(+)-PINORESINOL CAS 487-36-5

Introduction：Basic information about (+)-PINORESINOL CAS 487-36-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

(+)-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

(+)-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
• Major Application: cleaning products cosmetics food and beverages personal care
• 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
• Storage Class: 11 - Combustible Solids

(+)-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