34444-37-6

Basic information

• Product Name: (-)-NORTRACHELOGENIN
• Synonyms: (-)-NORTRACHELOGENIN;(-)-Wikstromol;(3S)-4,5-Dihydro-4β-(4-hydroxy-3-methoxybenzyl)-3-(4-hydroxy-3-methoxybenzyl)-3β-hydroxyfuran-2(3H)-one;(3S,4S)-4,5-Dihydro-3,4-bis(4-hydroxy-3-methoxybenzyl)-3-hydroxyfuran-2(3H)-one;(3S,4S)-4,5-Dihydro-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]furan-2(3H)-one;Pinopalustrin;2(3H)-Furanone,dihydro-3-hydroxy-3,4-bis((4-hydroxy-3-methoxyphenyl)methyl)-,(3R-cis);8'-(R)-4,4',8-Trihydroxy-3,3'-dimethoxylignanolide
• CAS NO: 34444-37-6
• Molecular Formula: C₂₀H₂₂O₇
• Molecular Weight: 374.38
• EINECS: 200-158-5
• Mol File: 34444-37-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 609.1 °C at 760 mmHg
• Flash Point: 217.3 °C
• Appearance: /
• Density: 1.37 g/cm³
• Vapor Pressure: 1.08E-15mmHg at 25°C
• Refractive Index: 1.629
• CAS DataBase Reference: (-)-NORTRACHELOGENIN(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-NORTRACHELOGENIN(34444-37-6)
• EPA Substance Registry System: (-)-NORTRACHELOGENIN(34444-37-6)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• Hazardous Substances Data: 34444-37-6(Hazardous Substances Data)

Usage

General Description

(-)-NORTRACHELOGENIN is a naturally occurring phytochemical compound found in various plants, including the seeds of celery and parsley. It belongs to the class of compounds known as furanocoumarins, which are known for their antifungal and antimicrobial properties. Nortrachelogenin has been investigated for its potential therapeutic benefits, including its potential use in the treatment of cancer and infectious diseases. Studies have also demonstrated its ability to inhibit certain cytochrome P450 enzymes, which are involved in drug metabolism. Additionally, (-)-nortrachelogenin has been found to exhibit anti-inflammatory, antioxidant, and anti-osteoporotic properties, making it a compound of interest for further research and potential pharmaceutical development.

InChI:InChI=1/C20H22O7/c1-25-17-8-12(3-5-15(17)21)7-14-11-27-19(23)20(14,24)10-13-4-6-16(22)18(9-13)26-2/h3-6,8-9,14,21-22,24H,7,10-11H2,1-2H3

Upstream product

• 124988-56-3 (2S,3S)-2,3-bis(4-benzyloxy-3-methoxybenzyl)-2-hydroxy-4-butanolide 
• 72724-00-6 1-(benzyloxy)-4-(bromomethyl)-2-methoxybenzene 
• 111266-03-6 (R)-(+)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone 
• 111194-07-1 (3R,4R)-3,4-bis(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one 
• 336101-54-3 (2R,3S)-2-(4-Benzyloxy-3-methoxy-benzyl)-3-hydroxy-succinic acid 
• 336101-52-1 (2R,3S)-2-[4-(benzyloxy)-3-methoxybenzyl]-3-hydroxybutanedioic acid diisopropyl ester 
• 336101-58-7 (R)-3-(4-Benzyloxy-3-methoxy-phenyl)-2-((2S,4S)-2-tert-butyl-5-oxo-[1,3]dioxolan-4-yl)-propionic acid 
• 336101-59-8 (2R,2'S,4'S)-2-{4-[4-(benzyloxy)-3-methoxybenzyl]-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-yl}-3-[4'-(benzyloxy)-3'-methoxyphenyl]propanoic acid 
• 116185-15-0 dihydro-3-hydroxy-3,4-bis<<3-methoxy-4-(phenylmethoxy)phenyl>methyl>-2,(3H)-furanone 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 1135-23-5 3-(4-hydroxy-3-methoxyphenyl)propionic acid 
• 30034-49-2 β-(4-benzyloxy-3-methoxyphenyl)propionic acid 
• 116185-12-7 2,3-bis<<3-methoxy-4-(phenylmethoxy)phenyl>methyl>-butanedioic acid 
• 116185-11-6 benzyl 3-[4-(benzyloxy)-3-methoxyphenyl]propanoate 

Downstream Products

• 33464-73-2 (-)-O-methyltrachelogenine 
• 146196-54-5 (-)-O-dimethyltrachelogenine 
• 58139-12-1 7-hydroxysecoisolariciresinol 
• 33464-73-2 3,4-bis<(3,4-dimethoxyphenyl)methyl>dihydro-3-hydroxy-2(3H)-furanone 
• 33464-73-2 3,4-bis<(3,4-dimethoxyphenyl)methyl>dihydro-3-hydroxy-2(3H)-furanone 

Relevant articles and documents

Radical and superoxide scavenging activities of matairesinol and oxidized matairesinol

The radical and superoxide scavenging activities of oxidized matairesinols were examined. It could be assumed that the free benzylic position was important for higher radical scavenging activity. The different level of activity was observed between 7′-oxomatairesinol (Mat 2) and 7-oxomatairesinol (Mat 3). The activity of 8-hydroxymatairesinol was lower than that of matairesinol (Mat 1). The superoxide scavenging activity of the oxidized matairesinols was also demonstrated for the first time. It is assumed that the pKa value of phenol in the oxidized matairesinols affected this activity.

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Racemic and optically active α,β-dibenzyl-γ-butyrolactones (of synthetic origin) were hydroxylated in the α position with respect to the carbonyl group, using oxygen in the presence of LHDS. This led to (-)-trachelogenin 1, (-)-nortrachelogenin 2 and (+)-

Total Synthesis of (+/-)-Wikstromol

The antineoplastic prototype lignan natural product wikstromol was synthesized in racemic form by a straightforward sequence involving, as its key transformations,oxidative coupling of a carboxylic acid dianion,generation and stereoselective oxidation of a potassium enolate,and a deprotection step.The overall yield for nine steps is 29percent.Depending on the choice of oxidants for the enolate,considerable modification in the ratio of stereoisomeric products is possible.