17-Hydroxyandrostan-3-one , CAS No.15

CAS: 15 Cat. No.: H1328194 Fórmula: C₁₉H₃₀O₂ Peso molecular: 290.4

Storage

Room temperature

Especificações

Condições de armazenamento de armazenamento

Room temperature

Nomes e identificadores

Sorrisos canónicos

CC12CCC(=O)CC1CCC3C2CCC4(C3CCC4O)C

IUPAC Name

17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one

InChIKey

NVKAWKQGWWIWPM-UHFFFAOYSA-N

INCHI

1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-17,21H,3-11H2,1-2H3

Peso molecular

290.4

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Steroids and steroid derivatives
      • Subclass Androstane steroids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Steroids and steroid derivatives
• Subclass: Androstane steroids
• Intermediate Tree Nodes: Not available
• Direct Parent: Androgens and derivatives
• Alternative Parents: 3-oxosteroids 17-hydroxysteroids Secondary alcohols Cyclic ketones Cyclic alcohols and derivatives Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Androgen-skeleton - 3-oxosteroid - 17-hydroxysteroid - Oxosteroid - Hydroxysteroid - Cyclic alcohol - Cyclic ketone - Secondary alcohol - Ketone - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Organic oxide - Alcohol - Aliphatic homopolycyclic compound
• Descrição: This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
• External Descriptors: a small molecule

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Propriedades químicas e físicas

• Peso molecular: 290.400 g/mol
• XLogP3: 3.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 290.225 Da
• Monoisotopic Mass: 290.225 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 458.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 7
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No manufacturer-tested application protocols are provided for this item in the Product Data.

General note:

• For any use (e.g., analytical standard preparation, receptor assays), develop and validate in-house protocols appropriate to your instrumentation and biological model. Refer to peer-reviewed literature and your institutional SOPs for detailed steps.

Please consult the SDS and CoA for handling guidance and batch-specific attributes before designing protocols.

Biological Roles

Literature overview (for context; not item-specific claims):

• Endogenous function: The name 17β-hydroxy-5α-androstan-3-one corresponds to dihydrotestosterone (DHT), a high-affinity agonist of the androgen receptor (AR). It is formed from testosterone via 5α-reductase and subsequently interconverted by 3α/3β- and 17β-hydroxysteroid dehydrogenases.
• Molecular mechanism: DHT binds AR, promoting receptor dimerization, nuclear translocation, and regulation of androgen response elements, influencing transcription of target genes in diverse tissues.
• Metabolism: Phase I pathways include oxidation/reduction at C3 and C17, and conjugation (glucuronidation/sulfation) to enhance excretion. Tissue-specific enzymes (e.g., UGT2B, SULT2A families) modulate local concentrations.
• Physicochemical context: High hydrophobicity and protein binding (to SHBG and albumin, literature) limit free concentrations; intracellular levels are shaped by local synthesis and uptake.

Research implications:

• Serves as a benchmark agonist in AR functional assays and in studies of endocrine signaling, steroidogenesis, and metabolic enzyme profiling.
• Used as a positive control standard to validate AR pathway inhibitors/antagonists and to calibrate bioanalytical quantification of androgens.

Note: This section summarizes biochemical roles reported in the literature for the named scaffold. It does not constitute medical or clinical claims and does not specify properties of the particular item/batch.

Buffer Applications

Not typically applicable. 17-Hydroxyandrostan-3-one is a hydrophobic small molecule and does not serve as a buffering agent or pH stabilizer.

Practical handling note (general literature guidance):

• When dosing into aqueous buffers or culture media, prepare concentrated stocks in DMSO or ethanol and dilute into buffer with vigorous mixing to avoid precipitation. Maintain consistent vehicle content across controls (e.g., 0.1–0.2% v/v DMSO).
• If precipitation occurs, incorporate a small co-solvent fraction (e.g., ≤0.5% ethanol) or use carrier proteins (e.g., BSA) where compatible with the assay.

For true buffering needs, select established buffer systems (phosphate, HEPES, Tris), separate from this compound’s role.

Green Alternatives

While the compound itself is not a solvent or reagent easily substituted, greener considerations relate to solvent choice and process design when handling steroidal ketol-alcohols.

• Greener solvent swaps (literature guidance):

  • Replace dichloromethane or chloroform for extractions with ethyl acetate or 2-methyltetrahydrofuran (2-MeTHF) when feasible.
  • Substitute DMF/NMP with Cyrene, propylene carbonate, or dimethyl isosorbide for certain transformations, assessing solubility and reactivity.
  • Favor ethanol or isopropanol over methanol for solution preparation where biological compatibility allows.

• Comparison snapshot (general):

  • DCM vs. EtOAc: EtOAc offers lower toxicity and better environmental profile; may require altered workup due to different partitioning.
  • DMF vs. Cyrene: Cyrene can mimic DMF polarity with improved safety; stability toward strong bases/acids must be evaluated.
  • THF vs. 2-MeTHF: 2-MeTHF is bio-based and less miscible with water, aiding separations; peroxide formation risk persists—test and manage.

• Process considerations:

  • Minimize DMSO/DMF volumes by preparing concentrated stock solutions and immediate dilution at point-of-use.
  • Use solid-phase extraction (SPE) instead of large-volume liquid–liquid extraction where applicable.
  • Implement solvent recovery and recycling for chromatographic purifications (normal-phase to ethyl acetate/hexane systems with reduced chlorinated usage).

All substitutions must be validated for your assay chemistry, solubility, and regulatory context.

Pharmaceutical Uses

Item-specific pharmacopeial status and formulation role: Not specified for this item; refer to CoA/Spec Sheet.

Literature-based and industry practice (non-clinical, non-therapeutic):

• Reference standard: Employed as a system suitability, calibration, or control standard for bioanalytical LC-MS/MS methods quantifying androgens and metabolites in nonclinical studies, in vitro ADME assays, and manufacturing QC of research materials.
• Formulation research: Used as a model hydrophobic steroid to evaluate solubilization strategies (cyclodextrin inclusion, lipid emulsions, self-emulsifying systems) in pre-formulation research. These activities are for research applications and method development only.
• Impurity profiling: Utilized to map degradation pathways (oxidation at C17/C3, epimerization) and to qualify stabilization strategies (antioxidants, desiccation, light protection) for steroidal actives.

Regulatory note: No pharmacopeial monograph or grade is cited in the Product Data for this item. If you require compendial compliance (USP/EP) or certified reference materials (CRM), please contact us with your specifications.

Physical Properties

Item-specific specifications (authoritative values):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Other measured specifications (mp, bp, density, refractive index, UV cutoff, residuals): Not specified for this item; refer to CoA/Spec Sheet.

Literature or general properties for the named scaffold (for planning only; not item specifications):

• Typical physical state for androstane steroids with 17-OH/3-one: white to off-white crystalline solid.
• Melting point (literature, for 17β-hydroxy-5α-androstan-3-one/DHT): ~175–178 °C.
• Boiling point: not applicable (decomposes before boiling under ambient pressure); steroids are usually characterized by mp rather than bp.
• Aqueous solubility: negligible; commonly handled as concentrated stock solutions in polar aprotic organics.
• Solubility (literature trends): soluble in DMSO, DMF, ethanol, methanol; sparingly soluble in isopropanol; insoluble in water and alkanes.
• logP/logD (literature, for DHT): logP ~3–3.5, indicating high hydrophobicity.

Practical notes:

• Prepare analytical stocks in anhydrous DMSO or ethanol for reproducibility; filter-sterilize through 0.2 μm PTFE if needed for cell-based assays.
• Given hydrophobicity, adsorption to plastic can occur at low μM–nM levels; pre-wetting or using glass vials can improve dose accuracy.

Always confirm item-specific values on the CoA/SDS; do not treat literature values as specifications.

Quality and Grades

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

General notes on quality for steroidal analytical materials (literature/practice):

• Research grade vs. analytical/reference grade: Reference-standard material is typically accompanied by certified purity (HPLC/GC), water content (Karl Fischer), and identity (1H/13C NMR, HRMS). Research grade may provide assay by HPLC and identity by NMR/IR without full certification.
• UV behavior: Conjugation in typical androstane scaffolds is minimal; however, carbonyl absorption (n→π*) can contribute to UV at ~240–280 nm. For LC-UV quantitation, verify extinction coefficients experimentally.
• Impurities of concern: residual solvents, oxidized steroids (e.g., 17-ketones/diols), isomeric epimers, and moisture. If your application is bioassay-sensitive, request a CoA with detailed chromatographic purity and residual solvent data.
• Retest/expiry: absent explicit stability data, many solid steroids are stable >24 months at ambient, dry, and dark conditions. Confirm with the specific batch CoA.

Practical recommendation:

• If using as a calibration or bioassay control, obtain batch-specific CoA including: HPLC area% purity, water (KF), residual solvents, and structural confirmation. Without item-specific grade, set acceptance criteria aligned with your method validation.

Reaction and Applications

Applications focus on the compound’s steroidal 17β-ol/3-one motif (literature-based; not item-specific):

• Receptor biology and assay development:

  • Widely used as a tool ligand in androgen receptor (AR) binding and transactivation assays (e.g., luciferase reporter systems) to calibrate potency/efficacy and benchmark antagonists.
  • Employed as a positive control in AR nuclear translocation and chromatin recruitment studies.

• Bioanalytical workflows:

  • Utilized as a calibration/quality-control standard for LC-MS/MS quantification of androgens and their metabolites in complex matrices (after appropriate derivatization if required).

• Synthetic chemistry:

  • Serves as a substrate for site-selective oxidations/reductions at C3/C17 to map catalytic selectivity of enzymes (e.g., 17β-HSDs, 3α/3β-HSDs) and to develop small-molecule catalysts.
  • Protecting-group chemistry (e.g., silylation of 17-OH) enables divergent functionalization, while stereoretentive transformations preserve the steroidal framework.

Practical tips:

• Dry conditions improve reproducibility in acylation/silylation at the 17-OH; employ 4 Å molecular sieves or anhydrous solvents.
• For receptor assays, prepare fresh working solutions and minimize freeze–thaw; adsorption to plastics can lower effective concentrations—use glass vials or low-bind plastics.

Note: No manufacturer-specific application details were provided for this item; the above are general literature practices for the named scaffold and should be adapted to your validated protocols.

Reaction Conditions

General conditions reported in the literature for transforming 17-hydroxy/3-one androstane scaffolds (not item-specific):

• 17-OH protection:

  • Silylation (TBSCl, imidazole, DMF or CH2Cl2, rt to 40 °C, 2–12 h). Typical isolated yields: 80–95%.
  • Acetylation (Ac2O, pyridine or DMAP, CH2Cl2, 0 °C→rt, 1–4 h). Yields: 85–95%.

• 3-ketone reduction:

  • NaBH4 in MeOH/THF at 0–5 °C gives predominantly 3β-ol; Luche reduction (NaBH4/CeCl3·7H2O, MeOH, 0 °C) enhances 3β selectivity. 70–95% yield typical.
  • Stereochemical outcome depends on approach to the A-ring; confirm by NMR (H-3 coupling constants) and specific rotation.

• Mitsunobu inversion at C17:

  • DIAD/PPh3, appropriate acid, THF, 0 °C→rt; subsequent hydrolysis furnishes 17-epi derivatives. Variable yields (50–80%) depending on sterics.

• Oxime formation at C3:

  • NH2OH·HCl, pyridine or Et3N, EtOH, reflux 2–6 h. 70–90% yield. Useful for purification and downstream Beckmann-type rearrangements.

• Analytical/assay preparations:

  • DMSO stock solutions (10–50 mM), filter 0.2 μm PTFE, store aliquots at −20 °C to minimize freeze–thaw (literature practice). Final assay carrier ≤0.1–0.2% v/v.

These conditions are representative literature guidelines. Optimize for scale, substrate substitution, and equipment constraints. Always confirm identity/stereochemistry after transformations.

Safety and Handling

Safety information specific to this item:

• GHS classification, hazard statements, signal word, and pictograms: Not specified for this item; refer to the SDS for definitive safety information.
• Storage conditions (from Product Data): store at room temperature.

General handling guidance for steroidal ketol-alcohols (literature-based; not item-specific):

• Potential hazards: may cause irritation upon contact; avoid inhalation of dusts and aerosolized particles. Hormone-like compounds should be handled to minimize dermal exposure.
• Engineering controls: use in a chemical fume hood or ventilated enclosure when weighing or preparing solutions.
• PPE: lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Consider double-gloving for extended handling of concentrated solutions.
• Hygiene: avoid skin contact; wash thoroughly after handling. Prevent environmental release of solutions/solids.
• Incompatibilities: strong oxidizing agents can react with organic substrates; avoid strong bases/acids that may induce undesired degradation or isomerization.
• First aid (overview; consult SDS):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation continues.
  • Ingestion: rinse mouth; seek medical advice.
• Spills: avoid dust generation; collect mechanically or with damp disposable towels; dispose according to local regulations.

Always defer to the product SDS for authoritative hazard classification and emergency measures.

Solvent Selection

This compound class is hydrophobic and poorly water-soluble; solvent choice focuses on achieving complete dissolution and compatibility with downstream assays.

• Polarity/miscibility profile (literature-based for androstane 17-ol/3-one):

  • Water: effectively insoluble.
  • DMSO: highly soluble; preferred for concentrated stocks (10–50 mM typical).
  • DMF/NMP: good solubility; use with care due to cytotoxicity in cell assays.
  • Ethanol/Methanol: moderate-to-good solubility; often used for biochemical assays (prepare 10–100 mM stocks, dilute to ≤0.1–0.5% v/v in final media).
  • Isopropanol/Acetonitrile: variable solubility; test empirically.
  • Nonpolar solvents (hexanes, toluene): limited use due to low polarity of the OH; dissolution can be sluggish.

• Practical selection guidance:

  • For cell biology: DMSO stocks are most common; keep final DMSO ≤0.1–0.2% v/v to minimize carrier effects, or match vehicle controls.
  • For LC/MS reference solutions: acetonitrile or methanol with ≤0.1% formic acid can improve ionization; dissolve first in a small volume of DMSO if needed.
  • For chemical transformations: anhydrous THF, toluene, or dichloromethane are typical media for protection/oxidation steps; polar aprotics (DMSO/DMF) for oxidation or Mitsunobu-like conversions.

• Small comparison (pros/cons):

  • DMSO: maximal solubility; may affect biological systems at >0.2%.
  • Ethanol: biologically tolerated up to ~0.5% v/v; lower solubility than DMSO.
  • Methanol/ACN: analytical-friendly; watch for assay toxicity.

Always verify solubility with your specific lot and application.

Storage and Reconstitution

• Storage conditions (from Product Data): store at room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution guidance (item-specific instructions not provided): Not specified for this item; refer to CoA/Spec Sheet.

General literature-based advice (not item-specific):

• Solid material: keep tightly closed, dry, and protected from light to preserve integrity. For long-term archival, many labs store steroids desiccated at 2–8 °C or −20 °C, though Product Data indicates room temperature is acceptable.
• Solution stocks: prepare concentrated stocks in anhydrous DMSO or ethanol; dispense single-use aliquots to avoid repeated freeze–thaw and adsorption losses. Store aliquots at −20 °C, protected from light; equilibrate to room temperature before opening to minimize condensation.
• Compatibility: avoid aqueous storage; hydroalcoholic mixtures can promote slow degradation. Use amber vials or wrap in foil to limit photodegradation.

Always follow the batch-specific CoA and SDS for authoritative storage and handling instructions. Research use only.

Structure and Identity

Brief overview: 17-Hydroxyandrostan-3-one is a saturated C19 steroid (androstane framework) bearing a hydroxyl and a ketone on opposite termini of the tetracyclic sterane core.

• Item-specific identifiers (from Product Data):

  • SKU: H1328194
  • Product name: 17-Hydroxyandrostan-3-one
  • CAS: 15 (as provided; atypical format)
  • PubChem CID: 15 (as provided)
  • InChIKey: 248950 (as provided)
  • 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.

• Structural features (general, literature-based for the named scaffold):

  • Core: tetracyclic cyclopentanoperhydrophenanthrene (sterane) skeleton (rings A–D fused trans).
  • Functional groups: one secondary alcohol at C17 (17-hydroxyl) and one ketone at C3 (3-one).
  • Saturation: fully saturated androstane (no Δ4 or other double bonds; “5α-androstane” framework when applicable).
  • Stereochemistry: multiple defined stereocenters intrinsic to the sterane framework (8β/9α/10β/13β/14α configuration typical of androstane derivatives). Exact stereodescriptors for this specific item are not provided in Product Data.

• Literature identity note (for context only, not item-specific): the name 17β-hydroxy-5α-androstan-3-one corresponds to dihydrotestosterone (DHT), with typical identifiers MF = C19H30O2 and MW ≈ 290.44 g/mol. These are provided as literature context and are not specifications for this product listing.

Synthetic Utility

Literature-based perspective on the androstane 17-ol/3-one scaffold as a synthetic intermediate:

• Functional group handles:

  • C17 secondary alcohol: amenable to acylation (acyl chlorides/anhydrides), sulfonylation (Ms/Ts), and silylation (TBDMS/TBS) to direct subsequent chemistry. Mitsunobu-type inversions enable access to 17-epi derivatives.
  • C3 ketone: supports selective reduction (NaBH4, Luche conditions) to 3α- or 3β-ols, or formation of oximes/hydrazones for further manipulation. Enolization (under strong base) must consider steroid stereocontrol.

• Ring-selective modifications:

  • Electrophilic substitutions at activated positions (e.g., halogenation at C9/C11 under forcing conditions) and directed oxidations (SeO2 allylic-type when unsaturation is introduced post-modification).
  • Radical or photochemical approaches to install side-chain surrogates on ring D following protection of 17-OH.

• Biocatalysis:

  • Hydroxysteroid dehydrogenases enable stereospecific interconversion at C3/C17, offering high selectivity under mild conditions—a valuable route to reference epimers for analytical use.

• Retrosynthetic value:

  • A versatile branch point for accessing 17-esters/ethers, 3-ols/oximes, and deoxygenated analogs; preserving the rigid steroidal topology while modulating polarity and receptor affinity.

Process tips:

• Protect 17-OH during strong-base manipulations to prevent elimination or rearrangement. Use anhydrous, oxygen-limited conditions to curb oxidative side reactions.
• Monitor diastereomer ratios by 1H NMR (C18/C19 methyl signals) and chiral/2D LC where needed.

Target Specificity

Item-specific target information (antigen/clone/isotype/species), tested cross-reactivity, and application validations: Not applicable and not provided for this chemical product. This section generally pertains to biological affinity reagents (e.g., antibodies, ligands supplied with validated bioactivity data). For receptor-binding studies with this compound, consult primary literature and validate in your assay system.