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
• Article Data: 7

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

General Description

Hesperetin dihydrochalcone is a type of flavonoid compound found in citrus fruits, particularly oranges and lemons. It is known for its sweet taste and is commonly used as a flavoring in the food and beverage industry. Additionally, hesperetin dihydrochalcone has been found to have antioxidant properties, which may help protect cells from damage caused by free radicals. It also has potential anti-inflammatory and anti-cancer properties, making it an interesting compound for further research into its potential health benefits. Overall, hesperetin dihydrochalcone is a versatile compound with potential uses in the food, beverage, and pharmaceutical industries.

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 
• 520-33-2 hesperetin 
• 20702-77-6 neohesperidin 

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.

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.

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.