amber vials and argon headspace (aligns with product guidance).
  • Avoid strong acids/bases and prolonged high temperatures, which may induce isomerization (e.g., Δ5↔Δ4 shifts) or H/D exchange (literature).

Expected performance (literature):

• With internal standards, method precision (CV) typically improves to <10% across QC levels in validated assays; yields in derivatization often >90% when water is rigorously excluded.

Safety and Handling

Hazard classification details are not provided for this specific item. Always consult the SDS for authoritative information.

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

General laboratory safety guidance for steroidal small molecules (literature/best practice):

• PPE: Wear lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Avoid inhalation of dust/aerosols; handle powders in a fume hood or ventilated enclosure.
• Avoid exposure: Although intended for research use only, treat as potentially bioactive. Prevent skin contact and accidental ingestion. Deuteration does not inherently reduce biological activity.
• Handling: Minimize light and air exposure per product guidance; this item is supplied argon charged and should be protected from light. Cap promptly after use.
• Incompatibilities: Strong oxidizers may react with secondary alcohols/ketones; strong bases/acids may cause degradation or isomerization (literature). Avoid prolonged exposure to moisture.
• First aid (general): If on skin, wash with soap and water. If in eyes, rinse cautiously with water for several minutes and seek medical advice. If inhaled, move to fresh air. If ingested, rinse mouth and seek medical attention. Provide SDS to medical personnel.
• Waste: Dispose according to institutional chemical waste procedures; avoid drain disposal.

Note: Always defer to the product SDS and institutional EHS policies for specific requirements.

Solvent Selection

This deuterated steroidal standard is typically handled in organic solvents for analytical workflows.

General solvent behavior (literature):

• Polarity and miscibility: Poorly soluble in water; good solubility in polar organic solvents (methanol, ethanol, acetonitrile, acetone) and in polar aprotics like DMSO. Solubility often increases with gentle heating and sonication.
• LC–MS compatibility: Methanol and acetonitrile (with 0.1% formic acid or ammonium formate/acetate) are standard for reverse-phase methods. For stock solutions, anhydrous methanol or acetonitrile are preferred to minimize hydrolysis or isomerization pathways.
• GC–MS workflows: Derivatization (e.g., silylation with BSTFA + 1% TMCS) in dry acetonitrile or pyridine is common to increase volatility of hydroxy-steroids (literature). Ensure absence of water.

Comparison notes (general):

• Methanol vs acetonitrile: MeOH enhances solubility for many steroids; ACN often yields sharper LC peaks and lower backpressure.
• DMSO: Excellent solvency for concentrated stocks (e.g., 10–50 mM), but use low final percentages (<1–2%) to avoid chromatographic suppression or ion-source contamination.
• Isopropanol: Useful as a co-solvent to prevent precipitation during sample dilution.

Always confirm your instrument’s solvent compatibility. Item-specific solubility limits are Not specified for this item; refer to CoA/Spec Sheet.

Storage and Reconstitution

Follow the item-specific storage guidance provided and standard practices for light- and air-sensitive steroidal standards.

• Storage conditions (from Product Data): Store at 2–8 °C, protected from light, argon charged. Shipments are on wet ice.
• Container handling: Keep tightly closed. Purge headspace with argon after each use. Use amber vials or foil wrapping to minimize photodegradation.
• Reconstitution (general guidance):
  • Solvents: LC–MS–grade methanol or acetonitrile are typical. DMSO can be used for highly concentrated stocks. Verify compatibility with your analytical method.
  • Concentration: Prepare a primary stock (e.g., 0.1–1 mg/mL) and dilute to working levels with 50:50 MeOH:water or mobile phase. Filter through 0.2 μm PTFE if particulate is observed.
  • Aliquoting: Divide into single-use aliquots to avoid repeated freeze–thaw and atmospheric exposure. Maintain inert headspace.
• Stability: Item-specific stability data, water/peroxide limits, and light sensitivity kinetics are Not specified for this item; refer to CoA/Spec Sheet. As a precaution, avoid prolonged exposure to room temperature and strong light.
• Research use only: Not for human or animal administration.

Before first use, allow container to equilibrate to room temperature in the dark to prevent moisture condensation, then open under inert atmosphere if possible.

Structure and Identity

A deuterium-labeled steroid standard corresponding to 16α-hydroxydehydroepiandrosterone (16α-OH DHEA), i.e., a hydroxylated DHEA metabolite bearing an additional hydroxyl at C16α. The exact deuterium labeling pattern for this catalog item is not specified.

• SKU: H1440762
• Product name: 16α-Hydroxydehydroepiandrosterone-d (deuterated analog)
• CAS: 97453-29-7
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (Note: the non-deuterated parent 16α-OH DHEA is C19H28O3, literature.)
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Deuteration typically increases MW by +1 per D, literature.)

Structural features (general, literature):

• Steroid tetracyclic cyclopentanoperhydrophenanthrene core (rings A–D).
• Unsaturation at Δ5 (androst-5-ene system) as in DHEA.
• Hydroxyl at C3β and an additional hydroxyl at C16α; ketone at C17.
• Multiple stereocenters inherent to the androstane framework; 16α configuration at the added hydroxyl.

2D description in words (literature):

• A fused 6-6-6-5 ring system with a 17-ketone on ring D, a 3β-alcohol on ring A, a double bond between C5–C6, and a secondary alcohol at C16 pointing below the plane (α). Deuterium substitution(s) occur at unspecified carbon(s) relative to the parent structure.

Synthetic Utility

While primarily an analytical standard, the underlying functional groups of 16α-hydroxy-DHEA (and by extension its deuterated analog) offer instructive chemistry for steroidal transformations (literature/general):

Key functional elements:

• 3β- and 16α-secondary alcohols: amenable to selective protection (e.g., silyl ethers such as TBS/TBDMS), acylation, Mitsunobu inversion (with caution due to neighboring group effects), and oxidations (e.g., Dess–Martin) to corresponding ketones.
• 17-ketone: participates in oxime/hydrazone formation, reductive amination (with prior protection), or Wolff–Kishner/clemmensen-type manipulations under carefully chosen conditions to preserve other centers.
• Δ5-alkene: subject to epoxidation (m-CPBA), hydroboration–oxidation, or catalytic hydrogenation, often with facial selectivity dictated by the steroid framework.

Applications of deuterated analogs (general):

• Mechanistic probes: Non-exchangeable deuterium can reveal kinetic isotope effects or migration pathways in rearrangements, provided labeling sites are known (not specified for this item; consult CoA).
• Isotope tracing: Track fate of specific hydrogens during enzymatic hydroxylation or redox processes by MS.

Caveat:

• If employed in synthesis, be aware of potential H/D exchange under acidic/basic, catalytic hydrogenation, or metal-catalyzed conditions. Verify retention of deuterium by HRMS after key steps.

Target Specificity

Not applicable. This product is a small-molecule deuterated steroid standard, not a biological targeting reagent (e.g., antibody, ligand conjugate). There is no antigen, clone, isotype, or species reactivity associated with this item.

For analytical specificity, see Reaction & Applications and Application Protocols regarding isotope-dilution mass spectrometry.

よくある質問

How should this product be stored?

Store at 2–8 °C, protected from light, under argon. It is supplied under an argon blanket; reseal under inert gas after each use.

How is this product shipped?

This product ships chilled on wet ice. 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 97453-29-7, the molecular formula is C19H22D6O3, and the molecular weight is 310.46 g/mol.

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.