11-Ketodihydrotestosterone - ≥98% , CAS No.32694-37-4

CAS: 32694-37-4 Cat. No.: K651369 Fórmula: C19H28O3 Peso molecular: 304.42 PubChem CID: 11197479
Disponible para pedir
GRADE & PURITY ≥98%
Synonyms
5.ALPHA.-ANDROSTANE-3,11-DIONE-17.BETA.-OL | Androstane-3,11-dione, 17-hydroxy-, (5.alpha.,17.beta.)- | MS-24402 | 17-Hydroxyandrostane-3,11-dione # | DX994972WA | (5alpha,17beta)-17-Hydroxyandrostane-3,11-dione | PD044172 | 5alpha-Androstane-3,11-dione,
Storage
Store at -20°C
Shipped In
Ice chest + Ice pads
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Size
Alemania (EU)
USA*
Price
Qty
5mg
K651369-5mg
Fabricado bajo pedido · 8–12 semanas
608,20€
10mg
K651369-10mg
Fabricado bajo pedido · 8–12 semanas
1.094,13€
50mg
K651369-50mg
Fabricado bajo pedido · 8–12 semanas
3.211,42€
100mg
K651369-100mg
Fabricado bajo pedido · 8–12 semanas
4.946,89€
Enter a quantity for the sizes you want to add.
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Why this grade

≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

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Storage & shipping

Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.

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Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

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Literature proof

Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Descripción general

11-Ketodihydrotestosterone (11-KDHT; 5α-Dihydro-11-keto testosterone) is an endogenous steroid and a metabolite of 11β-Hydroxyandrostenedione. 11-Ketodihydrotestosterone is an active androgen and is also a potent androgen receptor (AR) agonist with a K i of 20.4 nM and an EC 50 of 1.35 nM for human AR . 11-Ketodihydrotestosterone drives gene regulation, protein expression and cell growth in androgen-dependent prostate cancer cells

In Vitro

11-Ketodihydrotestosterone (11-KDHT; 1-10 nM; 24 hours; LNCaP and VCaP cells) treatment induces significant cell proliferation. 11-Ketodihydrotestosterone (11-KDHT; 0.1-10 nM; 7-10 days; LNCaP and VCaP cells) treatment results in the significant upregulation of KLK3 , TMPRSS2 and FKBP5 in both LNCaP and VCaP cells, with the exception of KLK3 at 1 nM in LNCaP cells. In PNT2 cells, only 20% of 11β-hydroxyandrostenedione (11OHA4) and 11β-hydroxytestosterone (11OHT) are metabolised with the former yielding 11keto-androstenedione (11KA4), 11-Ketodihydrotestosterone (11-KDHT) and 11β-hydroxy-5α-androstanedione (11OH-5αDIONE) and the latter yielding 11OHA4, 11KT and 11-Ketodihydrotestosterone with downstream products <0.03 μM. In prostate cancer tissue, C11-oxy C19 metabolites at significantly higher levels than the C19 steroids are detected, with unconjugated 11-Ketodihydrotestosterone, 11KT and 11OHA4 levels ranging between 13 and 37.5 ng/g. Analyses of total steroid levels in plasma show significant levels of 11OHA4 (≈230-440 nM), 11KT (≈250-390 nM) and 11-Ketodihydrotestosterone (≈19 nM). MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Proliferation AssayCell Line: LNCaP and VCaP cells Concentration: 0.1 nM, 1 nM or 10 nM Incubation Time: 7 days (LNCaP cells) or 10 days (VCaP cells) Result: Induced significant cell proliferation. RT-PCRCell Line: LNCaP and VCaP cells Concentration: 1 nM, 10 nM Incubation Time: 24 hours Result: Resulted in the significant upregulation of KLK3 , TMPRSS2 and FKBP5 in both LNCaP (Fig 3) and VCaP (Fig 4) cells.

Form:Solid

IC50& Target:Ki: 20.4 nM (Human androgen receptor), EC50: 1.35 nM (Human androgen receptor)

Specifications

Sinónimos
5.ALPHA.-ANDROSTANE-3,11-DIONE-17.BETA.-OL | Androstane-3,11-dione, 17-hydroxy-, (5.alpha.,17.beta.)- | MS-24402 | 17-Hydroxyandrostane-3,11-dione # | DX994972WA | (5alpha,17beta)-17-Hydroxyandrostane-3,11-dione | PD044172 | 5alpha-Androstane-3,11-dione,
Especificaciones y pureza
≥98%
Mecanismos bioquímicos y fisiológicos
11-Ketodihydrotestosterone (11-KDHT; 5α-Dihydro-11-keto testosterone) is an endogenous steroid and a metabolite of 11β-Hydroxyandrostenedione. 11-Ketodihydrotestosterone is an active androgen and is also a potent androgen receptor (AR) agonist with a K i
Condiciones de almacenamiento de almacenamiento
Store at -20°C
Enviado en
Ice chest + Ice pads
Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.
Tipo de acción
AGONIST
Pureza
≥98%
Nombres e identificadores
Sonrisas canónicas
CC12CCC(=O)CC1CCC3C2C(=O)CC4(C3CCC4O)C
IUPAC Name
(5S,8S,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-2,4,5,6,7,8,9,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
InChIKey
RSQKILYTRHKUIJ-HZGXJFKTSA-N
INCHI
1S/C19H28O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h11,13-14,16-17,22H,3-10H2,1-2H3/t11-,13-,14-,16-,17+,18-,19-/m0/s1
Isómeros SMILES
C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2C(=O)C[C@]4([C@H]3CC[C@@H]4O)C
CAS alternativo
32694-37-4
PubChem CID
11197479
Términos de entrada MeSH
11-ketodihydrotestosterone
Peso molecular
304.42

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

Download SDS →

✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

Look up COA →

📊 Datasheet

Quick-reference summary of product specifications and applications.

View datasheet →

🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

View spec sheet →

Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClaseSteroids and steroid derivatives
SubclassAndrostane steroids
Intermediate Tree Nodes Not available
Direct ParentAndrogens and derivatives
Alternative Parents 3-oxo-5-alpha-steroids  17-hydroxysteroids  11-oxosteroids  Secondary alcohols  Cyclic ketones  Cyclic alcohols and derivatives  Organic oxides  Hydrocarbon derivatives  
Molecular FrameworkAliphatic homopolycyclic compounds
Substituents Androgen-skeleton - 3-oxosteroid - Hydroxysteroid - 11-oxosteroid - Oxosteroid - 17-hydroxysteroid - 3-oxo-5-alpha-steroid - Cyclic alcohol - Ketone - Secondary alcohol - Cyclic ketone - Organic oxygen compound - Organooxygen compound - Alcohol - Carbonyl group - Hydrocarbon derivative - Organic oxide - Aliphatic homopolycyclic compound
DescripciónThis 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 Not available
Estructura 3D
Modelo de Estructura Química Interactiva





Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
SolubilidadDMSO : 100 mg/mL (328.49 mM; Need ultrasonic)
Peso molecular304.400 g/mol
XLogP32.300
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass304.204 Da
Monoisotopic Mass304.204 Da
Topological Polar Surface Area54.400 Ų
Heavy Atom Count22
Formal Charge0
Complexity527.000
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds0
Covalently-Bonded Unit Count1
Calculadoras de soluciones
Reseñas

Reseñas de cliente

Application Protocols

No vendor-validated biological assay protocols are provided for this item. The following are general, literature-informed procedures for handling hydrophobic steroidal ligands in research settings. Adjust to your system and validate internally.

A. Preparation of concentrated stocks

  • Weigh compound quickly into an amber vial.
  • Add anhydrous DMSO (or ethanol) to prepare a 10 mM stock. Vortex and, if needed, sonicate briefly at room temperature until fully dissolved.
  • Optionally sterile-filter through 0.2 µm PTFE for cell-based work. Aliquot and store at −20 °C.

B. Working solution for cell assays

  • Thaw an aliquot on ice; dilute into pre-warmed culture medium to desired concentration, keeping final DMSO ≤0.1–0.2% v/v (as tolerated by cells).
  • Include 0.1% fatty-acid-free BSA to minimize adsorption/precipitation if compatible.
  • Prepare vehicle controls matched for solvent content.

C. LC–MS/MS reference standard curve

  • Prepare serial dilutions in 50:50 ACN:water with 0.1% formic acid (or matrix-matched diluent) from a validated intermediate stock.
  • Spike stable-isotope internal standard if available.
  • Store calibrators and QCs at −20 °C; minimize freeze–thaw.

D. Solid-phase extraction (typical research method)

  • Condition mixed-mode cartridge; load sample; wash with aqueous buffer; elute with MeOH or ACN containing 0.1–1% NH4OH if needed; evaporate and reconstitute for LC–MS.

Note: These are general guidelines; follow institutional SOPs and method validation requirements.

Biological Roles

Literature context (for research interpretation; not a medical/clinical claim)

  • Pathway: 11-Ketodihydrotestosterone (11-keto-DHT) is part of the 11-oxygenated androgen axis. It can arise via oxidation of 11β-hydroxylated androgens and retains the 5α-reduced androstane core typical of potent androgenic ligands.
  • Putative interactions: As a dihydrotestosterone analog with an additional 11-keto group, it is studied for binding/activation properties at the androgen receptor (AR) and for its susceptibility to metabolizing enzymes (e.g., 11β-HSDs, AKR1C isoforms) in cell-free or cellular systems (literature).
  • Physicochemical implications: The added C11 carbonyl increases polarity relative to DHT, potentially affecting receptor affinity, protein binding, metabolic stability, and tissue distribution—factors commonly investigated in SAR and metabolism studies.
  • Metabolic transformations: Enzymatic interconversion between 11-hydroxy and 11-keto forms (redox cycling) and phase II conjugation at the 17β–OH (glucuronidation/sulfation) are frequently profiled in vitro to map clearance routes (literature trends for steroidal alcohols/ketones).
  • Analytical relevance: Serves as a target/analyte in LC–MS/MS panels quantifying steroid profiles in biological matrices for research. Solid-phase extraction with mixed-mode sorbents and stable-isotope internal standards are common for robust quantification.

Note: All roles summarized here are intended strictly for basic and translational research settings. This product is labeled “For research use only” and is not intended for human or veterinary use.

Buffer Applications

This compound is not a buffer component and does not form buffering systems in the physiological pH range. Accordingly, there are no standard “buffer recipes” for 11-Ketodihydrotestosterone.

Practical notes for using in aqueous buffers (general)

  • Stock preparation: dissolve in DMSO or ethanol to 1–10 mM; dilute into the desired buffer (e.g., PBS, HBSS, assay media) with vigorous mixing.
  • Carrier proteins: to avoid precipitation and adsorption losses, include 0.1–0.5% fatty-acid-free BSA or 0.1–1% serum in biological buffers when compatible with the assay.
  • Surfactants: 0.01–0.05% nonionic surfactants (e.g., Tween 20, Pluronic F-68) can improve solubilization in cell-based assays; validate for assay compatibility.
  • Adsorption control: precondition plasticware with buffer containing carrier protein or use low-binding tubes/plates to reduce loss of hydrophobic steroids.

If a true buffering agent is required, select a dedicated buffer system (HEPES, MOPS, Tris, phosphate) appropriate to your pH and ionic strength requirements and prepare the steroid as a separate cosolvent stock.

Green Alternatives

Because 11-Ketodihydrotestosterone is a solid analyte/tool compound rather than a process solvent or bulk reagent, “green alternatives” considerations focus on solvent choice and sample handling rather than replacing the compound itself.

Greener solvent strategies (literature/general)

  • Prefer ethanol or 2-propanol over chlorinated solvents for routine weighing/dissolution when solubility permits.
  • Use aqueous-buffered formulations with small amounts of ethanol or DMSO, combined with serum albumin or cyclodextrins, to reduce neat organic solvent usage in bioassays.
  • For chromatography, explore water–acetonitrile gradients (ACN has favorable safety/energy profile in UHPLC) and minimize MeOH/THF. Consider supercritical CO2 for preparative separations when infrastructure exists.

Comparison (typical dissolution/media choices)

  • DMSO: highest solubilizing power; not green but used at very low final % in assays. Manage by preparing concentrated stocks to minimize volume.
  • Ethanol: renewable feedstock, lower toxicity; may precipitate upon aqueous dilution without carriers.
  • 2-MeTHF/CPME: less relevant for analytical stocks but useful as greener extraction/flash solvents compared with DCM/THF.

Operational improvements

  • Right-size aliquots to avoid freeze–thaw cycles and unnecessary solvent disposal.
  • Adopt microscale assay formats to reduce solvent volumes.
  • Implement solvent recycling for prep-scale purifications where applicable.

Note: No greener “substitute molecule” is applicable—this compound’s structure-specific interactions are often the experimental objective.

Pharmaceutical Uses

No therapeutic, diagnostic, or clinical uses are claimed or supported for this catalog item. For research use only.

Formulation and manufacturing context (general, literature-informed)

  • Reference standard: employed as a primary or secondary standard in analytical methods for research and development workflows (e.g., impurity profiling, process tracking in steroid synthesis).
  • Excipient status: not an excipient; however, knowledge of solubility in pharmaceutically acceptable solvents (ethanol, PEGs, polysorbates) can aid in preformulation research, such as screening delivery vehicles for steroidal actives in model systems.
  • Stability studies: solid-state stability can be evaluated under ICH-like conditions for method development; pay attention to humidity and light. In solution, forced degradation (oxidation, base/acid, light) can support stability-indicating method validation.
  • Regulatory status: not a compendial article to our knowledge; no USP/EP monograph is indicated. Any use in regulated studies requires independent qualification of reference standards and validation of analytical methods.

Handling implications for formulation research

  • Prepare aliquoted, low-water-content stocks (e.g., in anhydrous ethanol or DMSO) to maintain consistency across experiments.
  • Use glass vials with PTFE-lined caps to minimize adsorption and vapor ingress during long-term storage of solutions.
Physical Properties

Item-specific specifications

  • Appearance: 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.

Literature/general physicochemical information (for context; not product specifications)

  • Aggregate state: typically a white to off-white crystalline solid for analogous androstane ketols.
  • Melting point: not widely reported for this specific analog; many 11-oxygenated androgens melt in the 170–220 °C range (literature, compound-dependent). Consult CoA for the exact value for this lot.
  • Solubility: very low in water; readily soluble in DMSO and DMF; soluble to moderately soluble in ethanol and methanol; sparingly soluble in isopropanol and acetone (literature trends for hydrophobic steroids). Aqueous buffers generally require cosolvent or carrier protein (e.g., serum/BSA) to prevent precipitation.
  • Partitioning: expected high hydrophobicity (logP typically ~3–4 for 5α-androstanes; literature). Actual value for this item is not specified; see CoA if available.
  • pKa: no titratable groups in physiological range; phenolic/acidic sites absent. The 17β–OH is a weak alcohol (pKa > 14; literature), and carbonyls are H-bond acceptors only.
  • UV: lacks strong chromophores; typical steroidal UV absorbance is weak above 240–260 nm (literature). For quantitative HPLC, use ELSD, MS, or UV at short wavelengths if validated.
  • Stability: generally stable as a dry solid under inert, cool storage. In solution, prolonged exposure to light/air may promote slow oxidation or isomerization; prepare fresh working solutions when possible (general guidance).
Quality and Grades

Item-specific information

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

How to interpret grades/purity for this compound class (general guidance)

  • Research grade steroidal standards are typically qualified by identity (1H/13C NMR, HRMS) and purity (HPLC/UPLC area %). When HPLC grade is indicated for small molecules, it usually targets low UV background and high chromatographic purity; for steroids, UV is modest, so MS or ELSD may be preferred for release testing.
  • Residual solvents, water content, and inorganic residues may be controlled depending on grade; exact limits for this catalog item are not specified here. Always consult the CoA for your lot for numeric specifications.

Practical implications for users

  • Analytical verification: for quantitative bioassays or as an LC–MS reference standard, confirm purity by an orthogonal technique (e.g., qNMR or LC–MS) upon receipt if your application is highly purity-sensitive.
  • Isomerism/impurities: steroidal materials can contain epimeric or positional isomers formed during synthesis or workup (e.g., minor 17-epimers, hydrate/hemiketal traces). Chromatographic methods should resolve these when present.
  • Stabilizers: none are indicated for this item. If stabilizers are required for your workflow (e.g., antioxidant in long-term solutions), add them in-house following validated methods.
  • Documentation: retain CoA/SDS with your records; if regulatory or method-validation work is planned (e.g., GLP), request any additional characterization data you require prior to study start.
Reaction and Applications

This compound is primarily used as a research-grade androgenic steroid reference and tool compound rather than a bulk reaction solvent or reagent. However, its functional groups and rigid scaffold enable several useful chemical and analytical applications.

Applications (research/analytical)

  • Reference standard: calibration and system suitability for LC–MS/MS methods targeting 11-oxygenated androgen pathways (literature). Employed in metabolism studies and enzymology panels (e.g., 11β-HSD/AKR families) without implying clinical use.
  • Ligand studies: biochemical binding/activation studies with nuclear receptors (e.g., AR) and steroid-binding proteins in vitro (literature). Use validated assay conditions and appropriate controls.

Transformations enabled by its functionality (synthetic context)

  • Carbonyl chemistry at C3/C11: reversible formation of oximes/hydrazones for derivatization or protection; selective reduction (e.g., L-Selectride, NaBH4/CeCl3) to access diols for SAR libraries.
  • 17β–OH derivatization: esterification (acid chlorides/anhydrides, DMAP) to modulate lipophilicity or generate pro-analogs for delivery studies; carbonate/carbamate formation for tagging.
  • Enolate/ketone reactivity: mild enolization at C3 under base enables electrophilic trapping (e.g., O-silylation with TMSCl/Et3N; limited scope due to steric constraints).

Practical tips

  • Chemoselectivity: C3 is typically more reactive than C11 toward hydride reduction; temperature and reagent control are critical to avoid over-reduction.
  • Protection strategies: ketalization (ethylene glycol, p-TsOH, Dean–Stark) can mask C3 or C11 during selective transformations; 17-O-protection as TBDMS or acetate aids chromatographic handling.
  • Analysis: steroids often require MS or ELSD detection due to weak UV; derivatization (e.g., dansylation of alcohols) can enhance sensitivity.
Reaction Conditions

General literature-style conditions for representative transformations on 11-keto-androstane frameworks (guidance only; not product specifications):

  • Selective C3 reduction

    • Reagents: NaBH4 (1.0–2.0 equiv)
    • Solvent: MeOH or MeOH/THF (4:1)
    • Temperature/time: 0–5 °C, 0.5–2 h
    • Notes: Quench with NH4Cl, extract; low temperature favors kinetic selectivity at C3 over C11.
  • Chemoselective hydride reduction (enhanced control)

    • Reagents: L-Selectride (1.2–1.5 equiv)
    • Solvent: dry THF
    • Temperature/time: −78 to −20 °C, 0.5–2 h
    • Notes: Improved stereocontrol at C3; avoid warming to prevent over-reduction.
  • Oxime formation at C3/C11

    • Reagents: hydroxylamine hydrochloride (2–5 equiv), pyridine or Et3N (2–3 equiv)
    • Solvent: EtOH or MeOH
    • Temperature/time: rt–50 °C, 2–16 h
    • Notes: Useful for protection or analytical derivatization; E/Z isomerism may occur.
  • 17β–O-acylation

    • Reagents: acyl chloride (1.2–1.5 equiv), DMAP (0.1 equiv)
    • Solvent: CH2Cl2 or THF; base: pyridine or Et3N (2–3 equiv)
    • Temperature/time: 0 °C to rt, 1–4 h
    • Notes: Monitor by TLC/LC–MS; avoid strong base if carbonyl protection is absent.
  • Ketalization (carbonyl protection)

    • Reagents: ethylene glycol (5–10 equiv), p-TsOH (5–10 mol%)
    • Solvent: toluene, Dean–Stark apparatus
    • Temperature/time: reflux, 2–6 h
    • Notes: Typically targets the more reactive C3 carbonyl first; confirm site by NMR.

Yields vary with substrate and conditions; consult primary literature and optimize on small scale before scale-up.

Safety and Handling

Authoritative safety information should be taken from the product’s SDS. The following summarizes available item data and general best practices for handling hydrophobic steroidal small molecules in the lab.

Item-specific safety data

  • GHS Classification: Not specified for this item; refer to SDS.
  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements/Pictograms: Not specified for this item; refer to SDS.
  • Storage: Store at −20 °C (per Product Data). Shipments are provided cold (ice chest + ice pads).

General laboratory precautions (literature/best practice)

  • PPE: wear lab coat, nitrile gloves, and safety glasses. Avoid skin contact and inhalation of dust.
  • Engineering controls: handle powders in a fume hood or ventilated enclosure to minimize airborne particulates.
  • Avoid: heat, direct light, and prolonged exposure to air when in solution; incompatible with strong oxidants and strong bases that can induce aldol-type side reactions or enolization at the C3/C11 carbonyls.
  • First aid (overview; see SDS for details): in case of skin contact, wash with soap and water; for eye exposure, rinse cautiously with water for several minutes; if inhaled, move to fresh air; if ingested, rinse mouth. Seek medical advice if symptoms persist.
  • Waste: dispose of solutions and contaminated materials as organic chemical waste per institutional and local regulations.
  • Special note: although intended strictly for research use, treat steroidal ligands as potentially bioactive; minimize exposure and avoid release to drains. Use closed containers and clearly labeled secondary containment during transport within the facility.
Solvent Selection

Solvation behavior (general, literature-informed for androstane ketols)

  • Polarity: highly hydrophobic core with limited polar functionality (two ketones, one secondary alcohol); behaves as a weakly polar, largely lipophilic analyte.
  • Preferred solvents: DMSO and DMF (excellent), ethanol and methanol (good), acetonitrile (moderate), isopropanol and acetone (variable), ethyl acetate and dichloromethane (good for preparative handling), water (poor without cosolvent or carrier protein).
  • Aqueous work: prepare concentrated DMSO or ethanol stocks (e.g., 1–10 mM), then dilute into buffer containing serum/BSA or a nonionic surfactant to minimize precipitation. Keep final DMSO ≤0.1–0.5% v/v where compatible with biology.

Comparison and selection tips

  • DMSO vs ethanol: DMSO maximizes solubility and stability for freezer stocks; ethanol offers greener credentials and lower viscosity for quick dilutions but may precipitate upon aqueous dilution without protein carriers.
  • ACN vs MeOH (chromatography): for RP-HPLC/UPLC, both are viable. ACN often gives sharper peaks and lower backpressure; MeOH can improve selectivity for steroid separations via subtle H-bonding differences.
  • Nonpolar organic (DCM/EtOAc/MTBE): useful for extraction or flash chromatography. Avoid prolonged contact with basic alumina which can promote undesired isomerization.

Practical handling

  • Warm gently (room temperature) and vortex to dissolve; avoid heating above ~40 °C to limit degradation (general precaution).
  • Filter solutions (0.2 µm PTFE) prior to analytical work to remove particulates.
  • Validate solvent choice against your assay tolerance and the compound’s stability in that matrix.
Storage and Reconstitution

Item-specific instructions (from Product Data)

  • Storage: Store at −20 °C.
  • Shipping: Shipped in an ice chest with ice pads to maintain a cold chain.

General best practices for this compound class

  • Solid storage: keep tightly closed in an amber vial, under dry, inert conditions (desiccant recommended). Limit headspace and avoid repeated warming cycles.
  • Solution storage: prepare concentrated stocks in dry DMSO or ethanol. Aliquot into small, single-use volumes to avoid freeze–thaw; store at −20 °C. Protect from light.
  • Reconstitution suggestions: for biochemical work, dissolve to 10 mM in DMSO; for less polar matrices, ethanol or DMF are viable. Mix thoroughly (vortex/brief sonication). Confirm complete dissolution before dilution into aqueous media.
  • In-use stability: use freshly thawed aliquots the same day when working at low micromolar concentrations in aqueous buffers to minimize adsorption losses and degradation. Discard any solutions showing turbidity or precipitation.
  • Compatibility: when diluting into water-based buffers, add slowly with vigorous mixing and include carrier protein (e.g., 0.1% BSA) if permitted by the assay to maintain solubility.
  • Labeling/documentation: record preparation date, solvent, and concentration on each aliquot. Refer to the CoA/Spec Sheet for any lot-specific stability information.

Research Use Only

  • This product is intended for research use only and is not for human or veterinary use.
Structure and Identity

Overview of a 5α-reduced androgen bearing an additional ketone at C11; steroidal androstane nucleus (three fused cyclohexanes + one cyclopentane, trans-fused A/B rings typical of 5α-androstanes). 11-Ketodihydrotestosterone is commonly described as 5α-androstan-3,11-dione-17β-ol (literature), i.e., two carbonyls (C3 and C11) and a 17β-hydroxyl.

Item-specific identifiers (from Product Data)

  • CAS: 32694-37-4
  • InChIKey: 324981 (as supplied; verify on CoA/SDS if needed)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Computed/literature identifiers and features (informational; not item specifications)

  • Common synonyms (literature): 11-keto-DHT; 5α-androstan-3,11-dione-17β-ol; 11-oxo-dihydrotestosterone.
  • Molecular formula (literature): C19H28O3 (reflecting an additional carbonyl relative to DHT).
  • Molecular weight (literature): ~304.43 g/mol.
  • Stereochemistry (literature): 5α-configuration; 8β/9α/10β/13β junctions characteristic of the androstane framework; 17β-hydroxy.
  • Functional groups: two ketones (A-ring C3 enone-equivalent reduced to ketone; additional C11 ketone), one secondary alcohol at C17; multiple tertiary C–H stereocenters.

2D structure, described verbally

  • Ring system: tetracyclic androstane core (A/B/C six-membered rings, D five-membered ring).
  • Polar handles: C3=O and C11=O increase H-bond acceptor count; C17–OH provides single H-bond donor/acceptor site.
  • Overall topology: compact, rigid, hydrophobic scaffold with a single polar substituent at the D-ring and two carbonyls on A- and C-rings.
Synthetic Utility

Functional group leverage on the androstane scaffold enables diverse, chemoselective transformations useful for SAR exploration and derivatization.

Transformations centered on the carbonyls (literature)

  • Selective reduction: C3 ketone is typically more accessible than C11; NaBH4 at 0–5 °C in MeOH/THF can preferentially reduce C3 to a 3β- or 3α-alcohol depending on conditions; L-Selectride or K-Selectride in THF at −78 to −20 °C offers improved stereocontrol.
  • Oxime/hydrazone formation: C3 and/or C11 react with hydroxylamine/hydrazines (pyridine or AcOH, rt–50 °C) for derivatization, protection, or analytical tagging.
  • Ketal protection: ethylene glycol or 1,3-propanediol with catalytic p-TsOH in toluene (Dean–Stark) to mask one carbonyl during selective modifications at the other.

Manipulation of the 17β–OH

  • Esterification: acyl chlorides/anhydrides (pyridine, DMAP, rt) to tune lipophilicity or as pro-moieties; carbonates/carbamates for linker installation.
  • Silylation: TBDMS-Cl/imidazole (DMF, rt) or TBSOTf/2,6-lutidine (−20 to 0 °C) to protect the alcohol during enolate chemistry at C3.

C–H and enolate chemistry

  • Mild enolization at C3 with LDA or KHMDS (THF, −78 to −40 °C) followed by electrophiles (TMSCl, acylation) can be achieved; the rigid framework demands careful control to avoid rearrangements.

Analytical derivatization

  • For GC/MS, convert to trimethylsilyl ethers (BSTFA + 1% TMCS, 60–70 °C) to enhance volatility and sensitivity; for LC–MS, dansylation of the alcohol can boost ESI response.

Note: Conditions are literature-style guidance; optimize for your substrate, scale, and stereochemical goals.

Target Specificity

This section typically applies to biologics (e.g., antibodies) with defined antigen/epitope specificity. 11-Ketodihydrotestosterone is a small-molecule steroid, not an antibody or affinity reagent.

  • Item-specific targeting data (clone, isotype, species reactivity): Not applicable.
  • For receptor/ligand studies (general, literature): Investigations often probe interactions with the androgen receptor and steroid-metabolizing enzymes, but no product-specific binding data are provided here. Design assay conditions and controls according to your research question and consult the literature for affinity/efficacy parameters.

Preguntas frecuentes

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.
What is the purity of this product?
This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.
How is this product shipped?
This product ships in an insulated container with ice pads. 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 32694-37-4, the molecular formula is C19H28O3, and the molecular weight is 304.42 g/mol. InChIKey RSQKILYTRHKUIJ-HZGXJFKTSA-N.

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