57765-66-9

Usage

Uses

Used in Pharmaceutical Industry:
ERIODICTYOL DIHYDROCHALCONE is used as an antioxidant for its ability to neutralize free radicals and protect cells from oxidative damage, which is a major contributor to aging and various diseases.
Used in Anticancer Applications:
ERIODICTYOL DIHYDROCHALCONE is used as an anticancer agent for its effects on human cancer cell lines. It has been shown to inhibit the growth and proliferation of cancer cells, making it a promising candidate for the development of novel cancer treatments.
Used in Cosmetic Industry:
ERIODICTYOL DIHYDROCHALCONE is used as an ingredient in cosmetics for its antioxidant properties, which help protect the skin from environmental stressors and promote a healthier, more youthful appearance.
Used in Food Industry:
In the food industry, ERIODICTYOL DIHYDROCHALCONE is used as a natural antioxidant to extend the shelf life of products and maintain their freshness and quality.
Used in Research:
ERIODICTYOL DIHYDROCHALCONE is also used in scientific research as a model compound to study the mechanisms of oxidative stress and cancer cell biology, contributing to the advancement of medical knowledge in these areas.

Upstream product

• 480-70-6 aureusidin 
• 4049-38-1 eriodictyol 
• 552-58-9 eriodictyol 
• 60-82-2 3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on 

Downstream Products

• 65236-01-3 3-(3,4-dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)propan-1-one 
• 861381-26-2 3,4,2',4',6'-pentamethoxydihydrochalcone 
• 6027-43-6 3′-C-β-D-glucopyranosyl-2′,3,4,4′,6′-pentahydroxydihydrochalcone 
• 122554-95-4 5,7-dihydroxy-3-(3,4-dihydroxybenzyl)chromone 

Relevant academic research and scientific papers

Enzymatic conversion of flavonoids using bacterial chalcone isomerase and enoate reductase

Flavonoids are a large group of plant secondary metabolites with a variety of biological properties and are therefore of interest to many scientists, as they can lead to industrially interesting intermediates. The anaerobic gut bacterium Eubacterium ramulus can catabolize flavonoids, but until now, the pathway has not been experimentally confirmed. In the present work, a chalcone isomerase (CHI) and an enoate reductase (ERED) could be identified through whole genome sequencing and gene motif search. These two enzymes were successfully cloned and expressed in Escherichia coli in their active form, even under aerobic conditions. The catabolic pathway of E. ramulus was confirmed by biotransformations of flavanones into dihydrochalcones. The engineered E. coli strain that expresses both enzymes was used for the conversion of several flavanones, underlining the applicability of this biocatalytic cascade reaction.

Regioselective hydroxylation of phloretin, a bioactive compound from apples, by human cytochrome p450 enzymes

Phloretin, the major polyphenol compound in apples and apple products, is interesting because it shows beneficial effects on human health. It is mainly found as a form of glucoside, phlorizin. However, the metabolic pathway of phloretin in humans has not been reported. Therefore, identifying phloretin metabolites made in human liver microsomes and the human cytochrome P450 (P450) enzymes to make them is interesting. In this study, the roles of human liver P450s for phloretin oxidation were examined using human liver microsomes and recombinant human liver P450s. One major metabolite of phloretin in human liver microsomes was 3‐OH phloretin, which is the same product of a bacterial CYP102A1‐catalyzed reaction of phloretin. CYP3A4 and CYP2C19 showed kcat values of 3.1 and 5.8 min?1, respectively. However, CYP3A4 has a 3.3‐fold lower Km value than CYP2C19. The catalytic efficiency of a CYP3A4‐catalyzed reaction is 1.8‐fold higher than a reaction catalyzed by CYP2C19. Whole‐cell biotransformation with CYP3A4 was achieved 0.16 mM h?1 productivity for 3‐OH phlorein from 8 mM phloretin at optimal condition. Phloretin was a potent inhibitor of CYP3A4‐catalyzed testosterone 6β‐hydroxylation activity. Antibodies against CYP3A4 inhibited up to 90% of the microsomal activity of phloretin 3‐hydroxylation. The immunoinhibition effect of anti‐2C19 is much lower than that of anti‐CYP3A4. Thus, CYP3A4 majorly contributes to the human liver microsomal phloretin 3‐hydroxylation, and CYP2C19 has a minor role.

Examination of the phenolic profile and antioxidant activity of the leaves of the australian native plant smilax glyciphylla

Together with the sweet principle component glycyphyllin A (3), seven phenolic compounds including two new dihydrochalcone rhamnopyranosides, glycyphyllin B (1) and glycyphyllin C (2), and five known flavonoids, catechin (4), kaempferol-3-O-β-d-glucopyranoside (5), quercetin-3-O-β-d- glucopyranoside (6), kaempferol-3-O-β-neohesperidoside (7), and 2R,3R-dihydrokaempferol-3-O-β-d-glucopyranoside (8), have been isolated from the ethanolic extract of the leaves of Smilax glyciphylla for the first time. The structures of these compounds were characterized by spectroscopic methods including UV, MS, and 1D and 2D NMR. In vitro antioxidant capacity tests employing FRAP and DPPH assays indicated that 1, 4, and 6 exhibited potent antioxidant activity and are the key phenolics responsible for the antioxidant activity of the leaf extract of S. glyciphylla.

AROMA COMPOSITIONS OF ALKAMIDES WITH HESPERETIN AND/OR 4-HYDROXYDIHYDROCHALCONES AND SALTS THEREOF FOR ENHANCING SWEET SENSORY IMPRESSIONS

The invention primarily relates to aroma compositions of (i) certain saliva-stimulating alkamides having a tingling, pungent and/or hot flavor (such as for example pellitorines, spilanthol) with (ii) hesperetin (5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-chroman-4-one) or the enantiomers and/or salts thereof and/or (iii) 4-hydroxydihydrochalcones (3-(4-hydroxyphenyl)-1-phenylpropan-1-ones) and/or the salts thereof, the use thereof to enhance the sweet flavor of sweet-tasting substances or the sweet odor impression of aroma substances which give rise to a sweet odor impression, but in particular to enhance the sweet initial flavor or odor (initial sweetness). The invention thus relates to the use of said aroma compositions as general sweetness enhancers and enhancers of initial sweetness. The invention further relates to certain preparations which contain an effective amount of said aroma compositions of (i) alkamides (such as in particular pellitorines, spilanthol) with (ii) hesperetin or the enantiomers and/or salts thereof and/or (iii) 4-hydroxydihydrochalcones and/or the salts thereof and methods for enhancing the sweet flavor or initial sweetness of a sweet-tasting substance or the sweet odor impression or initial sweetness of an aroma substance which gives rise to a sweet odor impression. The invention also relates to the use of certain alkamides (i) to enhance the initial sweetness of a preparation comprising (ii) hesperetin or the enantiomers and/or salts thereof and/or (iii) 4-hydroxydihydrochalcones and/or the salts thereof and (b) sweet-tasting substances and/or (c) aroma substances which give rise to a sweet odor impression.

Dihydrochalcones: Evaluation as novel radical scavenging antioxidants

Dihydrochalcones are a family of bicyclic flavonoids, defined by the presence of two benzene rings joined by a saturated three carbon bridge. In the present study, we systematically examined the antioxidant activities of dihydrochalcones against the stable free radical (1,1-diphenyl-2-picrylhydrazyl) and lipid peroxidation in the erythrocyte membrane. All dihydrochalcones exhibited higher antioxidant activities than the corresponding flavanones. The 1H NMR analysis indicated that the active dihydrochalcone has a time-averaged conformation in which the aromatic A ring is orthogonal to the carbonyl group, while the inactive dihydrochalcone such as 2′-O-methyl-phloretin has a strongly hydrogen-bonded phenolic hydroxyl group, suggestive of a coplanar conformation. A hydroxyl group at the 2′-position of the dihydrochalcone A ring, newly formed by reduction of the flavanone C ring, is an essential pharmacophore for its radical scavenging potential.

Anti-ulcer agent comprising chalcone derivative as effective ingredient and novel chalcone derivative

The present invention relates to an anti-ulcer agent comprising a compound represented by the following general formula I as the effective ingredient, and a novel chalcone derivative included in the compound represented by this general formula I: STR1 wherein X and Y independently stand for a hydrogen atom or together form a single bond, R1 stands for a hydroxyl group, an acetoxy group, a carboxymethoxy group or a methoxycarbonylmethoxy group, R2 stands for a hydrogen atom, an isoprenyl group, isopentyl group or a propyl group, R3 stands for hydroxyl group or a methoxy group, R4 stands for a hydrogen atom, a hydroxyl group or a methoxy group, R5 stands for a hydrogen atom, a hydroxyl group, a methoxy group or an isopentyl group, R6 stands for a hydroxyl group, a methoxy group or a carboxymethoxy group, and R7 stands for a hydrogen atom or a methoxy group.

CATALYTIC TRANSFER HYDROGENATION, A FACILE CONVERSION OF HYDROXYFLAVANONES INTO HYDROXYDIHYDROCHALCONES

Catalytic transfer hydrogenation of naringenin, hesperetin and eriodictyol using sodium formate as the donor and commercially available Pd/C gives the respective hydroxydihydrochalcones in good yields.The method is an excellent alternative to catalytic hydrogenation.