5,7,4'-trihydroxy-3,8,3'-trimethoxy-flavone
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| Category | Others |
| Catalog number | BBF-04960 |
| CAS | 14965-08-3 |
| Molecular Weight | 360.31 |
| Molecular Formula | C18H16O8 |
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Specification
| Synonyms | Gossypetin 3,8,3'-trimethyl ether; 5,7,4'-Trihydroxy-3,8,3'-trimethoxyflavone; 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,8-dimethoxy- |
| IUPAC Name | 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,8-dimethoxychromen-4-one |
| Canonical SMILES | COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)OC)OC)O |
| InChI | InChI=1S/C18H16O8/c1-23-12-6-8(4-5-9(12)19)15-18(25-3)14(22)13-10(20)7-11(21)16(24-2)17(13)26-15/h4-7,19-21H,1-3H3 |
| InChI Key | XZGZRRSEIISPEP-UHFFFAOYSA-N |
Properties
| Boiling Point | 627.3±55.0°C at 760 mmHg |
| Melting Point | 213.5-215°C |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. Xanthine oxidase inhibiting flavonol glycoside from Amberboa ramosa
Sher Bahadar Khan, Nighat Afza, Abdul Malik, Azhar-Ul-Haq, Shagufta Perveen, Ijaz Ahmad, Asma Ejaz, M Iqbal Choudhary Nat Prod Res. 2006 Apr;20(4):335-9. doi: 10.1080/14786410500182110.
A new flavonol glycoside (1) has been isolated from the ethyl acetate soluble fraction of Amberboa ramosa and assigned the structure 5,7,4'-trihydroxy-3,8-dimethoxylflavone 5-O-beta-D-gluco-pyranoside (1). In addition, 6,4'-dihydroxy-3,5,7-trimethoxyflavone (2), 5,7-dihydroxy-4'-methoxyflavone (3) and (23R)-5alpha-cycloart-24-ene-3beta,21,23-triol (4) have also been reported for the first time from this species. The structures were deduced on the basis of 1D and 2D NMR techniques. The compounds 1-3 displayed weak to moderate inhibition against the xanthine oxidase enzyme.
2. 6-C-methyl flavonoids isolated from Pinus densata inhibit the proliferation and promote the apoptosis of the HL-60 human promyelocytic leukaemia cell line
Rongcai Yue, Bo Li, Yunheng Shen, Huawu Zeng, Bo Li, Hu Yuan, Yiren He, Lei Shan, Weidong Zhang Planta Med. 2013 Aug;79(12):1024-30. doi: 10.1055/s-0033-1350617. Epub 2013 Jul 22.
Three structurally related 6-C-methyl flavonoids isolated from Pinus densata, including 5,4'-dihydroxy-3,7,8-trimethoxy-6-C-methylflavone (PD1), 5,7,4'-trihydroxy-3,8-dimethoxy-6-C-methylflavone (PD2), and 5,7,4'-trihydroxy-3-methoxy-6-C-methylflavone (PD3), were tested for their ability to inhibit the proliferation and promote the apoptosis of the HL-60 human leukaemia cell line. Cytotoxicity assays in the HL-60 human cancer cell line demonstrated that 5,4'-dihydroxy-3,7,8-trimethoxy-6-C-methylflavone exhibited the most potent cytotoxicity of the three structurally related 6-C-methyl flavonoids. 5,4'-Dihydroxy-3,7,8-trimethoxy-6-C-methylflavone inhibited the proliferation of HL-60 cells in a dose-dependent manner with an IC₅₀ of 7.91 µM (48 h treatment). Furthermore, 5,4'-dihydroxy-3,7,8-trimethoxy-6-C-methylflavone-induced apoptosis was associated with mitochondrial membrane disruption and cytochome c release. Flow cytometry analyses revealed an increase in the hypodiploid population in 5,4'-dihydroxy-3,7,8-trimethoxy-6-C-methylflavone-treated HL-60 cells. Treatment with a concentration of 5,4'-dihydroxy-3,7,8-trimethoxy-6-C-methylflavone that induced apoptosis activated caspase-3 but did not activate caspase-1. A caspase-3 inhibitor (Ac-DEVD-CHO), but not a caspase-1 inhibitor (Ac-YVAD-CHO), reversed the cytotoxic effects of 5,4'-dihydroxy-3,7,8-trimethoxy-6-C-methylflavone in HL-60 cells. These data demonstrated that 5,4'-dihydroxy-3,7,8-trimethoxy-6-C-methylflavone effectively induced the apoptosis of HL-60 cells and exhibited significant anticancer activity via the mitochondrial caspase-3-dependent apoptosis pathway.
3. Chemical constituents of Picea neoveitchii
Zhijun Song, Weiquan Chen, Xiaoying Du, Heng Zhang, Lijing Lin, Hanhong Xu Phytochemistry. 2011 Apr;72(6):490-4. doi: 10.1016/j.phytochem.2011.01.018. Epub 2011 Feb 19.
Four flavonoids, 5,7,4'-trihydroxy-3,8,-dimethoxy-6-C-methylflavone (1), 5,8,4'-trihydroxy-3,7-dimethoxy-6-C-methylflavone (2), 7-methoxy-6-C-methylkaempferol (3) and kaempferol-7-O-(2″-E-p-coumaroyl)-α-l-arabinofuranoside (4), together with 15 known compounds, were isolated from the twigs and leaves of Picea neoveitchii Mast. Their structures were elucidated on the basis of analyses of spectroscopic data. Compound 4 showed strong anti-fungal activity against Fusarium oxysporum whereas compounds 1-4 were all active against Rhizoctonia solani.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
