GRADE & PURITYMoligand™?Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools.≥98%
Moligand™, ≥98% Moligand™ for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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Storage & shipping
Store at -20°C,Argon charged 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 1 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Overview
16α-Hydroxy Progesterone a hydroxylated metabolite of Progesterone that binds to human progesterone receptors hPR-A and hPR-B and act as an agonist for both receptors.
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
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives
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
Not applicable. No validated antibody-style application protocols (WB, IHC, IF, FC) apply to this small-molecule product.
General handling suggestions for assay stocks (research use only)
Prepare a concentrated stock in DMSO or ethanol (e.g., 10–50 mM).
Vortex and, if needed, warm gently to fully dissolve; avoid prolonged heating.
For aqueous assays, add stock to buffer with rapid mixing to keep final organic content low (≤1% v/v) and prevent precipitation.
Filter sterilize through 0.22 μm PTFE for cell-free systems if particulate-free solutions are required.
Biological Roles
General context (literature; not a claim about this product’s use in humans/animals)
16α-Hydroxyprogesterone is a known oxidative metabolite of progesterone formed by cytochrome P450 enzymes (e.g., hepatic and placental CYP pathways) via regio- and stereoselective hydroxylation at C16.
The introduction of a 16α-hydroxyl increases polarity relative to progesterone, influencing receptor binding, metabolic clearance, and conjugation (e.g., glucuronidation/sulfation) in vivo.
In biochemical studies, 16α-hydroxylated steroids are used to probe structure–activity relationships at steroid receptors and metabolizing enzymes.
Laboratory relevance
Serves as a reference analyte for LC–MS/MS method development in steroid panels; fragmentation commonly involves neutral loss from the side chain and water loss from the 16α-OH.
Useful substrate/standard in enzymology assays investigating regioselective hydroxylations, phase II conjugations, and stereochemical outcomes of steroid metabolism.
Notes
Any biological exploration with this product must be for research use only, in controlled laboratory settings.
No medical, diagnostic, or therapeutic applications are implied or supported for this catalog item.
Buffer Applications
This product is a neutral, poorly water-soluble steroid and is not used as a buffering agent or pH stabilizer.
Practical note
When introducing into aqueous buffers for biochemical assays, prepare a concentrated stock in DMSO or ethanol and dilute with vigorous mixing to keep final organic content low (typically ≤1% v/v). Consider cyclodextrin inclusion or serum proteins to enhance apparent solubility if consistent with the experimental design.
For actual buffering needs
Select established buffer systems (e.g., phosphate, HEPES, Tris) appropriate to your assay’s pH; this steroid does not contribute to buffering capacity.
Green Alternatives
Because 16α-hydroxyprogesterone is a substrate rather than a solvent or reagent, “green alternatives” pertain to solvent and reagent choices during its handling and derivatization.
Greener solvent swaps (general guidance)
Replace DCM with ethyl acetate or 2-MeTHF for extractions and chromatography when feasible.
Use 2-MeTHF or CPME instead of THF for moisture-tolerant transformations (e.g., acylations, silylations) to reduce peroxide risk and improve sustainability.
Favor ethanol or isopropanol over methanol where reaction compatibility allows.
Oxidation/reduction choices
Prefer catalytic oxidations (e.g., TEMPO/O2, Oxone under buffered conditions) over chromium(VI) reagents; Dess–Martin Periodinane is effective but consider hypervalent iodine waste.
For reductions, transfer hydrogenation (HCOONH4, HCOONa) or catalytic hydrogenation with recyclable Pd/C under low pressure can reduce solvent and energy footprint.
Process considerations
Implement solvent recycling for DMSO/MeOH/EtOAc streams.
Minimize protecting group manipulations by selecting chemoselective conditions (e.g., acylation with catalytic DMAP, mild bases) to reduce steps and waste.
Illustrative comparison (general)
DCM vs EtOAc: Similar extraction power for steroids; EtOAc is biodegradable and has a better EHS profile, with slightly higher boiling point and sometimes larger volumes needed.
THF vs 2-MeTHF: 2-MeTHF is bio-derived, forms fewer peroxides, and facilitates phase-splitting in workups; solubility of highly crystalline steroids may be lower, requiring adjustment.
Pharmaceutical Uses
Scope (non-clinical, research/QC context only)
16α-Hydroxyprogesterone can function as a reference or process-related impurity standard in pharmaceutical analytical development for progesterone-derived APIs.
Employed in method validation (specificity, linearity, accuracy) for HPLC/UPLC or LC–MS/MS steroid panels.
Formulation/excipient role
Not used as an excipient or functional additive in dosage forms; rather, it may be spiked into matrices for recovery studies or stability-indicating method development.
Pharmacopeial status
No specific pharmacopeial monograph is cited here. Check the relevant pharmacopoeias and your regulatory strategy if a compendial reference is required.
Practical considerations for QC labs (general)
Ensure traceability of standards and document purity and uncertainty from the CoA when using as a system suitability or impurity marker.
Store working standards under the same protective conditions as the neat solid (low temperature, inert gas, protected from light) to ensure stability over the study period.
No therapeutic, diagnostic, or clinical claims are made for this product; it is intended strictly for research use only.
Physical Properties
Item-specific specifications (from Product Data)
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/typical data for 16α-hydroxyprogesterone (reference only; not item specifications)
Solubility profile: sparingly soluble in water; soluble in polar aprotic and protic organic solvents (DMSO, DMF, acetone, ethanol, methanol); limited solubility in nonpolar hexanes; higher solubility in dichloromethane/ethyl acetate.
Thermal behavior: high-melting steroid that may char/decompose before boiling under ambient pressure; drying under vacuum at moderate temperature is typical.
UV/Vis: weak chromophore (Δ4-3-ketone) with n→π*/π→π* absorption in the near-UV; often suitable for HPLC-UV detection around 240–254 nm (method-dependent).
Acid/base: essentially neutral molecule; contains one secondary alcohol (pKa of conjugate acid very high); behaves as a weak hydrogen bond donor/acceptor.
Partitioning: lipophilic steroid; exhibits strong retention on C18 in RP-HPLC; requires MeOH/ACN with aqueous modifier for elution.
Practical notes (general)
Prepare concentrated stocks in DMSO or ethanol; dilute into aqueous media with co-solvent to avoid precipitation.
Hygroscopicity is typically low for ketosteroids, but protect from moisture to maintain assay integrity.
Quality and Grades
Item-specific quality details
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Additives: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting typical grades for small-molecule research materials (general guidance)
Research grade: Suitable for synthetic and analytical work where trace impurities minimally impact outcomes; verification by NMR/HPLC recommended for sensitive applications.
Reference standard/CRM grades: Where applicable, provided with certified purity/uncertainty and traceability—useful for impurity profiling and method validation in QC environments.
Low-water/anhydrous claims: For steroidal solids, moisture is less critical than for reactive salts, but water can influence crystallinity and accurate weighing; confirm Karl Fischer only if specified in the CoA.
Practical quality considerations for 16α-hydroxyprogesterone (general)
Key impurities: Positional/stereoisomers (e.g., 16β-OH), over-oxidized (16-oxo) or reduced species, and residual protecting groups from synthesis.
Analytical control: RP-HPLC/UPLC with UV detection (≈240–254 nm) offers robust assay; confirm identity by 1H/13C NMR and HRMS; monitor specific optical rotation if stereochemistry is critical.
Solid-state form: Polymorphs/solvates may exist for steroids; drying under vacuum and reporting loss on drying (LOD) can improve between-batch comparability.
Consult the item’s CoA/Spec Sheet for definitive purity, residual solvent limits, and assay values.
Reaction and Applications
Applications (research use only)
Analytical standard: Useful as a reference analyte for steroid metabolism studies (CYP-mediated 16α-hydroxylation pathways) and impurity profiling of progesterone-derived APIs.
Synthetic intermediate: The 16α-OH provides a handle for selective derivatization to generate esters, carbonates, ethers, and further oxidized derivatives (e.g., 16-oxo). Retention of 3,20-dione permits classic steroid transformations.
O-Acylation: 16α-OH acylated with acid chlorides/anhydrides (pyridine, DMAP) to give 16-acyl esters; control acyl selectivity vs possible 20-ketal formation by protecting 20-ketone when needed.
Silylation: Protection as TBDMS or TBS ether (TBDMS-Cl/imidazole, DMF) to mask 16-OH during reactions at C3/C20.
Oxidation: TEMPO/BAIB, Dess–Martin, or Swern to 16-oxo, enabling subsequent Wittig/aldol chemistry on the D-ring side chain.
Mitsunobu substitution: Inversion at C16 to access 16β-derivatives using DEAD/DIAD and PPh3 with a nucleophile; requires careful control to avoid competing reactions at the enolizable 3-keto.
Hydrogenation/Isomerization: Selective reduction of the Δ4 double bond (e.g., Pd/C, H2) to modulate A-ring saturation where desired.
Practical tips
Protect 3-keto as a ketal or enone as an enol ether if strong nucleophiles/bases are used.
Control moisture and oxygen to limit side reactions (over-oxidation or aldol-type condensations); employ argon or nitrogen atmosphere.
Monitor reactions by TLC (anisaldehyde/sulfuric stains) or LC–MS for improved sensitivity with low UV response.
Reaction Conditions
General literature guidance for common transformations on 16α-hydroxyprogesterone (reference only; optimize per lab):
O-acylation (selective at 16-OH)
Solvent: DCM or DMF
Reagents: RCOCl (1.1–1.5 eq) or (RCO)2O (1.5 eq), DMAP (5–10 mol%), base (pyridine or NEt3, 2–3 eq)
Temperature/time: 0 °C to rt, 1–4 h
Notes: Protect 3/20 carbonyls if over-acylation is observed; minimal base suppresses enolization.
Silyl protection (TBDMS/TBS ethers)
Solvent: DMF or DCM
Reagents: TBDMS-Cl (1.2–1.5 eq), imidazole (2 eq)
Temperature/time: rt, 2–12 h
Notes: Monitor by TLC; acid-labile—remove with TBAF or HF·pyridine.
Notes: Protect carbonyls if necessary; carefully remove hydrazide byproducts.
Purification
Normal-phase silica: DCM/EtOAc/MeOH gradients; detect with anisaldehyde or phosphomolybdic acid stains.
RP-HPLC: Water/ACN or water/MeOH with 0.1% formic/acetic acid; typical retention on C18 is high—use strong organic to elute.
All conditions are literature-style guidance; adapt to your substrate and scale.
Safety and Handling
Item-specific hazard data (from Product Data)
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
General laboratory safety guidance for steroidal ketols (literature/general)
Potential hazards: May cause irritation to skin/eyes/respiratory tract. As a steroidal compound, avoid inhalation/ingestion and skin contact to minimize unintended biological exposure.
PPE: Use appropriate lab coat, nitrile gloves, and safety glasses. Handle powders within a fume hood or containment to control dust/aerosols.
Engineering controls: Work in a chemical fume hood; employ local exhaust during weighing and transfers.
Incompatibilities: Strong oxidizing agents (can over-oxidize alcohol functionality), strong bases (may promote aldolization/enolization at C3/C20), and strong acids (possible dehydration at C16 under forcing conditions). Avoid prolonged exposure to light/air to limit oxidative degradation.
First aid (overview; defer to SDS): Inhalation—move to fresh air; Skin—wash with soap/water; Eyes—rinse with water for several minutes; Ingestion—rinse mouth, seek medical attention.
Spill cleanup: Avoid dust; gently sweep or use HEPA-filtered vacuum; place waste in labeled container.
Waste disposal: Dispose according to institutional and local regulations for organic laboratory chemicals; do not release to drain.
Always consult the product-specific SDS for authoritative hazard classifications and response procedures.
Solvent Selection
Polarity and miscibility (general behavior of 16α-hydroxyprogesterone)
Non-ionizable, moderately lipophilic molecule with one secondary alcohol and two ketones.
Poorly soluble: Water and aliphatic hydrocarbons (hexanes, heptane); limited in toluene unless warmed.
Practical selection by task
Stock solutions for bioassays: DMSO (most common) or ethanol; prepare concentrated stock (e.g., 10–50 mM) and dilute into aqueous buffers with 0.1–1% co-solvent to prevent precipitation.
Synthetic transformations: Use anhydrous chlorinated (DCM) or ethereal solvents (THF, 2-MeTHF) for acylations/silylations; polar aprotic media (DMF/MeCN) for Mitsunobu or coupling steps.
Purification: RP-HPLC (water/MeOH or water/ACN, 0.1% acid optional) or normal-phase silica (DCM/MeOH or DCM/EtOAc). Avoid strong basic modifiers that can induce enolization.
Comparison notes (general)
DMSO vs ethanol: DMSO provides highest solubility and stability; ethanol is more volatile and easier to remove but may form azeotropes and can promote transesterification under strong acid/base.
DCM vs EtOAc for workup: DCM extracts efficiently and evaporates rapidly; EtOAc is greener, with slightly lower extraction efficiency for highly lipophilic steroids.
Storage and Reconstitution
Item-specific storage and shipping (from Product Data)
Storage: Store at -20°C, Argon charged.
Shipped in: Ice chest + Ice pads.
General stability guidance for steroidal solids
Protect from light, air, and moisture to minimize oxidative or photochemical degradation. Keep container tightly closed under inert gas (argon or nitrogen).
Allow vial to equilibrate to room temperature before opening to prevent condensation. Reseal promptly and purge headspace with inert gas after use.
Solvents: DMSO or ethanol recommended for concentrated stocks; soluble also in DMF, acetone, and dichloromethane for synthetic use.
Typical stock concentrations: 10–50 mM in DMSO or ethanol. Verify complete dissolution by visual inspection; gentle warming (≤40°C) and vortexing may help.
Aliquoting: Prepare single-use aliquots to minimize freeze–thaw cycles; store aliquots at −20°C under inert atmosphere and protected from light.
Aqueous dilutions: Add organic stock to buffer with vigorous mixing; consider using solubilizing agents (e.g., 0.1–1% v/v co-solvent) to prevent precipitation.
Shelf-life
Not specified for this item; refer to CoA/Spec Sheet. Periodic re-analysis by HPLC or NMR is prudent for long-term stored materials.
Structure and Identity
Steroidal progestin metabolite bearing a secondary alcohol at C16α on the pregn-4-ene-3,20-dione framework.
Item-specific (from Product Data)
SKU: H336075
Product name: 16α-Hydroxy Progesterone
CAS: 438-07-3
PubChem CID: 243761
InChIKey: 205291 (as provided; appears truncated—see literature identifiers below)
Storage: Store at -20°C, Argon charged; shipped in ice chest with ice pads
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers and description (for reference; not item specifications)
Core features: tetracyclic cyclopentanoperhydrophenanthrene skeleton; Δ4-ene; 3-keto and 20-keto groups; 16α-secondary alcohol; multiple defined stereocenters consistent with the pregnane series.
2D structural description (general)
A fused 6-6-6-5 ring system with a Δ4 double bond in ring A.
Carbonyls at C3 (A-ring) and C20 (side chain on D-ring).
A hydroxyl at C16 in the α-orientation (below the plane), providing a polar handle on the D-ring side chain.
Synthetic Utility
Functional group set
16α-Secondary alcohol: amenable to esterification, etherification, silyl protection, oxidation to ketone, and Mitsunobu inversion/substitution.
3- and 20-ketones: enable enol/enolate chemistry, selective reduction, protection as ketals/oximes, and participation in conjugate additions when A-ring enone is engaged.
Strategic value in steroid synthesis (literature/general)
Divergent derivatization at C16: Access to 16-oxo, 16β-substituted, or 16-ester series, providing entry to families of progestins and intermediates.
Orthogonal protection schemes: Temporary masking of 16-OH (TBDMS, TBS) while modifying C3/C20; or conversely, protect carbonyls (ethylene glycol ketals) while functionalizing 16-OH.
Late-stage diversification: The stereodefined C16 center makes it a useful chiral handle for installing side-chain functionality via substitution or oxidation–olefination sequences.
Representative transformations
Esterification: RCOCl or anhydrides, catalytic DMAP, pyridine or NEt3, DCM/DMF.
Oxidation at C16: Dess–Martin or Swern to 16-ketone; follow with Wittig/HWE to reconfigure side chain geometry.
Mitsunobu: 16α-OH inversion with carboxylic acids or phenols to 16β-esters/ethers; hydrolysis gives 16β-OH analogs.
Reductions: Selective NaBH4/CeCl3 (Luche) for 3-keto vs 20-keto; catalytic hydrogenation for Δ4 reduction without affecting protected 16-O functionality.
Analytical control
Stereochemical verification by NOESY/ROESY and coupling constants at C16; confirm mass balance via HRMS and purity by RP-HPLC.
Target Specificity
Not applicable. This product is a small-molecule steroid standard/intermediate, not an antibody, enzyme, or targeted biological. No antigen/epitope, isotype, or species reactivity applies.
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