34209-69-3

Basic information

• Product Name: Trachelogenin
• Synonyms: Trachelogenin;(3S,4S)-4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone
• CAS NO: 34209-69-3
• Molecular Formula: C₂₁H₂₄O₇
• Molecular Weight: 388.41106
• Mol File: 34209-69-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 582.7°Cat760mmHg
• Flash Point: 203.8°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 2.02E-14mmHg at 25°C
• Refractive Index: 1.598
• CAS DataBase Reference: Trachelogenin(CAS DataBase Reference)
• NIST Chemistry Reference: Trachelogenin(34209-69-3)
• EPA Substance Registry System: Trachelogenin(34209-69-3)

Safety Data

• Hazardous Substances Data: 34209-69-3(Hazardous Substances Data)

Usage

General Description

Trachelogenin is a naturally occurring chemical compound found in various plants, including the bark of the Trachelospermum jasminoides plant. It belongs to a group of compounds known as cardenolides, which have been traditionally used in herbal medicine for their potential cardiac effects. Trachelogenin has been studied for its potential anti-cancer properties, specifically its ability to inhibit the growth of cancer cells. Additionally, it has been investigated for its potential use in the treatment of cardiovascular diseases, as it has shown to have positive effects on heart function and blood pressure regulation. Overall, trachelogenin shows promise as a therapeutic compound for various health conditions, although further research is needed to fully understand its mechanisms and potential applications.

InChI:InChI=1/C21H24O7/c1-25-17-7-5-13(9-19(17)27-3)8-15-12-28-20(23)21(15,24)11-14-4-6-16(22)18(10-14)26-2/h4-7,9-10,15,22,24H,8,11-12H2,1-3H3/t15-,21+/m1/s1

Upstream product

• 124887-01-0 (-)-O-benzyltrachelogenine 
• 106647-13-6 trachelogenin 4'-O-β-gentiobioside 
• 123251-05-8 (3R,4R)-3-[(3-methoxy-4-benzyloxyphenyl)methyl]-4-[(3,4-dimethoxyphenyl)methyl] dihydro-2-(3H)-furanone 
• 108102-77-8 (R)-4-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one 
• 33464-71-0 trachelogenin glucoside 

Downstream Products

• 74861-37-3 trachelogenin diacetate 
• 74861-44-2 5-hydroxytrachelogenin 
• 74861-38-4 5-acetoxytrachelogenin diacetate 
• 33464-73-2 (-)-O-methyltrachelogenine 

Relevant articles and documents

Lignan glucosides and serotonin phenylpropanoids from the seeds of Leuzea carthamoides

Two lignan glucosides, the known tracheloside and the new carthamoside, together with their two known aglycones, trachelogenin and (7E,8'S)-7,8- didehydroarctigenin (cf. carthamogenin), were isolated from the seeds of Leuzea carthamoides. Additional four phenyl-propanoid derivatives of tryptamine, the E and Z isomers of N-feruloylserotonin and N-isoferuloylserotonin, were also isolated and identified. Their structure determination and Identification were performed by spectroscopic, mainly NMR analysis.

TOTAL SYNTHESES OF (-)-TRACHELOGENIN, (-)-NORTRACHELOGENIN AND (+)-WIKSTROMOL

The title compounds were obtained by α-hydroxylation of the corresponding α,β-dibenzyl-γ-butyrolactones (lignans of synthetic origin), and were correlated to (+/-)-methyltrachelogenin 9 whose relative structure was definitely established by X-ray cristallography. (-)-Trachelogenin 1 and (-)-nortrachelogenin 12 thus have the (8S,8'S) absolute configuration, whereas (+)-nortrachelogenin 20 (or wikstromol) has the (8R,8'R) absolute configuration.