(3beta,5alpha,12beta,13beta,22S,23R)-3-hydroxy-5,6,12,13-tetrahydro-17,23-epoxyveratraman-11-one

Base Information

• Chemical Name: (3beta,5alpha,12beta,13beta,22S,23R)-3-hydroxy-5,6,12,13-tetrahydro-17,23-epoxyveratraman-11-one
• CAS No.: 24508-94-9
• Molecular Formula: C27H43 N O3
• Molecular Weight: 429.6352
• Mol file: 24508-94-9.mol

Synonyms:Jervine, 5a,6,12b,13a-tetrahydro- (8CI); Veratraman-11-one,17,23-epoxy-5,6,12,13-tetrahydro-3-hydroxy-, (3b,5a,12b,13b,23b)-; 5a,6,12b,13a-Tetrahydrojervine; Tetrahydrojervine

Chemical Property of (3beta,5alpha,12beta,13beta,22S,23R)-3-hydroxy-5,6,12,13-tetrahydro-17,23-epoxyveratraman-11-one

Chemical Property:

• Vapor Pressure: 4.31E-15mmHg at 25°C
• Boiling Point: 564.5°Cat760mmHg
• Flash Point: 295.2°C
• Density: 1.15g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: (3beta,5alpha,12beta,13beta,22S,23R)-3-hydroxy-5,6,12,13-tetrahydro-17,23-epoxyveratraman-11-one, also known as Jervine or Tetrahydrojervine, is a steroidal alkaloid derived from plants of the *Veratrum* genus. It is characterized by a complex tetracyclic structure with hydroxyl and epoxy functional groups, contributing to its biological activity. (3beta,5alpha,12beta,13beta,22S,23R)-3-hydroxy-5,6,12,13-tetrahydro-17,23-epoxyveratraman-11-one has been studied for its potential teratogenic effects, particularly in disrupting embryonic development, as well as its interactions with cellular signaling pathways such as the Hedgehog pathway. Its structural features and stereochemistry are critical for its pharmacological properties, making it a subject of interest in toxicology and medicinal chemistry research.

Technology Process of (3beta,5alpha,12beta,13beta,22S,23R)-3-hydroxy-5,6,12,13-tetrahydro-17,23-epoxyveratraman-11-one

There total 6 articles about (3beta,5alpha,12beta,13beta,22S,23R)-3-hydroxy-5,6,12,13-tetrahydro-17,23-epoxyveratraman-11-one 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:

(22Ξ,23S)-17,23-epoxy-(5β,17αH)-veratrane-3,11-dione (14425-18-4,14425-27-5) → 22,27-Imino-17,23-oxido-5β-jervan-3α-ol-11-on (14425-29-7,24508-94-9)

Guidance literature:

With potassium hydroxide; hydrogen; platinum; In ethanol; for 4h; Ambient temperature;

DOI:10.1016/S0040-4020(01)82558-8

Reference yield:

→ 5α,12β,13αH-Tetrahydrojervin (24508-94-9)

Guidance literature:

With acetic acid; platinum; Hydrogenation;

DOI:10.1021/ja01651a005

Reference yield:

(22Ξ,23S)-17,23-epoxy-11α-hydroxy-(5β,17αH)-veratran-3-one (14425-17-3,14425-25-3) → 22,27-Imino-17,23-oxido-5β-jervan-3α-ol-11-on (14425-29-7,24508-94-9)

Guidance literature:

Multi-step reaction with 2 steps

1: CrO₃, H₂SO₄ / dimethylformamide / 48 h / Ambient temperature

2: H₂, KOH / Pt / ethanol / 4 h / Ambient temperature

With chromium(VI) oxide; potassium hydroxide; sulfuric acid; hydrogen; platinum; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)82558-8

upstream raw materials:

jervine

(22Ξ,23S)-17,23-epoxy-(5β,17αH)-veratrane-3,11-dione

(22Ξ,23S)-17,23-epoxy-11α-hydroxy-(5β,17αH)-veratran-3-one

(22Ξ,23S)-17,23-epoxy-(17αH)-veratr-5-ene-3β,11α-diol