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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H22O6
Molecular Weight 358.3851
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PINORESINOL

SMILES

COC1=CC(=CC=C1O)[C@H]2OC[C@H]3[C@@H]2CO[C@@H]3C4=CC(OC)=C(O)C=C4

InChI

InChIKey=HGXBRUKMWQGOIE-AFHBHXEDSA-N
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

HIDE SMILES / InChI

Molecular Formula C20H22O6
Molecular Weight 358.3851
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Pinoresinol is a common component of the lignan fraction found in olive oil, in Styrax sp. and in Forsythia suspense and in other plants. Many experimental studies have been focused on the strong antioxidant activity of pinoresinol. Enzymatic hydrolysis of maltose is inhibited by (+)-pinoresinol through competitive and noncompetitive manners. Pinoresinol caused an upregulation of the CDK inhibitor p21(WAF1/Cip1) both at mRNA and protein levels so suggesting that this could be a mechanism by which pinoresinol reduced proliferation and induced differentiation on HL60 leukemia cells. Pinoresinol may have a therapeutic potential to prevent breast cancer development via the reduction of intracellular oxidative stress and DNA damage in human mammary epithelial cells. In vivo, pinoresinol ameliorates CCl4-induced acute liver injury, and this protection is likely due to anti-oxidative activity and down-regulation of inflammatory mediators through inhibition of NF-kappaB and AP-1.

Approval Year

PubMed

PubMed

TitleDatePubMed
Balanochalcone, a new chalcone from Balanophora laxiflora Hemsl.
2018-04
Association between dietary phytoestrogens intakes and prostate cancer risk in Sicily.
2018-03
Characterization and evaluation of phenolic profiles and color as potential discriminating features among Spanish extra virgin olive oils with protected designation of origin.
2018-02-15
Inositol Derivatives and Phenolic Compounds from the Roots of Taraxacum coreanum.
2017-08-14
Differences in Chemical Component and Anticancer Activity of Green and Ripe Forsythiae Fructus.
2017
A Novel Soybean Dirigent Gene GmDIR22 Contributes to Promotion of Lignan Biosynthesis and Enhances Resistance to Phytophthora sojae.
2017
Influence of Boiling Duration of GCSB-5 on Index Compound Content and Antioxidative and Anti-inflammatory Activity.
2016-09-25
Phenolic constituents from Parakmeria yunnanensis and their anti-HIV-1 activity.
2013-10
Anti-AIDS agents. 46. Anti-HIV activity of harman, an anti-HIV principle from Symplocos setchuensis, and its derivatives.
2001-07
Patents

Sample Use Guides

Rat: 1 or 2 mg/kg b.w. in 0.5 mL saline solution
Route of Administration: Intravenous
The percentage of non-tumorigenic human mammary epithelial cells death following treatment with 0.001 uM pinoresinol was much lower (10 %) than in breast cancer cells (29 % for MDA-MB-231 and 20 % for MCF7 cells).
Substance Class Chemical
Created
by admin
on Mon Mar 31 20:04:17 GMT 2025
Edited
by admin
on Mon Mar 31 20:04:17 GMT 2025
Record UNII
V4N1UDY811
Record Status Validated (UNII)
Record Version
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Name Type Language
PINORESINOL
Common Name English
NSC-35444
Preferred Name English
PHENOL, 4,4'-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYLBIS(2-METHOXY-, (1S-(1.ALPHA.,3A.ALPHA.,4.ALPHA.,6A.ALPHA.))-
Common Name English
PHENOL, 4,4'-((1S,3AR,4S,6AR)-TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS(2-METHOXY-
Common Name English
PINORESINOL, (+)-
Common Name English
D-PINORESINOL
Common Name English
(+)-PINORESINOL
Common Name English
Code System Code Type Description
WIKIPEDIA
PINORESINOL
Created by admin on Mon Mar 31 20:04:17 GMT 2025 , Edited by admin on Mon Mar 31 20:04:17 GMT 2025
PRIMARY
CHEBI
40
Created by admin on Mon Mar 31 20:04:17 GMT 2025 , Edited by admin on Mon Mar 31 20:04:17 GMT 2025
PRIMARY
FDA UNII
V4N1UDY811
Created by admin on Mon Mar 31 20:04:17 GMT 2025 , Edited by admin on Mon Mar 31 20:04:17 GMT 2025
PRIMARY
CAS
487-36-5
Created by admin on Mon Mar 31 20:04:17 GMT 2025 , Edited by admin on Mon Mar 31 20:04:17 GMT 2025
PRIMARY
NSC
35444
Created by admin on Mon Mar 31 20:04:17 GMT 2025 , Edited by admin on Mon Mar 31 20:04:17 GMT 2025
PRIMARY
PUBCHEM
73399
Created by admin on Mon Mar 31 20:04:17 GMT 2025 , Edited by admin on Mon Mar 31 20:04:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID20964099
Created by admin on Mon Mar 31 20:04:17 GMT 2025 , Edited by admin on Mon Mar 31 20:04:17 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
1,1-Diphenyl-2-picrylhydrazyl radical scavenging assay(DPPH) IC50 expressed as ug/mL = 34.7+/- 5.0. In vitro hydroxyl radical scavenging assay(Hydroxy Radical) IC50 expressed as ug/mL = 1.8+/- 0.20.