| Identification | More | [Name]
Naringin dihydrochalcone | [CAS]
18916-17-1 | [Synonyms]
1-[4-[[2-o-(6-deoxy-l-mannopyranosyl)-d-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone
NARINGIN DIHYDROCHALCONE
NARINGIN DIHYDOROCHALCONE
NAGINGINDIHYDROCHALCONE
Naringin DC
NARINGINDIHYDROHALCONE
1-[4-[[2-O-(6-Deoxy-L-mannopyranosyl)-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone
Senior saccharin
1-Propanone,1-[4-[[2-O-(6-deoxy-α-L-mannopy
2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-
ranosyl)-β-D-glucopyranosyl]oxy]- | [EINECS(EC#)]
700-320-7 | [Molecular Formula]
C27H34O14 | [MDL Number]
MFCD08436145 | [Molecular Weight]
582.55 | [MOL File]
18916-17-1.mol |
| Chemical Properties | Back Directory | [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 | [form ]
Powder | [pka]
6.85±0.40(Predicted) | [color ]
White to Off-white | [JECFA Number]
2208 | [Major Application]
food and beverages | [InChIKey]
CWBZAESOUBENAP-CUDWAMJSNA-N | [SMILES]
O1[C@H]([C@@H]([C@@H]([C@H]([C@@H]1C)O)O)O)O[C@H]2[C@@H](O[C@@H]([C@H]([C@@H]2O)O)CO)Oc3cc(c(c(c3)O)C(=O)CCc4ccc(cc4)O)O | [LogP]
-0.703-1.01 at 22.6℃ and pH5-9 | [CAS DataBase Reference]
18916-17-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [WGK Germany ]
WGK 1 | [HS Code ]
29329990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Description]
Naringin dihydrochalcone is an artificial sweetener and flavonoid that has been isolated from various plants and has antioxidant activity.1,2 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).2 | [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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