| Identification | More | [Name]
7-(2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavone | [CAS]
10236-47-2 | [Synonyms]
4',5,7-TRIHYDROXYFLAVANONE 7-RHAMNOGLUCOSIDE
FEMA 2769
ISOHESPERIDIN
NARINGENIN-7-NEOHESPERIDOSIDE
NARINGENIN-7-O-NEOHESPERIDOSIDE
NARINGENIN-7-RHAMNOGLUCOSIDE
NARINGENINE-7-RHAMNOSIDOGLUCOSIDE
NARINGIN
(s)-yranosyl]oxy]-
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)-,(S)-
4h-1-benzopyran-4-one,7-[[2-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucop
7-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-4H-1-Benzopyran-4-one
naringenin-7-beta-neohesperidoside
naringoside
NARINGIN FROM CITRUS FRUIT
4H-1-Benzopyran-4-one, 7-2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyloxy-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-
(2S)-7-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
7-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-4H-1-Benzopyran-4-one
7-(2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavone
7-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-5-hydroxy-2(S)-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | [EINECS(EC#)]
233-566-4 | [Molecular Formula]
C27H32O14 | [MDL Number]
MFCD00148888 | [Molecular Weight]
580.53 | [MOL File]
10236-47-2.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
QN6340000
| [F ]
3 | [TSCA ]
Yes | [HS Code ]
29389000 |
| Hazard Information | Back Directory | [Description]
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. | [Chemical Properties]
beige to yellowish powder | [Physical properties]
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 . | [Uses]
antihaemorrhagic, antiinflammatory | [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. | [General Description]
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 | [Flammability and Explosibility]
Notclassified | [Biochem/physiol Actions]
Naringin, a flavanoid in grapefruit and other citrus fruits, potently inhibits intestinal organic anion-transporting polypeptide 1A2 (OATP1A2). Grapefruit juice thereby reduces bioavailability of many pharmacological agents taken at the same time. | [Pharmacology]
Analgesic and Anti-inflammatory Effects
The writhing times of mice were found to be significantly reduced after intragastric
administration of naringin at the dose of 60, 120, and 180 mg/kg. The swelling
degree of ear was inhibited after intragastric administration of naringin at the dose
of 120, 180, and 240 mg/kg. The peritoneal exudate was significantly reduced after
intragastric administration of naringin at the dose of 120, 180, and 240 mg/kg. The
inflammatory swelling caused by rat paw injection of protein was inhibited after
intragastric administration of naringin at the dose of 60, 120, and 180 mg/kg/day for
consecutive 3 days, and the anti-inflammatory mechanism may be related to the
inhibitory effects on the process of synthesizing or releasing of inflammatory medi ators PGE2
Anti-apoptosis, Anti-radiation, and Cancer Prevention
Naringin was found to inhibit the liver damage caused by TNF releasing induced by
lipopolysaccharide, which may be used to reduce the damage to liver and the inci dence of liver cancer . The anticancer effect of naringin was a comprehensive
result caused by many physiological activities, including the effect of antioxidantand anti-free radicals, inhibiting the proliferation of cancer cells, inducing the apop tosis of tumor cells, and inhibiting the expression of cancer gene, among which
inducing tumor cell apoptosis was an important way of naringin to prevent cancer
Protective Effects on Early Diabetes and Complications
Naringin was reported to promote the decomposition of sugar in the liver and
decrease glycogen concentration by inhibiting the apoptosis of pancreatic B cells
caused by oxidation and regulating the expressing and activity of fatty acid, choles terol, and glucose metabolism enzyme .
Naringin is the important component of traditional Chinese medicine drynaria
rhizome. Experiment results have proved that naringin can inhibit many kinds of
inflammation effects including osteoarthritis. Besides, naringin was found to have
the effects of promoting osteoblast proliferation and differentiation as well as inhib iting the activity of osteoclast | [Clinical Use]
It was used for the treatment of bacterial infection, calm, and cancer prevention | [Purification Methods]
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.] |
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