E-Guggulsterone

Base Information

• Chemical Name: E-Guggulsterone
• CAS No.: 39025-24-6
• Deprecated CAS: 137682-27-0
• Molecular Formula: C₂₁H₂₈O₂
• Molecular Weight: 312.452
• UNII: 9B259YE66O
• DSSTox Substance ID: DTXSID6033538
• Wikipedia: Guggulsterone
• Wikidata: Q10910387
• Pharos Ligand ID: L818G9DRGCV3
• Metabolomics Workbench ID: 133669
• ChEMBL ID: CHEMBL402063
• Mol file: 39025-24-6.mol

Synonyms:(E)-guggulsterone;(Z)-guggulsterone;guggulsterone;pregna-4,17-diene-3,16-dione;pregna-4,17-diene-3,16-dione, (17E)-isomer;pregna-4,17-diene-3,16-dione, (17Z)-isomer

Chemical Property of E-Guggulsterone

Chemical Property:

• Vapor Pressure: 9.21E-09mmHg at 25°C
• Melting Point: 170-171.5°
• Refractive Index: 1.557
• Boiling Point: 463.3 °C at 760 mmHg
• Flash Point: 172.3 °C
• PSA: 34.14000
• Density: 1.1 g/cm³
• LogP: 4.64360
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble5mg/mL
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 312.208930132
• Heavy Atom Count: 23
• Complexity: 640

Purity/Quality:

95%-98% ^*data from raw suppliers

(E)-Guggulsterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37-52/53
• Safety Statements: 61-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C1C(=O)CC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
• Isomeric SMILES: C/C=C\1/C(=O)C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
• Uses: (E)-Guggulsterone acts as an α-glucosidase inhibitor also known as a hypolipidemic agent.

Technology Process of E-Guggulsterone

There total 7 articles about E-Guggulsterone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

4,17(20)-E-pregnadien-3-one-16α-ol → E-guggulsterone (39025-23-5,39025-24-6,95975-55-6)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 20 ℃; for 1 - 2h; Product distribution / selectivity;

Reference yield: 92.0%

5,17(20)-E-pregnadiene-3β,16α-diol (3347-58-8,10070-16-3,10106-43-1,95118-98-2,139563-13-6) → E-guggulsterone (39025-23-5,39025-24-6,95975-55-6)

Guidance literature:

With cyclohexanone; aluminum isopropoxide; In benzene; at 80 ℃; for 2h; Product distribution / selectivity; Heating / reflux;

Reference yield: 64.4%

E-guggulsterone (39025-23-5,39025-24-6,95975-55-6) → Z-guggulsterone (39025-23-5,39025-24-6,95975-55-6)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; at 80 ℃; for 1h; Product distribution / selectivity; Heating / reflux;

upstream raw materials:

5,17(20)-E-pregnadiene-3β,16α-diol

E-guggulsterone

Downstream raw materials:

Z-guggulsterone

guggulsterol-VI

16β-hydroxy-4-pregnen-3-one

Refernces

Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone

10.1021/acs.orglett.1c02173

The research presents a novel method for enone transposition using a silyl group masking strategy. The purpose of the study was to develop a reliable and efficient method for transposing enones, which are versatile intermediates in organic synthesis, with highlights such as enantioswitching, substituent shuffling, and Z-selectivity. The researchers utilized key chemicals like PhMe2SiLi (phenyldimethylsilyllithium) for the addition to carbonyl groups, acetonitrile and water as solvents, and TFA (trifluoroacetic acid) for catalysis. The developed method was successfully applied to the first total synthesis and structural revision of peribysin D, a bioactive natural product, as well as the formal synthesis of E-guggulsterone and E-volkendousin. The study concludes that the silyl-based masking group approach is highly effective for enone transposition, offering a practical and versatile tool for organic synthesis, with potential applications in the synthesis of other bioactive compounds and natural products.

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