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Details

Stereochemistry ACHIRAL
Molecular Formula C21H22O9
Molecular Weight 418.394
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 5-HYDROXY-3,6,7,8,3',4'-HEXAMETHOXYFLAVONE

SMILES

COC1=C(OC)C=C(C=C1)C2=C(OC)C(=O)C3=C(O)C(OC)=C(OC)C(OC)=C3O2

InChI

InChIKey=JDVPHCLYMGBZLE-UHFFFAOYSA-N
InChI=1S/C21H22O9/c1-24-11-8-7-10(9-12(11)25-2)16-18(26-3)14(22)13-15(23)19(27-4)21(29-6)20(28-5)17(13)30-16/h7-9,23H,1-6H3

HIDE SMILES / InChI

Molecular Formula C21H22O9
Molecular Weight 418.394
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
5-Hydroxy-3,6,7,8,3'4'-hexamethoxyflavone inhibits nitric oxide production in lipopolysaccharide-stimulated BV2 microglia via NF-κB suppression and Nrf-2-dependent heme oxygenase-1 induction.
2013-07
Quantitative analysis of hydroxylated polymethoxyflavones by high-performance liquid chromatography.
2010-08
Inhibitory effects of 5-hydroxy polymethoxyflavones on colon cancer cells.
2010-07
Simultaneous determination of four 5-hydroxy polymethoxyflavones by reversed-phase high performance liquid chromatography with electrochemical detection.
2010-01-29
Polymethoxyflavones activate Ca2+-dependent apoptotic targets in adipocytes.
2009-07-08
Monodemethylated polymethoxyflavones from sweet orange (Citrus sinensis) peel inhibit growth of human lung cancer cells by apoptosis.
2009-03
Inhibitory effect of citrus 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone on 12-O-tetradecanoylphorbol 13-acetate-induced skin inflammation and tumor promotion in mice.
2007-12
5-Hydroxy-3,6,7,8,3',4'-hexamethoxyflavone induces apoptosis through reactive oxygen species production, growth arrest and DNA damage-inducible gene 153 expression, and caspase activation in human leukemia cells.
2007-06-27
Isolation and syntheses of polymethoxyflavones and hydroxylated polymethoxyflavones as inhibitors of HL-60 cell lines.
2007-05-15
Polymethoxylated flavones induce Ca(2+)-mediated apoptosis in breast cancer cells.
2006-12-23
Genetic toxicity of a standardized mixture of citrus polymethoxylated flavones.
2002-05
Substance Class Chemical
Created
by admin
on Mon Mar 31 23:34:23 GMT 2025
Edited
by admin
on Mon Mar 31 23:34:23 GMT 2025
Record UNII
07JTS22V9J
Record Status Validated (UNII)
Record Version
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Name Type Language
5-HYDROXY-3,6,7,8,3',4'-HEXAMETHOXYFLAVONE
Systematic Name English
NSC-618935
Preferred Name English
FLAVONE, 5-HYDROXY-3,3',4',6,7,8-HEXAMETHOXY-
Systematic Name English
4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIMETHOXYPHENYL)-5-HYDROXY-3,6,7,8-TETRAMETHOXY-
Systematic Name English
Code System Code Type Description
NSC
618935
Created by admin on Mon Mar 31 23:34:23 GMT 2025 , Edited by admin on Mon Mar 31 23:34:23 GMT 2025
PRIMARY
CAS
1176-88-1
Created by admin on Mon Mar 31 23:34:23 GMT 2025 , Edited by admin on Mon Mar 31 23:34:23 GMT 2025
PRIMARY
FDA UNII
07JTS22V9J
Created by admin on Mon Mar 31 23:34:23 GMT 2025 , Edited by admin on Mon Mar 31 23:34:23 GMT 2025
PRIMARY
PUBCHEM
136417
Created by admin on Mon Mar 31 23:34:23 GMT 2025 , Edited by admin on Mon Mar 31 23:34:23 GMT 2025
PRIMARY
EPA CompTox
DTXSID50151834
Created by admin on Mon Mar 31 23:34:23 GMT 2025 , Edited by admin on Mon Mar 31 23:34:23 GMT 2025
PRIMARY
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PARENT -> CONSTITUENT ALWAYS PRESENT
56% Cell growth rate of human acute promyelocytic leukemia HL-60 cells at 50 uM of compound vs control