Naringenin supplier | CasNO.480-41-1

Name
Naringenin
EINECS 207-550-2
CAS No. 480-41-1
Article Data75
CAS DataBase
Density 1.485 g/cm³
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
Appearance beige-brown powder
Safety 26-36-37/39
Risk Codes 36/37/38-22
Molecular Structure
Hazard Symbols Xn,Xi
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)-;
PSA 86.99000
LogP 2.50990

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

Conditions	Yield
With hydrogenchloride; water at 80℃; for 1h;	A n/a B 72%

: 10236-47-2
naringin

: 480-41-1
naringenin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With Aspergillus saitoi In water; dimethyl sulfoxide at 30℃; pH=5.0;	A n/a B 5% C 13.7%

...Expand

: 529-41-9, 19253-00-0, 23711-00-4
(2S)-(-)-naringenin-5-O-β-D-glucopyranoside

: 480-41-1
naringenin

Conditions

Conditions	Yield
With formic acid; ethylene glycol

: 112294-87-8
4,2',4',6'-tetrahydroxychalchone 4'-glucoside

: 480-41-1
naringenin

Conditions

Conditions	Yield
acid and enzymatic hydrolysis;

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

: 480-41-1
naringenin

Conditions

Conditions	Yield
With hydrogenchloride for 4h; Heating;

: 2''-O-p-coumaroylprunin

: 480-41-1
naringenin

Conditions

Conditions	Yield
With hydrogenchloride for 4h; Heating;

: 520-29-6, 2957-21-3, 17784-36-0, 118244-13-6
(-)-(S)-sakuranetin

A: 480-41-1
naringenin

B: (2S)-naringenin 4′-O-sulphate

Conditions

Conditions	Yield
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

B: 480-41-1, 17654-19-2, 67604-48-2, 93602-28-9
(+)-Naringenin

Conditions

Conditions	Yield
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;

: 10236-47-2
naringin

A: 529-55-5, 88275-21-2, 127469-97-0
prunin

B: 480-41-1
naringenin

Conditions

Conditions	Yield
With 2,4-Dichlorophenoxyacetic acid at 25℃; for 120h; Darkness;
With naringinase from Penicillium decumbens immobilized on glutaraldehyde modified silica ITQ-2 zeolite In aq. buffer at 50℃; for 0.5h; pH=4.5; Reagent/catalyst; Green chemistry; Enzymatic reaction;

: 10236-47-2
naringin

A: 492-61-5
β-D-glucose

B: 6014-42-2
L-rhamnose

C: 529-55-5, 88275-21-2, 127469-97-0
prunin

D: 480-41-1
naringenin

Conditions

Conditions	Yield
With naringinase In tetrahydrofuran at 45℃; pH=4; Kinetics; Solvent; Concentration; aq. acetate buffer;

...Expand

: 10236-47-2
naringin

A: 2280-44-6
D-Glucose

B: 73-34-7
L-rhamnose

C: 529-55-5, 88275-21-2, 127469-97-0
prunin

D: 480-41-1
naringenin

Conditions

Conditions	Yield
With naringenase from Pencillium decumbens at 30℃; under 1125110 Torr; pH=4; Kinetics; Equilibrium constant; Thermodynamic data; Pressure; Temperature; Concentration; aq. acetate buffer; Enzymatic reaction;
With α-L-rhamnosidase from Alternaria alternata SK37.001 In aq. acetate buffer at 40℃; for 0.166667h; pH=5.5; Enzymatic reaction;

...Expand

: 25515-46-2
naringenin chalcone

: 480-41-1
naringenin

Conditions

Conditions	Yield
With Trigonella foenum-graecum L. chalcone isomerase 1 at 36℃; pH=7.5 - 8; Kinetics; aq. buffer; Enzymatic reaction;

: 529-55-5, 88275-21-2, 127469-97-0
prunin

A: 492-62-6
alpha-D-glucopyranose

B: 480-41-1
naringenin

Conditions

Conditions	Yield
With β-D-glucosidase In aq. buffer at 50 - 100℃; for 0.166667h; pH=5; Enzymatic reaction;

: 10236-47-2
naringin

A: 492-61-5
β-D-glucose

B: 6014-42-2
L-rhamnose

C: 480-41-1
naringenin

Conditions

Conditions	Yield
With Novosphingobium sp. PP1Y protein extract In aq. phosphate buffer at 35℃; for 3h; pH=8.5; pH-value; Solvent; Enzymatic reaction;

...Expand

: 10236-47-2
naringin

A: 19949-48-5
2-O-α-L-rhamnopyranosyl-β-D-glucopyranose

B: 480-41-1
naringenin

Conditions

Conditions	Yield
With sulfuric acid In methanol; water for 6h; Reflux;

: 529-55-5, 88275-21-2, 127469-97-0
prunin

: 480-41-1
naringenin

Conditions

Conditions	Yield
With β-D-glucosidase In aq. buffer at 50 - 100℃; for 0.583333h; pH=4; Kinetics; Enzymatic reaction;

: 60-18-4
L-tyrosine

A: 961-29-5, 13745-20-5
isoliquirtigenin

B: 7400-08-0
p-Coumaric Acid

C: 578-86-9
liquiritigenin

D: 480-41-1
naringenin

Conditions

Conditions	Yield
With isopropyl β-D-thiogalactopyranoside at 30℃; for 24h; Reagent/catalyst; Microbiological reaction;

...Expand

: 60-18-4
L-tyrosine

A: 7400-08-0
p-Coumaric Acid

B: 480-41-1
naringenin

Conditions

Conditions	Yield
With isopropyl β-D-thiogalactopyranoside at 30℃; for 24h; Reagent/catalyst; Microbiological reaction;

: 520-29-6, 2957-21-3, 17784-36-0, 118244-13-6
(-)-(S)-sakuranetin

A: 93012-86-3
7-methoxy-3',4',5-trihydroxyflavanone

B: 552-58-9
eriodictyol

C: 21785-09-1
7-methoxyflavanone

D: 480-41-1
naringenin

Conditions

Conditions	Yield
With cytochromes P450 in human liver microsomes Kinetics; Enzymatic reaction;

...Expand

: 520-29-6, 2957-21-3, 17784-36-0, 118244-13-6
(-)-(S)-sakuranetin

A: 552-58-9
eriodictyol

B: 480-41-1
naringenin

Conditions

Conditions	Yield
With cytochromes P450 in human liver microsomes Kinetics; Enzymatic reaction;

: 186581-53-3, 908094-01-9
diazomethane

: 480-41-1
naringenin

: 520-29-6, 2957-21-3, 17784-36-0, 118244-13-6
(-)-(S)-sakuranetin

Conditions

Conditions	Yield
In methanol; diethyl ether at 20℃; for 6h;	100%
In diethyl ether Ambient temperature;	75%

: 2106-10-7
1-deoxy-1-fluoro-α-D-glucose

: 480-41-1
naringenin

: naringenin 7-α-O-glucoside

Conditions

Conditions	Yield
With α-glucosidase from sulfolobus solfataricus In dimethyl sulfoxide at 45℃; for 2h; pH=9; Enzymatic reaction;	99%

: 480-41-1
naringenin

: 7,4'-di-O-hexylnaringenin oxime

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In ethanol at 40 - 50℃; for 25h;	98.6%

: 7732-18-5
water

: 142-71-2
copper diacetate

: 480-41-1
naringenin

: trans-di(aqua) bis(7-hydroxy-2-(4-hydroxyphenyl)-4-oxo-5-chromanolato) copper (II)

Conditions

Conditions	Yield
In ethanol at 60 - 65℃; for 1h; pH=7;	95%

...Expand

: 100-39-0
benzyl bromide

: 480-41-1
naringenin

: 7,4'-O,O-dibenzyl naringenin

Conditions

Conditions	Yield
Stage #1: naringenin With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 1h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 40℃; Temperature; Inert atmosphere;	92.29%

: 142-61-0
Hexanoyl chloride

: 480-41-1
naringenin

: 5,7,4'-tri-O-hexanoyl-naringenin

Conditions

Conditions	Yield
With dmap; triethylamine In N,N-dimethyl-formamide at 20℃; for 4.5h; Cooling with ice;	92%
With dmap; triethylamine In N,N-dimethyl-formamide

: 480-41-1
naringenin

: naringenin oxime

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydroxide In ethanol for 3h; Reflux;	88%
With hydroxylamine hydrochloride; sodium acetate In methanol at 40℃; for 48h; Reflux;	87.9%
With hydroxylamine hydrochloride; sodium acetate trihydrate In ethanol; water for 4h; Reflux;	76%
With hydroxylamine hydrochloride; sodium acetate In ethanol at 40 - 50℃;

: 107-15-3
ethylenediamine

: 480-41-1
naringenin

: 1,2-di(4-iminenaringenin)ethane

Conditions

Conditions	Yield
With acetic acid In ethanol for 5h; Inert atmosphere; Reflux;	87%

: 480-41-1
naringenin

: 520-36-5
5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

Conditions

Conditions	Yield
With iodine In pyridine at 90℃; for 8h;	86%
With flavone synthase I Product distribution;
With GLUTATHIONE; N-[tris(hydroxymethyl)methyl]glycine; flavone synthase II; NADPH; potassium hydroxide at 25℃; for 0.5h; pH=7.9; Enzymatic reaction;
With 2,3-dicyano-5,6-dichloro-p-benzoquinone

: 70223-96-0, 4753-07-5, 5160-10-1, 14206-57-6, 14227-66-8, 14257-35-3, 42385-75-1, 67650-37-7, 68682-05-3, 69308-57-2, 69349-74-2, 70223-97-1, 71276-38-5, 85248-99-3, 118493-15-5, 120575-76-0
2,2',3,3',4',6,6'-hepta-O-acetyl-β-D-cellobiosyl bromide

: 480-41-1
naringenin

: 7-O-(heptaacetyl--D-cellobiosyl)naringenin

Conditions

Conditions	Yield
With quinoline; silver (II) carbonate at 20℃; for 3h; Koenigs-Knorr Glycosidation;	86%

: 107-15-3
ethylenediamine

: 480-41-1
naringenin

: 1,2-di(4'-iminonaringenin)ethane

Conditions

Conditions	Yield
With acetic acid In ethanol for 72h; Reflux;	85%

: 480-41-1
naringenin

Beauveria bassiana AM 278 grown on a sabouraud medium: Beauveria bassiana AM 278 grown on a sabouraud medium

: naringenin 7-O-β-D-(4''-O-methyl)glucopyranoside

Conditions

Conditions	Yield
In dimethyl sulfoxide for 168h; Microbiological reaction; regioselective reaction;	82%

: 100-39-0
benzyl bromide

: 480-41-1
naringenin

: 88607-79-8
(E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one

Conditions

Conditions	Yield
With potassium carbonate In acetone Heating;	81%
With potassium carbonate In acetone Heating / reflux;	81%

: 142-71-2
copper diacetate

: 480-41-1
naringenin

: Cu(naringenin)2

Conditions

Conditions	Yield
With triethylamine In methanol; water at 20℃; for 3h;	80%

: 480-41-1
naringenin

: 7-O-hexylnaringenin oxime

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In ethanol at 40 - 50℃; for 5h;	79.1%

: 66-71-7
1,10-Phenanthroline

: copper(II) perchlorate

: 480-41-1
naringenin

: C27H21CuN2O6(1+)*ClO4(1-)*H2O

Conditions

Conditions	Yield
In methanol for 8h; Reflux;	79%

...Expand

: 366-18-7
[2,2]bipyridinyl

: copper(II) choride dihydrate

: 480-41-1
naringenin

: Cu(naringenin)(2,2'-bipyridine)

Conditions

Conditions	Yield
With triethylamine In methanol; water at 20℃; for 6h;	79%

...Expand

: 50-00-0
formaldehyd

: 617-89-0
furan-2-ylmethanamine

: 480-41-1
naringenin

: 9-(furan-2-ylmethyl)-2-(3-(furan-2-ylmethyl)-3,4-dihydro-2H-benzo[e][1,3]oxazin-6-yl)-5-hydroxy-2,3,9,10-tetrahydrochromeno[8,7-e][1,3]oxazin-4(8H)-one

Conditions

Conditions	Yield
In toluene at 100℃; for 3h;	79%

...Expand

: 542-69-8
1-iodo-butane

: 480-41-1
naringenin

: 7-O-butylnaringenin

Conditions

Conditions	Yield
With potassium carbonate In acetone at 40 - 45℃; regioselective reaction;	78.7%

: 505-18-0
2,3,4,5-tetrahydropyridine

: 480-41-1
naringenin

: 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(piperidin-2-yl)chroman-4-one

Conditions

Conditions	Yield
at 80℃; Mannich Aminomethylation; Inert atmosphere; regioselective reaction;	78%

: 480-41-1
naringenin

: 18107-18-1
diazomethyl-trimethyl-silane

: (S)-5-hydroxy-2-(4-methoxyphenyl)-7-methoxy-2,3-dihydro chromen-4-one

Conditions

Conditions	Yield
In methanol; hexane; dichloromethane at 20℃; for 12h;	77%

: 110-91-8
morpholine

: 50-00-0
formaldehyd

: 480-41-1
naringenin

: 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(morpholinomethyl)chroman-4-one

Conditions

Conditions	Yield
In methanol at 65℃; Mannich Aminomethylation; regioselective reaction;	76%

...Expand

: 50-00-0
formaldehyd

: 80518-57-6
ethyl 4-(piperazin-1-yl)benzoate

: 480-41-1
naringenin

: ethyl 4-(4-((5, 7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochroman-6-yl)methyl) piperazin-1-yl)benzoate

Conditions

Conditions	Yield
In methanol at 65℃; Mannich Aminomethylation; regioselective reaction;	76%

...Expand

: 50-00-0
formaldehyd

: 62-53-3
aniline

: 480-41-1
naringenin

: C31H26N2O5

Conditions

Conditions	Yield
Stage #1: formaldehyd; naringenin In toluene at 20℃; for 0.166667h; Mannich Aminomethylation; Stage #2: aniline In toluene at 100℃; for 4h;	76%

...Expand

: 77-78-1
dimethyl sulfate

: 480-41-1
naringenin

: 520-29-6, 2957-21-3, 17784-36-0, 118244-13-6
(-)-(S)-sakuranetin

Conditions

Conditions	Yield
With potassium carbonate In acetone at 50℃; for 12h;	76%

: 480-41-1
naringenin

Absidia coerulea AM 93 grown on a sabouraud medium: Absidia coerulea AM 93 grown on a sabouraud medium

: 529-55-5, 88275-21-2, 127469-97-0
prunin

Conditions

Conditions	Yield
In dimethyl sulfoxide for 168h; Microbiological reaction; regioselective reaction;	73%

: 100-39-0
benzyl bromide

: 480-41-1
naringenin

: 88607-75-4
C22H18O5

Conditions

Conditions	Yield
With tertamethylammonium iodide In N,N-dimethyl-formamide at 20℃; for 48h;	72%

: 2050-77-3
Iododecane

: 480-41-1
naringenin

: 7-O-decylnaringenin

Conditions

Conditions	Yield
With potassium carbonate In acetone at 40 - 45℃; regioselective reaction;	70.8%

: 79074-45-6
2-(bromomethyl)-3,5,6-trimethylpyrazine

: 480-41-1
naringenin

: (E)-1-(2-hydroxy-4,6-bis((3,5,6-trimethylpyrazin-2-yl)methoxy)phenyl)-3-(4-((3,5,6-trimethylpyrazin-2-yl)methoxy)phenyl)prop-2-en-1-one

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide; acetone for 2h; Inert atmosphere;	70%

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

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, Harmful Xn
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.

Product Name

Naringenin

Synthetic route

Naringenin Chemical Properties

Naringenin Toxicity Data With Reference

Naringenin Safety Profile

Naringenin Specification

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