4049-38-1

Usage

Uses

Used in Pharmaceutical Industry:
Eriodictyol is used as a pharmaceutical agent for its potent antioxidant properties. It helps in protecting the body from oxidative stress and free radicals, which are known to cause cellular damage and contribute to various diseases.
Used in Cosmetics Industry:
Eriodictyol is used as an ingredient in the cosmetics industry for its antioxidant and anti-inflammatory properties. It is often included in skincare products to help protect the skin from environmental stressors and promote a healthy, radiant complexion.
Used in Food and Beverage Industry:
Eriodictyol is used as a natural antioxidant in the food and beverage industry to extend the shelf life of products and maintain their freshness. It can be found in various food products, such as fruit juices, to help prevent spoilage and preserve their nutritional value.
Used in Nutraceutical Industry:
Eriodictyol is used as a nutraceutical ingredient for its potential health benefits, including its antioxidant and anti-inflammatory properties. It can be found in dietary supplements and functional foods, aiming to support overall health and well-being.

InChI:InChI=1/C15H12O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-5,13,16-19H,6H2/t13-/m1/s1

Upstream product

• 14917-41-0 2',3,4,4',6'-pentahydroxychalcone 
• 10496-67-0 3-(3,4-dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 314734-03-7 2'-hydroxy-3,4,4',6'-tetrakis(methoxymethoxy)chalcone 
• 108-73-6 3,5-dihydroxyphenol 
• 618910-88-6 eriodictyol-7-O-β-D-glucuronopyranoside 
• 128837-28-5 3,4-Di(ethoxymethoxy)benzaldehyde 
• 128837-25-2 1-[2,4-bis(ethoxymethoxy)-6-hydroxyphenyl]ethan-1-one 
• 17060-20-7 2,3-dihydro-5,7-dimethoxy-2-(4'-dimethoxyphenyl)-4H-1-benzopyran-4-one 
• 114021-60-2 2'-hydroxy-3,4,4',6'-tetramethoxychalcone 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 215257-15-1 3,3',4',5,7-pentahydroxy flavanone 

Downstream Products

• 6599-89-9 5,7,3',4'-tetrahydroxyflavanone tetraacetate 
• 57765-66-9 eriodictoyl dihydrochalcone 
• 93012-86-3 7-methoxy-3',4',5-trihydroxyflavanone 
• 123477-16-7 3,4,2',4',6'-pentaacetoxy-chalcone 
• 446-06-0 2-(3,4-dihydroxyphenyl)chromane-5,7-diol 
• 4250-76-4 3’,4’-dimethyleriodictyol 
• 446-71-9 (+/-)-homoeriodictyol 
• 17654-26-1 (2S,3R)-cis-dihydroquercetin 
• 17654-26-1 trans-dihydroquercetin 
• 491-70-3 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on 

Relevant academic research and scientific papers

Total synthesis of novel skeleton flavan-alkaloids

The first total synthesis of novel skeleton natural compounds kinkeloids A and B, a group of newly discovered flavan alkaloids isolated fromthe African plant Combretum micranthum, are described in this study. The key and final step are achieved by Mannich reaction, through which the piperidine moiety couples to the flavan moiety. The identities of synthesized kinkeloids were further confirmed through a comparison with the ones in the plant leaves extract using LC/MS.

Biological Properties and Absolute Configuration of Flavanones From Calceolaria thyrsiflora Graham

Flavanones (–)-(2S)-5,4’-dihydroxy-7-methoxyflavanone (1) and (–)-(2S)-5,3’,4’-trihydroxy-7-methoxyflavanone (2) were isolated from the extracts of Calceolaria thyrsiflora Graham, an endemic perennial small shrub growing in the central zone of Chile. The absolute configuration of these compounds was resolved by optical rotation experiments and in silico calculations. Three analogs (3, 4, and 5) were synthesized to do structure-activity relationships with the biological assays studied. Biological tests revealed that only flavanone 2 exhibited a moderate inhibitory activity against the methicillin-resistant strain S. aureus MRSA 97-77 (MIC value of 50 μg/ml). In addition, flavanone 2 showed a potent, selective, and competitive inhibition of 5-hLOX, which supports the traditional use of this plant as an anti-inflammatory in diseases of the respiratory tract. Also, 2 exhibited cytotoxic and selective effects against B16-F10 (8.07 ± 1.61 μM) but 4.6- and 17-fold lesser activity than etoposide and taxol.

Use of flavone and flavanone derivatives in preparation of sedative and hypnotic drugs

Disclosed is a use of flavones derivatives and flavanone derivatives in preparation of sedative and hypnotic drugs.

Eriodictyol synthesis method

The invention provides an eriodictyol synthesis method. According to the eriodictyol synthesis method, isovanillin and 2,4,6-trihydroxyacetophenone are selected as starting materials, and eriodictyol is obtained through the following five steps: firstly, performing MOMCl protection on a hydroxyl of isovanillin; secondly, performing MOMCl protection on a hydroxyl of 2,4,6-trihydroxyacetophenone; thirdly, performing an aldol condensation reaction to generate chalcone; fourthly, performing Michael addition and cyclization; finally, carrying out MOM deprotection to obtain eriodictyol of which the total yield is 50-65%. As isovanillin and 2,4,6-trihydroxyacetophenone are selected as the starting materials, the eriodictyol synthesis method is high in yield and suitable for industrialized production.

USE OF FLAVONE AND FLAVANONE DERIVATIVES IN PREPARATION OF SEDATIVE AND HYPNOTIC DRUGS

Disclosed is a use of flavones derivatives and flavanone derivatives in preparation of sedative and hypnotic drugs.

Production of hydroxlated flavonoids with cytochrome P450 BM3 variant F87V and their antioxidative activities

A variant of P450 BM3 with an F87V substitution [P450 BM3 (F87V)] is a substrate-promiscuous cytochrome P450 monooxygenase. We investigated the bioconversion of various flavonoids (favanones, chalcone, and isoflavone) by using recombinant Escherichia coli cells, which expressed the gene coding for P450 BM3 (F87V), to give their corresponding hydroxylated products. Potent antioxidative activities were observed in some of the products.

DPPH radical scavenging reaction of hydroxy- and methoxychalcones

The DPPH radical scavenging activity of 2′,4′,6′- trihydroxy- and 2′-hydroxy-4′,6′-dimethoxychalcones carrying a 2,3- and 3,4-dihydroxylated, and 3,4,5-trihydroxylated B-ring was evaluated in alcoholic and non-alcoholic solvents. All test compounds scavenged more than two equivalent of radicals by a possible conversion to the corresponding B-ring quinones and in most cases subsequently underwent cyclization to aurones and flavanones, these being identified in the reaction solutions by an in situ NMR analysis. Interestingly, the reaction between 2′,3,4-trihydroxy-4′, 6′-dimethoxychalcone and the DPPH radical was significantly affected by the solvent used, which might be accounted for by the difference in readiness for cyclization to an aurone.

(±)-Diinsininone: made nature's way

We report the synthesis of diinsininone (33), the aglycone of (±)-diinsinin (2). Thereby, we complete the first construction of a proanthocyanidin (PA) type-A compound incorporating a [3.3.1]-bicyclic ketal as its characteristic core. Our strategy utilizes a coupling between a benzopyrilium salt and a flavanone that proves applicable to other PA type-A compounds. During this undertaking, treatment of naringenin (9) with 2-iodoxybenzoic acid (IBX) followed by reductive work-up affords eriodictyol (10). This reactivity mirrors that of catechol hydroxylase (F3H) found in the flavonoid pathway. Other interesting transformations include the formation of flavonoids through an ortho-quinone methide (o-QM) cycloaddition-oxidation sequence and regioselective β-glycosidations of several unprotected flavanones suggesting a likely synthesis of 2 from the aglycone 33.