Coprostanone , CAS No.601-53-6

CAS: 601-53-6 Cat. No.: C1051703 Formula: C₂₇H₄₆O Peso molecolare: 386.65 PubChem CID: 92132

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

• Sorrisi canonici: CC(C)CCCC(C)C1CCC2C1(CCC3C2CCC4C3(CCC(=O)C4)C)C
• IUPAC Name: (5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• InChIKey: PESKGJQREUXSRR-JDIFZLMISA-N
• INCHI: 1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-20,22-25H,6-17H2,1-5H3/t19-,20-,22+,23-,24+,25+,26+,27-/m1/s1
• Isomeri SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CCC(=O)C4)C)C
• PubChem CID: 92132
• Peso molecolare: 386.65

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Steroids and steroid derivatives
• Subclass: Cholestane steroids
• Intermediate Tree Nodes: Not available
• Direct Parent: Cholesterols and derivatives
• Alternative Parents: 3-oxo-5-beta-steroids Cyclic ketones Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Cholesterol-skeleton - 3-oxo-5-beta-steroid - Oxosteroid - 3-oxosteroid - Cyclic ketone - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homopolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as cholesterols and derivatives. These are compounds containing a 3-hydroxylated cholestane core.
• External Descriptors: Cholesterol and derivatives

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

Proprietà chimiche e fisiche

• Peso molecolare: 386.700 g/mol
• XLogP3: 8.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 386.355 Da
• Monoisotopic Mass: 386.355 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 579.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No assay-specific, vendor-validated protocols are provided for this item. For general use as an analytical standard or synthetic intermediate:

• Preparation of stock solutions:
  • Dissolve in CHCl3, DCM, EtOAc, or DMSO to prepare concentrated stocks (e.g., 10–50 mg/mL); warm gently and sonicate if needed.
• GC–MS derivatization (example workflow):
  • Reduce aliquot to coprostanol (NaBH4/MeOH), extract, dry; derivatize with BSTFA (60 °C, 30 min); inject on non-polar column (e.g., 5% phenyl‑methylpolysiloxane). Include internal standard appropriate for sterols.
• Oxime formation (analytical characterization):
  • Treat with hydroxylamine·HCl (pyridine, 60 °C, 1 h), extract; confirm by IR (C=N) and MS.

These are illustrative literature-style procedures. Adjust to your instrumentation and safety practices. Refer to peer-reviewed methods for validated parameters.

Biological Roles

Literature/general information (not product specifications):

• Coprostanone (5β‑cholestan‑3‑one) is a neutral sterol metabolite related to the anaerobic bacterial transformation of cholesterol in the gut. It is structurally intermediate between cholesterol and coprostanol, lacking the C5–C6 double bond and bearing a 3‑keto group.
• In biochemical studies, coprostanone is analyzed alongside coprostanol and cholestanone as part of sterol reduction/oxidation pathways, providing insight into microbial metabolism and hydrogenation of the steroid nucleus.
• Due to its high hydrophobicity and absence of polar functionalities beyond the C3 carbonyl, it partitions strongly into lipid phases and model membranes, a property leveraged in lipidomics workflows.
• As an authentic standard, coprostanone assists in method development and quantitation (e.g., GC–MS, LC–MS after derivatization) of fecal neutral sterols and environmental sterol biomarkers.

Notes:

• The above describes general roles in biochemistry and analytical chemistry. It does not imply any medical or clinical application. For regulated bioanalytical use, verify identity and purity via CoA and orthogonal methods (NMR, HRMS, IR).

Buffer Applications

Not typically applicable. Coprostanone is a highly hydrophobic neutral sterol and is not used to prepare aqueous buffer systems. For aqueous work, dissolve first in a suitable co-solvent (e.g., DMSO or ethanol) and then dilute into buffer below the solubility limit, or employ carrier lipids/micelles if required for biochemical assays.

Green Alternatives

While coprostanone itself is a solid analyte/building block, greener choices can be made for solvents and reagents used alongside it.

Greener solvent substitutions (general guidance):

• Replace chloroform or DCM with ethyl acetate or 2‑MeTHF when feasible (workups, chromatography, extractions)
• Use ethanol or isopropanol as protic media for reductions instead of methanol when compatible with selectivity
• Prefer heptane/cyclohexane over hexane for reduced toxicity in normal-phase chromatography

Comparison (general):

• DCM vs EtOAc
  • DCM: Excellent solvency, low bp, halogenated, higher environmental impact
  • EtOAc: Good solvency for steroids, biodegradable, renewable feedstock options available
• THF vs 2‑MeTHF
  • THF: Highly used, forms peroxides, petroleum-derived
  • 2‑MeTHF: Bio-based, less miscible with water (easier separations), good for NaBH4 reductions; may alter stereochemical outcomes—validate selectivity

Reagent considerations:

• For reducing the C3 ketone, explore transfer hydrogenation (e.g., catalytic isopropanol) as an alternative to stoichiometric hydrides where applicable.

Caveats:

• Solubility and stereoselectivity in steroid reductions are sensitive to solvent polarity and coordinating ability; run small-scale trials when changing to greener media.

Pharmaceutical Uses

No excipient or pharmacopeial role is specified for this item; refer to CoA/Spec Sheet.

General/literature context:

• Coprostanone may be employed as an analytical reference standard or system suitability compound in pharmaceutical and nutraceutical testing laboratories when monitoring sterol profiles or validating derivatization-based GC–MS workflows.
• Its saturated steroidal framework and lack of strong chromophores make it suitable primarily for mass spectrometric or evaporative detection; UV detection is limited to low-wavelength end absorption.

Compliance note:

• This product is for research use only and is not intended for human or veterinary use, formulation into drug products, or clinical diagnostics.

Physical Properties

Item-specific specs were not provided for this listing. The following are general/literature characteristics for 5β-cholestan-3-one (for reference only; not product specifications):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula and weight (literature): C27H46O; ~386.65 g/mol
• Phase at ambient: Non-volatile, crystalline solid (typical for neutral steroids; literature)
• Solubility (literature/general):
  • Practically insoluble in water
  • Soluble in nonpolar and moderately polar organic solvents (e.g., chloroform, dichloromethane, ethyl acetate, acetone); sparingly to moderately soluble in ethanol/methanol; dissolves in DMSO at elevated concentration
• Partitioning (literature/general): Highly lipophilic; very high logP expected for cholestane derivatives (qualitative)
• UV/Vis: Lacks strong chromophores; weak end-absorbance in UV (literature/general for saturated steroids)
• Volatility: Negligible under ambient conditions

Notes and practical implications:

• Owing to hydrophobicity, prepare stock solutions in CHCl3, DCM, EtOAc, or DMSO; gentle warming and sonication can aid dissolution.
• Avoid stating melting/boiling points or refractive indices without batch-specific documentation; Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay and impurity profile.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Context and expectations for this compound class:

• Neutral steroidal ketones are typically provided as high-purity crystalline solids suitable for analytical reference, metabolism studies, or synthetic use. For reference-standard applications (e.g., GC–MS derivatization studies), low levels of residual moisture and non-volatile residues are desirable.
• If HPLC or GC reference-grade material is required, confirm:
  • Assay by HPLC/GC ≥98–99% (as needed)
  • Low UV background is typical due to lack of conjugation, but confirm chromatographic suitability (baseline stability) if using UV detection at low wavelengths
  • Residual solvent content and identification (per ICH if applicable)
• Stabilizers: None are ordinarily required for saturated steroids; they are generally air- and light-stable. Any stabilizer content would be declared on the CoA if used.

Documentation:

• Always verify batch-specific specifications (purity, identification by NMR/IR/MS, water content, residual solvents) on the CoA/Spec Sheet before regulated or quantitative work.

Reaction and Applications

As a saturated 3‑ketosteroid (5β‑cholestan‑3‑one), coprostanone is widely used in:

• Analytical/biochemical applications (literature):
  • Reference standard for fecal neutral sterol profiling
  • Derivatization target for GC–MS (e.g., O‑trimethylsilyl ethers after reduction or oximes from the 3‑ketone)
• Reductive transformations (synthetic):
  • NaBH4 or catalytic hydrogenation with transfer-hydrogen donors to give coprostanol (5β‑cholestan‑3β‑ol) or stereoisomeric 3‑ols; reagent/solvent/temperature modulate α/β selectivity
  • Luche reduction (NaBH4/CeCl3) can enhance 3β selectivity in protic solvents
• Carbonyl derivatizations:
  • Formation of oximes (hydroxylamine), hydrazones/semicarbazones for characterization or protection of the C3 carbonyl
  • Ketalization with ethylene glycol (acid-catalyzed) for temporary protection during side-chain manipulations
• Enolate/adduct chemistry (ring A):
  • Under strong base, limited enolization at C2/C4 may allow selective α‑functionalizations (e.g., halogenation, deuteration) though reaction control is critical due to sterics
• Oxidation chemistry:
  • The saturated framework resists over-oxidation; Baeyer–Villiger of the 3‑ketone in rigid A‑ring systems is less common but documented in steroid chemistry with appropriate peracids/catalysts (literature examples)

Practical tips:

• Ensure anhydrous conditions for protective group strategies; steroids often crystallize slowly—seed to induce crystallization.
• For GC–MS work, confirm complete derivatization; residual 3‑ketone can tail without derivatization.

Reaction Conditions

General literature guidance for common transformations of coprostanone (5β‑cholestan‑3‑one). These are not product specifications; optimize per your laboratory conditions.

• Stereoselective reduction of C3 ketone:
  • NaBH4 (0.5–2.0 equiv) in MeOH or EtOH, 0–25 °C, 0.5–4 h; workup by quench, extract, and purify. Luche variant: NaBH4 (1–1.5 equiv) with CeCl3·7H2O (1–2 equiv) in MeOH at 0–5 °C to favor 3β‑ol.
  • Alternative: NaBH(OAc)3 in THF/AcOH (mild) or transfer hydrogenation (e.g., Ru or Ir catalysts, iPrOH) with careful control to avoid over-reduction elsewhere.
• Oxime formation (C3): Hydroxylamine hydrochloride (1.2–2.0 equiv), pyridine or EtOH with base (e.g., NaOAc), 50–80 °C, 1–4 h; isolate E/O isomers as applicable.
• Ketalization/protection: Ethylene glycol (excess), p‑TsOH (cat.), toluene or benzene with Dean–Stark, reflux until water removal complete; neutralize and purify.
• Silylation for GC–MS (after reduction to alcohol or with oxime): BSTFA (N,O‑bis(trimethylsilyl)trifluoroacetamide) ± TMCS, acetonitrile or pyridine, 60–70 °C, 15–60 min; analyze promptly to minimize hydrolysis.

Chromatography:

• Normal phase (silica) with hexanes/EtOAc or hexanes/DCM gradients is standard. Add 0.1% Et3N if tailing is observed with carbonyl derivatives.

Notes:

• The rigid steroid framework can slow reactions; ensure adequate mixing and, when safe, modest heating.
• Monitor stereochemical outcomes by 1H/13C NMR (diagnostic H3/H5 signals) and chiral or derivatization-based GC where applicable.

Safety and Handling

Item-specific hazard classifications were not provided for this product. Always consult the Aladdin Scientific SDS for authoritative safety information.

• GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
• General hazards (class-based): Neutral steroidal ketones are typically of low volatility and low acute inhalation hazard but may cause irritation upon contact or ingestion. Handle as a combustible organic solid.
• Personal Protective Equipment (PPE):
  • Lab coat, safety glasses or goggles, and appropriate chemically resistant gloves (e.g., nitrile)
  • Use in a chemical fume hood when weighing, dissolving, or transferring organic solutions
• Handling advice:
  • Avoid dust generation; though low, fine particulates can be irritants
  • Prevent skin/eye contact; wash thoroughly after handling
  • Avoid open flames and strong ignition sources when using organic solvents for dissolution
• Incompatibilities (general): Strong oxidizing agents; strong acids/bases may promote unwanted reactions (e.g., aldol-type or enolization at C3 under forcing conditions)
• First-aid overview (general):
  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists
  • Inhalation of dust: Move to fresh air; seek medical attention if symptoms occur
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention
• Waste: Dispose according to local regulations for non-halogenated organic waste or mixed solvent/solid waste streams.
• Defer to SDS for: toxicological endpoints, exposure limits, transport classification, and spill/cleanup procedures.

Solvent Selection

Coprostanone is a hydrophobic, neutral steroidal ketone. Solvent choice is usually dictated by dissolution and the downstream application (e.g., derivatization, reduction, GC–MS sample prep).

• Polarity/miscibility profile (general):
  • Practically insoluble in water
  • Soluble in nonpolar to moderately polar organics: chloroform, dichloromethane, ethyl acetate, acetone; soluble in DMSO; limited solubility in alcohols
• Selection guidance:
  • Preparative workup/crystallization: Hexanes/EtOAc or hexanes/CH2Cl2 mixtures provide tunable elution and crystallization windows
  • NMR: CDCl3 typically affords sharp resonances for steroids; DMSO‑d6 or CD2Cl2 are alternatives when higher solubility is needed
  • Derivatization for GC–MS: Use anhydrous pyridine or acetonitrile as reaction/dilution media prior to silylation/oximation
  • Reductions (e.g., NaBH4): Alcoholic solvents (MeOH/EtOH) or THF/MeOH mixtures; control temperature to tune 3β/3α selectivity

Practical comparison (general):

• CHCl3 vs DCM: CHCl3 offers higher solubility and better NMR compatibility; DCM is lower boiling for faster evaporation
• EtOAc vs acetone: Both dissolve well; EtOAc is greener and less aggressive toward certain plastics; acetone is fully miscible with alcohols for mixed-solvent protocols.

Storage and Reconstitution

Item-specific:

• Storage conditions: Room temperature (per Product Data)
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for this compound class:

• Keep container tightly closed in a dry, well-ventilated place. Protect from prolonged exposure to strong light and heat.
• For long-term analytical integrity, store desiccated; neutral steroids are typically stable for years at ambient when dry.
• Reconstitution/solution prep:
  • Dissolve in CHCl3, DCM, ethyl acetate, acetone, or DMSO. Gentle warming (30–40 °C) and sonication can help complete dissolution.
  • For aqueous assay systems, first prepare a concentrate in DMSO or ethanol, then dilute into buffer with vigorous mixing; consider carriers (e.g., Tween, BSA, liposomes) to avoid precipitation.
• Freeze–thaw: Not generally required for solids. If storing solutions, aliquot to avoid repeated freeze–thaw; store organic solutions in amber vials at 2–8 °C or −20 °C depending on solvent stability.

Research use only: This product is intended for laboratory research use and is not for human or veterinary applications.

Structure and Identity

Coprostanone is a saturated steroidal ketone (a cholestane derivative) bearing a carbonyl at C3 with 5β (cis-fused A/B rings) configuration; commonly named 5β-cholestan-3-one.

Item-specific (from Product Data):

• CAS: 601-53-6
• PubChem CID: 92132
• InChIKey: 275473 (truncated as provided; full 27-character InChIKey not specified for this item; refer to CoA/Spec Sheet.)
• Storage conditions: Room temperature
• Category: Life Science (全部 / 可售 / 生命科学)

Literature/structural notes (reference information):

• Molecular formula (literature): C27H46O (neutral steroid ketone)
• Molecular weight (literature): ~386.65 g/mol
• Preferred name/synonyms: 5β-cholestan-3-one; coprostan-3-one; cholestan-3-one (5β)
• 2D structural description: Tetracyclic perhydrophenanthrene core (rings A–D) fully saturated; A/B ring junction cis (5β), one carbonyl (ketone) at C3 on ring A; side chain at C17 is the saturated cholestane C8 aliphatic chain; multiple defined stereocenters across the steroid framework; no heteroatoms other than the C3 carbonyl oxygen.
• SMILES/InChI: Not specified for this item; refer to CoA/Spec Sheet.

Functional groups and features:

• One secondary cyclic ketone (C3)
• Hydrophobic steroidal framework (no aromaticity, fully saturated)
• Multiple stereocenters; typical steroid topology influences reactivity and solubility.

Synthetic Utility

Coprostanone is a versatile entry point into a variety of steroid transformations owing to its single, well-defined C3 carbonyl within a rigid 5β-cholestane framework.

Key functional elements and transformations:

• C3 Ketone chemistry:
  • Stereoselective reduction to 3β‑ or 3α‑alcohols (coprostanol is the 3β‑ol); selectivity tuned by solvent, temperature, and additives (e.g., Luche conditions)
  • Carbonyl protection as ketals/acetals to permit selective modifications on the side chain (C17) or rings C/D
  • Oxime/hydrazone formation for characterization, protection, or traceless activation
• A-ring enolization (under strong base):
  • α‑Functionalizations (halogenation, deuteration, limited aldol-type reactions) with careful control due to steric hindrance and conformational bias
• Side-chain modifications:
  • Oxidations, cross-metathesis after side-chain activation, or radical halogenation at terminal positions following protection of the C3 carbonyl
• Derivatization for analytics:
  • Silylation (e.g., BSTFA) to generate volatile derivatives post-reduction for GC–MS; oxime–TMS dual derivatization to improve chromatographic behavior

Retrosynthetic value:

• Serves as a saturated, de-olefinated scaffold relative to cholesterol, enabling studies that isolate the influence of the C5–C6 unsaturation on physical and biological properties.

Target Specificity

Not applicable. This product is a small-molecule steroidal ketone, not an antibody, enzyme, or affinity reagent. No target/epitope specificity, clone, isotype, or species reactivity applies.