54107-66-3

Basic information

• Product Name: 4H-1-benzopyran-4-one, 2,3-dihydro-5,7-diMethoxy-
• Synonyms: 4H-1-benzopyran-4-one, 2,3-dihydro-5,7-diMethoxy-;5,7-DiMethoxychroMan-4-one;5,7-DIMETHOXY-3,4-DIHYDRO-2H-1-BENZOPYRAN-4-AMINE;5,7-dimethoxy-4-Chromanone
• CAS NO: 54107-66-3
• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 208.21058
• Mol File: 54107-66-3.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4H-1-benzopyran-4-one, 2,3-dihydro-5,7-diMethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-benzopyran-4-one, 2,3-dihydro-5,7-diMethoxy-(54107-66-3)
• EPA Substance Registry System: 4H-1-benzopyran-4-one, 2,3-dihydro-5,7-diMethoxy-(54107-66-3)

Safety Data

• Hazardous Substances Data: 54107-66-3(Hazardous Substances Data)

Usage

General Description

The chemical 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dimethoxy- is a type of organic compound with the molecular formula C11H12O4. It belongs to the class of flavonoids and is also known as sakurannin. 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dimethoxy- is found in various natural products and plants, and it has been studied for its potential biological activities. It is considered to have antioxidant, anti-inflammatory, and potential medicinal properties. Its structure contains a benzopyran ring system with two methoxy groups at positions 5 and 7, and a carbonyl group at position 4. This chemical compound has shown promise in various pharmaceutical and agrochemical applications due to its diverse biological activities and relatively low toxicity.

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Downstream Products

• 1392217-69-4 5,7-dimethoxy-3-(2′hydro-xybenzyl)-4-chromanone 
• 1036-72-2 5,7-dimethoxyflavone 
• 66074-95-1 4',5,7-trimethoxyflavanone 
• 17060-20-7 2,3-dihydro-5,7-dimethoxy-2-(4'-dimethoxyphenyl)-4H-1-benzopyran-4-one 
• 105245-63-4 3-(3,4-dimethoxybenzyl)-5,7-dimethoxychroman-4-one 
• 246244-10-0 rac-5,7-dimethoxy-3-(4-methoxybenzyl)-chroman-4-one 
• 76672-84-9 3-benzyl-5,7-dimethoxychroman-4-one 

Relevant articles and documents

Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids

A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.

Synthetic method for portulacanone compounds and their derivatives and anti-inflammatory pharmaceutical compounds containing thereof

The present inventors synthesized described portulacanone derivatives (compound 1: R^1, R^2 = H; and compound 2: R^1, R^2 = H), natural homoisoflavonoids (andplusmn;)-portulacanone A-C (compound 4: R^1 = OMe, R^2 = H; compound 8: R^1, R^2 = OMe; and compound 9: R^1 = OH, R^2 = OMe), and derivatives thereof (compound 3: R^1 = OMe, R^2 = H; compound 5: R^1 = OH, R^2 = H, and compound 7: R^1, R^2 = OMe), and thus evaluated ability to inhibit NO production in LPS-induced RAW 264.7 macrophages as an indicator of anti-inflammatory activity. All tested compounds showed no clear cytotoxicity and inhibited NO production in a concentration dependent manner in RAW 264.7 macrophages. A compound 3 (97.2% inhibition at 10 andmu;M; IC50 = 1.26 andmu;M) shows a significant inhibition effect compared to a compound 1 (91.4% inhibition at 10 andmu;M; IC50 = 1.75 andmu;M) and a compound 7 (83.0% inhibition at 10 andmu;M; IC50 = 2.91 andmu;M). Compounds of the present invention are useful for developing NO producing targeted anti-inflammatory drugs.COPYRIGHT KIPO 2019

Synthesis and in vitro evaluation of homoisoflavonoids as potent inhibitors of nitric oxide production in RAW-264.7 cells

Syntheses of natural homoisoflavonoids, (±)-portulacanones A–C (4, 8 and 9), portulacanone D (6), isolated from Portulaca oleracea L. (POL) and their derivatives (3, 5 and 7) have been achieved for the first time along with the synthesis of known derivatives (1 and 2) and their in vitro inhibitory effect against NO production in LPS-induced RAW-264.7 macrophages was evaluated as an indicator of anti-inflammatory activity. All the compounds tested had a concentration-dependent inhibitory effect on NO production by RAW-264.7 macrophages without obvious cytotoxicity. Compounds 3 (97.2% at 10 μM; IC50 = 1.26 μM) followed by 6 (portulacanone D) (92.5% at 10 μM; IC50 = 2.09 μM), 1 (91.4% at 10 μM; IC50 = 1.75 μM) and 7 (83.0% at 10 μM; IC50 = 2.91 μM) were the most potent from the series. This finding was further correlated with the suppressed expression of iNOS induced by LPS. Our promising preliminary results may provide the basis for the assessment of compound 3 as a lead structure for a NO production-targeted anti-inflammatory drug development and also could support the usefulness of POL as a folklore medicinal plant in the treatment of inflammatory diseases.