(+)-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

InChI

InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3/t13-,14-,19+,20+/m0/s1

InChIKey

HGXBRUKMWQGOIE-AFHBHXEDSA-N

SMILES

O1C[C@]2([H])[C@@H](C3=CC=C(O)C(OC)=C3)OC[C@]2([H])[C@H]1C1=CC=C(O)C(OC)=C1

LogP

1.591 (est)

Safety Information

WGK Germany 

3

(+)-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.

References

[1] ALICIA LóPEZ-BIEDMA . The biological activities of natural lignans from olives and virgin olive oils: A review[J]. Journal of Functional Foods, 2016, 26: Pages 36-47. DOI: 10.1016/j.jff.2016.07.005
[2] DAN-QI LI. Antioxidant and cytotoxic lignans from the roots of Bupleurum chinense[J]. Journal of Asian Natural Products Research, 2017, 19 1: 519-527. DOI: 10.1080/10286020.2016.1234456
[3] ARIN WIKUL . (+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase[J]. Bioorganic & Medicinal Chemistry Letters, 2012, 22 16: Pages 5215-5217. DOI: 10.1016/j.bmcl.2012.06.068
[4] SEO-JI IN. Lignans and neolignans from the stems of Vibrunum erosum and their neuroprotective and anti-inflammatory activity[J]. Archives of Pharmacal Research, 2014, 38 1: 26-34. DOI: 10.1007/s12272-014-0358-9

(+)-PINORESINOL(487-36-5)Related Product Information

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