35400-60-3

Basic information

• Product Name: HESPERETIN DIHYDROCHALCONE
• Synonyms: 4-METHOXY-2',4',6',3-TETRAHYDROXYDIHYDROCHALCONE;HESPERETIN DIHYDROCHALCONE;HESPERIDINDIHYDROCHALCONE;1-Propanone, 3-(3-hydroxy-4-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)-;3-(3-Hydroxy-4-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone;Hesperitin dihydrochalcone;3-(3-hydroxy-4-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
• CAS NO: 35400-60-3
• Molecular Formula: C₁₆H₁₆O₆
• Molecular Weight: 304.29
• Product Categories: Chalcones
• Mol File: 35400-60-3.mol

Chemical Properties

• Boiling Point: 553.1 °C at 760 mmHg
• Flash Point: 207 °C
• Appearance: /
• Density: 1.409 g/cm³
• Vapor Pressure: 7.68E-13mmHg at 25°C
• Refractive Index: 1.659
• PKA: 7.16±0.40(Predicted)
• CAS DataBase Reference: HESPERETIN DIHYDROCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: HESPERETIN DIHYDROCHALCONE(35400-60-3)
• EPA Substance Registry System: HESPERETIN DIHYDROCHALCONE(35400-60-3)

Safety Data

• Hazardous Substances Data: 35400-60-3(Hazardous Substances Data)

Usage

Uses

Used in Food and Beverage Industry:
Hesperetin dihydrochalcone is used as a natural flavoring agent for its sweet taste, enhancing the flavor profiles of various food and drink products while offering a healthy alternative to artificial sweeteners.
Used in Pharmaceutical Research:
Hesperetin dihydrochalcone is utilized in pharmaceutical research as a potential antioxidant, anti-inflammatory, and anti-cancer agent. Its ability to combat free radicals and modulate inflammatory responses makes it a candidate for the development of treatments targeting a range of health conditions.
Used in Health Supplements:
Given its potential health benefits, hesperetin dihydrochalcone is incorporated into health supplements aimed at promoting overall well-being and supporting the body's natural defenses against oxidative stress and inflammation.

InChI:InChI=1/C16H16O6/c1-22-15-5-3-9(6-12(15)19)2-4-11(18)16-13(20)7-10(17)8-14(16)21/h3,5-8,17,19-21H,2,4H2,1H3

Upstream product

• 520-33-2 (S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone 
• 20702-77-6 neohesperidin 
• 520-33-2 hesperetin 

Downstream Products

• 122554-94-3 5,7-dihydroxy-3-(3-hydroxy-4-methoxybenzyl)chromone 

Relevant articles and documents

Identification of Interleukin-8-Reducing Lead Compounds Based on SAR Studies on Dihydrochalcone-Related Compounds in Human Gingival Fibroblasts (HGF-1 cells) in Vitro

Background: In order to identify potential activities against periodontal diseases, eighteen dihydrochalcones and structurally related compounds were tested in an established biological in vitro cell model of periodontal inflammation using human gingival fibroblasts (HGF-1 cells). Methods: Subsequently to co-incubation of HGF-1 cells with a bacterial endotoxin (Porphyromonas gingivalis lipopolysaccharide, pgLPS) and each individual dihydrochalcone in a concentration range of 1 μM to 100 μM, gene expression of interleukin-8 (IL-8) was determined by qPCR and cellular interleukin-8 (IL-8) release by ELISA. Results: Structure–activity analysis based on the dihydrochalcone backbone and various substitution patterns at its aromatic ring revealed moieties 20,4,40,60-tetrahydroxy 3-methoxydihydrochalcone (7) to be the most effective anti-inflammatory compound, reducing the pgLPS-induced IL-8 release concentration between 1 μM and 100 μM up to 94%. In general, a 2,4,6-trihydroxy substitution at the A-ring and concomitant vanilloyl (4-hydroxy-3-methoxy) pattern at the B-ring revealed to be preferable for IL-8 release inhibition. Furthermore, the introduction of an electronegative atom in the A,B-linker chain led to an increased anti-inflammatory activity, shown by the potency of 4-hydroxybenzoic acid N-vanillylamide (13). Conclusions: Our data may be feasible to be used for further lead structure designs for the development of potent anti-inflammatory additives in oral care products.

USE OF 3-(3-HYDROXY-4-METHOXY-PHENYL)-1-(2,4,6-TRIHYDROXY-PHENYL) PROPAN-1-ONE

The present invention concerns the use of 3-(3-Hydroxy-4-methoxy-phenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one for masking, reducing or suppressing an unpleasant taste impression, preferably bitter, sour and/or astringent taste impression of unpleasant-t

SWEETNESS AND TASTE IMPROVEMENT OF STEVIOL GLYCOSIDE AND MOGROSIDE SWEETENERS WITH DIHYDROCHALCONES

Compositions and consumables comprising certain sweeteners and at least one dihydrochalcone of Formula I are provided herein, wherein the at least one sweetener is selected from certain steviol glycoside and/or mogroside sweeteners in sweetening amounts.

α-Rhamnosidase activity in the marine isolate Novosphingobium sp. PP1Y and its use in the bioconversion of flavonoids

Crude protein extracts of Novosphingobium sp. PP1Y, a microorganism isolated from polluted marine waters in Pozzuoli (Italy), were analyzed for the presence of glycosidase activities. Particular attention was devoted to a α-L-rhamnosidase activity able to hydrolyze several flavonoids of interest for the pharmaceutical and food industries. This activity had an alkaline pH optimum and a moderate tolerance to the presence of organic solvents, appealing features for its possible biotechnological uses. An increase of the α-L-rhamnosidase activity in PP1Y crude extracts was induced by adding naringin to the growth medium, suggesting the possibility to use material from Citrus industrial waste to induce the glycosidase activity expressed by strain PP1Y and produce simultaneously high-added-value molecules from the hydrolysis of their flavonoids. In order to investigate on the enzymatic mechanism of PP1Y α-L-rhamnosidase activity, hydrolysis products of PNP-α-L- rhamnopyranoside were analyzed by 1H-NMR experiments. The kinetic behaviour clearly indicated an inverting mechanism of hydrolysis for this novel enzymatic activity.

Diarylalkanes as potent inhibitors of binuclear enzymes

The present invention implements a strategy that combines an enzyme inhibition assay with a chemical dereplication process to identify active plant extracts and the particular compounds—diarylalkanes and/or diarylalkanols within those extracts that specifically inhibit binuclear enzyme function. Included in the present invention are compositions of matter comprised of one or more of diarylalkanes and/or diarylalkanols, which inhibit the activity of binuclear enzymes, particularly tyrosinase and which prevent melanin overproduction. The present invention also provides a method for inhibiting the activity of a binuclear enzyme, particularly tyrosinase and a method for preventing and treating diseases and conditions related to binuclear enzyme function. The present invention further includes a method for preventing and treating melanin overproduction and diseases and conditions of the skin related thereto. The method for preventing and treating diseases and conditions related to binuclear enzyme function and melanin overproduction is comprised of administering to a host in need thereof an effective amount of a composition comprising one or more diarylalkanes and/or diarylalkanols synthesized and/or isolated from one or more plants together with a pharmaceutically acceptable carrier.

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.

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.