Naringin dihydrochalcone Chemical Properties

Melting point:

131-132°C

Boiling point:

916.8±65.0 °C(Predicted)

Density 

1.63±0.1 g/cm3(Predicted)

vapor pressure 

0Pa at 20-50℃

FEMA 

4495 | NARINGIN DIHYDROCHALCONE

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Soluble in DMSO

pka

6.85±0.40(Predicted)

form 

Powder

color 

White to Off-white

JECFA Number

2208

InChIKey

CWBZAESOUBENAP-CUDWAMJSNA-N

LogP

-0.703-1.01 at 22.6℃ and pH5-9

CAS DataBase Reference

18916-17-1(CAS DataBase Reference)

Safety Information

HS Code 

29329990

Naringin dihydrochalcone Usage And Synthesis

Description

Naringin dihydrochalcone is an artificial sweetener and flavonoid that has been isolated from various plants and has antioxidant activity. It scavenges ABTS (Item No. 27317), oxygen, and 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in cell free assays (IC50s = 24, 322.8, and 318.9 μM, respectively).

Uses

Naringin Dihydrochalcone is an intense sweetener and strong antioxidant compound which displays anti-allegeric activity.

Definition

ChEBI: Naringin dihydrochalcone is a member of flavonoids and a glycoside.

Synthesis

Naringin was used as a raw material to synthesize 1-(4-((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-2,6-dihydroxyphenyl)-3-( 4-hydroxyphenyl)propan-1-one was prepared in the following general procedure: 120 g of the natural extract (containing 600 g of 8% naringin) was dissolved in potassium hydroxide solution and filtered to obtain a clarified solution. The filtrate was transferred to a 2000 ml autoclave and 200 g of ethanol and 3 g of palladium carbon catalyst were added. Hydrogen was introduced at 55°C, maintaining the pressure at 1~2MPa, and the reaction was carried out for 5~7 hours until the hydrogen absorption was basically completed. The reaction solution was removed and filtered to remove the palladium-carbon catalyst. Subsequently, the hydrogenated solution was acidified with hydrochloric acid, the pH was adjusted to 5-7, and stirred thoroughly to induce crystallization, and a white solid was rapidly precipitated. The mixture was cooled to 20 °C and filtered, and the resulting wet product was dried under reduced pressure at 60 °C to give 118 g of dihydronaringenin chalcone as a white powder with 98.9% liquid phase purity and 98% molar yield. The product needs to be stored in a cool place under light nitrogen protection.

target

NF-κB

References

[1] Patent: CN105801636, 2016, A. Location in patent: Paragraph 0022
[2] Journal of Agricultural and Food Chemistry, 2003, vol. 51, # 11, p. 3309 - 3312

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