7-(2-O-(6-Desoxy-α-L-mannopyranosyl)-β-D-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavon Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
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. It tastes bitter and is
naturally existed in the skin and flesh of Rutaceae like grapefruit, mandarin orange,
and orange. It is also one of the active ingredients in many traditional Chinese medi cines like Rhizoma Drynariae, Immature Bitter Orange, Fructus Aurantii, and
Exocarpium Citri Grandis. The contents of naringin in different plants vary greatly
with the category and origin, and the content of naringin is high in immature fruits
. 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.
Chemische Eigenschaften
beige to yellowish powder
Physikalische Eigenschaften
Appearance: white to light yellow crystalline powder. Solubility: soluble in metha nol, ethanol, acetone, acetic acid, dilute alkali solution, and hot water and insoluble
in nonpolar solvent like petroleum benzin, ether, benzene, and chloroform. Melting
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.
Definition
ChEBI: A disaccharide derivative that is (S)-naringenin substituted by a 2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosi
ic linkage.
Allgemeine Beschreibung
This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG
Clinical Use
It was used for the treatment of bacterial infection, calm, and cancer prevention
läuterung methode
This bitter principle from grape juice crystallises from water to give the hydrate with 6-8 H2O which when dried at 110o gives the dihydrate. Its solubility in H2O is 0.1% at 40o and 10% at 75o. The 2,4-dinitrophenylhydrazone crystallises from aqueous dioxane with m 246-247o [Douglass et al. J Am Chem Soc 73 4023 1951]. [Pulley & von Loesecke J Am Chem Soc 61 175 1939, Beilstein 18 III/IV 2637, 18 V 528.]
7-(2-O-(6-Desoxy-α-L-mannopyranosyl)-β-D-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavon Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
