7-(2-O-(6-Desoxy-α-L-mannopyranosyl)-β-D-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavon
FEMA 2769 · NARINGENIN-7-O-NEOHESPERIDOSIDE · Naring · Cabinda bark extract · naringoside · (2S)-Naringin · NARINGIN WITH HPLC · Citrus grandis Osbeck
Identifikatoren & physikalische Daten
| CAS No. | 10236-47-2 |
|---|---|
| Summenformel | C27H32O14 |
| Durchschnittliche Molmasse | 580,5 g/mol |
| Monoisotopische Masse | 580,17920569 g/mol |
| SMILES | CC1OC(OC2C(Oc3cc(O)c4c(c3)OC(c3ccc(O)cc3)CC4=O)OC(CO)C(O)C2O)C(O)C(O)C1O |
| InChIKey | DFPMSGMNTNDNHN-UHFFFAOYSA-N |
| PubChem CID | 4441 |
| DTXSID | DTXSID10860071 |
| Lokaler Name | 7-(2-O-(6-Desoxy-α-L-mannopyranosyl)-β-D-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavon |
Chemische & physikalische Eigenschaften
| XLogP | -0,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 225 |
| H-Brücken-Donoren | 8 |
| H-Brücken-Akzeptoren | 14 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 41 |
| Formalladung | 0 |
| Komplexität | 884 |
| Schmelzpunkt | 166 °C |
| Siedepunkt | 559.35°C (rough estimate) |
| Dichte | 1.3285 (rough estimate) |
| Dampfdruck | 2.25Pa at 20℃ |
| Brechungsindex | -84 ° (C=2, EtOH) |
| FEMA | 2769 | NARINGEN EXTRACT (CITRUS PARADISI MACF.) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | DMSO : 1 mg/mL (1.72 mMNeed ultrasonic)H2O : 1 mg/mL (1.72 mMultrasonic and warming and heat to 80°C)Soluble in water, alcohol, acetone and warm acetic acid. |
| Aggregatzustand | crystalline |
| pKa (Säurekonstante) | 7.17±0.40(Predicted) |
| Farbe | off-white |
| Biologische Quelle | citrus fruit |
| Merck | 14,6425 |
| BRN | 102012 |
| Hauptanwendungen | cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN PROTECTING |
| InChIKey | DFPMSGMNTNDNHN-JJLSSNRUSA-N |
| SMILES | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2Oc3cc(O)c4C(=O)CC(Oc4c3)c5ccc(O)cc5)[C@H](O)[C@H](O)[C@H]1O |
| LogP (Verteilungskoeffizient) | -0.44 at 20℃ |
| CAS Datenbank | 10236-47-2(CAS DataBase Reference) |
| EPA chemische Informationen | 4H-1-Benzopyran-4-one, 7-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)- (10236-47-2) |
Sicherheit & Vorschriften
| Regulatorische Informationen | Naringin: Does not have an individual approval but may be used under an appropriate group standard |
|---|---|
| F | 3 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29389090 |
| RTECS-Nr. | QN6340000 |
| R-Sätze (R) | 22-36/37/38 |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 22-24/25-36-26 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 Oral |
Anwendungen & Verwendung
Beschreibung
Naringin is also called naringoside, hesperidin, and isohesperidin. It is a pale yellow flavanone compound extracted from immature or nearly mature outer layer of C. paradisi Macfad which belongs to Citrus grandis (L.) Osbeck. In terms of traditional Chinese medicine, the flavor of grapefruit is sweet and sour, and the nature is cold; the flavors of its peel are sweet, pungent, and bitter, and the nature of its peel is warm. Both the pulp and the peel of grapefruit have the bio logical function including reducing phlegm, helping digestion, relieving abdominal distention, and fast diaphragm. And they are mainly used for the treatment of cough with asthma, sense of suppression in the chest, coldness and pain in abdomen, dys peptic retention, and hernia.
History
Naringin is mainly existed in the peel of grapefruit, lime, and their varieties; it has multiple biological activities and is widely applied in the fields of medicine, food, and cosmetics. In the 1930s, Harvey and Rygg obtained naringin through the method of isolation and extraction. They also established a colorimetric method for the determination of naringin, which laid the foundation for the following researches . Booth and other researchers conducted the systematic researches on the narin gin metabolites . In the 1960s, Hagen and other researchers established a fluores cence chromatography method for the determination naringin . In addition, the biological activity of naringin was evaluated. It was observed to improve ascites, experimental pulmonary edema, peritonitis, and oxygenation . At present, the extraction methods of naringin are hot water extraction, alkali extraction, and acid precipitation and organic solvent extraction. A series of pharmacological activity studies have been conducted and demonstrated its various biological activities .
Verwenden
Naringoside is a metabolite of Naringin (N378980), a major flavonoid found in grapefruit juice. It has antioxidant, lipid lowering, and anticancer activities. It is also an inhibitor of cytochrome P450 enzymes, affecting drug metabolism and thus drug absorption in humans.