6879-01-2

Basic information

• Product Name: tuberostemonine
• Synonyms: tuberostemonine;(7aR,8aβ,11aβ,11bα,11cβ)-2β-[(2S,4S)-Tetrahydro-4-methyl-5-oxofuran-2-yl]-8β-ethyltetradecahydro-11β-methylfuro[2,3-h]pyrrolo[3,2,1-jk][1]benzoazepine-10-one;2β-[(2S,4S)-Tetrahydro-4-methyl-5-oxofuran-2-yl]stenine;Nsc366235;TUBERSTEMONINE(P);TuberosteMonin;Tuberostemonine, 98%, from Stemona tuberosa L.
• CAS NO: 6879-01-2
• Molecular Formula: C22H33NO4
• Molecular Weight: 375.506
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 6879-01-2.mol

Chemical Properties

• Melting Point: 86～88℃
• Boiling Point: 554.2 °C at 760 mmHg
• Flash Point: 289 °C
• Appearance: /
• Density: 1.19 g/cm³
• Vapor Pressure: 2.52E-12mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: 2-8°C(protect from light)
• PKA: 8.90±0.70(Predicted)
• CAS DataBase Reference: tuberostemonine(CAS DataBase Reference)
• NIST Chemistry Reference: tuberostemonine(6879-01-2)
• EPA Substance Registry System: tuberostemonine(6879-01-2)

Safety Data

• Hazardous Substances Data: 6879-01-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
Tuberostemonine is used as a therapeutic agent for treating cigarette smoke-induced acute lung inflammation. Its presence as one of the major components of Radix Stemonae contributes to its medicinal value, making it a promising candidate for further research and development in the pharmaceutical industry.
Used in Traditional Medicine:
As a component of Radix Stemonae, tuberostemonine is utilized in traditional medicine for its various therapeutic effects. Its presence in the plant material has been recognized for centuries, and it continues to be an essential part of herbal remedies and treatments.
Used in Chemical Research:
Tuberostemonine's unique chemical properties and reactivity make it an interesting subject for chemical research. Its various salts, melting points, and reactions with different reagents provide valuable information for understanding its structure and potential applications in the field of chemistry.
Used in Drug Development:
The therapeutic effects of tuberostemonine against cigarette smoke-induced acute lung inflammation suggest its potential use in drug development. Further research and development could lead to the creation of new drugs or therapies targeting lung inflammation and related conditions, benefiting patients suffering from respiratory issues.

References

Kondo, Suzuki, Satomi.,J. Pharrn. Soc., Japan, 54,96 (1934) Kondo, Suzuki, Satomi., ibid, 59, 177 (1939) Kondo, Suzuki, Satomi., ibid, 60, 149 (1940) Kondo, Suzuki, Satomi., ibid, 61, 111 (1941) Kaneko., Ann. Rep. ITSUU Lab. (Tokyo), 11,45 (1960) Gotz, Bogri, Gray., Tetrahedron Lett., 707 (1961) Edwards, Feniak, Handa., Can. J. Chern., 40,455,2416 (1962) Crystal structure: Harada et ai., Chern. Cornrnun., 460 (1967)

InChI:InChI=1/C22H33NO4/c1-4-13-14-7-5-6-8-23-16(17-9-11(2)21(24)26-17)10-15(19(14)23)18-12(3)22(25)27-20(13)18/h11-20H,4-10H2,1-3H3

Upstream product

• 486421-60-7 8-des-ethyl-(8S)-phenylseleno-(-)-tuberostemonine 
• 486421-61-8 C₂₂H₃₁NO₄ 
• 486421-59-4 N,N-dimethyl-2R,S-[2S-(4S-methyl-5-oxotetrahydrofuran-2-yl)-1,2S,4,5,6,7,7aS,10,10aR,10bS-decahydroazepino[3,2,1-hi]indol-10-yl]propionamide 
• 486421-52-7 (2S,3¹S,7aS,10aR)-methyl 8-oxo-1,2,3¹,4,7,7a,8,10a-octahydroazepino[3,2,1-hi]indole-2-carboxylate 
• 828921-50-2 (-)-8-des-ethyl,(8S)-phenylseleno-13-epituberostemonine 
• 828921-47-7 N,N-dimethyl-2R,S-[2S-(4S-methyl-5-oxotetrahydrofuran-2-yl)-(1,2S,4,5,6,7,7aS,8S,10aR,10bS)-decahydroazepino[3,2,1-hi]indol-10-yl]propionamide 
• 486421-66-3 (2S,7aS,10aS,10bR)-8-Oxo-10-phenylsulfanyl-1,2,4,7,7a,8,9,10,10a,10b-decahydro-azepino[3,2,1-hi]indole-2-carboxylic acid methyl ester 
• 486421-62-9 8-des-ethyl-(8S)-allyl-(-)-tuberostemonine 
• 486421-47-0 6-(tert-butyldimethylsilanyloxy)-(2S,3,3aR,6S,7,7aR)-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 486421-49-2 6-(tert-butyldimethylsilanyloxy)-1-(3-phenylallyl)-(2S,3,3aR,6S,7,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester 
• 486421-55-0 8-(tert-butyldimethylsilanyloxy)-(1,2S,4,7,7aS,8,10aR,10bS)-decahydroazepino[3,2,1-hi]indole-2-carboxylic acid methoxymethyl amide 
• 486421-54-9 8-(tert-butyldimethylsilanyloxy)-(1,2S,4,7,7aS,8,10aR,10bS)-decahydroazepino[3,2,1-hi]indole-2-carboxylic acid methyl ester 
• 486421-51-6 7-allyl-1-(3-phenylallyl)-6-oxo-(2S,3,3aR,6,7,7aR)-hexahydro-1H-indole-2-carboxylic acid methyl ester 
• 486421-58-3 (5S)-(8-hydroxy-(1,2S,4,5,6,7,7aS,8S,10aR,10bS)-decahydroazepino[3,2,1-hi]indol-2-yl)-(3S)-methyldihydrofuran-2-one 

Downstream Products

• 20675-62-1 (3aS,12aS)-5c-ethyl-4t-hydroxy-3t-methyl-11c-((2S)-4c-methyl-5-oxo-tetrahydro-[2r]furyl)-(3ar)-3,3a,4,5,6,7,8,9,11,12-decahydro-azepino[3,2,1-hi]furo[2,3-d]indole 
• 106861-40-9 didehydrotuberostemonine 

Relevant articles and documents

Asymmetric total syntheses of tuberostemonine, didehydrotuberostemonine, and 13-epituberostemonine

Detailed experimental approaches toward the pentacyclic Stemona alkaloids tuberostemonine and didehydrotuberostemonine and the close analogue 13-epituberostemonine are described. The syntheses originate with a hydroindolinone derivative that can be obtain

Total synthesis of (-)-tuberostemonine

The first total synthesis of the complex pentacyclic Stemona alkaloid tuberostemonine was accomplished in 24 steps and in 1.4% overall yield from a hydroindole intermediate which is readily obtained in three steps from Cbz-L-tyrosine. An innovative synthe