(+)-Pinoresinol
Basic information
- CAS
487-36-5- Standard SMILES
COc1cc([C@H]2OC[C@H]3[C@@H]2CO[C@@H]3c2ccc(O)c(OC)c2)ccc1O- InChIKey
HGXBRUKMWQGOIE-AFHBHXEDSA-N- Molecular formula
- C20H22O6
- Average molar mass
- 358.4 g/mol
- Monoisotopic mass
- 358.14163842
Overview
(+)-pinoresinol is an enantiomer of pinoresinol having (+)-1S,3aR,4S,6aR-configuration. It has a role as a hypoglycemic agent, a plant metabolite and a phytoestrogen.
Names & identifiers
- Preferred name
- (+)-Pinoresinol
- IUPAC
- 4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
- English name
- (+)-PINORESINOL
- Molecular formula
- C20H22O6
- Molecular weight
- 358.39
Names & synonyms
Pinoresinol(+)-Pinoresinol487-36-5V4N1UDY811DTXSID20964099NSC-35444CHEBI:40(7alpha,7'alpha,8alpha,8'alpha)-3,3'-dimethoxy-7,9':7',9-diepoxylignane-4,4'-diolpino-resinolPhenol, 4,4'-(tetrahydro-1H,3H-furo(3,4-c)furan-1,4-diylbis(2-methoxy-, (1S-(1alpha,3aalpha,4alpha,6aalpha))-4-((3S,3aR,6S,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro(3,4-c)furan-3-yl)-2-methoxyphenol4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
Show more names
80% ee)(+)-Piresil(+/-)-Pinoresinol(+)-Pinoresinol-RM(+)-Pinoresinol (>(+)-Pinoresinol (>80% ee)Pinoresinol, 10 mM in DMSO(+)-Pinoresinol,Pinoresinol(1β,5β)-2β,6β-Bis(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclo[3.3.0]octane
RefChem:44689CHEBI:8225DTXCID8017670634-((3R,3aR,6S,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro(3,4-c)furan-3-yl)-2-methoxyphenol4-((3R,3aS,6R,6aS)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro(3,4-c)furan-3-yl)-2-methoxyphenolD-PINORESINOLMFCD07784516NSC 35444
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 77.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 4
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 431
Physicochemical properties
- Melting point
- 112 °C · 112 °C
- Boiling point
- 556.5 · 556.5±50.0 °C(Predicted)
- Density
- 1.385 g/cm3 · 1.385 g/cm3
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 6 mg/mL · DMSO: ≥6mg/mL
- pka
- 9.54 · 9.54±0.35(Predicted)
- form
- Solid
- color
- white to tan
- Major Application
- cleaning productscosmeticsfood and beveragespersonal 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 · 1.591 (est)
- FDA UNII
- 4 N1UDY811 · V4N1UDY811
- UNSPSC Code
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
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.
Additional notes
DefinitionChEBI: An enantiomer of pinoresinol having (+)-1S,3aR,4S,6aR-configuration.
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