Pinoresinol

Base Information

• Chemical Name: Pinoresinol
• CAS No.: 487-36-5
• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.391
• UNII: V4N1UDY811
• DSSTox Substance ID: DTXSID20964099
• Nikkaji Number: J322.968H
• Wikipedia: Pinoresinol
• Wikidata: Q3388802
• Metabolomics Workbench ID: 52793
• ChEMBL ID: CHEMBL260183
• Mol file: 487-36-5.mol

Synonyms:pino-resinol;pinoresinol

Chemical Property of Pinoresinol

Chemical Property:

• Melting Point: 112 °C
• Boiling Point: 556.5 °C at 760 mmHg
• PKA: 9.54±0.35(Predicted)
• Flash Point: 290.4 °C
• PSA: 77.38000
• Density: 1.287 g/cm³
• LogP: 3.19020
• Storage Temp.: ?20°C
• Solubility.: DMSO: ≥6mg/mL
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 358.14163842
• Heavy Atom Count: 26
• Complexity: 431

Purity/Quality:

≥98% ^*data from raw suppliers

(+)-Pinoresinol(>80%ee) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)O
• Isomeric SMILES: COC1=C(C=CC(=C1)[C@@H]2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC(=C(C=C4)O)OC)O
• 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.

Technology Process of Pinoresinol

There total 75 articles about Pinoresinol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(1R,2R,5R,6S)-2-(4-methanesulfonyloxy-3-methoxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octane (651779-99-6) → (+)-epipinoresinol (487-36-5,4263-88-1,7452-03-1,10061-38-8,18779-41-4,18779-51-6,24404-50-0,81446-29-9,146338-76-3)

Guidance literature:

With potassium hydroxide; In 1,4-dioxane; methanol; water; at 50 ℃; for 40h;

DOI:10.1021/jo035365r

Reference yield:

(7S,8R,7′S,8′R)-(-)-pinoresinol-4-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside → D-glucose (50-99-7) + pinoresinol (4263-88-1,7452-03-1,10061-38-8,18779-41-4,18779-51-6,24404-50-0,81446-29-9,146338-76-3,487-36-5)

Guidance literature:

With β-glucosidase; water; In ethyl acetate; at 37 ℃; for 24h; Enzymatic reaction;

DOI:10.1016/j.bioorg.2020.104312

Reference yield:

(7S,8R,7′S,8′R)-(-)-pinoresinol-4-O-β-D-glucopyranosyl-(1→3)-β-D-glucopyranoside → D-glucose (50-99-7) + pinoresinol (4263-88-1,7452-03-1,10061-38-8,18779-41-4,18779-51-6,24404-50-0,81446-29-9,146338-76-3,487-36-5)

Guidance literature:

With β-glucosidase; water; In ethyl acetate; at 37 ℃; for 24h; Enzymatic reaction;

DOI:10.1016/j.bioorg.2020.104312

upstream raw materials:

Diacetate of (+)-epipinoresinol

Versicoside

pinoresinol

(1R,2R,5R,6S)-2-(4-methanesulfonyloxy-3-methoxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octane

Downstream raw materials:

5,5'-Bis-[(3aR)-4c-(4-hydroxy-3-methoxy-phenyl)-(3ar,6ac)-tetrahydro-furo[3,4-c]furan-1c-yl]-3,3'-dimethoxy-biphenyl-2,2'-diol

Diacetate of (+)-epipinoresinol

eudesmin

(+)-epipinoresinol

Refernces

• 1、 Davin, Laurence B.,Hwang, Julianne K.,Lewis, Norman G.,Moinuddin, Syed G. A.. "Pinoresinol-lariciresinol reductase: Substrate versatility, enantiospecificity, and kinetic properties". . . Retrieved 2020/03/26.
• 2、 Zhou, Le,Han, Feng-Ying,Lu, Li-Wei,Yao, Guo-Dong,Zhang, Ying-Ying,Wang, Xiao-Bo,Lin, Bin,Huang, Xiao-Xiao,Song, Shao-Jiang. "Isolation of enantiomeric furolactones and furofurans from Rubus idaeus L. with neuroprotective activities". . p. 122 - 129. Retrieved 2019/05/29.