ChemicalBook Product Catalog Biochemical Engineering Plant extracts 3,3',4',5,6,7-HEXAHYDROXYFLAVONE

3,3',4',5,6,7-HEXAHYDROXYFLAVONE

Product Name3,3',4',5,6,7-HEXAHYDROXYFLAVONE
CAS90-18-6
MFC15H10O8
MW318.24
EINECS201-973-6
MOL File90-18-6.mol

Chemical Properties

Melting point	>300°C
Boiling point	732.4±60.0 °C(Predicted)
Density	1.912±0.06 g/cm3(Predicted)
storage temp.	Store at -20°C
solubility	DMSO : 125 mg/mL (392.79 mM; Need ultrasonic)
form	A crystalline solid
pka	6.12±0.40(Predicted)
color	Light yellow to yellow
Cosmetics Ingredients Functions	SKIN PROTECTING
InChI	InChI=1S/C15H10O8/c16-6-2-1-5(3-7(6)17)15-14(22)13(21)10-9(23-15)4-8(18)11(19)12(10)20/h1-4,16-20,22H
InChIKey	ZVOLCUVKHLEPEV-UHFFFAOYSA-N
SMILES	C1(C2=CC=C(O)C(O)=C2)OC2=CC(O)=C(O)C(O)=C2C(=O)C=1O
LogP	2.230 (est)

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Uses

Quercetagetin (6-Hydroxyquercetin) is a flavonoid[1]. Quercetagetin is a moderately potent and selective, cell-permeable pim-1 kinase inhibitor (IC50, 0.34 μM)[2]. Anti-inflammatory and anticancer properties.

Definition

ChEBI: A hexahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 5, 6, 7, 3' and 4' respectively.

Biological Activity

Cell permeable: yes', 'Primary Target
PIM1 kinase', 'Product competes with ATP.', 'Reversible: yes', 'Target IC50: 340 nM against PIM1 kinase

in vivo

Quercetagetin significantly inhibits UVB-induced skin cancer development. Topical application of 4 or 20 nmol of Quercetagetin to mouse skin reduces tumor incidence by 32.0% and 46.7%, respectively^[3].

Animal Model:	SKH-1 hairless mice model^[3]
Dosage:	4 or 20 nmol
Administration:	Topical application; 28 weeks
Result:	Inhibited UVB-induced skin tumorigenesis in SKH-1 hairless mice models. Delayed the development of tumors and reduced tumor volumes in an SKH-1 hairless mice model.

IC 50

PIM1: 0.34 μM (IC₅₀); PIM2: 3.45 μM (IC₅₀); RSK2: 2.82 μM (IC₅₀); PKA: 21.2 μM (IC₅₀)

References

[1] Yang X, et al. Isolation and identification of an antioxidant flavonoid compound from citrus-processing by-product. J Sci Food Agric. 2011 Aug 15;91(10):1925-7. DOI:10.1002/jsfa.4402
[2] Holder S, et al. Characterization of a potent and selective small-molecule inhibitor of the PIM1 kinase. Mol Cancer Ther. 2007 Jan;6(1):163-72. DOI:10.1158/1535-7163.MCT-06-0397
[3] Baek S, et al. Structural and functional analysis of the natural JNK1 inhibitor quercetagetin. J Mol Biol. 2013 Jan 23;425(2):411-23. DOI:10.1016/j.jmb.2012.10.019

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