A lignan with diverse biological activities
Related Products
Enantiomer(s)
27700(+)-Pinoresinol
Isomer(s)
10005174Matairesinol
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(−)-Pinoresinol

Item No. 36850

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4,4′-[(1R,3aS,4R,6aS)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[2-methoxy-phenol
CAS Number
81446-29-9
Molecular Formula
C20H22O6
Formula Weight
358.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetone: solubleChloroform: solubleDichloromethane: solubleDMSO: solubleEthyl Acetate: soluble
SMILES
[H][C@](OC1)(C2=CC(OC)=C(O)C=C2)[C@@]3([H])[C@]1([H])[C@]([H])(C4=CC(OC)=C(O)C=C4)OC3
InChi Code
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+/m1/s1
InChi Key
HGXBRUKMWQGOIE-NSMLZSOPSA-N
Origin
Plant/Eucommia ulmoides Oliver
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

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    Product Description

    (−)-Pinoresinol is a lignan that has been found in Manihot esculenta and has diverse biological activities.1,2,3 It scavenges DPPH (Item No. 14805) and ABTS (Item No. 27317) radicals in cell-free assays (EC50s = 0.2 and 0.055 mg/ml, respectively).1 (−)-Pinoresinol selectively inhibits 5-lipoxygenase (5-LO) and 15-LO over COX-2 (IC50s = 13.8, 3.5, and >100 µM, respectively).2 It also inhibits LPS-induced nitric oxide (NO) production in BV-2 microglial cells (IC50 = 34.25 µM).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yi, B., Hu, L., Mei, W., et al. Antioxidant phenolic compounds of cassava (Manihot esculenta) from Hainan. Molecules 16(12), 10157-10167 (2011).

    2. Deng, S., Palu, A.K., West, B.J., et al. Lipoxygenase inhibitory constituents of the fruits of noni (Morinda citrifolia) collected in Tahiti. J. Nat. Prod. 70(5), 859-862 (2007).

    3. Suh, W.S., Subedi, L., Kim, S.Y., et al. Bioactive lignan constituents from the twigs of Sambucus williamsii. Bioorg. Med. Chem. Lett. 26(8), 1877-1880 (2016).