10236-47-2 Usage
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
Different sources of media describe the Uses of 10236-47-2 differently. You can refer to the following data:
1. antihaemorrhagic, antiinflammatory
2. 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.
3. Naringin has been used:as a bitter tastant to compare the behavioral response of the Drosophila larva and adult(2)to study its anti-inflammatory property and to determine its effect on nucleus pulposus (NP) cells(3)to determine its effect on bone metabolism like osteogenic differentiation, inhibition of osteoclast formation(4)
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 EffectsThe 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 PreventionNaringin 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 cancerProtective Effects on Early Diabetes and ComplicationsNaringin 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.]
Check Digit Verification of cas no
The CAS Registry Mumber 10236-47-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,2,3 and 6 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 10236-47:
(7*1)+(6*0)+(5*2)+(4*3)+(3*6)+(2*4)+(1*7)=62
62 % 10 = 2
So 10236-47-2 is a valid CAS Registry Number.
10236-47-2Relevant articles and documents
Chiral separation of hesperidin and naringin and its analysis in a butanol extract of Launeae arborescens
Belboukhari, Nasser,Cheriti, Abdelkrim,Roussel, Christian,Vanthuyne, Nicolas
, p. 669 - 681 (2010)
Two flavanone glycosides were isolated from the aerial part of Launeae arborescens (Asteraceae), which were identified as hesperidin and naringin. They are the most abundant flavonoids in the edible parts of many species of citrus fruits. In this study, we were interested in the chiral separation and determination of the diastereomerisation barriers of hesperidin and naringin by HPLC methods. The chiral separation HPLC screening of diastereomers of hesperidin and naringin by HPLC methods was accomplished in the normal-phase mode using 11 chiral stationary phases and various n-hexane/alcohol mobile phases. The rate constants and activation energy of diastereomerisation (G#) of flavanones, naringin and hesperidin were determined, respectively, on Chiralpak IC and Chiralpak IA. The analysis of flavanones isolated in butanol extracts of Launeae arborescens were confirmed by HPLC on Chiralpak IC.
Enthalpy-entropy compensation effect in the chalcone formation from naringin in water-ethanol mixtures
Gonzalez, Evangelina A.,Nazareno, Monica A.,Borsarelli, Claudio D.
, p. 2052 - 2056 (2007/10/03)
The isomerisation equilibrium between the flavanone and chalcone forms of the naturally occurring flavonoid naringin (7-rhamnoglucosyl-4′,5-dihydroxyflavanone) has been studied in water-ethanol mixtures in the presence of NaOH. The variation of the observed pseudo-first order rate constant for the equilibrium reaction, kobs, and the equilibrium composition were determined as a function of the base concentration (-4.0 w ≤ 1.00) of the solvent mixture. The variation of the ring opening kop, and the cyclisation kcy, rate constants with the base concentration and solvent composition indicated that the isomerisation reaction is mediated by a carbanion intermediate. The temperature effect on kop and kcy showed that only the activation enthalpy and entropy changes for the ring-opening reaction, ΔHop? and ΔSop?, were dependent on the solvent composition. In fact, a good linear correlation of a plot of ΔHop? vs. ΔSop?, indicate the existence of an enthalpy-entropy compensation effect. This result was associated with changes in the balance of hydrogen-bonding interactions between the intermediate carbanion and its solvation sphere as solvent composition was modified.
Synthesis and taste of some isomers of naringin
Kamiya,Konishi,Esaki
, p. 1887 - 1888 (2007/10/10)
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