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Naringenin

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Name

Naringenin

EINECS 207-550-2
CAS No. 480-41-1 Density 1.485 g/cm3
PSA 86.99000 LogP 2.50990
Solubility almost insoluble in water Melting Point 247-250 °C
Formula C15H12O5 Boiling Point 577.5°C at 760mmHg
Molecular Weight 272.257 Flash Point 224.7°C
Transport Information N/A Appearance beige-brown powder
Safety 26-36-37/39 Risk Codes 36/37/38-22
Molecular Structure Molecular Structure of 480-41-1 (Naringenin) Hazard Symbols HarmfulXn,IrritantXi
Synonyms

4H-1-Benzopyran-4-one,2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (S)-;Flavanone,4',5,7-trihydroxy- (8CI);Naringenin (6CI);(-)-(2S)-Naringenin;(2S)-4',5,7-Trihydroxy-flavanone;(2S)-Naringenin;(S)-Naringenin;(2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-on;(S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;Naringenine;S-Dihydrogenistein;Salipurol;4H-1-benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)-;

Article Data 75

Naringenin Synthetic route

1160434-47-8

(2S)-naringenin 5,4'-di-O-β-D-glucopyranoside

A

50-99-7

D-glucose

B

480-41-1

naringenin

Conditions
ConditionsYield
With hydrogenchloride; water at 80℃; for 1h;A n/a
B 72%
10236-47-2

naringin

480-41-1

naringenin

Conditions
ConditionsYield
With hydrogenchloride In water at 100℃; for 1h; Temperature;26.9%
With glucosidase Rohapect(R) D5L; citric-phosphorus acid McIlvaine buffer at 37℃; for 24h; pH=5.5;12 mg
Multi-step reaction with 2 steps
1: naringinase from Aspergillus aculeatus JMUdb058 / aq. buffer / 0.58 h / 50 - 100 °C / pH 4 / Enzymatic reaction
2: β-D-glucosidase / aq. buffer / 0.58 h / 50 - 100 °C / pH 4 / Enzymatic reaction
View Scheme
With sulfuric acid at 90℃;4.62 g
With sulfuric acid In water at 90℃; for 2h;

naringin

480-41-1

naringenin

Conditions
ConditionsYield
With sulfuric acid; water at 20℃; for 0.166667h;21%
10236-47-2

naringin

A

480-41-1

naringenin

B

5,6,7,4′-tetrahydroxyflavanone

C

5,7,8,4′-tetrahydroxyflavanone

Conditions
ConditionsYield
With Aspergillus saitoi In water; dimethyl sulfoxide at 30℃; pH=5.0;A n/a
B 5%
C 13.7%
529-41-9, 19253-00-0, 23711-00-4

(2S)-(-)-naringenin-5-O-β-D-glucopyranoside

480-41-1

naringenin

Conditions
ConditionsYield
With formic acid; ethylene glycol
112294-87-8

4,2',4',6'-tetrahydroxychalchone 4'-glucoside

480-41-1

naringenin

Conditions
ConditionsYield
acid and enzymatic hydrolysis;

naringenin 7-O-(6-O-((E)-p-coumaroyl)-β-D-glucopyranoside)

480-41-1

naringenin

Conditions
ConditionsYield
With hydrogenchloride for 4h; Heating;

2''-O-p-coumaroylprunin

480-41-1

naringenin

Conditions
ConditionsYield
With hydrogenchloride for 4h; Heating;

A

480-41-1

naringenin

B

(2S)-naringenin 4′-O-sulphate

Conditions
ConditionsYield
With Cunninghamella elegans NRRL 1392; water In N,N-dimethyl-formamide for 240h;A 60.0 mg
B 110 mg
480-41-1

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

A

480-41-1

naringenin

Conditions
ConditionsYield
Resolution of racemate;
With chiral β-cyclodextrin column In methanol; water Resolution of racemate; stereospecific reaction;
With trifluoroacetic acid In ethanol; hexane Resolution of racemate;

Naringenin Chemical Properties

Molecular Structure of Naringenin (CAS NO.480-41-1):


IUPAC Name: (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Molecular Formula: C15H12O5
Formula Weight: 272.26g/mol
Appearance: yellow crystalline powder
Density: 1.485g/cm3
Melting Point: 247-250 °C
Boiling Point: 577.5°C at 760mmHg
Flash Point: 224.7°C
Vapor Pressure: 6.18E-14 mmHg at 25°C
EINECS: 207-550-2
liansport Information: OTH
Freely Rotating Bonds: 4
Index of Refraction: 1.692
Molar Refractivity: 70.25 cm3
Molar Volume: 183.2 cm3
Polarizability: 27.85 10-24cm3
Surface Tension: 72.8 dyne/cm
Enthalpy of Vaporization: 89.65 kJ/mol
Solubility: dissolved in ethanol, ether and benzene, almost insoluble in water,475.2mg/L in water at 25°C
InChI
InChI=1/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2
Smiles
c12c(O[C@@H](c3ccc(O)cc3)CC1=O)cc(O)cc2O
Product Categories: Flavanones; Natural Plant Extract; Inhibitors

Naringenin Toxicity Data With Reference

1.    

dnd-rat-lvr 20 µmol/L

    FCTOD7    Food and Chemical Toxicology. 35 (1997),443.

Naringenin Safety Profile

Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Codes:  Xi,HarmfulXn
Risk Statements:  36/37/38-22.
22:  Harmful if swallowed.
36/37/38:  Irritating to eyes, respiratory system and skin.
Safety Statements:  26-36-37/39.
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
36:  Wear suitable protective clothing.
37/39:  Wear suitable gloves and eye/face protection.

Naringenin Specification

  Naringenin, with CAS number of 480-41-1, can be called 4H-1-Benzopyran-4-one,2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (S)- ; Naringenin (6CI) ; (2S)-4',5,7-Trihydroxy-flavanone ; (2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-on ; (S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one ; 4H-1-benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)- ; 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (S)- . Naringenin (CAS NO.480-41-1) is a beige-brown powder, It can be used as antibacterial , anti-inflammatory, anti-cancer and anti-oxidation.

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