Altrenogest-d , CAS No.A1455374

CAS: A1455374 Cat. No.: A1455374 Formula: C₂₁H₂₁D₅O₂ Molecular Weight: 315.46

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Altrenogest-d 5 is the deuterium labeled Altrenogest. Altrenogest (Allyltrenbolone) is a progestogen structurally related to veterinary steroid trenbolone.

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

315.46

Application Protocols

No item-specific, vendor-validated protocols are provided in the Product Data. Below is a general LC–MS/MS isotope-dilution workflow for deuterated small-molecule standards; adapt per your SOP.

• Internal standard (IS) stock preparation:

  • Accurately weigh the solid into a volumetric flask (amber). Dissolve in MeOH or DMSO to prepare a primary stock (e.g., 1–10 mM; choose based on expected working range). Record exact mass and volume.
  • Prepare intermediate and working IS solutions in MeOH or 50:50 MeOH:water. Store aliquots at −20°C (amber vials).

• Calibration standards and QCs:

  • Spike unlabeled analyte into blank matrix or solvent at a series of concentrations spanning expected sample levels. Add a constant IS amount to all calibrators, QCs, and study samples.

• Sample extraction (example, protein precipitation):

  • Add IS to sample, vortex. Add 3–4 volumes of cold ACN or MeOH, vortex 1 min, incubate on ice 10 min, centrifuge (≥12,000 g, 10 min). Transfer supernatant, dilute with water, inject or proceed to SPE.

• LC–MS/MS analysis:

  • Use reversed-phase C18 column; mobile phases water + 0.1% formic acid and MeOH (or ACN). Optimize gradient and MRM transitions for both analyte and IS.

• Data analysis:

  • Construct calibration curve using analyte/IS peak area ratio; apply appropriate weighting (e.g., 1/x or 1/x²). Evaluate accuracy, precision, recovery, and matrix effects per validation guidance.

Biological Roles

• Item-specific biological data: Not specified for this item; refer to CoA/Spec Sheet.

• General/literature context (parent compound altrenogest):

  • Functional class: Synthetic progestin; agonist activity at the progesterone receptor (PR) has been described in the literature for related compounds.
  • Research relevance: Frequently used in animal reproduction research and as an analytical target in environmental/food testing laboratories.

• Deuterated analog relevance:

  • The deuterated form is not intended for biological effect studies but serves as an isotopically distinguishable surrogate to quantify the unlabeled analyte and track fate/transport in experimental systems.
  • Because deuteration minimally alters receptor binding relative to hydrogen at most non-exchangeable positions, co-elution and similar extraction efficiency with the parent are typically observed, making it suitable for isotope-dilution workflows (literature/general).

• Precautions in biological matrices:

  • Add internal standard early (pre-extraction) to correct for recovery and matrix effects.
  • Avoid conditions that promote H/D back-exchange; keep extractions brief and control pH.

No medical or clinical claims are made; this product is for research use only.

Buffer Applications

This product is a hydrophobic, neutral, small-molecule analytical standard and is not typically employed to make laboratory buffers.

• Practical note:
  • For LC–MS sample preparation, aqueous buffers (e.g., ammonium formate/acetate at 1–10 mM with 0.1% formic acid) are commonly combined with organic modifiers (MeOH or ACN) to aid solubility and chromatographic performance (literature/general). Optimize pH and ionic strength for your stationary phase and ionization mode.

For classical buffer-making guidance (pH control in biochemistry), please refer to dedicated buffering agents such as phosphate, Tris, HEPES, or acetate.

Green Alternatives

Greener handling focuses on solvent choices and waste minimization; the active compound class itself has limited green alternatives due to analytical specificity requirements.

• Greener solvent substitutions (general guidance):

  • Replace acetonitrile with methanol or ethanol in extraction/mobile phases when chromatographic performance allows; expect changes in retention and ionization.
  • Use aqueous-organic mixtures with lower organic content by optimizing column chemistry (e.g., core–shell C18, phenyl-hexyl) to maintain resolution.
  • Employ 2-propanol as a stronger eluent in place of halogenated solvents for cleanup steps.

• Process improvements:

  • Miniaturize sample prep (microextraction, SPME, or 96-well SPE) to reduce solvent volumes.
  • Implement closed-vial evaporation and solvent recycling where feasible.
  • Use solid dispensing of standards with gravimetric dilution to reduce solvent usage and improve accuracy.

• Trade-offs:

  • Methanol is greener than acetonitrile but may increase viscosity and backpressure; ionization efficiency can differ.
  • Ethanol is safer but less volatile, potentially lengthening drying times.

• Comparison (general):

  • MeOH: Renewable routes available; good LC–MS compatibility.
  • ACN: Petrochemical-derived; excellent chromatographic performance but higher toxicity.
  • IPA/Ethanol: Safer handling; may need higher percentages to elute strongly retained hydrophobes.

These suggestions are general. Validate any solvent change for your specific chromatographic method and detection limits.

Pharmaceutical Uses

• Item-specific pharmacopeial/grade information: Not specified for this item; refer to CoA/Spec Sheet.

• General research/manufacturing context (no therapeutic claims):

  • Deuterated altrenogest standards can be used in quality control laboratories to assay altrenogest content and impurity profiles in research formulations by LC–MS or HPLC-UV/MS.
  • Serve as system suitability and method performance markers in validation (linearity, accuracy, precision, carryover) for analytical procedures targeting the unlabeled active.
  • Stability-indicating methods: Employed to monitor degradation pathways during forced-degradation studies (acid/base/oxidation/light) of research samples.

• Not an excipient:

  • Deuterated analogs are not used as formulation excipients; their role is analytical quantification and tracing only.

Always consult internal QA/QC requirements and pharmacopeial monographs (where applicable for the unlabeled parent) to align system suitability and acceptance criteria.

Physical Properties

• Item-specific properties (specs for this catalog number):

  • 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: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Melting/boiling points, density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

• General/literature expectations for steroidal progestins (context, not specifications):

  • Physical state: Typically crystalline or amorphous solid at ambient conditions.
  • Polarity/partitioning: Highly lipophilic; low aqueous solubility; good solubility in polar aprotic and protic organic solvents such as DMSO, methanol, ethanol, acetone, and acetonitrile.
  • Acid–base behavior: Neutral molecule (no strongly ionizable groups); pKa not typically defined for the core structure.
  • Stability: Generally stable under dry, cool, light-protected storage; can undergo photodegradation and slow oxidation under harsh conditions.
  • Isotopic substitution: Deuteration raises exact mass by +1 Da per D and may slightly alter volatility and vibrational spectra without changing connectivity.

• Practical notes (general):

  • Prepare concentrated stock solutions in anhydrous DMSO or methanol for analytical applications; aliquot to avoid repeated freeze–thaw.
  • For LC–MS, solutions in MeOH, ACN, or 1:1 MeOH:water with 0.1% formic acid are commonly used carrier matrices (literature guidance).

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• General guidance for deuterated reference standards:

  • Isotopic enrichment: Typically reported as percent deuterium incorporation at specified positions (e.g., ≥98 atom% D at labeled sites). Exact enrichment and labeling pattern determine suitability as internal standard; verify on the CoA.
  • Chemical purity: Reported as area% or weight% by HPLC/GC/NMR. For quantitative LC–MS, high chemical purity reduces interference and ion suppression.
  • Residual solvents/inorganics: CoA may include residual solvent by GC and metal/ash content; review if your analytical method is sensitive.
  • Identity confirmation: Often documented by 1H/13C NMR (with reduced 1H signals at labeled positions), HRMS (exact mass shift), and sometimes IR.

• What this means in practice:

  • For isotope-dilution LC–MS/MS, choose lots with clear isotopic labeling information and minimal isotopic impurity (e.g., unlabeled parent content) to prevent bias at low analyte levels.
  • Stabilizers: Not typically used for solid steroidal standards; if present, they will be disclosed on the CoA. Absent such disclosure, do not assume any stabilizer.

• Documentation:

  • Request the lot-specific CoA and Spec Sheet for definitive grade/purity, labeling pattern, and analytical characterization supporting your validation package.

Reaction and Applications

• Primary research applications (general for deuterated altrenogest):

  • Internal standard for quantitative LC–MS/MS of altrenogest in complex matrices (feed, environmental samples, biological extracts) via isotope-dilution calibration.
  • Tracer for metabolism and stability studies to distinguish analyte from background using characteristic mass shifts.
  • Recovery and matrix-effect assessments in method validation (spike-and-recover, post-extraction spiking).

• Practical tips (analytical workflows):

  • Prepare a concentrated stock (e.g., in DMSO or MeOH) and serially dilute with MeOH or ACN:water to obtain calibration levels; record exact gravimetric concentrations.
  • Spike internal standard at a constant concentration across all calibrators, QCs, and samples prior to extraction for best compensation of losses and ion suppression.
  • Verify isotopic purity to ensure chromatographic co-elution without interference from unlabeled parent.

• Synthetic/chemical applications (general):

  • Deuterated analogs can be used to probe kinetic isotope effects or H/D exchange pathways in steroid chemistry; conditions must avoid back-exchange.

• Noteworthy considerations:

  • Avoid acidic or basic aqueous incubations that promote H/D exchange at labile positions (allylic/benzylic or enolizable sites), which can diminish isotopic label integrity.
  • Protect solutions from prolonged light exposure to minimize photodegradation of conjugated enone systems (general for steroidal enones).

Reaction Conditions

For this deuterated analytical standard, "reaction conditions" typically refers to analytical sample preparation and chromatography rather than synthetic transformations. The following are general/literature guidelines; adjust to your method and instrument.

• Stock and calibration solutions:

  • Dissolve in anhydrous MeOH or DMSO to prepare a primary stock (gravimetrically quantified). Prepare serial dilutions in MeOH or 50:50 MeOH:water.
  • Store aliquots at −20°C; minimize light exposure and freeze–thaw cycles.

• LC–MS/MS (ESI+ or APCI+, general starting points):

  • Mobile phases: A = water + 0.1% formic acid or 2 mM ammonium formate; B = MeOH or ACN.
  • Gradient: Begin at 40–60% B, ramp to 90–98% B over 3–6 min for reversed-phase C18; re-equilibrate adequately.
  • Source: Moderate temperature and drying gas; monitor in-source fragmentation of steroidal enones.
  • MRM transitions: Select precursor m/z corresponding to the deuterated analog; product ions analogous to the unlabeled parent but shifted by the deuterium count (optimize empirically).

• Sample prep (biological matrices):

  • Add internal standard pre-extraction; perform protein precipitation with ACN or MeOH (3–4× volume), vortex, centrifuge; dilute supernatant with water before injection.
  • For cleaner extracts, consider SPE (C18 or polymeric reversed-phase) with MeOH/ACN elution.

• Stability checks:

  • Include short-term, freeze–thaw, and post-preparative stability experiments to confirm absence of H/D back-exchange and acceptable autosampler stability.

Safety and Handling

• GHS/SDS information for this specific item:

  • Signal word: Not specified for this item; refer to SDS.
  • Hazard statements (H-codes): Not specified for this item; refer to SDS.
  • GHS classification and pictograms: Not specified for this item; refer to SDS.

• General safety considerations (literature/general for steroidal small molecules):

  • Avoid inhalation/ingestion/skin contact. Use in a chemical fume hood.
  • Wear appropriate PPE: lab coat, nitrile gloves, safety glasses; consider double-gloving and dedicated tools to prevent cross-contamination when handling analytical standards.
  • Potential hazards: Hormone-like activity is possible for the non-deuterated parent. Treat unknown powders of steroidal nature as potentially bioactive; prevent exposure and environmental release.
  • Incompatibilities: Strong oxidizers; strong acids/bases may cause degradation; avoid prolonged exposure to light and elevated temperature.

• First aid (overview, defer to SDS):

  • Skin/eye contact: Rinse with plenty of water for ≥15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

• Spills and waste:

  • Small spills: Absorb with inert material (e.g., vermiculite), collect in a sealable container for disposal as hazardous chemical waste.
  • Disposal: Follow institutional and governmental regulations; minimize hormone-like substance release to drains.

Always consult the product-specific SDS for authoritative safety data and emergency measures.

Solvent Selection

This product behaves as a hydrophobic, neutral, steroid-like small molecule. Solvent choices below are general/literature guidance for handling and LC–MS workflows; they are not item-specific specifications.

• Primary solvents for stocks:

  • DMSO: Excellent solvating power for steroids; compatible with bioanalytical workflows at low final %.
  • Methanol or ethanol: Good solubility; volatile; LC–MS friendly.
  • Acetonitrile (ACN): Often used in mobile phases and for precipitation of proteins; moderate solubility for steroids.

• Working solutions (analytical):

  • 50:50 MeOH:water or ACN:water with 0.1% formic acid or 1–2 mM ammonium formate/acetate are common starting points for LC–MS/MS.

• Miscibility and polarity (general):

  • Immiscible with water at high concentrations; form clear solutions in polar organic solvents.
  • LogP expected to be high (lipophilic), favoring organic-rich media.

• When to choose what:

  • DMSO stock + dilution into MeOH:water for robust solubilization of standards.
  • Pure MeOH stock for maximum volatility and ease of evaporation during sample prep.
  • ACN-rich solutions for workflows using protein precipitation from biological matrices.

• Small comparison (general):

  • DMSO: Highest solubility; lowest volatility.
  • MeOH/Ethanol: Good solubility; high volatility; greener profile than ACN.
  • ACN: LC–MS gold standard mobile phase component; toxic and less green than MeOH.

Storage and Reconstitution

• Storage (item-specific from Product Data):

  • Store at −20°C.
  • Shipped in: Ice chest + ice pads.

• General handling guidance:

  • Protect from light and moisture. Allow container to equilibrate to room temperature before opening to avoid condensation.
  • Reseal tightly under inert atmosphere (if available) or promptly purge headspace with dry nitrogen/argon after use.
  • Minimize freeze–thaw cycles by preparing single-use aliquots of stock solutions.

• Reconstitution (general, not item-specific specifications):

  • Prepare primary stock in anhydrous methanol or DMSO at a convenient concentration for your assay. Vortex and, if necessary, sonicate briefly to ensure complete dissolution.
  • Filter working solutions (0.2 µm PTFE) if particulate is observed prior to LC–MS injection.
  • For aqueous working solutions, dilute the organic stock into water or buffer while vortexing to prevent precipitation; maintain organic content sufficient to keep the compound in solution (often ≥10–20% MeOH or ACN, method-dependent).

• Stability checks:

  • Verify solution stability at bench-top, autosampler (4–10°C), and long-term frozen conditions as part of method validation. Monitor for any evidence of H/D back-exchange over time by HRMS or MRM transitions.

• Research use note:

  • For research use only.

Structure and Identity

Brief overview: Altrenogest-d is a deuterium-labeled analog of altrenogest intended for research and analytical use (e.g., as an internal standard). Specific structural identifiers for this catalog item are not supplied in the Product Data.

• Item-specific identifiers (this product):

  • CAS: Not specified for this item; refer to CoA/Spec Sheet.
  • 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.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

• General/literature context (for the non-deuterated parent, altrenogest):

  • Class: Synthetic progestin (steroidal framework) bearing an enone and allyl substituent at C17.
  • Typical features: Tetracyclic cyclopentanoperhydrophenanthrene core; conjugated enone; secondary alcohol at C17; multiple defined stereocenters characteristic of steroids.

• What “-d” denotes:

  • Indicates one or more hydrogens of the parent structure are replaced by deuterium (2H) for isotopic tracing and mass spectrometric discrimination.
  • Exact number/positions of deuterium atoms for this item: Not specified for this item; refer to CoA/Spec Sheet.

• 2D structure description (general, steroid framework):

  • Four fused rings (three cyclohexane-like and one cyclopentane), a C3-ketone conjugated to a Δ4-double bond, and a C17 substituent (allyl and hydroxyl in the parent). Deuteration does not alter connectivity but increases exact mass at labeled positions (literature/general).

Synthetic Utility

While primarily intended as an analytical internal standard, a deuterated steroidal enone such as altrenogest-d can have niche synthetic and mechanistic utility (general/literature context):

• Mechanistic probes:

  • Kinetic isotope effect (KIE) studies to interrogate rate-limiting C–H vs C–D bond cleavage in steroid functionalization (allylic oxidation, hydrogenation, or enolization steps).
  • H/D scrambling assessments in catalytic systems to map enolization or isomerization pathways of enone-containing steroids.

• Label tracing:

  • Positional analysis by NMR/HRMS to follow migration or retention of deuterium during derivatizations (e.g., O-silylation at C17-OH, oxime/semicarbazone formation at C3=O).

• Derivatization for analytics:

  • Formation of more MS-responsive adducts/derivatives (e.g., PFB oxime for GC-MS of ketosteroids) while preserving the deuterium label enables improved sensitivity and selectivity.

• Constraints:

  • Avoid strongly acidic/basic or protic conditions that catalyze H/D exchange at activated positions (enolizable alpha to carbonyl, allylic benzylic sites) to maintain isotopic integrity.
  • Thermal and photostability should be considered when planning high-temperature GC methods; LC–MS is generally preferred for labile steroidal enones.

These uses are general and should be validated for the exact labeling pattern documented on the product’s CoA.

Target Specificity

Not applicable. This product is a small-molecule, deuterated analytical standard, not an antibody or affinity reagent. No clone/isotype/species reactivity data are relevant.