1358-76-5

Basic information

• Product Name: koumine
• Synonyms: koumine;(3R,7alpha,20alpha)-1,2,18,19-Tetradehydro-3,17-epoxy-7,20(2H,19H)cyclovobasan;7,20(2H,19H)-Cyclovobasan, 1,2,18,19-tetradehydro-3,17-epoxy-, (3R,7alpha,20alpha)-
• CAS NO: 1358-76-5
• Molecular Formula: C₂₀H₂₂N₂O
• Molecular Weight: 306.407
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Alkaloids
• Mol File: 1358-76-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 168℃
• Boiling Point: 436.5 °C at 760 mmHg
• Flash Point: 217.8 °C
• Appearance: /
• Density: 1.42
• Refractive Index: 1.763
• Storage Temp.: 2-8°C
• PKA: 8.67±0.40(Predicted)
• CAS DataBase Reference: koumine(CAS DataBase Reference)
• NIST Chemistry Reference: koumine(1358-76-5)
• EPA Substance Registry System: koumine(1358-76-5)

Safety Data

• Hazardous Substances Data: 1358-76-5(Hazardous Substances Data)

Usage

Description

Koumine, an alkaloid derived from Gelsemium elegans Benth, is a component of the Chinese drug 'Kou-wen.' It forms rhombic prisms from Me2 CO and has a specific optical rotation of [α]23D 265° (EtOH). Koumine also forms a crystalline hydrochloride with a melting point of 255°C (dec.) and a hydrobromide with a melting point of 269°C (dec.).

Uses

Used in Anti-Inflammatory Applications:
Koumine is used as an anti-inflammatory agent for attenuating lipopolysaccharide-stimulated inflammation in RAW264.7 macrophages. This application is particularly relevant in the context of inflammatory diseases and conditions where reducing inflammation is a key therapeutic goal.
Used in Pharmaceutical Industry:
Koumine is used as a pharmaceutical compound for its potential therapeutic applications. As an alkaloid with anti-inflammatory properties, it may be further researched and developed for use in the treatment of various diseases and conditions where inflammation plays a significant role.
Used in Research and Development:
Koumine is used as a research compound for studying its chemical properties, structural characteristics, and potential applications in various fields, including pharmaceuticals, biotechnology, and material science. Its unique properties and structural features make it an interesting subject for scientific investigation and potential development of new drugs or materials.

References

Chou, Pak, Hou., Chin. 1. Physiol., 5, 345 (1931) Chou, Wang, Chen., ibid, 8,40 (1934) Chi, Kao, Huang., 1. Amer. Chem. Soc., 60, 1723 (1938)

InChI:InChI=1/C20H22N2O/c1-3-19-11-22(2)16-9-20(19)13-6-4-5-7-15(13)21-18(20)17-8-14(19)12(16)10-23-17/h3-7,12,14,16-17H,1,8-11H2,2H3/t12?,14-,16?,17-,19+,20?/m1/s1

Upstream product

• 119184-21-3 (1R,3S)-(+)-methyl 2,9-dibenzyl-3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate 
• 119184-23-5 (6R,10R)-(+)-methyl 5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole-8-carboxylate 
• 119184-32-6 (E)-(+)-(16S)-12-benzyl-10-desoxy-18-oxo-18-methoxysarpagine 
• 119184-32-6 (Z)-(+)-(16S)-12-benzyl-10-desoxy-18-oxo-18-methoxysarpagine 
• 119184-33-7 (E)-(+)-(16S)-12-benzyl-10-desoxy-18-hydroxysarpagine 
• 119184-33-7 (Z)-(+)-(16S)-12-benzyl-10-desoxy-18-hydroxysarpagine 
• 119184-29-1 (E)-(2S,6R,12bR)-(+)-methyl 12-benzyl-13-oxo-1,2,3,4,5,6,7,12,12b-octahydro-2,6-methanoindolo<2,3-a>quinolizine-3-ethylidenoate 
• 119184-29-1 (Z)-(2S,6R,12bR)-(+)-methyl 12-benzyl-13-oxo-1,2,3,4,5,6,7,12,12b-octahydro-2,6-methanoindolo<2,3-a>quinolizine-3-ethylidenoate 
• 128466-35-3 (+)-18-hydroxy-N-carbomethoxytaberpsychine 
• 128466-35-3 C₂₁H₂₄N₂O₄ 
• 119184-34-8 (E)-(+)-(16S)-10-desoxy-18-hydroxysarpagine 
• 119184-34-8 (+)-18-hydroxykoumidine 
• 129784-64-1 N¹-benzyl-(L)-tryptophan methyl ester 

Downstream Products

• 113900-75-7 koumine N-oxide 
• 113900-75-7 C₂₀H₂₂N₂O₂ 

Related news

Development and in-house validation of a sensitive LC–MS/MS method for simultaneous quantification of gelsemine, koumine (cas 1358-76-5) and humantenmine in porcine plasma09/02/2019

Three monomers of G. elegans indole alkaloids (gelsemine, koumine and humantenmine) were simultaneously detected in porcine plasma for the first time with the development and validation of a sensitive and reliable LC-ESI-MS/MS method. Using a gradient mobile phase at a constant flow rate of 0.2 ...detailed

Relevant articles and documents

Asymmetric Total Synthesis of Sarpagine-Related Indole Alkaloids Hydroxygardnerine, Hydroxygardnutine, Gardnerine, (E)-16-epi-Normacusine B, and Koumine

Sarpagine-related indole alkaloids (-)-hydroxygardnerine, (+)-hydroxygardnutine, (-)-gardnerine, (+)-(E)-16-epi-normacusine B, and (-)-koumine were divergently synthesized via a common intermediate possessing a piperidine ring with an exocyclic (E)-ethylidene side chain, which was constructed by a gold(I)-catalyzed 6-exo-dig cyclization strategy.

BIOMIMETIC SYNTHESIS OF KOUMINE BY THE PALLADIUM-CATALYZED INTRAMOLECULAR COUPLING REACTION OF 18-HYDROXYTABERPSYCHINE (18-HYDROXYANHYDROVOBASINEDIOL)

A principal Gelsemium alkaloid, koumine (1) was synthesized from 18-hydroxygardnutine (3) via the demethoxylation from the indole ring and the palladium-catalyzed cyclization between C7 and C20 of the hypothetical biogenetic intermediate, 18-hydroxytaberpsychine (2).