Diethylstilbestrol-d , CAS No.58322-36-4

CAS: 58322-36-4 Cat. No.: D1451607 Fórmula: C₁₈H₁₇D₃O₂ Peso molecular: 271.37

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Visão geral

Diethylstilbestrol-d 3 is deuterium labeled Diethylstilbestrol.

Specifications

Condições de armazenamento de armazenamento

Store at -20°C

Enviado em

Ice chest + Ice pads

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Nomes e identificadores

• Peso molecular: 271.37

Application Protocols

General workflow examples for research use (no item-specific validated protocols are provided):

• LC–MS internal standardization:

  1. Prepare a 1–5 mM stock in methanol or acetonitrile. Store aliquots at −20 °C, protected from light.
  2. Spike samples with a fixed amount of Diethylstilbestrol-d prior to extraction (typical final 1–100 ng/mL depending on matrix and instrument sensitivity; literature/practice).
  3. Perform sample cleanup (e.g., protein precipitation with MeOH/ACN; or SPE using reversed-phase cartridges).
  4. Analyze by LC–MS/MS monitoring the unlabeled DES and the deuterated analog in parallel channels. Optimize MRM/PRM transitions empirically based on the actual deuterium content (not specified for this item).

• Receptor-binding/cell-based assays (exploratory research):

  1. Prepare DMSO stocks (e.g., 10 mM). Dilute into assay buffer to desired concentrations, maintaining ≤0.1–0.5% DMSO.
  2. Include vehicle controls and, if needed, unlabeled DES standards for comparative binding curves.

Notes:

• Exact masses/transitions and extinction coefficients are not provided; determine experimentally for the received lot.
• Validate linearity, recovery, matrix effects, and stability per your laboratory’s SOPs.

Biological Roles

Context (literature/general for the parent scaffold):

• Diethylstilbestrol (DES) is a synthetic, nonsteroidal estrogen that binds estrogen receptors ERα and ERβ, acting as an agonist. The phenolic groups and planar conjugated framework mimic key pharmacophores of endogenous estrogens.
• Mechanistic features: ligand binding induces receptor dimerization, DNA binding to estrogen response elements, and transcriptional modulation (biochemical description). Coactivator recruitment is ligand- and receptor-isoform dependent.
• Metabolism: Phase II conjugation (UDP-glucuronosyltransferases; sulfotransferases) yields glucuronides and sulfates; oxidative metabolites may form under specific conditions (literature/general). These pathways are often characterized using isotopically labeled analogs.

Relevance of deuteration (general):

• Deuteration increases mass without significantly altering receptor affinity or basic biochemical interactions, enabling selective MS detection as a tracer/internal standard.
• Exchangeable vs non-exchangeable D: placement matters for metabolic tracing; consult CoA for labeling positions to interpret any observed deuterium loss through H/D exchange.

Use-cases in life science research (for research use only):

• Quantifying receptor engagement or cellular uptake using parallel-labeled and unlabeled analytes.
• Tracking biotransformation products and assessing enzyme kinetics via isotope-dilution LC–MS.

No medical or clinical claims are made; this product is intended strictly for research applications.

Buffer Applications

This product is not a buffering agent and is not typically used to prepare buffer systems. For assays involving Diethylstilbestrol-d:

• Prepare concentrated stocks in an appropriate organic solvent (e.g., DMSO, methanol) and dilute into the desired biological buffer (e.g., PBS, HEPES) while controlling final organic content (commonly ≤0.1–0.5% v/v in cell-based assays; literature/general practice).
• If increased apparent solubility is needed, limited use of co-solvents or serum proteins (binding carriers) may be considered, ensuring that controls account for vehicle effects.

No buffer recipes or pH ranges are applicable specifically to this analyte.

Green Alternatives

Green chemistry considerations center on solvent and waste selection rather than replacement of the analyte:

• Prefer greener solvents for stock preparation and chromatography where compatible:
  • Ethanol or methanol instead of chlorinated solvents (literature/general).
  • Aqueous-organic mobile phases (water + MeOH/ACN) with volatile modifiers (formic acid, ammonium acetate) to facilitate low-impact waste handling.
• Minimize DMSO where possible due to persistence; if required for solubility, keep volumes small and segregate waste streams appropriately.
• Employ microscale workflows (low-volume sample prep, 96/384-well formats) to reduce solvent consumption in LC–MS assay development.

Comparison (general):

• Methanol: renewable routes available; readily biodegradable; excellent LC–MS compatibility.
• Ethanol: bio-based, low toxicity, suitable for UV/fluorescence assays; check assay tolerance.
• Acetonitrile: strong LC performance but less green; use efficiently (short columns, UHPLC) to reduce volumes.

Process suggestions:

• Use light-protective glassware to reduce photodegradation, decreasing the need for repeat preparations.
• Optimize sample cleanup (e.g., SPE) to lower injection solvent strength and volumes, cutting overall solvent use.

Note: No greener substitute exists for the analyte itself when isotopic fidelity to DES is required for analytical accuracy.

Pharmaceutical Uses

Formulation/manufacturing context (general):

• Diethylstilbestrol-d, as a deuterated analog, is used primarily as an analytical internal standard in method development, validation, and quality control for the detection/quantitation of diethylstilbestrol and related metabolites by LC–MS or GC–MS.
• Typical roles: system suitability standard, recovery surrogate, and calibration spike for isotope-dilution quantitation.

Notes:

• This product is designated for research use only (per Product Data) and is not an excipient or therapeutic agent.
• When used in regulated environments, confirm traceability, isotopic enrichment, and purity per internal SOPs and applicable guidelines. Ensure solvent residues or stabilizers (if present; not specified for this item) are compatible with the analytical procedure.

Pharmacopeial status:

• No pharmacopeial monograph for the deuterated analog is cited here. If alignment to compendial methods is required, adapt procedures validated for the unlabeled parent, using the deuterated standard for internal standardization (general guidance).

Physical Properties

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula and weight: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index, density, UV cutoff, water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general values for the unlabeled parent (Diethylstilbestrol, for context only):

• Typical melting point (literature, parent DES): ~168–171 °C (depends on polymorph and purity).
• Solubility profile (literature): sparingly soluble in water; soluble in polar organic solvents (methanol, ethanol, acetonitrile) and in aprotic solvents (DMSO, DMF); enhanced solubility in basic media via phenolate formation.
• pKa (phenolic OH, literature, parent DES): weakly acidic, pKa typically in the 10 range for phenolic groups; actual values depend on substitution and medium.
• LogP (literature, parent DES): high hydrophobicity consistent with a hydrophobic nonsteroidal estrogen; exact value varies by source.

Notes for deuterated analogs:

• Deuteration minimally alters bulk physical properties (mp, solubility) but increases exact mass proportionally to D content (literature/general). Users should consult the specific CoA for exact isotopic enrichment, deuterium number, and any salt/hydrate form that may affect handling.

Quality and Grades

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

Context for isotopically labeled analytical standards (general):

• Isotopic labeling (deuterium) is commonly used to create internal standards for quantitative LC–MS/GC–MS. Key quality attributes include isotopic enrichment (atom % D), labeling positions, chemical purity, and residual unlabeled parent content. These directly impact quantitative accuracy and isotope-dilution methodologies.
• Documentation: For rigorous analyses, refer to the CoA for exact deuterium count, isotopic purity (e.g., %D, %H), residual solvents, and any stabilizers.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. If present, stabilizers can influence chromatographic baselines or ionization and should be considered when developing methods (general guidance).
• Regulatory/traceability: For research use only (per Product Data). If used as an analytical standard in regulated workflows, ensure appropriate qualification/verification against in-house criteria.

What to verify upon receipt:

• Confirm lot-specific isotopic distribution by HRMS where critical.
• Verify chromatographic purity and absence of significant isomeric impurities (e.g., cis/trans mixtures) when relevant to your method.

Reaction and Applications

Primary applications (research/analytical; literature/general):

• Isotope-dilution quantitation: Diethylstilbestrol-d is suited as an internal standard for LC–MS workflows targeting DES in environmental, metabolomic, or endocrine-disruptor exposure studies. Deuteration provides a characteristic mass shift enabling co-elution and correction for matrix effects.
• Metabolic fate studies: Tracing conjugation pathways (e.g., glucuronidation, sulfation) of the parent scaffold by monitoring deuterated mass channels.
• Binding/biophysics: Use in receptor-binding assays (ERα/ERβ) to differentiate specific vs nonspecific signals via parallel isotopic channels, without altering receptor interactions substantially (literature: deuteration typically has minimal effect on binding energetics).

Chemical reactivity/derivatization (literature/general for phenolic stilbenes):

• Phenolic O-acylation/alkylation to tune lipophilicity or for immobilization on solid supports.
• Protection strategies (e.g., MOM, Bn) to facilitate multi-step manipulations if the labeled scaffold is used in probe synthesis.
• Sensitivity to photochemical isomerization (E↔Z) across the stilbene double bond; protect from light during reactions and storage.

Practical tips:

• Prepare fresh stock solutions and verify isotopic integrity by MS prior to critical quantitation campaigns.
• Avoid prolonged exposure to strong bases/acids and oxidants that can induce degradation or isotope scrambling (where exchangeable positions exist).

Reaction Conditions

Analytical preparation (general):

• Stock solutions: common concentrations 1–10 mM in DMSO, methanol, ethanol, or acetonitrile (literature practice). Filter (0.2 µm PTFE) if particulate is present. Protect from light.
• LC–MS: employ water/MeOH or water/ACN with volatile modifiers (e.g., 0.1% formic acid or ammonium acetate). Column choices include C18 or phenyl-hexyl to leverage π–π interactions; gradients typically 20–95% organic over 5–15 min. Optimize source conditions for phenolic analytes.

Derivatization (if required; literature/general for phenols):

• O-acylation: acyl chloride/anhydride, mild base (e.g., pyridine, DMAP catalysis), 0–25 °C, minutes to hours.
• O-methylation: MeI/Me2SO4 with base (e.g., K2CO3) in acetone/DMF, 0–25 °C.
• Caution: Conditions that facilitate H/D exchange can erode isotopic labeling; maintain neutral to mildly basic conditions, low water content, and minimal heating.

Biochemical assays (general):

• Receptor-binding or cell assays often use final concentrations in the nM–µM range with vehicle ≤0.1–0.5% DMSO. Pre-equilibrate solutions and verify adsorption losses (glass vs plastic) due to hydrophobicity.

Yields/timings: Not applicable to this item as a supplied standard; any reaction yields depend on specific derivatization chosen and are not specified.

Safety and Handling

• 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 considerations (literature/general):

• Synthetic estrogens such as diethylstilbestrol exhibit potent endocrine activity. Handle as a hazardous laboratory chemical, minimizing exposure via inhalation, ingestion, and skin contact. Work in a certified fume hood.
• PPE: lab coat, nitrile gloves (double-gloving recommended for extended work), safety glasses or face shield. Change gloves frequently and avoid contamination of common surfaces.
• Avoid dust/aerosol generation; keep containers tightly closed. Clean spills with absorbent pads while wearing appropriate PPE and dispose of waste as hazardous chemical waste per institutional guidelines.
• Incompatibilities: strong oxidizing agents; strong bases/acids may lead to salt/ester formation or degradation (literature/general). Protect from light to minimize potential photodegradation of stilbene systems.
• First aid (overview; consult SDS): in case of skin contact, wash immediately with soap and water; for eye exposure, flush with water for ≥15 minutes and seek medical evaluation; if inhaled, move to fresh air; if ingested, do not induce vomiting and seek medical attention.
• Environmental note: prevent release to the environment due to potential bioactivity (literature/general). All disposal should follow local regulations.

Always defer to the product-specific SDS for authoritative hazard classification and response procedures.

Solvent Selection

Solubility guidance (literature/general for DES-like scaffolds):

• Preferred solvents for stock solutions: DMSO, methanol, ethanol, acetonitrile. Aqueous solubility is poor; prepare concentrated stocks in an organic solvent and dilute into assay buffers with cosolvent control.
• pH effects: Phenolic OH groups allow limited solubility increase in basic aqueous media via formation of phenolate salts; however, strong base may risk degradation over time.
• Polarity/miscibility: Choose polar aprotic or protic organic solvents depending on the analytical platform (e.g., MeOH/ACN for LC–MS).

Practical selection for common use-cases:

• LC–MS internal standard: MeOH or ACN (0.1% formic acid often used in mobile phase; assess ionization of phenolic species accordingly).
• Bioassays/receptor studies: DMSO stocks (e.g., 10–20 mM) with final assay DMSO ≤0.1–0.5% v/v to minimize biological interference (general practice).
• Spectroscopy: Ethanol or methanol provides clean UV backgrounds; avoid strongly absorbing stabilizers.

Comparison (literature/general):

• DMSO: Highest solvating power; hygroscopic; may affect some bioassays.
• Methanol/Ethanol: Greener, volatile, LC-compatible; lower maximum solubility than DMSO.
• Acetonitrile: LC–MS friendly, low viscosity; less green; handle with ventilation.

Always confirm actual solubility and stability for this lot/formulation; item-specific solubility data are not specified for this product.

Storage and Reconstitution

• Storage conditions (item-specific): Store at −20 °C (per Product Data). Protect from light. Avoid repeated freeze–thaw cycles by aliquoting upon first use.
• Shipping: Shipped in ice chest with ice pads (per Product Data) to maintain low temperature during transit.

Reconstitution/preparation (general guidance):

• Solvents: DMSO, methanol, ethanol, or acetonitrile are typical for stock solution preparation of DES-like compounds. Use anhydrous solvents where feasible to limit hydrolysis/oxidation.
• Concentration: Prepare 1–10 mM stocks depending on downstream use; verify complete dissolution by gentle vortexing/sonication.
• Filtration: If particulate is present, filter through 0.2 µm PTFE. Avoid cellulose-based filters that may adsorb hydrophobic phenolics.

Stability notes (literature/general):

• Phenolic stilbenes can undergo photochemical isomerization and slow oxidative degradation; store in amber vials under inert gas if long-term storage is required.
• Solution stability improves at −20 °C; assess by periodic LC–MS or HPLC purity checks. Specific shelf-life for this item is not specified; refer to CoA/Spec Sheet.

Research Use Note: For research use only (per Product Data). Ensure compliance with institutional handling and disposal policies for bioactive small molecules.

Structure and Identity

• SKU: D1451607
• Product name: Diethylstilbestrol-d
• CAS: 58322-36-4
• 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 overview (literature, parent scaffold):

• Diethylstilbestrol (DES) is a synthetic, nonsteroidal estrogen of the stilbene family featuring a central trans-ethenyl (stilbene) linkage connecting two para-hydroxylated phenyl rings, each bearing an ethyl substituent at the α-carbon relative to the double bond.
• Key functional groups: two phenolic hydroxyls (weakly acidic), an internal C=C double bond (E-stilbene core), and alkyl (ethyl) substituents that increase hydrophobicity.
• Isotopic labeling note: the “-d” indicates deuterium incorporation; the number and positions of deuteria are not specified for this item. Isotopic labeling does not change bonding topology but increases exact mass according to the number of D atoms (literature/general).

2D description in words (literature, parent scaffold): a trans-stilbene backbone where each phenyl ring is para-hydroxylated; ethyl groups are located vicinal to the ethenyl linkage. The molecule is planar around the C=C with extended conjugation across the aromatic rings. Deuteration replaces one or more hydrogens with deuterium at specified positions (not provided here).

Synthetic Utility

As a finished, isotopically labeled analyte, Diethylstilbestrol-d is primarily used analytically rather than as a synthetic reagent. Nonetheless, for researchers modifying the scaffold (literature/general for phenolic stilbenes):

• Functional handles: two phenolic OH groups enable derivatization (O-acylation, O-alkylation, carbonate/carbamate formation) to modulate polarity or tether to supports/fluorophores.
• Stilbene reactivity: the central C=C can undergo E/Z photoisomerization; hydrogenation yields bibenzyl derivatives. Oxidation at benzylic/allylic positions should be performed cautiously to preserve isotopic labels.
• Isotopic integrity: If synthetic steps are planned, avoid conditions that promote H/D exchange at labeled positions (strong acids/bases, metal-catalyzed exchange, or protic solvents at elevated temperature).

Retrosynthetic considerations (general):

• Label introduction strategies include use of deuterated building blocks or catalytic H/D exchange on activated aromatic/benzylic positions. The choice impacts isotopic stability during downstream transformations.

In most workflows, the labeled compound is not further transformed but used directly as a calibration/internal standard to ensure measurement trueness and precision.

Target Specificity

Not applicable. This product is a small-molecule, isotopically labeled standard and is not an antibody or affinity reagent. No antigen, clone, isotype, or species reactivity data apply. For biochemical context regarding receptor interactions, refer to the Biological Roles section.