28115-68-6

Basic information

• Product Name: pluviatolide
• Synonyms: pluviatolide;(3R,4R)-4-[(1,3-Benzodioxol-5-yl)methyl]-4,5-dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]furan-2(3H)-one;3α-(4-Hydroxy-3-methoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one;4,5-Dihydro-4β-[(1,3-benzodioxole-5-yl)methyl]-3α-(4-hydroxy-3-methoxybenzyl)furan-2(3H)-one;trans-Pluviatolide
• CAS NO: 28115-68-6
• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.3692
• Mol File: 28115-68-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 569.5°Cat760mmHg
• Flash Point: 205.4°C
• Appearance: /
• Density: 1.337g/cm³
• Vapor Pressure: 1.43E-13mmHg at 25°C
• Refractive Index: 1.616
• CAS DataBase Reference: pluviatolide(CAS DataBase Reference)
• NIST Chemistry Reference: pluviatolide(28115-68-6)
• EPA Substance Registry System: pluviatolide(28115-68-6)

Safety Data

• Hazardous Substances Data: 28115-68-6(Hazardous Substances Data)

Usage

Description

Pluviatolide is a lignan that has been found in B. chinense and has diverse biological activities, including antioxidant, enzyme inhibitory, and antispasmodic properties. It scavenges ABTS and 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals in cell-free assays (IC50s = 23.2 and 88.5 μM, respectively). Pluviatolide inhibits matrix metalloproteinase-7 (MMP-7) with an IC50 value of 260 μM. It decreases contractions induced by acetylcholine in isolated guinea pig ileum when used at concentrations of 30 and 100 μM.

Definition

ChEBI: A butan-4-olide that is dihydrofuran-2(3H)-one which is substituted by a vanillyl group at position 3 and by a 3,4-methylenedioxybenzyl group at position 4 (the R,R stereoisomer).

InChI:InChI=1/C20H20O6/c1-23-18-8-13(2-4-16(18)21)7-15-14(10-24-20(15)22)6-12-3-5-17-19(9-12)26-11-25-17/h2-5,8-9,14-15,21H,6-7,10-11H2,1H3/t14-,15+/m0/s1

Upstream product

• 120-57-0 piperonal 
• 96548-65-1 3-(benzo[d][1,3]dioxol-5-ylmethyl)-4-methoxy-4-oxobutanoic acid 
• 84736-28-7 (methylenedioxy-3,4 benzylidene) α-hemisuccinate de methyle 
• 80483-34-7 4-(1,3-benzodioxol-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one 
• 84755-36-2 2-(4-benzyloxy-3-methyoxybenzyl)-3-(3,4-methylenedioxybenzyl)-γ-butyrolactone 
• 158665-03-3 (3R,4R,5R)-4-<1,3-Benzodioxol-5-ylbis(phenylthio)methyl>-3-<(4-(benzyloxy)-3-methoxyphenyl)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone 
• 6302-93-8 5-[Bis(phenylsulfanyl)methyl]-1,3-benzodioxole 
• 33693-48-0 4-benzyloxy-3-methoxybenzyl alcohol 
• 72724-00-6 1-(benzyloxy)-4-(bromomethyl)-2-methoxybenzene 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 158705-72-7 (3R,4R)-4-(1,3-Benzodioxol-5-ylmethyl)-3-<(4-(benzyloxy)-3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 

Relevant articles and documents

Design and synthesis of novel arctigenin analogues for the amelioration of metabolic disorders

Analogues of the natural product (-)-arctigenin, an activator of adenosine monophosphate activated protein kinase, were prepared in order to evaluate their effects on 2-deoxyglucose uptake in L6 myotubes and possible use in ameliorating metabolic disorders. Racemic arctigenin 2a was found to display a similar uptake enhancement as does (-)-arctigenin. As a result, the SAR study was conducted utilizing racemic compounds. The structure-activity relationship study led to the discovery of key substitution patterns on the lactone motif that govern 2-deoxyglucose uptake activities. The results show that replacement of the para-hydroxyl group of the C-2 benzyl moiety of arctigenin by Cl has a pronounced effect on uptake activity. Specifically, analogue 2p, which contains the p-Cl substituent, stimulates glucose uptake and fatty acid oxidation in L6 myotubes.

Synthesis of (±)-pluviatolide and (±)-isopluviatolide

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