beta-CHLOROGENIN

Base Information

• Chemical Name: beta-CHLOROGENIN
• CAS No.: 41743-71-9
• Molecular Formula: C27H44O4
• Molecular Weight: 432.644
• UNII: R88XV7YUIG
• Nikkaji Number: J1.514.228F
• Wikidata: Q27287965
• Metabolomics Workbench ID: 35112
• Mol file: 41743-71-9.mol

Synonyms:5 beta-spirostane-3 beta,6 alpha-diol;ruizgenin;ruizgenin, (3beta,5alpha,6alpha,25R)-isomer;ruizgenin, (3beta,5alpha,6alpha,25S)-isomer;ruizgenin, (3beta,5alpha,6beta,25R)-isomer

Chemical Property of beta-CHLOROGENIN

Chemical Property:

• Vapor Pressure: 2.07E-14mmHg at 25°C
• Boiling Point: 550.5°Cat760mmHg
• Flash Point: 286.7°C
• PSA: 58.92000
• Density: 1.16g/cm³
• LogP: 4.76460
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 432.32395988
• Heavy Atom Count: 31
• Complexity: 726

Purity/Quality:

99% ^*data from raw suppliers

3β,6β-Chlorogenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC(C6C5(CCC(C6)O)C)O)C)C)OC1
• Isomeric SMILES: C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4C[C@H]([C@@H]6[C@@]5(CC[C@@H](C6)O)C)O)C)C)OC1
• General Description: Ruizgenin (also known as chlorogenin) is a steroidal compound characterized by hydroxyl groups at positions 3 and 6, with confirmed beta and alpha configurations, respectively. Its structure and properties were elucidated through chemical reactions, including reductions and oxidations, which supported its identification as a spirostan derivative with specific stereochemistry.

Technology Process of beta-CHLOROGENIN

There total 28 articles about beta-CHLOROGENIN 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: 93.0%

diosgenin (512-04-9) → chlorogenin (511-91-1,562-33-4,562-34-5,32562-83-7,41743-71-9,72203-51-1,74609-42-0)

Guidance literature:

diosgenin; With diborane; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

With sodium hydroxide; In tetrahydrofuran; at 0 ℃; for 0.75h;

With dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 3h;

Reference yield: 86.0%

(25R)-3β-hydroxy-5α-spirostan-6-one (20470-24-0,62212-10-6,1177-71-5) → (3β,5α,6β,25R)-spirostan-3,6-diol (41743-71-9)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethanol; for 4h; under 1034.3 Torr;

DOI:10.1080/00397919808006836

Reference yield: 86.0%

(25R)-5α-spirostan-3,6-dione (3514-59-8) → (3β,5α,6β,25R)-spirostan-3,6-diol (41743-71-9)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethanol; under 1034.32 Torr;

DOI:10.1039/b007656m

upstream raw materials:

aluminum isopropoxide

isopropyl alcohol

(25R)-5α-spirostan-3,6-dione

(25R)-6α-hydroxy-5α-spirostan-3-one

Downstream raw materials:

(25R)-3β-hydroxy-5α-spirostan-6-one

(23S,25R)-5α-spirostan-3β,6β,23-triol

(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.0^2,9.0^4,8.0^13,18]icosa-16,18-diene-6,2'-oxane]

Di-O-benzoyl-chlorogenin

Refernces

CONTRIBUTION FROM THE SCHOOL OF CHEMISTRY AND PHYSICS OF THE PENNSYLVANIA STATE COLLEGE: Sterols. CII. Chlorogenin

10.1021/ja01866a074

The study investigates the structure and properties of chlorogenin and its related compounds. Chlorogenin is a sterol compound with hydroxyl groups at positions 3 and 6, which are confirmed to be in the beta and alpha configurations respectively. The researchers used various chemical reactions and reduction methods to synthesize and analyze chlorogenin and its derivatives. For instance, chlorogenone was reduced with sodium in ethanol to obtain chlorogenin, and catalytic reduction with hydrogen and platinum oxide catalyst yielded beta-chlorogenin. The study also involved the oxidation of digitogenin residues to produce chlorogenone, and the reduction of cholestanedione-3,6 with sodium and ethanol to obtain a diol for comparison. These experiments provided evidence supporting the proposed structure of chlorogenin and helped elucidate the configurations of its hydroxyl groups.

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