A derivative of quercetin with diverse biological activities
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3,5,7,3′,4′-Pentamethoxyflavone

Item No. 46065

Technical Information
Formal Name
2-(3,4-dimethoxyphenyl)-3,5,7-trimethoxy-4H-1-benzopyran-4-one
CAS Number
1247-97-8
Synonyms
  • KPMF-8
  • PMF
  • NSC 115922
  • NSC 618936
  • Quercetin 3,5,7,3’,4’-Pentamethyl ether
Molecular Formula
C20H20O7
Formula Weight
Purity
≥98%
A solid
DMSO: Soluble: ≥ 10 mg/ml
SMILES
O=C1C(OC)=C(C2=CC=C(OC)C(OC)=C2)OC3=CC(OC)=CC(OC)=C31
InChi Code
InChI=1S/C20H20O7/c1-22-12-9-15(25-4)17-16(10-12)27-19(20(26-5)18(17)21)11-6-7-13(23-2)14(8-11)24-3/h6-10H,1-5H3
InChi Key
ALGDHWVALRSLBT-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    3,5,7,3′,4′-Pentamethoxyflavone (PMF) is the pentamethyl ether derivative of quercetin (Item No. 10005169) that has been found in K. parviflora and has diverse biological activities.1,2,3 It is a SIRT1 activator that binds directly to SIRT1 and enhances its binding to the acetylated p53 peptide Ac-p53-AMC by 25-fold at 2 µM, an effect that is dependent on the SIRT1 N-terminal domain and the E230 residue of SIRT1.1 PMF (20 µM) increases deacetylase activity in SIRT1-expressing, but not SIRT1-knockdown, MCF-7 cells. It also binds to the minor groove of DNA, and it inhibits the formation of DNA single-strand breaks induced by hydrogen peroxide (H2O2) in mouse peripheral blood mononuclear cells (PBMCs) at 100 µg/ml but has weak antioxidant activity in a DPPH (Item No. 14805) assay (IC50 = 234.74 µg/ml).2 However, it reduces the levels of reactive oxygen species (ROS) and reverses cellular senescence in aged primary human dermal fibroblasts (HDFs) at 3 µg/ml.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhang, M., Lu, P., Terada, T., et alQuercetin 3,5,7,3',4'-pentamethyl ether from Kaempferia parviflora directly and effectively activates human SIRT1. Commun. Biol. 4(1), 209 (2021).

    2. Jakhar, R., Paul, S., Park, Y.R., et al3,5,7,3′,4′-Pentamethoxyflavone, a quercetin derivative protects DNA from oxidative challenges: Potential mechanism of action. J. Photochem. Photobiol. B 131, 96-103 (2014).

    3. Klinngam, W., Rungkamoltip, P., Thongin, S., et alPolymethoxyflavones from Kaempferia parviflora ameliorate skin aging in primary human dermal fibroblasts and ex vivo human skin. Biomed. Pharmacother. 145, 112461 (2022).