29424-96-2

Basic information

• Product Name: 4',7-Di-O-methylnaringenin
• Synonyms: 4',7-Di-O-methylnaringenin;(S)-5-Hydroxy-7,4'-dimethoxyflavanone;2,3-Dihydro-5-hydroxy-4',7-dimethoxyflavone;(S)-5-Hydroxy-7-Methoxy-2-(4-Methoxyphenyl)chroMan-4-one;(?)-5-Hydroxy-4′,7-dimethoxyflavanone;(S)-2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one;Naringenin 4′,7-dimethyl ether;Sakuranetin 4′-methyl ether
• CAS NO: 29424-96-2
• Molecular Formula: C₁₇H₁₆O₅
• Molecular Weight: 300.30594
• Mol File: 29424-96-2.mol

Chemical Properties

• Boiling Point: 524.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.281±0.06 g/cm3(Predicted)
• Storage Temp.: ?20°C
• PKA: 7.40±0.40(Predicted)
• CAS DataBase Reference: 4',7-Di-O-methylnaringenin(CAS DataBase Reference)
• NIST Chemistry Reference: 4',7-Di-O-methylnaringenin(29424-96-2)
• EPA Substance Registry System: 4',7-Di-O-methylnaringenin(29424-96-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-45
• WGK Germany: 3
• Hazardous Substances Data: 29424-96-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
4',7-Di-O-methylnaringenin is used as a therapeutic agent for its potential role in reducing the risk of cancer and cardiovascular diseases. Its antioxidant and anti-inflammatory properties make it a promising candidate for the development of treatments targeting these conditions.
Used in Metabolic Health Improvement:
4',7-Di-O-methylnaringenin is utilized as a dietary supplement to enhance metabolic health, potentially aiding in the management of obesity and related metabolic disorders.
Used in Menopause and Osteoporosis Management:
In the healthcare industry, 4',7-Di-O-methylnaringenin is used as a natural remedy to alleviate menopausal symptoms and improve bone health, thus reducing the risk of osteoporosis.
Used in Functional Foods and Beverages:
4',7-Di-O-methylnaringenin is incorporated into functional foods and beverages as a natural additive for its health-promoting properties, targeting consumers seeking natural ways to improve their overall well-being and reduce the risk of chronic diseases.

Upstream product

• 3420-72-2 2'-hydroxy-4,4',6'-trimethoxychalcone 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 17176-17-9 S-Adenosylmethionine 
• 20621-49-2 2',6'-dihydroxy-4,4'-dimethoxychalcone 
• 77-78-1 dimethyl sulfate 
• 480-41-1 naringenin 
• 123-11-5 4-methoxy-benzaldehyde 
• 3420-72-2 flavokawain A 
• 66074-95-1 4',5,7-trimethoxyflavanone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 491-69-0 (2S)-poncirenin 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 

Downstream Products

• 3791-75-1 2'-hydroxy-4,4',6'-trimethoxydihydrochalcone 
• 1390643-64-7 8-bromo-5-hydroxy-7,4'-dimethoxyflavone 
• 35095-48-8 6-bromo-5-hydroxy-7,4'-dimethoxyflavone 
• 529-53-3 scutellarein 
• 19103-54-9 5-hydroxy-4',6,7-trimethoxyflavone 
• 221257-06-3 7,4'-di-O-methylapigenin 5-O-1-β-xylopyranosyl(1->6)-β-glucopyranoside 
• 81148-82-5 5-acetoxy-7,4′-dimethoxyflavanone 
• 126116-61-8 N^α-benzyloxycarbonyl-N^ε-<(6'-hydroxy-4,4'-dimethoxydihydrochalcone)-2'-yloxy>acetyl-L-lysine benzyl ester 
• 126116-66-3 homoseryl>glycine benzyl ester 
• 126116-56-1 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-{3-hydroxy-5-methoxy-2-[3-(4-methoxy-phenyl)-propionyl]-phenoxy}-tetrahydro-pyran-4-yl ester 
• 126116-68-5 N-benzyloxycarbonyl-homoseryl>glycine ethyl ester 
• 126116-69-6 homoseryl>glycine 
• 126116-63-0 N-benzyloxycarbonyl-O-<(6'-hydroxy-4,4'-dimethoxydihydrochalcone)-2'-yl>homoserine methyl ester 
• 126116-64-1 N-benzyloxycarbonyl-O-<(6'-hydroxy-4,4'-dimethoxydihydrochalcone)-2'-yl>homoserine 

Relevant articles and documents

Flavanone compound as well as preparation method and application thereof

The invention belongs to the technical field of medicines, and particularly relates to a flavanone compound as well as a preparation method and application thereof. Specifically disclosed is a compound represented by formula (I) or a pharmaceutically acceptable salt thereof. The compound shown in the formula (I) can target hURAT1 and/or GLUT9, so that uric acid excretion is promoted, and the effect of reducing uric acid is achieved. The compound can be used for preparing medicines for treating and/or preventing and/or delaying and/or adjunctively treating and/or treating diseases related to hURAT1/GLUT9 activity, and has a good application prospect in preventing or treating diseases (such as gout, gouty arthritis, uric acid kidney stone and the like) related to hyperuricemia.

Semisynthesis of prunetin, a bioactive O-methylated isoflavone from naringenin, by the sequential deacetylation of chalcone intermediates and oxidative rearrangement

Prunetin (4′,5-dihydroxy-7-methoxyisoflavone) was semisynthesized in 8 steps from readily available naringenin in 26% total yield. The key reaction was chemoenzymatic sequential deacetylation to 6′-acetoxy-2′,4″-dihydroxy-4′-methoxychalcone, the in situ-formed precursor for thallium(III) nitrate-mediated oxidative rearrangement.

Synthesis and Evaluation of the Acetylcholinesterase Inhibitory Activities of Some Flavonoids Derived from Naringenin

Alzheimer's disease (AD) is an irreversible neurodegenerative disease that affects many older people adversely. AD has been putting a huge socioeconomic burden on the healthcare systems of many developed countries with aging populations. The need for new therapies that can halt or reverse the progression of the disease is now extremely great. A research approach in the finding new treatment for AD that has attracted much interest from scientists for a long time is the reestablishment of cholinergic transmission through inhibition of acetylcholinesterase (AChE). Naringenin is a flavonoid with the potential inhibitory activity against AChE. From naringenin, many other flavonoid derivatives, such as flavanones and chalcones, can be synthesized. In this study, by applying the Williamson method, nine flavonoid derivatives were synthesized, including four flavanones and five chalcones. The evaluation of AChE inhibitory activity by the Ellman method showed that there were four substances (2, 4, 5, and 7) with relatively good biological activities (IC50 100 μM), and these biological activities were better than that of naringenin. The molecular docking revealed that strong interactions with amino acid residue Ser200 of the catalytic triad and those of the peripheral region of the enzyme were crucial for strong effects against AChE. Compound 7 had the strongest AChE inhibitory activity (IC50 13.0 ± 1.9 μM). This substance could be used for further studies.

Total synthesis of agalloside, isolated from: Aquilaria agallocha, by the 5-O-glycosylation of flavan

Agalloside (1) is a neural stem cell differentiation activator isolated from Aquilaria agallocha by our group using Hes1 immobilized beads. We conducted the first total synthesis of agalloside (1) via the 5-O-glycosylation of flavan 25 using glycosyl fluoride 20 in the presence of BF3·Et2O. Subsequent oxidation with DDQ to flavanone 2 and deprotection successively provided agalloside (1). This synthetic strategy holds promise for use in the synthesis of 5-O-glycosylated flavonoids. The synthesized agalloside (1) accelerated neural stem cell differentiation, which is a result comparable to that for the naturally occurring compound 1.

A Biomimetic Strategy to Access the Silybins: Total Synthesis of (-)-Isosilybin A

(Figure Presented). We report the first asymmetric, total synthesis of (-)-isosilybin A. A late-stage catalytic biomimetic cyclization of a highly functionalized chalcone is employed to form the characteristic benzopyranone ring. A robust and flexible app

Efficient synthesis of scutellarein

Scutellarein is a component of Scutellaria, recently known as a potent cytotoxic agent on human leukaemia cells. The aim of this study was the synthesis of scutellarein and its methylated derivative. The new features are the innovating method to afford flavones from flavanones and the A-ring regioselective bromination step that lead to the target molecule by a facile and high-yielding pathway.

Purification and identification of naringenin 7-O-methyltransferase, a key enzyme in biosynthesis of flavonoid phytoalexin sakuranetin in rice

Sakuranetin, the major flavonoid phytoalexin in rice, is induced by ultraviolet (UV) irradiation, CuCl2 treatment, jasmonic acid treatment, and infection by phytopathogens. It was recently demonstrated that sakuranetin has anti-inflammatory activity, anti-mutagenic activity, anti-pathogenic activities against Helicobacter pylori, Leishmania, and Trypanosoma and contributes to the maintenance of glucose homeostasis in animals. Thus, sakuranetin is a useful compound as a plant antibiotic and a potential pharmaceutical agent. Sakuranetin is biosynthesized from naringenin by naringenin 7-O-methyl-transferase (NOMT). In previous research, rice NOMT (OsNOMT) was purified to apparent homogeneity from UV-treated wild-type rice leaves, but the purified protein, named OsCOMT1, exhibited caffeic acid O-methyltransferase (COMT) activity and not NOMT activity. In this study, we found that OsCOMT1 does not contribute to sakuranetin production in rice in vivo, and we purified OsNOMT using the oscomt1 mutant. A crude protein preparation from UV-treated oscomt1 leaves was subjected to three sequential purification steps, resulting in a 400-fold purification from the crude enzyme preparation. Using SDS-PAGE, the purest enzyme preparation showed a minor band at an apparent molecular mass of 40 kDa.Two O-methyltransferase-like proteins, encoded by Os04g0175900 and Os12g0240900, were identified from the 40-kDa band by MALDI-TOF/TOF analysis. Recombinant Os12g0240900 protein showed NOMT activity, but the recombinant Os04g0175900 protein did not. Os12g0240900 expression was induced by jasmonic acid treatment in rice leaves prior to sakuranetin accumulation, and the Os12g0240900 protein showed reasonable kinetic properties toOsNOMT.Onthe basis of these results, we conclude that Os12g0240900 encodes an OsNOMT.

Efficient one-pot synthesis of hydroxyflavanones by cyclization and O-demethylation of methoxychalcones

An efficient one-pot method for the synthesis of hydroxyflavanones is described. Methoxychalcones are treated with 36% HBr to afford cyclization and regioselective O-demethylation products (2a-i) while cyclization and complete O-demethylation products (3a

Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids

The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3′,4′,5,6,7,8- heptamethoxyflavone, quercetin and its derivatives were synthesized.

Total synthesis of flavocommelin, a component of the blue supramolecular pigment from Commelina communis, on the basis of direct 6-C-glycosylation of flavan

We succeeded in a first total synthesis of flavocommelin (1), a component of the blue supramolecular pigment, commelinin (2), from Commelina communis, by direct 6-C-glycosylation of the flavan 4 using perbenzylglucosyl fluoride 8 in the presence of MS 5 A in CH2Cl2 and a catalytic amount of BF3·Et2O. After 6-C-glycosylation of 4, oxidation with CAN to flavanone 18 and subsequent 4′-O-glycosylation, promoted with a combination of BF3·Et2O and DTBMP, afforded diglucosylflavanone 20. DDQ oxidation of 20 and deprotection successively gave 1.