E-Guggulsterone

Base Information

• Chemical Name: E-Guggulsterone
• CAS No.: 95975-55-6
• Deprecated CAS: 137682-27-0
• Molecular Formula: C21H28O2
• Molecular Weight: 312.452
• Hs Code.: 29147000
• UNII: 9B259YE66O
• DSSTox Substance ID: DTXSID6033538
• Wikipedia: Guggulsterone
• Wikidata: Q10910387
• Pharos Ligand ID: L818G9DRGCV3
• Metabolomics Workbench ID: 133669
• ChEMBL ID: CHEMBL402063
• Mol file: 95975-55-6.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:

• Appearance/Colour: Light yellow powder
• Vapor Pressure: 9.21E-09mmHg at 25°C
• 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: 5 mg/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:

99% ^*data from raw suppliers

Z/E-Guggulsterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37
• Safety Statements: 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: Guggulsterone is a broad spectrum steroid receptor ligand. Gum resin of Commiphora mukul marketed as an antihyperlipidemic drug.

Technology Process of E-Guggulsterone

There total 8 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

5,17⁽²⁰⁾-dien-pregna-3,16-diol

Downstream raw materials:

Z-guggulsterone

17α-hydroxy-16α-methylpregn-4-ene-3,20-dione

16β-hydroxy-4-pregnen-3-one

guggulsterol-VI

Refernces

• 1、 -. "PROCESS FOR PREPARING GUGGULSTERONES AND GUGGULSTEROL". Page 27; 55-56. . Retrieved 2010/02/09.