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(+)-PINORESINOL

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(+)-PINORESINOL Basic information

Product Name:
(+)-PINORESINOL
Synonyms:
  • (+)-PINORESINOL
  • (-)-4,4'-[[(3aα,6aα)-Tetrahydro-1H,3H-furo[3,4-c]furan]-1α,4α-diyl]bis(2-methoxyphenol)
  • (3aS,6aS)-3a,4,6,6a-Tetrahydro-3β,6β-bis(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan
  • (3R,3aβ,6aβ)-3β,6β-Bis(3-methoxy-4-hydroxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan
  • 2-Methoxy-4-[(1R)-4α-(3-methoxy-4-hydroxyphenyl)-3aα,4,6,6aα-tetrahydro-1H,3H-furo[3,4-c]furan-1α-yl]phenol
  • 4,4'-[[(3aα,6aα)-Tetrahydro-1H,3H-furo[3,4-c]furan]-1α,4α-diyl]bis(2-methoxyphenol)
  • (1S)-1β,4β-Bis(4-hydroxy-3-methoxyphenyl)-3aβ,4,6,6aβ-tetrahydro-1H,3H-furo[3,4-c]furan
  • (1β,5β)-2β,6β-Bis(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclo[3.3.0]octane
CAS:
487-36-5
MF:
C20H22O6
MW:
358.39
Product Categories:
  • Miscellaneous Natural Products
Mol File:
487-36-5.mol
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(+)-PINORESINOL Chemical Properties

Melting point:
112 °C
Boiling point:
556.5±50.0 °C(Predicted)
Density 
1.385 g/cm3
storage temp. 
Sealed in dry,Room Temperature
solubility 
DMSO: ≥6mg/mL
pka
9.54±0.35(Predicted)
form 
Solid
color 
white to tan
LogP
1.591 (est)
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Safety Information

WGK Germany 
3
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(+)-PINORESINOL Usage And Synthesis

Description

(+)-Pinoresinol is a lignan that has been found in Forsythia and virgin olive oils and has diverse biological activities, including antioxidant, anticancer, and anti-inflammatory properties. It is an inhibitor of α-glucosidase and maltase (IC50s = 492 and 34.3 μM in Baker’s yeast and rat small intestine, respectively). (+)-Pinoresinol scavenges ABTS , but not 2,2-diphenyl-1-picrylhydrazyl (DPPH; ), radicals in cell-free assays (IC50s = 13.43 and >200 μg/ml, respectively). It is cytotoxic to A549, HepG2, and MCF-7, but not U251 and Bcap-37, cells with IC50 values of 29.35, 62.35, 75.32, >80, and >80 μM, respectively. (+)-Pinoresinol prevents cell death induced by glutamate in HT22 cells (EC50 = 6.96 μM) and inhibits LPS-induced nitric oxide production in RAW 264.7 cells (IC50 = 7.89 μM).

Uses

(+)-Pinoresinol is a lignan found in olive oil and in other plants. This phenolic compound was reported to have antioxidant and anticancer potential.

Definition

ChEBI: An enantiomer of pinoresinol having (+)-1S,3aR,4S,6aR-configuration.

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