A quercetin derivative with diverse biological activities
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Pentaacetylquercetin

Item No. 26694

Technical Information
Formal Name
3,5,7-tris(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-4H-1-benzopyran-4-one
CAS Number
1064-06-8
Synonyms
  • NSC 115919
  • Peracetylated Quercetin
  • Quercetin Pentaacetate
Molecular Formula
C25H20O12
Formula Weight
Purity
≥95%
A crystalline solid
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH 7.2) (1:4): 1 mg/mlEthanol: 2 mg/ml
λmax
251, 299 nm
SMILES
CC(OC1=CC=C(C2=C(OC(C)=O)C(C(C(OC(C)=O)=CC(OC(C)=O)=C3)=C3O2)=O)C=C1OC(C)=O)=O
InChi Code
InChI=1S/C25H20O12/c1-11(26)32-17-9-20(35-14(4)29)22-21(10-17)37-24(25(23(22)31)36-15(5)30)16-6-7-18(33-12(2)27)19(8-16)34-13(3)28/h6-10H,1-5H3
InChi Key
JQUHMSXLZZWRHU-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Pentaacetylquercetin is a pentaacetylated derivative of the flavonoid quercetin (Item No. 10005169) that has diverse biological activities, including antioxidant, anti-inflammatory, and anticancer properties.1,2,3 It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in vitro (IC50 = 3.74 μg/ml) and inhibits iron(II) chloride-induced lipid peroxidation in rat liver mitochondria (IC50 = 20.2 μg/ml).1 Pentaacetylquercetin inhibits LPS-induced increases in nitrite (IC50 = 8.7 μM) and PGE2 (Item No. 14010) production, as well as inducible nitric oxide synthase (iNOS) and COX-2 levels, in RAW 264.7 cells when used at concentrations of 20 and 40 μM.2 It also inhibits the growth of HL-60, U937, and SK-MEL-1 cells (IC50s = 38, 25, and 58 μM, respectively).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chang, H.-F., and Yang, L.-L. Radical-scavenging and rat liver mitochondria lipid peroxidative inhibitory effects of natural flavonoids from traditional medicinal herbs. J. Med. Plant Res. 6(6), 997-1006 (2012).

    2. Chen, Y.-C., Shen, S.-C., Lee, W.-R., et alInhibition of nitric oxide synthase inhibitors and lipopolysaccharide induced inducible NOS and cyclooxygenase-2 gene expressions by rutin, quercetin, and quercetin pentaacetate in RAW 264.7 macrophages. J. Cell. Biochem. 82(4), 537-548 (2001).

    3. Díaz, J.G., Carmona, A.J., Torres, F., et alCytotoxic activities of flavonoid glycoside acetates from Consolida oliveriana. Planta Med. 74(2), 171-174 (2008).