4712-12-3

Usage

Uses

Used in Pharmaceutical Industry:
4'-Methylchrysoeriol is used as a potential therapeutic agent for various health conditions due to its antioxidant, anti-inflammatory, and anticancer properties. It may help in the development of new drugs targeting inflammation, oxidative stress, and cancer.
Used in Nutraceutical Industry:
4'-Methylchrysoeriol can be used as a dietary supplement or functional food ingredient, providing health benefits such as enhanced antioxidant capacity and reduced inflammation. Its presence in food products may contribute to overall health and well-being.
Used in Cosmetic Industry:
Due to its antioxidant and anti-inflammatory properties, 4'-methylchrysoeriol can be used in cosmetic products to protect the skin from oxidative damage, reduce inflammation, and promote skin health.
Used in Agricultural Industry:
4'-Methylchrysoeriol, being a natural compound, can be used in the development of biopesticides or as a natural alternative to synthetic chemicals in agriculture. Its potential antioxidant and anti-inflammatory properties may help in protecting plants from stress and promoting their growth.

InChI:InChI=1/C17H14O6/c1-21-13-4-3-9(5-15(13)22-2)14-8-12(20)17-11(19)6-10(18)7-16(17)23-14/h3-8,18-19H,1-2H3

Upstream product

• 480-66-0 2,4,6-trihydroxyacetophenone 
• 24824-54-2 3,4-dimethoxybenzoic anhydride 
• 108-73-6 3,5-dihydroxyphenol 
• 4687-37-0 ethyl 3,4-dimethoxybenzoylacetate 
• 5373-11-5 luteolin 7-O-glucoside 
• 74-88-4 methyl iodide 
• 62346-14-9 7,4′-dihydroxy-5,3′-dimethoxyflavone 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 127-09-3 sodium acetate 
• 203191-62-2 7-benzyloxy-2-(3,4-dimethoxy-phenyl)-5-methoxy-chromen-4-one 
• 34280-03-0 5,7-dihydroxy-3',4'-dimethoxyflavone 7-O-rhamnosyl(1->2)glucoside 
• 10544-05-5 2-(3,4-dimethoxy-phenyl)-7-hydroxy-5-methoxy-chromen-4-one 
• 491-70-3 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on 
• 485-80-3 S-adenosyl-L-methionine 

Downstream Products

• 742077-30-1 7-benzyloxy-2-(3,4-dimethoxy-phenyl)-5-hydroxy-chromen-4-one 
• 29080-58-8 5-hydroxy-3',4',7-trimethoxyflavone 
• 124281-55-6 2',4',6'-Trihydroxy-3,4-dimethoxydihydrochalcone 
• 84122-44-1 5,7-diacetoxy-2-(3,4-dimethoxy-phenyl)-chromen-4-one 
• 848734-07-6 6-acetyl-5,7-dihydroxy-3',4'-dimethoxyflavone 
• 203191-70-2 7-t-butyloxycarbonylmethyloxy-5-hydroxy-3',4'-dimethoxy flavone 
• 847909-45-9 7-ethyloxycarbonylmethyloxy-5-hydroxy-3',4'-dimethoxy flavone 
• 847909-48-2 7-carboxymethyloxy-3',4',5-trimethoxy flavone anhydride 
• 847909-44-8 7-carboxymethyloxy-3',4',5-trimethoxy flavone monohydrate 
• 203191-10-0 7-carboxymethyloxy-3',4',5-trimethoxy flavone 
• 1092093-60-1 7-(tetrazol-5-ylmethyloxy)-3',4',5-trimethoxyflavone 
• 1092093-74-7 C₂₀H₁₇NO₆ 
• 1092093-73-6 C₁₉H₁₅NO₆ 
• 203191-28-0 7-carboxymethyloxy-5-hydroxy-3',4'-dimethoxy flavone 

Relevant academic research and scientific papers

A new flavone glucoside from Stachys aegyptiaca

In addition to 5,7,3'-trihydroxy-6,4'-dimethoxyflavone, 5,7,3'-trihydroxy-6,8,4'-trimethoxyflavone, isoscutellarein, luteolin, and luteolin-7-O-glucoside, the methanol extract of the aerial parts of Stachys aegyptiaca yielded a new flavone identified as luteolin 3',4'-dimethylether-7-O- β-D-glucoside on the basis of chemical and spectroscopic methods.

Flavonoid glycosides with a triazole moiety for marine antifouling applications: Synthesis and biological activity evaluation

Over the last decades, antifouling coatings containing biocidal compounds as active ingre-dients were used to prevent biofouling, and eco-friendly alternatives are needed. Previous research from our group showed that polymethoxylated chalcones and glycosy

Influence of Substrate Binding Residues on the Substrate Scope and Regioselectivity of a Plant O-Methyltransferase against Flavonoids

Methylation of free hydroxyl groups is an important modification for flavonoids. It not only greatly increases absorption and oral bioavailability of flavonoids, but also brings new biological activities. Flavonoid methylation is usually achieved by a specific group of plant O-methyltransferases (OMTs) which typically exhibit high substrate specificity. Here we investigated the effect of several residues in the binding pocket of the Clarkia breweri isoeugenol OMT on the substrate scope and regioselectivity against flavonoids. The mutation T133M, identified as reported in our previous publication, increased the activity of the enzyme against several flavonoids, namely eriodictyol, naringenin, luteolin, quercetin and even the isoflavonoid genistein, while a reduced set of amino acids at positions 322 and 326 affected both, the activity and the regioselectivity of the methyltranferase. On the basis of this work, methylated flavonoids that are rare in nature were produced in high purity.

Synthesis of 5-Hydroxy-3′,4′,7-trimethoxyflavone and Related Compounds and Elucidation of Their Reversal Effects on BCRP/ABCG2-Mediated Anticancer Drug Resistance

3′,4′,7-Trimethoxyflavone (TMF) has been reported to show a potent reversal effect on drug resistance mediated by breast cancer resistance protein (BCRP)/ATP-binding cassette subfamily G member 2 (ABCG2). In this study, we designed and synthesized five derivatives with either a hydroxy group or a fluorine atom at C-5 and several kinds of capping moiety at the C-7 hydroxy group, on the same 3′,4′-dimethoxy-substituted flavone skeleton. We subsequently evaluated the efficacies of these compounds against BCRP-expressing human leukaemia K562/BCRP cells. Reversal of drug resistance was expressed as the concentration of compound causing a twofold reduction in drug sensitivity (RI50). Of the synthesized compounds, the reversal effect of 5-hydroxy-3′,4′,7-trimethoxyflavone (HTMF, RI50 7.2 nm) towards 7-ethyl-10-hydroxycamptothecin (SN-38) was stronger than that of TMF (RI50 18 nm). Fluoro-substituted 5-fluoro-3′,4′,7-trimethoxyflavone (FTMF, RI50 25 nm) and monoglycosylated 7-(β-glucosyloxy)-5-hydroxy-3′,4′-dimethoxyflavone (GOHDMF, 91 nm) also exhibited reversal effects, whereas the di- and triglycoside derivatives did not. TMF, HTMF and FTMF at 0.01–10 μm upregulated the K562/BCRP cellular accumulation of Hoechst 33342 nuclear staining dye. In addition, western blotting revealed that treatment of K562/BCRP cells with 0.1 μm TMF, HTMF or FTMT suppressed the expression of BCRP. HTMF showed the strongest inhibition of BCRP-mediated efflux and suppression of BCRP expression of the three effective synthesized flavones.

Structure-activity relationship of the inhibitory effects of flavonoids on nitric oxide production in RAW264.7 cells

We isolated flavonoids from herbal specimens from the Tibetan region (Sophora yunnanensis and Rhodiola sacra) that suppress nitric oxide (NO) production in macrophages stimulated by lipopolysaccharide and interferon-γ. The isolated flavonoids carry symmetric substitutions in the B ring (R3′= R5′). We analyzed the quantitative structure-activity relationship of the inhibitory activity by comparative molecular field analysis (CoMFA) using this series of flavonoids. Use of flavonoids with symmetrical substitutions in the B ring made it simpler to align molecules because it was not necessary to consider a huge number of combinations due to the B-ring conformation. The CoMFA model, whose cross-validated q2value was 0.705, suggested the existence of a hydroxy group at the 5-position, the choice of the A/C-ring scaffold (chromane or chromene) and electrostatic field around the B ring are important for NO inhibitory activity. Flavonoids synthesized based on the CoMFA model exhibited significant inhibitory potential against NO production, validating the predictive capability of the CoMFA model.

Whitening cosmetic composition comprising chromone derivatives

The present invention relates to a skin whitening cosmetic composition comprising chromone derivatives having a similar structure with aloesin derived from natural materials. According to the present invention, a chromone derivative compound has excellent abilities on inhibiting the activity of tyrosinase, can be synthesized in large quantity, shows an excellent skin whitening effect even if a small amount is applied, maximizes a whitening effect of skin whitening ingredients, and has few side effects by using derivatives derived from natural materials.

A new synthesis for acacetin, chrysoeriol, diosmetin, tricin and other hydroxylated flavones by modified Baker-Venkataraman transformation

Baker-Venkataraman (BV) rearrangement is the method of choice for the synthesis of flavones. The major limitation of BV is that it requires extensive protections and deprotections of hydroxyl groups which make the process lengthy and cumbersome. In the present study, a three step efficient method has been developed using simple protecting groups and easily available starting materials. New syntheses for acacetin, chrysoeriol, diosmetin, tricin and other hydroxylated flavones are described.

Modulation of human neutrophils' oxidative burst by flavonoids

Inflammation is a normal response towards tissue injury, but may become deleterious to the organism if uncontrolled. The overproduction of reactive species during the inflammatory process may cause or magnify the damage at inflammatory sites. Flavonoids have been suggested as therapeutic agents to avoid such damage, as these compounds exhibit anti-inflammatory activity, through the modulation of oxidative stress and signalling pathways. Both effects may attenuate neutrophils' activities at inflammatory sites. In this study,we investigated the structure/activity relationship of a series of flavonoids on the oxidative burst of human neutrophils in vitro, as a measure of its anti-inflammatory potential. Neutrophils were stimulated with phorbol-12-myristate-13-acetate, and fluorescence and chemiluminescence techniques were used to evaluate the generation of reactive oxygen species. All the tested flavonoids revealed the ability to modulate the neutrophil 's oxidative burst. From the obtained results, the pivotal role of the catechol group in the B-ringwas evidenced as well as the minor importance of the hydroxylations in the A-ring, which did not appear to be determinant for the activity, although clearly influencing the lipophilicity of the tested flavonoids. It is also clarified the importance of the methylation in the OH group at the B-ring catechol moiety. In conclusion, the obtained results uncover new possible strategies for the resolution of inflammatory processes, using flavonoids to modulate neutrophil's oxidative burst.

Chemical examination of juice of Citrus sinensis variety Jaffa

Phytochemical examination of Citrus sinensis juice var. Jaffa resulted in the isolation of 5,7-dihydroxy-3′,4′-dimethoxyflavanone 7-O-rhamnosyl(1→2)glucoside which is a hitherto unreported compound.

Solvent-free synthesis of functionalized flavones under microwave irradiation

(Chemical Equation Presented) Eco-friendly direct solvent-free synthesis of flavones is achieved by microwave irradiation of phloroglucinol and β-ketoesters. Heating with microwaves versus under classical conditions was shown to be higher yielding, cleaner, and faster. The reaction goes through a cycloaddition of an α-oxo ketene intermediate followed by an uncatalyzed thermal Fries rearrangement.