This compound belongs to the class of organic compounds known as androstane steroids. These are steroids with a structure based on the 19-carbon androstane skeleton.
External Descriptors
androstanoid
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.
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Application Protocols
No item‑specific tested application protocols are provided for this product. For general laboratory use:
Stock solution preparation: Dissolve an accurately weighed amount in anhydrous DMSO or ethanol to prepare concentrated stocks (e.g., 10–100 mM). Filter if particulate remains.
Analytical reference: Prepare calibration standards across the expected concentration range using matched solvent composition to minimize matrix effects. For LC‑MS, include 0.1% formic acid or ammonium formate as needed.
Synthetic operations: When performing functionalizations (oxidation, epoxidation, protection), run small‑scale trials to establish selectivity and monitor by NMR/MS.
Please refer to your internal SOPs and the product’s CoA/SDS for any validated methods specific to your application.
Biological Roles
General biochemical context (literature; not specific to this item)
Androstane derivatives constitute a major structural class of C19 steroids in vertebrates. They serve as scaffolds for androgens and related metabolites after specific oxidations/reductions and double‑bond migrations.
The 17β‑hydroxyl functionality is a hallmark of many bioactive steroids; enzymatic interconversion between 17β‑alcohols and 17‑ketones (via 17β‑HSDs) is common in steroid metabolism.
Double-bond localization in the A‑ring (e.g., Δ1, Δ2, Δ4) strongly influences receptor binding and metabolic stability across steroid families. Δ2 systems can act as precursors to enones upon allylic oxidation or dehydrogenation.
In biochemical assays, steroidal cores are frequently used as ligands or as negative/positive controls in receptor, transporter, or enzyme studies. When used as a reference material, confirm identity and purity by NMR/MS prior to assay setup.
Important
No medical, clinical, or therapeutic claims are made for this product. It is provided strictly for research use (per Product Data). Actual biological activity of this specific compound has not been established herein and should be determined experimentally where relevant.
Buffer Applications
This compound is a hydrophobic steroidal solid and is not typically used as a buffering agent or pH control component.
Practical notes
For studies requiring dispersion into aqueous buffers (e.g., biochemical assays), prepare concentrated stocks in DMSO or ethanol and dilute into the buffer with vigorous mixing, maintaining final organic content at minimal levels compatible with the system.
If sustained aqueous presence is needed, consider solubilization aids (cyclodextrins, nonionic surfactants) or liposomal formulations. Validate that additives do not interfere with your assay readout.
Green Alternatives
While 5α‑Androstan‑2‑en‑17β‑ol is itself a solid reagent, its handling and transformations can be made greener by solvent and reagent selection.
Greener solvent choices (general guidance)
Replace chlorinated solvents (CH2Cl2, CHCl3) with ethyl acetate, 2‑methyltetrahydrofuran (2‑MeTHF), cyclopentyl methyl ether (CPME), or toluene where feasible. For analytical work, ethanol or isopropanol can be viable co‑solvents for sample prep.
For reversed‑phase chromatography, prefer ethanol/water or methanol/water systems over acetonitrile when detection and resolution permit.
Greener oxidation/reduction strategies
Oxidations: Avoid Cr(VI) reagents (PCC, Jones). Consider TEMPO/bleach systems, catalytic IBX, or electrochemical oxidation for converting the 17β‑alcohol to ketone. Dess–Martin is effective but generates hypervalent iodine waste; plan for waste minimization.
Reductions: Use catalytic hydrogenation (H2, Pd/C) rather than stoichiometric hydrides when saturation of the Δ2 bond is required.
Comparison snapshot (literature/general)
CH2Cl2 vs EtOAc: EtOAc is bio‑derived and lower toxicity; however, CH2Cl2 often provides superior solubility and inertness. Start with EtOAc and escalate only if performance dictates.
Acetonitrile vs MeOH/EtOH: MeOH/EtOH are greener but may affect selectivity in some transformations (e.g., epoxidation or protection). Validate on small scale.
Process tips
Increase concentration and minimize solvent volumes for workups. Employ solid‑supported reagents/catalysts to streamline purification and reduce waste.
Pharmaceutical Uses
General formulation/manufacturing context (no therapeutic claims)
As a hydrophobic steroidal 17β‑alcohol, this compound may serve as an intermediate in the synthesis of androstane‑based active pharmaceutical ingredients or research tool compounds. It is not typically used as an excipient.
For preformulation studies, solubility screening in pharmaceutically acceptable solvents/co‑solvents (ethanol, PEG 400, propylene glycol) can inform downstream processing of related derivatives.
Analytical control: Due to weak UV chromophore, detection in QC workflows may benefit from ELSD/CAD or MS. Derivatization of the 17‑OH (e.g., benzoates) can enhance UV response for impurity profiling.
Solid‑state considerations: Steroidal molecules can exhibit polymorphism; if scaling synthetic steps, assess thermal behavior (DSC/TGA) and crystallinity (PXRD) to ensure lot‑to‑lot consistency.
Item-specific
No pharmacopeial designation, assay specification, or excipient role is specified for this item; refer to CoA/Spec Sheet.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations for steroidal 17β‑alcohols with Δ2 A‑ring (informational only)
Physical state: typically white to off‑white crystalline solid with low volatility.
Solubility profile: sparingly soluble in water; soluble in moderately polar to nonpolar organic solvents (e.g., ethanol, methanol, acetone, ethyl acetate, dichloromethane, chloroform). Often highly soluble in DMSO. Actual solubility depends on crystal form and purity.
Partitioning: hydrophobic core with a single secondary alcohol generally affords high logP; expect strong adsorption to silica/alumina unless modified.
UV characteristics: conjugation limited to a single Δ2 double bond; weak UV absorption above 210–230 nm; not optimized for UV detection. For analytical HPLC, consider ELSD/CAD or derivatization if sensitivity is needed.
Thermal behavior: many androstane derivatives melt in the 150–220 °C range and decompose before boiling under ambient pressure; gentle heating under vacuum is typically used for drying.
Important
Exact melting point, density, refractive index, pKa, logP, and UV cutoff are not specified for this item; refer to CoA/Spec Sheet. Literature values can vary with polymorph, solvate content, and measurement protocol.
Quality and Grades
Item-specific (from Product Data)
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades for this compound class (general)
Research grade: Suitable for synthetic work, method development, and biochemical assays after appropriate verification. For quantitative work, verify assay by qNMR or HPLC.
High-purity or ≥98% grade: Desirable for mechanistic and stereochemical studies; reduces ambiguity from minor epimers/oxidized analogs (e.g., 17‑ketones, Δ1/Δ4 isomers).
Chromatography suitability: If designated as HPLC grade solid (rare), expectation would be low UV-absorbing impurities; however, for non-UV active steroids, impurity profiling is often performed by ELSD/CAD/MS.
Stereochemical integrity: For androstane derivatives, minor epimerization at C17 or double-bond isomerization (Δ2 ↔ Δ1/Δ4) may occur during harsh processing. Vendors may indicate specific stereochemical purity (e.g., 17β/17α ratio) on the CoA.
Recommendations
Request the CoA for assay, residual solvents, and impurity profile. If your application is stereosensitive, confirm 17β-configuration and Δ2 location by 1H/13C NMR and NOE/2D experiments. Where applicable, verify water content by Karl Fischer and confirm absence of peroxides if stored with oxidants (not typically stabilized).
Reaction and Applications
This compound is a versatile steroidal building block. The Δ2 A‑ring olefin and the 17β‑secondary alcohol provide orthogonal reactivity that can be exploited in synthesis and derivatization.
Oxidation at C17: Convert 17β‑ol to the 17‑ketone using Dess–Martin periodinane, PCC, Swern, or TPAP/NMO. Oxidation state adjustments enable access to diverse androst‑2‑en‑17‑one derivatives.
Protection of 17β‑OH: Silyl ethers (TBS/TBDPS), benzyl/PMB ethers, or carbonate/ester protections (acetate, pivalate) to enable selective A‑ring chemistry without competitive reactions at C17.
A‑ring functionalization via the Δ2 olefin:
• Epoxidation (mCPBA) → 2,3‑epoxide, followed by regioselective opening to install C2/C3 functionality with stereochemical control dictated by the 5α framework.
• Hydroboration–oxidation → C3 alcohol introduction (anti‑Markovnikov) on the A‑ring side, though sterics may bias outcomes; conditions often require careful optimization.
• Electrophilic additions (HX, halogenation) to form 2,3‑dihalo or halo‑alcohol derivatives; useful for subsequent eliminations or substitutions.
• Allylic oxidation (SeO2 or Pd‑catalyzed) targeting C1/C2 region to access enone/enal motifs.
Hydrogenation: Selective reduction of the Δ2 double bond (H2, Pd/C) affords the fully saturated 5α‑androstane‑17β‑ol (androstane‑17β‑ol), enabling comparative SAR studies.
Conjugation: Formation of carbonate/ester linkers at C17 for immobilization, bioconjugation, or pro‑moiety introduction; carbamate formation is also viable after 17‑OH activation.
Applications
Intermediate for synthesizing labeled standards, affinity probes, and modified androstane libraries.
Reference material for chromatographic method development and stereochemical assignment within the androstane series.
Reaction Conditions
General conditions reported for related androstane Δ2 17β‑alcohols (guidance; optimize for your substrate)
Oxidation (17β‑OH → 17‑ketone):
• Dess–Martin periodinane (1.5–2.0 eq), CH2Cl2 or EtOAc, 0 °C to rt, 1–3 h; typical isolated yields 80–95% on steroids.
• Swern (oxalyl chloride/DMSO, −78 °C → 0 °C), CH2Cl2; quench with Et3N; 70–90%.
Protection (TBS ether): TBSCl (1.2–1.5 eq), imidazole (2–3 eq), DMF or CH2Cl2, rt to 40 °C, 2–16 h; 80–95%.
Epoxidation (Δ2): mCPBA (1.1–1.3 eq, 70–77%), NaHCO3 buffer, CH2Cl2, 0 °C to rt, 1–4 h; furnish 2,3‑epoxide with facial selectivity determined by 5α topology; 60–85%.
Hydrogenation (Δ2 → saturated): H2 (1–3 atm), Pd/C (5–10 wt%), EtOH/EtOAc/EtOAc–hexanes, rt to 40 °C, 2–8 h; 85–99%.
Hydroboration–oxidation: 9‑BBN (1.2 eq), THF, 0 °C to rt, then H2O2/NaOH; install C3‑OH with anti‑Markovnikov selectivity; yields vary (40–75%) due to sterics.
Allylic oxidation: SeO2 (0.5–1.0 eq), t‑BuOOH, dioxane or toluene, 60–90 °C; monitor for over‑oxidation; 30–70%.
Analytical/handling
Monitor by TLC (NP silica; hexanes/EtOAc 7:3 to 9:1) or RP‑HPLC with ELSD/CAD/MS. UV at 210–220 nm is possible but low sensitivity.
Drying: Vacuum (25–40 °C) to remove residual solvents without risking dehydration.
Notes
Values above are literature‑type ranges for closely related steroids and are provided as general guidance, not item specifications.
Safety and Handling
Item-specific (from Product Data)
GHS classification, signal word, pictograms, and H‑statements: Not specified for this item; refer to the SDS.
Storage conditions: Room temperature (per Product Data).
General laboratory safety guidance for steroidal alcohols (informational; not a substitute for SDS)
Hazards: Many steroids are bioactive; avoid inhalation of dust, skin contact, or accidental ingestion. Treat as a laboratory chemical of unknown toxicity.
PPE: Wear lab coat, safety glasses, and appropriate disposable gloves (e.g., nitrile). Change gloves frequently during weighing/handling to avoid trace contamination.
Engineering controls: Use a chemical fume hood when weighing, transferring, or preparing stock solutions to minimize airborne particulates and solvent vapors.
Handling: Minimize dust generation; use antistatic tools and weigh boats. For solutions, cap vials promptly to limit evaporation and adsorption to glass surfaces.
Incompatibilities: Strong oxidizers can convert the 17β‑alcohol to ketones/acids; strong acids/bases may induce dehydration or isomerization of the Δ2 double bond. Avoid prolonged exposure to UV/strong light which may promote peroxidation of trace impurities.
First aid (overview): In case of skin contact, wash with soap and water. If eye exposure occurs, rinse cautiously with water for several minutes and seek medical advice. If inhaled, move to fresh air. If ingested, rinse mouth and seek medical attention. Always follow the SDS.
Waste: Collect solid and solution waste in halogenated or non‑halogenated organic waste streams per your facility’s SOPs.
Solvent Selection
General guidance for 5α‑androstane Δ2 17β‑alcohols
Polarity class: Predominantly hydrophobic with a single secondary alcohol; behaves as a lipophilic neutral compound.
Preferred solvents for preparation of stock solutions: DMSO, ethanol, methanol, isopropanol, acetone, acetonitrile. For nonpolar media, chloroform, dichloromethane, toluene, and ethyl acetate are effective.
Aqueous work: Poor intrinsic water solubility. For aqueous systems, use co‑solvent strategies (1–5% DMSO or ethanol) or cyclodextrin/solubilizing excipients. Surfactants (e.g., Tween 80) can aid dispersion for analytical or materials studies.
Strong retention on normal‑phase silica due to hydrophobic interactions; elute with hexanes/ethyl acetate or dichloromethane/methanol gradients. On reversed‑phase C18, use high organic (acetonitrile or methanol) with formic acid or ammonium formate if MS detection is desired.
Avoid highly basic media during dissolution to limit E1 dehydration of the 17β‑alcohol and double-bond migration.
When to choose alternatives
If UV detection is required, derivatize the hydroxyl (e.g., p‑nitrobenzoate) or employ ELSD/CAD/MS detection to avoid forcing into strongly absorbing solvents.
For greener handling, consider bio‑based solvents (2‑MeTHF, CPME, EtOAc, ethanol) where compatible; see Green Alternatives tab for tradeoffs.
Storage and Reconstitution
Item-specific (from Product Data)
Storage conditions: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General best practices for steroidal solids
Container: Store in a tightly closed, chemically resistant container (amber glass vial recommended) to minimize adsorption and protect from light. Include a desiccant if ambient humidity is high.
Atmosphere: While not air‑sensitive, prolonged exposure to strong light/air can promote slow oxidation of impurities; store in the dark under ambient atmosphere or inert gas for long‑term archiving.
Reconstitution: For solution use, dissolve in dry DMSO, ethanol, methanol, or dichloromethane. Prepare single‑use aliquots to avoid repeated freeze‑thaw or extended bench exposure. Vortex/sonicate gently to assist dissolution.
Stability in solution: Steroidal alcohols are generally stable for days to weeks at 2–8 °C in anhydrous organic solvents. For extended storage, keep solutions at −20 °C in sealed vials. Verify integrity by LC‑MS or 1H NMR before critical uses.
Avoid: Strong acids/bases and oxidants during storage; these can induce dehydration, isomerization of the Δ2 bond, or oxidation at C17.
Note
For definitive shelf life, assay, and impurity limits, consult the item’s CoA and SDS. This product is for research use only (per Product Data).
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.
Literature/structural description
Core scaffold: androstane (C19 tetracyclic steroid nucleus), comprising four fused rings (A/B/C/D), typically trans-fused at A/B in the 5α series.
Unsaturation: “2-en” indicates a double bond in the A-ring between C2 and C3 (Δ2). The 5α designation denotes the hydrogen at C5 is α (below the plane), giving a trans A/B fusion and overall 5α-androstane configuration.
Functional groups: secondary alcohol at C17 with β-configuration (17β‑ol), no other heteroatoms. Hydrocarbon framework otherwise saturated except for the A-ring Δ2 olefin.
Stereochemistry: Stereocenters typical of androstane at C5, C8, C9, C10, C13, C14, and C17 (β‑OH). The β‑orientation at C17 places the hydroxyl on the same face as the angular 10β‑methyl group, consistent with many natural androgens.
2D description: Fused cyclohexane (A/B/C) and cyclopentane (D) rings; a C2=C3 double bond in the A-ring; methyl groups at C10 and C13; a 17β‑substituted secondary alcohol on the D-ring side chain terminus.
Notes
Structural identifiers (exact SMILES/InChI) can vary by stereochemical annotation; consult the CoA for the definitive line notation used for this item.
Synthetic Utility
Strategic features
Orthogonal handles: A‑ring Δ2 double bond and D‑ring 17β‑secondary alcohol.
Stereochemical control: The rigid 5α‑androstane framework provides predictable facial selectivity in additions/oxidations, enabling diastereocontrolled elaboration.
Build enone systems: Allylic/benzylic oxidation or dehydrogenation (e.g., DDQ, Pd/C–air, SeO2) to access 1‑ or 3‑enone motifs for Michael chemistry or Robinson annulations on the A‑ring.
Install leaving groups: Convert 17‑OH to mesylate/tosylate/carbonate for subsequent displacement, enabling introduction of heteroatom substituents or chain extensions at C17.
Epoxide route: mCPBA epoxidation of the Δ2 bond followed by regioselective nucleophilic opening to set contiguous stereocenters at C2/C3; nucleophiles include halides, azide, alcohols, or organocuprates.
Selective reductions: Hydrogenate Δ2 (H2, Pd/C) without affecting the 17‑OH; or use diimide for milder conditions.
Protection tactics: TBS/TBDPS ether formation at 17‑OH survives many A‑ring operations; deprotect under fluoride or mild acid as needed.
Labeling: Introduce stable isotopes (2H/13C) via catalytic exchange or through synthesis from labeled precursors to create internal standards for bioanalytical workflows.
Utility
Serves as a platform to access libraries of androstane analogs for SAR, materials, and analytical method development, where precise control over ring oxidation and substitution patterns is required.
Target Specificity
Not applicable. This product is a small‑molecule steroidal reagent, not an antibody, enzyme, or oligonucleotide. No antigen/epitope or species reactivity information applies.
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