This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Poids moléculaire
372.500 g/mol
XLogP3
3.100
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
3
Exact Mass
372.23 Da
Monoisotopic Mass
372.23 Da
Topological Polar Surface Area
60.400 Ų
Heavy Atom Count
27
Formal Charge
0
Complexity
722.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
7
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
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Application Protocols
No validated test applications or protocols are provided for this item in the Product Data.
General laboratory guidance for small-molecule handling in bioassays and analytics:
Stock solution preparation: dissolve in anhydrous DMSO or ethanol to a known concentration (e.g., 10–50 mM). Verify by UV or quantitative NMR if needed.
Dilution into assay media: add stock slowly with vigorous mixing; maintain final organic cosolvent at assay-tolerated levels. Include vehicle controls.
Plate-based assays: pre-dilute serially in DMSO/medium to minimize precipitation; consider using polypropylene plates to reduce adsorption of hydrophobic steroids.
LC–MS method sketch: reverse-phase C18 column, gradient elution with water (0.1% formic acid) and acetonitrile or methanol; monitor a characteristic [M+H]+ or [M–H]− ion. Validate linearity, precision, and stability (bench-top, autosampler, freeze–thaw).
Solid handling:
Allow vial to equilibrate to room temperature before opening to avoid condensation.
Briefly centrifuge before opening to collect material at the bottom of the container and minimize airborne particulates.
These are generic best practices; develop and validate protocols specific to your system and regulatory context.
Biological Roles
Scope: Research context only. No clinical or veterinary claims are made for this catalog item.
Literature overview for steroidal progestin analogs (e.g., norgestomet):
Mechanistic class: ligands for the progesterone receptor (PR), a nuclear hormone receptor that modulates gene transcription upon ligand binding. Steroid–receptor interactions depend on precise stereochemistry and functional group placement (e.g., A-ring enone, 17-substituent).
In vitro effects: binding to PR can recruit coactivator/corepressor complexes and alter transcriptional programs in PR-expressing cell lines. Cross-reactivity profiling commonly assesses activity against androgen, glucocorticoid, and mineralocorticoid receptors.
Metabolism (biochemistry): Phase I oxidative transformations (e.g., hydroxylation, dehydrogenation) by CYP450s and phase II conjugations (e.g., glucuronidation, sulfation) are frequently observed for steroidal esters; esterases may hydrolyze 17-esters to the corresponding alcohols.
Physicochemical determinants: hydrophobic surface area and polar carbonyl functions drive partitioning into membranes and binding pockets; protein binding in serum-containing media is usually high, which can influence apparent potency in cell-based assays.
Research utilities:
Tool compound in receptor binding, transactivation reporter assays, and chromatin immunoprecipitation workflows to interrogate PR-dependent gene networks.
Analytical control in metabolism/clearance studies using microsomes, S9 fractions, or recombinant enzymes.
Users should calibrate experimental systems with appropriate positive/negative controls and verify concentration–response relationships under their specific assay conditions.
Buffer Applications
This compound is a hydrophobic small-molecule solid and is not itself a buffering agent. It does not participate in classical acid–base buffer systems.
Practical handling in buffered systems (general guidance):
Prepare concentrated stocks in DMSO or ethanol, then dilute into the desired aqueous buffer (e.g., PBS, HBSS, assay media) with vigorous mixing or sonication to avoid precipitation. Maintain final organic cosolvent at assay-compatible levels (often ≤0.1–1% v/v).
Use carrier proteins (e.g., BSA) or cyclodextrins in buffer if enhanced apparent solubility is needed for in vitro studies; validate that carriers do not alter biological readouts.
Pre-warm buffers to room temperature and add compound slowly to minimize local supersaturation.
No item-specific buffer formulations are provided for this product; optimize empirically for your experimental context.
Green Alternatives
Context: Norgestomet is a hydrophobic solid and not itself a solvent; “green” considerations center on solvent and reagent choices for its handling, synthesis, and purification.
Greener solvent options (relative to common choices):
Comparison (general guidance)
Purpose: Dissolution for stock solutions
• Conventional: DMSO, DMF
• Greener alternatives: Ethanol (bio-derived), isopropanol
• Trade-offs: Alcohols are easier to remove and have better EHS profiles but may not dissolve as much material; risk of transesterification under harsh conditions.
Purpose: Workup/extraction
• Conventional: Dichloromethane, chloroform
• Greener alternatives: Ethyl acetate, methyl tert-butyl ether (MTBE), dimethyl carbonate (DMC)
• Trade-offs: Slightly lower solvating power for very hydrophobic steroids; DMC can participate in carbonylation chemistry under strong base.
Purpose: Chromatography
• Conventional: Hexane/ethyl acetate
• Greener alternatives: Cyclopentyl methyl ether (CPME), heptane/ethyl acetate, supercritical CO2 for preparative separations
• Trade-offs: Method development required; back-pressure and instrumentation constraints for scCO2.
Reagent choices:
Prefer catalytic hydrogenation over stoichiometric hydride where applicable.
Employ organocatalysts or benign Lewis acids (e.g., Zn(OTf)2, Sc(OTf)3) in place of more hazardous reagents for conjugate additions.
Energy and waste:
Use micro- or flow-scale screenings to minimize solvent consumption; recover/recycle eluents when feasible.
Pharmaceutical Uses
This listing is for research use only. No medical, clinical, or veterinary use is claimed or supported.
Formulation and analytical context (general information for steroidal small molecules):
Can serve as a reference standard during development of analytical methods (e.g., HPLC/LC–MS) assessing identity, assay, and stability in dosage-form development studies conducted in a laboratory setting.
Pre-formulation research may evaluate solubility, polymorphism, hygroscopicity, and compatibility with common excipients (e.g., lactose, microcrystalline cellulose) purely for methodological insight.
Solubilization strategies explored in research include cosolvents (ethanol, PEG 400), lipidic vehicles, cyclodextrin inclusion complexes, and solid dispersions; such studies inform basic physicochemical understanding without implying therapeutic application.
Stability-indicating methods can be established in the lab to resolve parent compound from degradants arising from hydrolysis, oxidation, or photolysis.
Quality references:
Where pharmacopeial monographs exist for related steroid classes, their analytical chapters can guide selection of chromatographic columns, mobile phases, and detection wavelengths. For this specific item, rely on the CoA/SDS and internal method development; no pharmacopeial status is provided here.
Physical Properties
Item-specific numeric specifications: Not specified for this item; refer to CoA/Spec Sheet.
General physical character (literature, for steroidal progestins like norgestomet):
Appearance: typically a white to off-white crystalline solid.
Solubility profile: sparingly soluble in water; soluble in polar aprotic and moderately polar organic solvents (e.g., DMSO, DMF, acetone, ethyl acetate, dichloromethane) and in alcohols (methanol/ethanol) to varying extents. Stock solutions for bioassays are commonly prepared in DMSO or ethanol.
Volatility: negligible (non-volatile solid). Vapor pressure is expected to be very low at ambient temperature due to high molecular mass and polarity from carbonyl groups.
UV characteristics: steroids with conjugated enones often show UV absorption in the 230–260 nm region; exact maxima and extinction coefficients should be determined experimentally for this item.
Typical ranges reported in the literature for related steroidal enones (context, not specs for this item):
Melting point: many acetate-bearing progesterone analogs melt in the 190–230 °C range (compound- and purity-dependent). Do not use as a specification.
LogP: hydrophobic; octanol/water partitioning is generally high for C21–C24 steroidal esters; consult experimental data for this exact compound.
Always rely on the item’s CoA for definitive properties needed for QC, method development, or formulation.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grades for small-molecule research chemicals (general guidance):
Research or analytical grades indicate material suitable for qualitative/quantitative laboratory studies. When purity is declared (e.g., ≥98%), it usually refers to HPLC area percent unless otherwise noted.
For receptor-binding, metabolism, or analytical reference uses, low residual solvent levels, tight melting range, and well-resolved HPLC purity are typically important. If you require trace impurity thresholds (e.g., steroidal isomers, de-acetylated analogs), request detailed chromatograms and impurity profiles.
If a stabilizer is employed (not specified for this item), it will be listed on the label/CoA. Stabilizers can influence UV spectra and biological assays; adjust controls accordingly.
Batch-specific data: Certificates of Analysis commonly include identity confirmation (e.g., 1H NMR, MS), purity (HPLC/GC), water (KF), and residual solvents. Where orthogonal ID is critical, request chiral HPLC or optical rotation to confirm stereochemical integrity for steroid frameworks.
Suggested QC on receipt (good practice):
Record appearance and lot information; acquire a reference spectrum (1H NMR in CDCl3 or DMSO-d6) and compare to literature patterns for steroidal enones/esters.
Verify purity by analytical HPLC with a gradient in acetonitrile/water + 0.1% formic acid; inspect for early/late eluting steroidal impurities.
Reaction and Applications
Manufacturer applications: Not specified beyond “For research use only.”
Research applications (general for steroidal progestin analogs like norgestomet):
Reference standard in analytical method development (HPLC/LC–MS quantification in formulation or in vitro matrices).
Ligand in biochemical studies of progesterone receptor (PR) binding, selectivity profiling against nuclear receptor panels, and structure–activity relationship (SAR) investigations. All uses confined to in vitro or ex vivo laboratory research.
Substrate for metabolism studies with hepatic microsomes, recombinant CYPs, and phase II enzymes to map oxidative and hydrolytic pathways (e.g., de-esterification, enone reduction).
Selective hydrolysis of the 17-ester to the corresponding alcohol; re-esterification or carbonate formation to tune lipophilicity.
1,4-conjugate additions to the A-ring enone under soft nucleophile conditions with Lewis acid mediation; careful control needed to retain stereochemistry.
Stereoselective reductions (e.g., Luche reduction) of the enone to allylic alcohols; hydrogenation of olefinic bonds when present.
Protective group interconversions at C17/C20 and oxidative transformations (e.g., Oppenauer oxidation) used in steroid tailoring.
Monitor reactions by TLC with steroid-sensitive stains (e.g., phosphomolybdic acid, anisaldehyde) and confirm by LC–MS; steroids often display weak UV at 254 nm unless conjugated.
Reaction Conditions
General conditions for typical transformations on steroidal enones/esters (literature guidance; not item-specific specifications):
Enone 1,4-reduction (Luche-type):
• Solvent: MeOH or EtOH
• Reagents: NaBH4 (0.5–1.5 equiv) with CeCl3·7H2O (1.0–2.0 equiv)
• Temperature: 0–25 °C
• Time: 0.5–2 h
• Notes: Preferential 1,2- vs 1,4-selectivity controlled by cerium(III); monitor carefully to avoid over-reduction.
Ester hydrolysis (to 17-alcohol):
• Solvent: MeOH/H2O or THF/H2O
• Base: Na2CO3, K2CO3, or NaOH (0.1–1.0 M)
• Temperature: 20–40 °C (basic), or catalytic acid (e.g., HCl/MeOH) under reflux for acidolysis
• Time: 1–6 h
• Notes: Avoid harsh conditions that may isomerize the enone; protect from light.
Re-esterification/Acylation at C17:
• Solvent: DCM, pyridine, or DMAP-catalyzed systems
• Reagents: Acyl chlorides or anhydrides (1.2–2.0 equiv), DMAP (5–10 mol%)
• Temperature: 0–25 °C
• Time: 1–12 h
• Notes: Strictly anhydrous; quench and wash thoroughly to remove pyridinium salts.
Conjugate addition (soft nucleophiles):
• Solvent: DCM, toluene, or MeCN
• Catalysts: Cu(I), Zn(II), or organocatalysts
• Temperature: 0–25 °C
• Notes: Stereocontrol is substrate-driven; minor isomer formation may require chromatographic resolution.
These conditions are representative for steroidal scaffolds and should be optimized for this specific compound via small-scale trials.
Safety and Handling
Item-specific GHS data: Not specified for this item; refer to SDS for authoritative hazard classification, pictograms, signal word, and H/P statements.
General safety notes for steroidal hormones and analogs (literature/precautionary guidance):
Potential hazards: Steroidal progestin analogs may exhibit bioactivity at very low levels. Avoid inhalation, ingestion, and skin contact. Use containment (weighing in a balance enclosure or fume hood) and minimize dust/aerosol formation.
PPE: lab coat, safety glasses, and appropriate gloves (e.g., nitrile). For weighing or handling powders, consider double-gloving and using disposable bench covers. Wash hands thoroughly after handling.
Engineering controls: handle inside a chemical fume hood or ventilated enclosure. For solution prep, closed transfer techniques are recommended to limit exposure.
Storage incompatibilities: keep away from strong oxidizers and strong bases or acids that could catalyze hydrolysis or degradation of ester/enone functionalities. Protect from prolonged light exposure.
First aid (overview; defer to SDS): in case of skin contact, wash with soap and water. Eye contact: rinse cautiously with water for several minutes and seek medical attention. If inhaled: move to fresh air and monitor. If swallowed: rinse mouth; seek medical advice.
Spill response: avoid raising dust; gently cover and collect with damp disposable towels or HEPA vacuum suitable for fine powders. Dispose per institutional and local regulations.
Always consult the current SDS for this catalog item before use.
Solvent Selection
Polarity and miscibility (general guidance for hydrophobic steroidal solids):
Water solubility is typically very low; dissolution is favored in polar aprotic media (DMSO, DMF) and chlorinated solvents (DCM, chloroform). Moderate solubility is often achievable in acetone, ethyl acetate, acetonitrile, and alcohols (methanol/ethanol), depending on temperature and concentration.
Practical recommendations:
For bioassays and stock solutions: prepare concentrated stocks in DMSO (e.g., 10–50 mM), then dilute into assay buffer with vigorous mixing; keep final DMSO ≤0.1–1% v/v as assay-compatible. Ethanol is an alternative cosolvent for receptor assays.
For synthetic manipulations: use anhydrous solvents when performing acylation, reduction, or conjugate addition to the enone. Ester hydrolysis/formation will require basic or acidic aqueous–organic systems; choose solvents that maintain phase separation and limit steroid precipitation (e.g., THF/MeOH–water systems).
Comparison and trade-offs (general):
DMSO: excellent solvating power; high boiling point can complicate removal; may interfere with certain spectroscopic/biological readouts.
Ethanol/methanol: facile removal; can participate in transesterification under basic/acidic conditions.
Acetonitrile/acetone: good balance of polarity and volatility; monitor for potential aldol/conjugate reactivity with strong bases or nucleophiles.
DCM/chloroform: strong solvents for steroids; consider safety and environmental profiles.
Note: No item-specific solubility numbers are provided for this product; users should establish working concentrations empirically.
Storage and Reconstitution
Item-specific storage: Room temperature (as provided in Product Data). Avoid direct sunlight and moisture ingress. Keep container tightly closed.
Shipping: Not specified for this item; refer to CoA/Spec Sheet. Given the solid, non-volatile nature typical of steroidal compounds, ambient shipping is commonly acceptable unless otherwise indicated.
Stability considerations (general for steroidal enones/esters):
Protect from prolonged light exposure to minimize photodegradation or isomerization.
Avoid extended contact with strong acids/bases, which can drive hydrolysis or rearrangement.
For long-term storage, a desiccated environment is beneficial; inert atmosphere (nitrogen/argon) is optional but can further limit oxidative processes.
Reconstitution guidance (general):
Prepare fresh stock solutions in anhydrous DMSO or ethanol. Filter through a 0.2 µm PTFE syringe filter if particulate matter is present.
For repeated use, aliquot stock solutions to minimize freeze–thaw and headspace exposure. Store aliquots at −20 °C protected from light when compatible with your workflow; verify stability by HPLC before critical assays.
Labeling and records:
Record preparation date, solvent, concentration, and lot number on each aliquot. Cross-check with CoA/SDS for any lot-specific handling notes.
Where stricter controls are required, base conditions on your internal stability studies for this exact lot.
Structure and Identity
Item-specific identifiers (from Product Data)
CAS: 25092-41-5
InChIKey: 152485 (as provided)
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.
Compound class (general literature):
Norgestomet is described in the literature as a steroidal progestin analog (a 19-norprogesterone derivative). Typical steroid cores are tetracyclic (cyclopentanoperhydrophenanthrene framework) with multiple chiral centers.
Literature depictions of norgestomet generally include an enone in the A-ring and an ester (often an acetate) at C17, alongside characteristic methyl substitution on the steroid scaffold. Exact substitution pattern and stereochemistry should be confirmed against the Certificate of Analysis for this specific lot.
2D structural features (literature description):
Four fused rings: three six-membered (A, B, C) and one five-membered (D) ring in a trans-fused arrangement.
Functional groups often reported: conjugated enone (C3), 17-ester functionality, and alkyl substituents (including a 13- or 18-methyl topology adjusted for 19-nor derivatives). Multiple stereocenters define the 3D shape critical for receptor recognition.
Note: Because several identifiers beyond CAS are not provided for this catalog item, users should verify exact structural representation (including stereochemistry and any protecting/esterifying group) from the CoA, spec sheet, or primary literature prior to quantitative work.
Synthetic Utility
Functional group landscape (literature description for norgestomet-like steroids):
Conjugated enone in the A-ring enables 1,4-addition and selective reductions (e.g., Luche conditions) to generate allylic alcohols or saturated ketones.
17-Ester function (commonly an acetate in literature descriptions) offers a handle for hydrolysis, transesterification, or conversion to carbonates/carbamates to probe structure–property relationships.
Multiple stereocenters provide opportunities for diastereoselective transformations under substrate control.
Retrosynthetic perspectives:
Access from 19-norprogesterone scaffolds via targeted oxidation and acylation at C17, with careful preservation of the Δ4-3-keto motif.
Late-stage diversification at the 17-position (ester interchange) and selective A-ring modifications enable libraries for SAR without re-entering the core steroid synthesis.
Derivatization examples (general):
Formation of oximes/hydrazones from the 3-ketone for analytical derivatization (GC/LC detectability), reversible under mild conditions.
Carbamate/carbonate pro-moieties at C17 to modulate lipophilicity and stability in in vitro delivery systems.
Photochemical or catalytic isomerization of double bonds (if present) to explore receptor binding conformational space.
Purification and analysis:
Normal-phase silica with hexane/ethyl acetate or heptane/EtOAc systems is standard; consider silver nitrate-doped silica for resolving closely related enones.
Structural verification by 1D/2D NMR (noting characteristic downfield enone protons), HRMS, and, where necessary, X-ray crystallography to unambiguously assign stereochemistry.
Target Specificity
No antibody/biologic attributes apply to this small-molecule product. Target-binding specificity data (e.g., receptor Ki/IC50) are not provided for this catalog item.
General literature context: Steroidal progestin analogs are studied for binding to the progesterone receptor and may be profiled against other nuclear receptors in vitro; specific potency/selectivity values must be obtained from primary literature or generated experimentally in your laboratory.
For this product, rely on your own in-house binding/functional assays or consult peer-reviewed reports; no item-specific target specificity data are supplied.
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