5523-49-9

Basic information

• Product Name: (15β,16E)-16,17,20,21-Tetradehydro-16-(hydroxymethyl)-18,19-secoyohimban-19-oic acid methyl ester
• Synonyms: (15β,16E)-16,17,20,21-Tetradehydro-16-(hydroxymethyl)-18,19-secoyohimban-19-oic acid methyl ester;Dihydrovallesiachotamine
• CAS NO: 5523-49-9
• Molecular Formula: C21H24N2O3
• Molecular Weight: 352.42686
• Mol File: 5523-49-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 563.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1.29±0.1 g/cm3(Predicted)
• PKA: 14.63±0.10(Predicted)
• CAS DataBase Reference: (15β,16E)-16,17,20,21-Tetradehydro-16-(hydroxymethyl)-18,19-secoyohimban-19-oic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (15β,16E)-16,17,20,21-Tetradehydro-16-(hydroxymethyl)-18,19-secoyohimban-19-oic acid methyl ester(5523-49-9)
• EPA Substance Registry System: (15β,16E)-16,17,20,21-Tetradehydro-16-(hydroxymethyl)-18,19-secoyohimban-19-oic acid methyl ester(5523-49-9)

Safety Data

• Hazardous Substances Data: 5523-49-9(Hazardous Substances Data)

Upstream product

• 114184-86-0 Methyl <12bS-(2α,12bα)>-1,2,6,7,12,12b-hexahydro-2-<(E/Z)-1-(methoxycarbonyl)prop-1-enyl>indolo<2,3-a>quinolizine-3-carboxylate 
• 10052-60-5 N-<β-Indolyl-3-ethyl>-3-t-butyloxycarbonylpyridiniumbromid 
• 135866-36-3 tert-Butyl <12bS-(2α,12bα)>-1,2,6,7,12,12b-hexahydro-2-<(E/Z)-1-(methoxycarbonyl)prop-1-enyl>indolo<2,3-a>quinolizine-3-carboxylate 
• 135887-52-4 tert-Butyl <12bS-(2α,12bα)>-1,2,6,7,12,12b-hexahydro-2-<(1R,2R)-2-hydroxy-1-(methoxycarbonyl)propyl>indolo<2,3-a>quinolizine-3-carboxylate 
• 135887-53-5 tert-Butyl <12bS-(2α,12bα)>-2-<(1R,2R)-2-acetoxy-1-(methoxycarbonyl)propyl>-1,2,6,7,12,12b-hexahydroindolo<2,3-a>quinolizine-3-carboxylate 
• 135887-51-3 tert-Butyl <12bS-(2α,12bα)>-2-<(5R)-2-tert-butyl-4-methyl-6-oxo-1,3-dioxan-5-yl>-1,2,6,7,12,12b-hexahydroindolo<2,3-a>quinolizine-3-carboxylate 
• 5523-37-5 (+/-)-vallesiachotaminen 
• 93862-67-0 ethyl vallesiachotamate 
• 4695-86-7 3-methoxycarbonyl-1-[2-(3-indolyl)ethyl]pyridinium bromide 
• 114197-78-3 ethyl 18,19-didehydro-19,20-dihydrovallesiachotamate 
• 114184-92-8 ethyl 18,19-didehydro-19,20-dihydro-18,18-bis(ethylthio)vallesiachotamate 
• 93862-65-8 (2R,12bS)-2-(Ethoxycarbonyl-trimethylsilanyl-methyl)-1,2,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizine-3-carboxylic acid methyl ester 
• 5523-37-5 (E)-vallesiachotamine 
• 19351-63-4 secologanin 

Downstream Products

• 5523-37-5 vallesiachotamine 
• 5552-25-0 tetrahydrovallesiachotamine 
• 5552-25-0 tetrahydrovallesiachotamine 
• 5523-37-5 (+/-)-vallesiachotaminen 
• 5523-37-5 Isovallesiachotamin 
• 5523-37-5 Vallesiachotamin 
• 5523-37-5 (E)-vallesiachotamine 
• 34384-71-9 isovallesiachotamine 

Relevant articles and documents

Bacterial biotransformation of 3α(S)-strictosidine to the monoterpenoid indole alkaloid vallesiachotamine

3α(S)-Strictosidine produced by heterologously expressed strictosidme synthase from Rauwolfia serpentina was used in biotransformation experiments with a series of 22 bacterial strains.All strains tested were found to deglucosylate and rearrange the alkaloid to vallesiachotamine, thereby providing an example of how gene technology and microbial biotransformation can be combined for the biotechnological production of alkaloidal natural products. - Keywords: Rauwolfia serpentina, Spodoptera frugiperda, baculovirus, strictosidine synthase, vallesiachotamine.

Addition von chiralen Nucleophilen an Pyridiniumverbindungen; Totalsynthese von (-)-Isovallesiachotamin und (+)-Vallesiachotamin

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Totalsynthese des Indolalkaloids Vallesiachotamin

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