545-16-4

Basic information

• Product Name: (3α)-Tazettine
• Synonyms: (3R,4aβ,6aα,13bS)-4,4a,5,6-Tetrahydro-3-methoxy-5-methyl-8H-[1,3]dioxolo[6,7][2]benzopyrano[3,4-c]indol-6a(3H)-ol;(3α)-Tazettine;3-Epitazettine;Criwelline
• CAS NO: 545-16-4
• Molecular Formula: C₁₈H₂₁NO₅
• Molecular Weight: 331.36304
• Mol File: 545-16-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 494.2°C at 760 mmHg
• Flash Point: 252.7°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 1.39E-10mmHg at 25°C
• Refractive Index: 1.66
• CAS DataBase Reference: (3α)-Tazettine(CAS DataBase Reference)
• NIST Chemistry Reference: (3α)-Tazettine(545-16-4)
• EPA Substance Registry System: (3α)-Tazettine(545-16-4)

Safety Data

• Hazardous Substances Data: 545-16-4(Hazardous Substances Data)

Usage

General Description

(3α)-Tazettine is a naturally occurring alkaloid found in various plant species, including Daffodils and Narcissus. This chemical compound belongs to the group of Amaryllidaceae alkaloids and is known for its potential biological activities. It has been studied for its anti-cancer properties, with research suggesting that it may have the ability to inhibit the growth of cancer cells. Additionally, (3α)-Tazettine has shown potential as an acetylcholinesterase inhibitor, making it a possible candidate for the treatment of neurodegenerative diseases such as Alzheimer's. Further research is ongoing to explore the pharmacological and therapeutic potential of this compound.

InChI:InChI=1/C18H21NO5/c1-19-9-18(20)17(4-3-12(21-2)6-16(17)19)13-7-15-14(22-10-23-15)5-11(13)8-24-18/h3-5,7,12,16,20H,6,8-10H2,1-2H3/t12-,16-,17-,18+/m0/s1

Upstream product

• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 466-73-9 6-epihaemanthidine 
• 67-56-1 methanol 
• 74-88-4 methyl iodide 
• 17245-16-8 pretazettine 
• 17322-84-8 pretazettine 
• 7732-18-5 water 
• 17245-16-8 (4aS)-3t-methoxy-5-methyl-(4ar,6ac,13btC¹)-3,4,4a,5,6,6a-hexahydro-8H-[1,3]dioxolo[4',5':6,7]isochromeno[3,4-c]indol-8ξ-ol 
• 60944-28-7 3t-acetoxy-3a-benzo[1,3]dioxol-5-yl-1-formyl-6t-methoxy-(3ar,7ac)-2,3,3a,6,7,7a-hexahydro-indole 
• 60944-23-2 3t-acetoxy-3a-benzo[1,3]dioxol-5-yl-6t-methoxy-(3ar,7ac)-1,3,3a,6,7,7a-hexahydro-indol-2-one 
• 60944-24-3 3a-benzo[1,3]dioxol-5-yl-5c-bromo-6t-methoxy-(3ar,7ac)-hexahydro-indole-2,3-dione 
• 35598-54-0 3a-benzo[1,3]dioxol-5-yl-(3ar,7ac)-3a,4,7,7a-tetrahydro-indole-2,3-dione 
• 60944-19-6 3t-acetoxy-3a-benzo[1,3]dioxol-5-yl-(3ar,7ac)-1,3,3a,4,7,7a-hexahydro-indol-2-one 

Downstream Products

• 65367-81-9 N-Methyl-8,9-methylenedioxy-phenantridinium chloride 
• 86046-50-6 4,5-methylenedioxy-4'-hydroxy-2-aldehyde[1,1'-biphenyl] 
• 4371-22-6 (6-phenyl-benzo[1,3]dioxol-5-yl)-methanol 
• 466-66-0 tazettadiol 
• 144-62-7 oxalic acid 
• 40141-98-8 N-methylcrinasiadine 
• 4371-22-6 6-phenylpiperonylalcohol 
• 73060-68-1 3α-hydroxy-3aβ-(2-hydroxymethyl-4,5-methylenedioxyphenyl)-6β-methoxy-N-methyl-2,3,6,7-tetrahydro-7aH-indole 
• 124339-69-1 (4aS)-6a-hydroxy-3t-methoxy-5,5-dimethyl-(4ar,6at,13btC¹)-3,4,4a,5,6,6a-hexahydro-8H-[1,3]dioxolo[4',5':6,7]isochromeno[3,4-c]indolium; picrate 

Relevant articles and documents

Total syntheses of (-)-haemanthidine, (+)-pretazettine, and (+)-tazettine

(matrix presented) Haemanthidine Pretazettine Tazettine The total syntheses of the amaryllidaceae alkaloids haemanthidine, pretazettine, and tazettine as optically pure enantiomers are reported. Using D-mannose as the starting material, the critical relat

ALKALOIDS FROM NARCISSUS CONFUSUS

Key Word Index - Narcissus confusus; Amaryllidaceae; haemanthamine; galanthamine; N-formylgalanthamine; pretazettine; two-dimensional NMR spectra.We report the isolation of haemanthamine, galanthamine, pretazettine and the new alkaloid N-formylgalanthamine from Narcissus confusus plants.Structural determination was carried out by spectroscopic analyses and application of two-dimensional NMR spectroscopy.

Transformation of tazettine to pretazettine

-