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

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

Uses

Used in Pharmaceutical Applications:
4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dimethoxyis used as a pharmaceutical agent for its potential medicinal properties. Its antioxidant and anti-inflammatory activities contribute to the development of treatments for various diseases and conditions.
Used in Agrochemical Applications:
In the agrochemical industry, 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dimethoxyis utilized for its potential applications in crop protection and enhancement of plant growth. Its biological activities can be harnessed to develop novel agrochemical products with improved efficacy and reduced environmental impact.
Used in Cosmetic Applications:
4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dimethoxyis employed in the cosmetic industry as an active ingredient for its antioxidant and anti-inflammatory properties. It can be incorporated into skincare products to provide benefits such as skin protection, hydration, and anti-aging effects.
Used in Food and Beverage Applications:
4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dimethoxycan also be used in the food and beverage industry as a natural preservative and flavor enhancer. Its antioxidant properties can help extend the shelf life of food products, while its potential medicinal properties may contribute to the development of functional foods and beverages with health benefits.

Upstream product

• 854678-45-8 β-(3,5-dimethoxyphenoxy)propionic acid 
• 501428-25-7 3-(3',5'-dimethoxyphenoxy)propionitrile 
• 500-99-2 3,5-dimethoxyphenol 
• 59887-91-1 5,7-dimethoxy-4H-chromen-4-one 
• 621-23-8 1,2,3-trimethoxybenzene 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 

Downstream Products

• 1282041-34-2 (E)-5,7-dimethoxy-3-(4-chlorobenzylidene)-4-chromanone 
• 1282041-32-0 (E)-5,7-dimethoxy-3-(benzylidene)chroman-4-one 
• 1282041-33-1 (E)-5,7-dimethoxy-3-(4'-hydroxybenzylidene)chroman-4-one 
• 27181-65-3 (E)-5,7-dimethoxy-3-(4-methoxybenzylidene)-4-chromanone 
• 1392217-69-4 5,7-dimethoxy-3-(2′hydro-xybenzyl)-4-chromanone 
• 17060-20-7 2,3-dihydro-5,7-dimethoxy-2-(4'-dimethoxyphenyl)-4H-1-benzopyran-4-one 
• 66074-95-1 4',5,7-trimethoxyflavanone 
• 1036-72-2 5,7-dimethoxyflavone 
• 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 

Relevant articles and documents

HETEROCYCLIC ACYL HYDRAZONE LINKERS, METHODS AND USES THEREOF

The present application is directed to compounds of Formula (I): compounds of Formula (II): compounds of Formula (III): and compounds of Formula (IV): compositions comprising these compounds and their uses, for example as medicaments and /or diagnostics.

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

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

Inventors of the present invention synthesized natural homoisoflavonoid portulacanone D (compound 6) isolated from Portulaca oleracea L (POL). An ability to inhibit NO production in LPS-induced RAW 264.7 macrophages was assessed as an indicator of anti-inflammatory activity. The tested portulacanone D did not show clear cytotoxicity and inhibited NO production in the RAW 264.7 macrophages in a concentration dependent manner. The portulacanone D exhibits 92.5% of NO production inhibition at 10 andmu;M and has an IC50 value of 2.09 andmu;M. The finding has additional correlation with the suppressed expression of iNOS induced by LPS. According to the information obtained from the study of the present invention, the portulacanone D can be used in the development of anti-inflammatory drugs targeting NO production.COPYRIGHT KIPO 2019

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.

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.

Novel homoisoflavanone derivatives, preparation method thereof, and pharmaceutical composition for use in preventing or treating ischemic brain damage and multiple sclerosis containing the same as an active ingredient

The present invention relates to: a homoisoflavanone compound; a manufacturing method thereof; and a pharmaceutical composition for preventing or treating ischemic brain damage and multiple sclerosis containing the homoisoflavanone compound as an active i

Anti-inflammatory activities of selected synthetic homoisoflavanones

Four homoisoflavanones of the 3-benzylidene-4-chromanone type, some of which were previously isolated from Caesalpinia pulcherrima, were synthesised to determine their anti-inflammatory activity and cytotoxicity. A range of four different homoisoflavanones (compounds 4a-4d) were synthesised from the corresponding substituted phenols.1H-and 13C-NMR data together with high-resolution mass spectroscopy data were employed to elucidate the structures. Anti-inflammatory activity was determined in mice with acute croton oil-induced auricular dermatitis. Invitro cytotoxicity was tested against a Chinese hamster ovarian cell line using the 3-(4,5-dimethylthiazol-2-yl)-2,5- diphenyltetrazoliumbromide (MTT) assay. Compound 4a exhibited a tendency to inhibit oedema in a dose-dependent manner after 3 and 6 h of treatment. Compounds 4b-4d also inhibited oedema, although a clear dose-response relationship was not observed. Compounds 4a-4c were found to be less cytotoxic than compound 4d. Compound 4b was the least cytotoxic. Compounds 4a-4d exhibited anti-inflammatory activity and varying levels of cytotoxicity.

Synthesis and NMR elucidation of homoisoflavanone analogues

A series of five homoisoflavanone analogues have been synthesized from the corresponding 3,5-methoxy phenols via chroman-4-one in three steps. The complete NMR elucidation of these homoisoflavanone analogues is reported. The use of 2D NMR techniques (COSY, NOESY, HSQC and HMBC) proved to be very useful tools in the elucidation of homoisoflavanone analogues. The homoisoflavanone analogues exhibit an AA0BB0 spin pattern in the ring B of the homoisoflavanone. These homoisoflavanone analogues are potential antifungal and anti-inflammatory agents. Springer Science+Business Media, LLC 2010.

Studies towards the stereoselective α-hydroxylation of flavanones. Biosynthetic significance

The enolates of various propiophenones, chromanones, and also analogues of naturally occurring flavanones were stereoselectively hydroxylated at the ?-position, by employing commercially available enantiopure oxaziridines, to afford the desired ?-hydroxylated target molecules in good to exceptional stereoselectivities and in moderate to good chemical yields. A mechanistic rationale is presented to account for the stereoselectivities achieved. These in vitro results were tentatively related to the stereoselective biosynthesis of enantio-enriched dihydroflavonols while questions were raised about the authenticity of certain natural compounds. CSIRO 2008.

Isomerisation of 3-Benzylidene-4-chromanones in Presence of Alkali

3-Benzylidene-4-chromanones (Ia-d) having 7-methoxy, 7-benzyloxy- or 5,7-dimethoxy groupings in ring-A undergo alkali isomerisation to yield both the corresponding 3-benzyl-4-chromones (IIa-d) and 3-methylflavones (IIIa-d).Hence both the types of isomeris