10308-13-1

Basic information

• Product Name: Vertine【alkaloid】
• Synonyms: (10α)-2'-Hydroxy-4'',5''-dimethoxylythran-12-one;Cryogenine【alkaloid】;Vertine;Vertine【alkaloid】
• CAS NO: 10308-13-1
• Molecular Formula: C₂₆H₂₉NO₅
• Molecular Weight: 435.51216
• Mol File: 10308-13-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Vertine【alkaloid】(CAS DataBase Reference)
• NIST Chemistry Reference: Vertine【alkaloid】(10308-13-1)
• EPA Substance Registry System: Vertine【alkaloid】(10308-13-1)

Safety Data

• Hazardous Substances Data: 10308-13-1(Hazardous Substances Data)

Usage

Description

This alkaloid has been isolated from Decodon verticillatus L. and forms colourless crystals from a mixture of MeOH and CHCl3. It has [α]D + 39° (c 0.95, CHCl3) and gives an ultraviolet spectrum with absorption maxima at 260 and 285 mJ.1. The acetyl derivative crystallizes from Et20 with m.p. 183-5°C; [α]D - 92.7° (c 0.96, CHCl3). Catalytic hydrogenation yields Decamine (q.v.).

References

Ferris., 1. Org. Chern., 27, 2985 (1962)

Upstream product

• 639458-43-8 (S)-2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 199942-74-0 (S)-2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 121169-17-3 3-iodo-4-(methoxymethoxy)benzaldehyde 
• 60032-63-5 4-hydroxy-3-iodo-benzaldehyde 
• 1007600-14-7 N-acetyl-L-leucine (S)-2-piperidineethanol 
• 1393603-59-2 (4S,9aS)-hexahydro-4-(2-(2'-tert-butyldimethylsiloxy-5'-vinylphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2yl-acrylate 
• 1393603-58-1 (4S,9aS)-hexahydro-4-(2-(2'-tert-butyldimethylsiloxy-5'-carboxaldehyphenyl)-4,5dimethoxy-phenyl)-1H-quinolizin-2yl-acrylate 
• 1393603-56-9 (4S,9aS)-hexahydro-4-(2-(2'-hydroxy-5'-carboxaldehyphenyl)-4,5-dimethoxy-phenyl)-1H-quinolizin-2yl-acrylate 
• 1393603-55-8 (4S,9aS)-hexahydro-4-(2-(2'-methoxymethoxy-5'-carboxaldehyphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2yl-acrylate 
• 1393603-54-7 (4S,9aS)-hexahydro-4-(2-(2'-methoxymethoxy-5'-carboxaldehyphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-ol 
• 1393603-53-6 (4S,9aS)-hexahydro-4-(2-(2'-methoxymethoxy-5'-methanolphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-ol 
• 1393603-52-5 (4S,9aS)-hexahydro-4-(2-(2'-methoxymethoxy-5'-carboxaldehyphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-one 
• 1393603-64-9 C₁₇H₂₂INO₃ 
• 1393603-61-6 C₁₇H₂₂INO₃ 

Downstream Products

• 76193-24-3 dihydro-13(S),17,22,23-tetramethoxylythran-11-one 
• 76193-27-6 12,13-dihydro-17,22,23-trimethoxy.13(S)-hydroxylythran-11-one 
• 28457-84-3 17,22,23-trimethoxylythran-11-one 
• 76193-25-4 12,13-dihydro-17-hydroxy-13(S),22,23-trimethoxylythran-11-one 

Relevant articles and documents

Asymmetric Total Synthesis of Biphenylquinolizidine Alkaloids 4″- O-Demethyllythridine and 14- epi-4″- O-Demethyllythridine

The first asymmetric total synthesis of new biphenylquinolizidine alkaloids 4″-O-demethyllythridine and 14-epi-4″-O-demethyllythridine isolated from Heimia salicifolia was accomplished. The key steps in the synthesis were a copper(I)-catalyzed asymmetric intramolecular aza-Michael reaction to build a chiral 4-arylquinolizidine unit and an intramolecular Suzuki-Miyaura cross-coupling reaction to construct a macrolactone ring comprising a biphenyl moiety.

ALKALOIDS OF HEIMIA MONTANA

The alkaloid composition of the little known Heimia species, H. montana has been determined.A new alkaloid, demethylvertine, has been isolated from this species and a close biogenetic correlation with other members of the genus has been established.Differences in alkaloid metabolism among the three species of Heimia have been demonstrated.