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Naringin
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Name

Naringin

 EINECS 233-566-4
CAS No. 10236-47-2 Density 1.66 g/cm3
PSA 225.06000 LogP -1.16520
Solubility Soluble in water, alcohol, acetone and warm acetic acid. Melting Point 166 °C
Formula C27H32O14 Boiling Point 928.1 °C at 760 mmHg
Molecular Weight 580.543 Flash Point 308.5 °C
Transport Information N/A Appearance beige to yellowish powder
Safety 22-24/25-36 Risk Codes 22
Molecular Structure Molecular Structure of 10236-47-2 (Naringin) Hazard Symbols IrritantXi
Synonyms

Nvaringin;Momordica grosvenori Extract;schizandra extract;Naringin 98% (HPLC);PolymethoxyLatecl Flavones (Nobiletin);Naringoside;4H-1-Benzopyran-4-one,7-[[2-O-(6-deoxy- R-L-mannopyranosyl)-a-D-glucopyranosyl]- oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-,(2S)-;Naringenin 7-O-[beta-L-rhamnosyl-(1->2)-beta-D-glucoside];45-diOH-Flavone-7-rhgluc;Naringenin 7-O-neohesperidoside;7-[[2-O-(6-Deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-5-hydroxy-2(S)-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;7-(2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavone;

Article Data 9

Naringin Synthetic route

50376-43-7

4'-rhamnoglucosyloxy-2',4,6'-trihydroxychalcone

10236-47-2

naringin

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 25℃; Kinetics; Equilibrium constant; Activation energy; Further Variations:; Solvents;
10236-47-2

naringin

480-41-1

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on

Conditions
ConditionsYield
With sulfuric acid In water at 121℃; for 2h;100%
10236-47-2

naringin

108-24-7

acetic anhydride

4',5-diacetoxy-7-[hexa-O-acetyl-(2-O-α-L-rhamnopyranoxyl-β-D-glucopyranosyl)oxy]flavan-4-one

Conditions
ConditionsYield
With pyridine; dmap at 20℃; for 2h; Inert atmosphere;99%
With sodium acetate for 4h; Acetylation; Heating;
10236-47-2

naringin

18916-17-1

[4-[[2-O-(6-deoxy-L-mannopyranosyl)-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen; potassium hydroxide In ethanol at 55℃; under 7500.75 - 15001.5 Torr; Temperature; Reagent/catalyst; Pressure; Autoclave;98%
With potassium hydroxide; hydrogen; palladium on activated charcoal at 30℃; under 2280 Torr; for 0.5h;
10236-47-2

naringin

112-24-3

triethylentetramine

N,N-1,1'-bis(naringin)triethylenetetraamine

Conditions
ConditionsYield
In methanol; ethanol at 50℃; for 1.5h;87%
10236-47-2

naringin

23643-71-2

2,6-dihydroxy-4-(β-neohesperidosyloxy)acetophenone

Conditions
ConditionsYield
With potassium hydroxide for 4h; Heating;64%
10236-47-2

naringin

221362-75-0

prunin

Conditions
ConditionsYield
With sulfuric acid In water at 121℃; for 0.5h; High pressure;58%
10236-47-2

naringin

77-78-1

dimethyl sulfate

5128-44-9

5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Conditions
ConditionsYield
Stage #1: naringin With pyridine; iodine Heating;
Stage #2: With sulfuric acid In ethanol Heating;
Stage #3: dimethyl sulfate With potassium carbonate In acetone at 45℃; for 0.5h; regioselective reaction;		44%
10236-47-2

naringin

A

2280-44-6

D-Glucose

B

221362-75-0

prunin

C

2781-65-9

2-O-α-L-rhamonopyranosyl-D-glucopyranose

D

480-41-1

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on

Conditions
ConditionsYield
With water at 120℃; for 45h;A 16 mg
B 13 mg
C 30 mg
D 30 mg
10236-47-2

naringin

7585-39-9

β‐cyclodextrin

C33H42O19

Conditions
ConditionsYield
With cyclodextrin glucanotransferase from alkanophilic Bacillus sp. AP A2-5a In water at 40℃; for 16h; other reagent;

Naringin Chemical Properties

IUPAC Name: 7-[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Synonyms of Naringin (CAS NO.10236-47-2): 5-Hydroxy-2-(4-hydroxyphenyl)-7-(2-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyloxy)-4-chromanon ; Naringenin-7-beta-neohesperidoside ; Naringoside ; 4H-1-Benzopyran-4-one, 7-((2-O-(6-deoxy-alpha-L-mannapyranosyl)-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-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)- ; 7-(2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavone
CAS NO: 10236-47-2
Molecular Formula: C27H32O14
Molecular Weight: 580.54
Molecular Structure:
H bond acceptors: 14
H bond donors: 8
Freely Rotating Bonds: 14
Polar Surface Area: 137.06 Å2
Index of Refraction: 1.708
Molar Refractivity: 135.63 cm3
Molar Volume: 347.8 cm3
Surface Tension: 101.2 dyne/cm
Density: 1.66 g/cm3
Flash Point: 308.5 °C
Enthalpy of Vaporization: 141.42 kJ/mol
Boiling Point: 928.1 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C
Melting Point: 166 °C
Alpha: -91 º (c=1, C2H5OH)
Storage temp: 0-6°C
Appearance: beige to yellowish powder
Product Categories of Naringin (CAS NO.10236-47-2): Flavanones;Biochemistry;Disaccharides;Flavonoids;Glycosides;Sugars;Natural Plant Extract

Naringin Uses

 Naringin (CAS NO.10236-47-2) has obvious anti-inflammation effect. Besides it can reduce blood viscosity and thrombosis. Naringin can also be used for analgesia, calm, and increase the secretion of bile of the experimental animals.

Naringin Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 2gm/kg (2000mg/kg)   Eksperimentalna Meditsina i Morfologiya. Vol. 19, Pg. 207, 1980.
rat LD50 intraperitoneal 2gm/kg (2000mg/kg)   Eksperimentalna Meditsina i Morfologiya. Vol. 19, Pg. 207, 1980.

Naringin Safety Profile

Safety information of Naringin (CAS NO.10236-47-2):
Hazard Codes: HarmfulXn
Risk Statements: 22
R22: Harmful if swallowed.
Safety Statements: 22-24/25-36
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

Naringin Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media: Use agent most appropriate to extinguish fire. 
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Storage: Store in a cool, dry place. Store in a tightly closed container.

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