10236-47-2 Usage
Uses
1. Used in Pharmaceutical Applications:
Naringin is used as an anti-inflammatory agent for studying its effect on nucleus pulposus (NP) cells and determining its impact on bone metabolism, such as osteogenic differentiation and inhibition of osteoclast formation.
2. Used in Anticancer Applications:
Naringin is used as an anticancer agent due to its antioxidant, lipid-lowering, and anticancer activities. It also inhibits cytochrome P450 enzymes, affecting drug metabolism and absorption in humans.
3. Used in Food Industry:
Naringin is used as a bitter tastant to compare the behavioral response of Drosophila larvae and adults.
4. Used in Traditional Chinese Medicine:
Naringin is used for its various biological functions, including reducing phlegm, aiding digestion, relieving abdominal distention, and fast diaphragm. It is primarily used for the treatment of cough with asthma, chest oppression, abdominal coldness and pain, dyspeptic retention, and hernia.
Physical Properties:
Naringin appears as a white to light yellow crystalline powder. It is soluble in methanol, ethanol, acetone, acetic acid, dilute alkali solution, and hot water, and insoluble in nonpolar solvents like petroleum benzin, ether, benzene, and chloroform. The melting point of naringin is not provided in the materials.
Chemical Properties:
Naringin is a disaccharide derivative that is (S)-naringenin substituted by a 2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It is a beige to yellowish powder in appearance.
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 .
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.
Preparation and evaluation of a triazole-bridged bis(β-cyclodextrin)–bonded chiral stationary phase for HPLC
Shuang, Yazhou,Liao, Yuqin,Wang, Hui,Wang, Yuanxing,Li, Laisheng
, p. 168 - 184 (2019/11/25)
A triazole-bridged bis(β-cyclodextrin) was synthesized via a high-yield Click Chemistry reaction between 6-azido-β-cyclodextrin and 6-propynylamino-β-cyclodextrin, and then it was bonded onto ordered silica gel SBA-15 to obtain a novel triazole-bridged bis (β-cyclodextrin)–bonded chiral stationary phase (TBCDP). The structures of the bridged cyclodextrin and TBCDP were characterized by the infrared spectroscopy, mass spectrometry, elemental analysis, and thermogravimetric analysis. The chiral performance of TBCDP was evaluated by using chiral pesticides and drugs as probes including triazoles, flavanones, dansyl amino acids and β-blockers. Some effects of the composition in mobile phase and pH value on the enantioseparations were investigated in different modes. The nine triazoles, eight flavanones, and eight dansyl amino acids were successfully resolved on TBCDP under the reversed phase with the resolutions of hexaconazole, 2′-hydroxyflavanone, and dansyl-DL-tyrosine, which were 2.49, 5.40, and 3.25 within 30 minutes, respectively. The ten β-blockers were also separated under the polar organic mode with the resolution of arotinolol reached 1.71. Some related separation mechanisms were discussed preliminary. Compared with the native cyclodextrin stationary phase (CDSP), TBCDP has higher enantioselectivity to separate more analytes, which benefited from the synergistic inclusion ability of the two adjacent cavities and bridging linker of TBCDP, thereby enabling it a promising prospect in chiral drugs and food analysis.
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.
Antimicrobial compositions of matter and a process for preparing antimicrobial compositions of matter from naturally occurring flavanoid glycosides
-
, (2008/06/13)
A process for the production of antimicrobial compositions from naturally occurring flavanoid glycosides. Flavanoid glycosides are acid hydrolyzed under substantially quiescent condition at a temperature within the range of about 60° C. and about 100° C. for a sufficient time to hydrolyze the flavanoid glycoside to partially hydrolyzed flavanoid compositions having antimicrobial activity.
