5,7-dimethoxyflavone

chrysin dimethyl ether

CAS: 21392-57-4 C17 H14 O4 MW: 282.29538000

Identification

Name5,7-dimethoxyflavone
IUPAC5,7-dimethoxy-2-phenylchromen-4-one
CAS Number21392-57-4
FDA UNIISearch
Molecular FormulaC17 H14 O4
Molecular Weight282.29538000
MDL NumberMFCD00016943
Nikkaji NumberJ145.247I
XlogP32.20 (est)

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 476.60 °C. @ 760.00 mm Hg (est)
Flash Point 416.00 °F. TCC ( 213.40 °C. ) (est)
logP (o/w) 3.270 (est)
Soluble in water, 11.42 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for 5,7-dimethoxyflavone usage levels up tonot for fragrance use.
Recommendation for 5,7-dimethoxyflavone flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

leptospermum scoparium

Synonyms

4H-1- benzopyran-4-one, 5,7-dimethoxy-2-phenyl- chrysin dimethyl ether chrysin dimethylether 5,7- dimethoxy-2-phenyl-4H-chromen-4-one 5,7- dimethoxy-2-phenylchromen-4-one PubMed: Identification and evaluation of anti-inflammatory compounds from Kaempferia parviflora. PubMed: A 5,7-dimethoxyflavone/hydroxypropyl-β-cyclodextrin inclusion complex with anti-butyrylcholinesterase activity. PubMed: The O-methylation of chrysin markedly improves its intestinal anti-inflammatory properties: Structure-activity relationships of flavones. PubMed: Novel formulation strategies for enhancing oral delivery of methoxyflavones in Kaempferia parviflora by SMEDDS or complexation with 2-hydroxypropyl-β-cyclodextrin. PubMed: Pharmacokinetics, bioavailability, tissue distribution, excretion, and metabolite identification of methoxyflavones in Kaempferia parviflora extract in rats. PubMed: Isoflavones inhibit the clonogenicity of human colon cancer cells. PubMed: 5,7-Dimethoxyflavone, an activator of PPARα/γ, inhibits UVB-induced MMP expression in human skin fibroblast cells. PubMed: Methylated chrysin reduced cell proliferation, but antagonized cytotoxicity of other anticancer drugs in acute lymphoblastic leukemia. PubMed: Methoxyflavone derivatives modulate the effect of TRAIL-induced apoptosis in human leukemic cell lines. PubMed: Kaempferia parviflora, a plant used in traditional medicine to enhance sexual performance contains large amounts of low affinity PDE5 inhibitors. PubMed: A chrysin analog exhibited strong inhibitory activities against both PGE2 and NO production. PubMed: 5, 7-Dimethoxyflavone sensitizes TRAIL-induced apoptosis through DR5 upregulation in hepatocellular carcinoma cells. PubMed: Methylated chrysin induces co-ordinated attenuation of the canonical Wnt and NF-kB signaling pathway and upregulates apoptotic gene expression in the early hepatocarcinogenesis rat model. PubMed: 5,7-dimethoxyflavone induces melanogenesis in B16F10 melanoma cells through cAMP-dependent signalling. PubMed: Antiproliferative activity of three methoxylated flavonoids isolated from Zeyheria montana Mart. (Bignoniaceae) leaves. PubMed: 5,7-Dimethoxyflavone and multiple flavonoids in combination alter the ABCG2-mediated tissue distribution of mitoxantrone in mice. PubMed: Suppressive effects of methoxyflavonoids isolated from Kaempferia parviflora on inducible nitric oxide synthase (iNOS) expression in RAW 264.7 cells. PubMed: Possible mechanisms of vasorelaxation for 5,7-dimethoxyflavone from Kaempferia parviflora in the rat aorta. PubMed: Effects of single and multiple flavonoids on BCRP-mediated accumulation, cytotoxicity and transport of mitoxantrone in vitro. PubMed: Chemical constituents from tiger's betel, Piper porphyrophyllum N.E.Br. (Fam. Piperaceae). PubMed: Amino and nitro derivatives of 5,7-dimethoxyflavone from Kaempferia parviflora and cytotoxicity against KB cell line. PubMed: Structural modification of 5,7-dimethoxyflavone from Kaempferia parviflora and biological activities. PubMed: Anticholinesterase activity of 7-methoxyflavones isolated from Kaempferia parviflora. PubMed: New 4'-substituted flavones from the fruit peels of Citrus limon (L.) Burm.f. PubMed: Cytotoxic effects of the dietary flavones chrysin and apigenin in a normal trout liver cell line. PubMed: Bioavailable flavonoids: cytochrome P450-mediated metabolism of methoxyflavones. PubMed: Aromatase inhibition by bioavailable methylated flavones. PubMed: Benzo[a]pyrene-induced cytochrome P450 1A and DNA binding in cultured trout hepatocytes - inhibition by plant polyphenols. PubMed: Modulation of function of multidrug resistance associated-proteins by Kaempferia parviflora extracts and their components. PubMed: Simultaneous identification and quantitation of 11 flavonoid constituents in Kaempferia parviflora by gas chromatography. PubMed: Cancer chemopreventive properties of orally bioavailable flavonoids--methylated versus unmethylated flavones. PubMed: Effects of Kaempferia parviflora extracts and their flavone constituents on P-glycoprotein function. PubMed: Accumulation and metabolism of the anticancer flavonoid 5,7-dimethoxyflavone compared to its unmethylated analog chrysin in the Atlantic killifish. PubMed: Inhibition of viral proteases by Zingiberaceae extracts and flavones isolated from Kaempferia parviflora. PubMed: Methylated flavonoids have greatly improved intestinal absorption and metabolic stability. PubMed: Methylation protects dietary flavonoids from rapid hepatic metabolism. PubMed: Cytochrome P450 1B1, a novel chemopreventive target for benzo[a]pyrene-initiated human esophageal cancer. PubMed: Inhibition of benzo[a]pyrene-activating enzymes and DNA binding in human bronchial epithelial BEAS-2B cells by methoxylated flavonoids. PubMed: Preferential induction of CYP1B1 by benzo[a]pyrene in human oral epithelial cells: impact on DNA adduct formation and prevention by polyphenols. PubMed: 5,7-Dimethoxyflavone downregulates CYP1A1 expression and benzo[a]pyrene-induced DNA binding in Hep G2 cells. PubMed: Flavanoids from Caesalpinia pulcherrima. PubMed: Novel compounds from Piper methysticum Forst (Kava Kava) roots and their effect on cyclooxygenase enzyme. PubMed: Pyrano chalcones and a flavone from Neoraputia magnifica and their Trypanosoma cruzi glycosomal glyceraldehyde-3-phosphate dehydrogenase-inhibitory activities. PubMed: Flavonoids from Leptospermum scoparium with affinity to the benzodiazepine receptor characterized by structure activity relationships and in vivo studies of a plant extract. PubMed: Anti-inflammatory activity of 5,7-dimethoxyflavone.