| Identification | Back Directory | [Name]
3,3',4',5,6,7-HEXAHYDROXYFLAVONE | [CAS]
90-18-6 | [Synonyms]
QUERCETAGIN
QUERCETAGENIN
QUERCETAGETIN
6-Hydroxyquercetin
6,7,4'-Quercetagetin
QUEBRACHITOL, (-)-(RG)
Quercetagetin 7-glucoside
3,3',4',5,6,7-HEXAHYDROXYFLAVONE
3,5,6,7,3',4'-HEXAHYDROXYFLAVONE
QuercetagitrinQuercetagetin 7-glucoside
2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4-benzopyrone
2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-1-benzopyran-4-one
2-(3,4-Dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4H-1-benzopyran-4-one
3,5,6,7-Tetrahydroxy-2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy- | [EINECS(EC#)]
201-973-6 | [Molecular Formula]
C15H10O8 | [MDL Number]
MFCD00017428 | [MOL File]
90-18-6.mol | [Molecular Weight]
318.24 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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) | [storage]
Store at -20°C | [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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