480-41-1

Basic information

• Product Name: Naringenin
• Synonyms: naringenine;naringetol;salipurol;salipurpol;5,7,4'-TRIHYDROXYFLAVANONE;5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)CHROMAN-4-ONE;(+/-)-4',5,7-TRIHYDROXYFLAVANONE;4',5,7-TRIHYDROXYFLAVANONE
• CAS NO: 480-41-1
• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.25
• EINECS: 266-769-1
• Product Categories: Flavanones;Natural Plant Extract;Inhibitors;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;natural product
• Mol File: 480-41-1.mol
• Article Data: 57

Chemical Properties

• Melting Point: 247-250 °C(lit.)
• Boiling Point: 335.31°C (rough estimate)
• Flash Point: 224.7°C
• Appearance: Beige-brown/Powder
• Density: 1.2066 (rough estimate)
• Vapor Pressure: 6.18E-14mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: 7.52±0.40(Predicted)
• CAS DataBase Reference: Naringenin(CAS DataBase Reference)
• NIST Chemistry Reference: Naringenin(480-41-1)
• EPA Substance Registry System: Naringenin(480-41-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 480-41-1(Hazardous Substances Data)

Usage

Pharmacological effects

Naringenin is the aglycone of naringin, it belongs to dihydro-flavonoids, at room temperature it is a white needle crystal(methanol), soluble in alcohol, ether and benzene, almost insoluble in water. In HCl-Mg powder reaction,it is cherry red ,in sodium borohydride reaction it is red purple, in molish reaction,it is negative. In the nature, it is mainly from the Rosaceae cherry (Prunus yedoensis Mate.) bud,and sumac plants (Amacardi-um occidentale L.)? fruits’ core-shell. Nucleus structure is similar among flavonoids, most of the components do not have ideal fat-soluble and water-soluble abilities, the bioavailability is low. By modifying its structure, the introduction of strongly fat-soluble or water-soluble groups can increase its fat-soluble or water-soluble abilities, thus improving the bioavailability. The structure modification includes alkylation, acylation, sulfonation,glycosidation? of hydroxyl groups and the formation of the metal complex. The effects of naringenin including: anti-bacterial, anti-inflammatory, antioxidant, cough expectorant,decreasing blood fat, anti-cancer and anti-tumor, antispasmodic, scavenging free radicals, prevention and treatment of liver disease, inhibition of platelet aggregation, anti-atherosclerosis and others , which can be widely used in medicine, food and other fields. 1. Antibacterial: it has a strong antibacterial effect on Staphylococcus aureus, Escherichia coli, Shigella dysenteriae, and Salmonella typhi. Naringenin also has effect on fungi? , 1000ppm is sprayed onto the rice, blast fungus infection can be reduced 40-90%,and it is not toxic to livestock and humans. 2. Anti-inflammatory: intraperitoneal injection of 20mg/kg per day for rats can inhibit the inflammatory process which caused by wool ball implantation. 3. Anticancer:? it displays action in L1210 leukemia and sarcomas in rats. 4. Antispasmodic and gallbladder: among the flavonoids,it has stronger effects. Naringenin has a strong effect on increasing bile secretion in experimental animals.

Application

It has anti-bacterial, anti-inflammatory, anti-cancer, antispasmodic and choleretic effects.

Chemical Properties

beige-brown powder

Uses

Different sources of media describe the Uses of 480-41-1 differently. You can refer to the following data:
1. The aglucon of Naringin. Inhibitory mechanism of Naringenin against carcinogenic acrylamide formation and nonenzymic browning in Maillard model reactions
2. antiulcer, antioxidant, immunomodulator, cholesterol lowering
3. (S)-Naringenin, an active flavanone, maintains antioxidative, anti-inflammatory and antitumorigenic activities. Used in the treatment of praquat (PQ)-induced oxidative stress.

Purification Methods

Crystallise it from EtOH or aqueous EtOH. It has UV: at 290nm (EtOH). The S(-)-enantiomer (natural form) has m 255-256o (from EtOH) and [] D -28.0o (c 2, EtOH), [] D -35.2o (c 1, pyridine).

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/t13-/m1/s1

Synthetic route

(2S)-naringenin 5,4'-di-O-β-D-glucopyranoside (1160434-47-8) → D-glucose (50-99-7) + naringenin (480-41-1)

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

naringin (10236-47-2) → naringenin (480-41-1)

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 → naringenin (480-41-1)

Conditions	Yield
With sulfuric acid; water at 20℃; for 0.166667h;	21%

naringin (10236-47-2) → naringenin (480-41-1) + 5,6,7,4′-tetrahydroxyflavanone + 5,7,8,4′-tetrahydroxyflavanone

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

(2S)-(-)-naringenin-5-O-β-D-glucopyranoside (529-41-9, 19253-00-0, 23711-00-4) → naringenin (480-41-1)

Conditions	Yield
With formic acid; ethylene glycol

4,2',4',6'-tetrahydroxychalchone 4'-glucoside (112294-87-8) → naringenin (480-41-1)

Conditions	Yield
acid and enzymatic hydrolysis;

naringenin 7-O-(6-O-((E)-p-coumaroyl)-β-D-glucopyranoside) → naringenin (480-41-1)

Conditions	Yield
With hydrogenchloride for 4h; Heating;

2''-O-p-coumaroylprunin → naringenin (480-41-1)

Conditions	Yield
With hydrogenchloride for 4h; Heating;

(-)-(S)-sakuranetin (520-29-6, 2957-21-3, 17784-36-0, 118244-13-6) → naringenin (480-41-1) + (2S)-naringenin 4′-O-sulphate

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

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on (480-41-1) → naringenin (480-41-1) + (+)-Naringenin (480-41-1, 17654-19-2, 67604-48-2, 93602-28-9)

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;

naringin (10236-47-2) → prunin (529-55-5, 88275-21-2, 127469-97-0) + naringenin (480-41-1)

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;

naringin (10236-47-2) → β-D-glucose (492-61-5) + L-rhamnose (6014-42-2) + prunin (529-55-5, 88275-21-2, 127469-97-0) + naringenin (480-41-1)

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

naringin (10236-47-2) → D-Glucose (2280-44-6) + L-rhamnose (73-34-7) + prunin (529-55-5, 88275-21-2, 127469-97-0) + naringenin (480-41-1)

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;

naringenin chalcone (25515-46-2) → naringenin (480-41-1)

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

prunin (529-55-5, 88275-21-2, 127469-97-0) → alpha-D-glucopyranose (492-62-6) + naringenin (480-41-1)

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

naringin (10236-47-2) → β-D-glucose (492-61-5) + L-rhamnose (6014-42-2) + naringenin (480-41-1)

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

naringin (10236-47-2) → 2-O-α-L-rhamnopyranosyl-β-D-glucopyranose (19949-48-5) + naringenin (480-41-1)

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

prunin (529-55-5, 88275-21-2, 127469-97-0) → naringenin (480-41-1)

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

L-tyrosine (60-18-4) → isoliquirtigenin (961-29-5, 13745-20-5) + p-Coumaric Acid (7400-08-0) + liquiritigenin (578-86-9) + naringenin (480-41-1)

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

L-tyrosine (60-18-4) → p-Coumaric Acid (7400-08-0) + naringenin (480-41-1)

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

(-)-(S)-sakuranetin (520-29-6, 2957-21-3, 17784-36-0, 118244-13-6) → 7-methoxy-3',4',5-trihydroxyflavanone (93012-86-3) + eriodictyol (552-58-9) + 7-methoxyflavanone (21785-09-1) + naringenin (480-41-1)

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

(-)-(S)-sakuranetin (520-29-6, 2957-21-3, 17784-36-0, 118244-13-6) → eriodictyol (552-58-9) + naringenin (480-41-1)

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

diazomethane (186581-53-3, 908094-01-9) + naringenin (480-41-1) → (-)-(S)-sakuranetin (520-29-6, 2957-21-3, 17784-36-0, 118244-13-6)

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

1-deoxy-1-fluoro-α-D-glucose (2106-10-7) + naringenin (480-41-1) → naringenin 7-α-O-glucoside

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

naringenin (480-41-1) → 7,4'-di-O-hexylnaringenin oxime

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

water (7732-18-5) + copper diacetate (142-71-2) + naringenin (480-41-1) → trans-di(aqua) bis(7-hydroxy-2-(4-hydroxyphenyl)-4-oxo-5-chromanolato) copper (II)

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

benzyl bromide (100-39-0) + naringenin (480-41-1) → 7,4'-O,O-dibenzyl naringenin

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%

Hexanoyl chloride (142-61-0) + naringenin (480-41-1) → 5,7,4'-tri-O-hexanoyl-naringenin

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

naringenin (480-41-1) → naringenin oxime

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℃;

ethylenediamine (107-15-3) + naringenin (480-41-1) → 1,2-di(4-iminenaringenin)ethane

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

naringenin (480-41-1) → 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (520-36-5)

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

2,2',3,3',4',6,6'-hepta-O-acetyl-β-D-cellobiosyl bromide (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) + naringenin (480-41-1) → 7-O-(heptaacetyl--D-cellobiosyl)naringenin

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

ethylenediamine (107-15-3) + naringenin (480-41-1) → 1,2-di(4'-iminonaringenin)ethane

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

naringenin (480-41-1) + Beauveria bassiana AM 278 grown on a sabouraud medium → naringenin 7-O-β-D-(4''-O-methyl)glucopyranoside

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

benzyl bromide (100-39-0) + naringenin (480-41-1) → (E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one (88607-79-8)

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

copper diacetate (142-71-2) + naringenin (480-41-1) → Cu(naringenin)2

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

naringenin (480-41-1) → 7-O-hexylnaringenin oxime

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

1,10-Phenanthroline (66-71-7) + copper(II) perchlorate + naringenin (480-41-1) → C27H21CuN2O6(1+)*ClO4(1-)*H2O

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

[2,2]bipyridinyl (366-18-7) + copper(II) choride dihydrate + naringenin (480-41-1) → Cu(naringenin)(2,2'-bipyridine)

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

formaldehyd (50-00-0) + furan-2-ylmethanamine (617-89-0) + naringenin (480-41-1) → 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	Yield
In toluene at 100℃; for 3h;	79%

1-iodo-butane (542-69-8) + naringenin (480-41-1) → 7-O-butylnaringenin

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

2,3,4,5-tetrahydropyridine (505-18-0) + naringenin (480-41-1) → 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(piperidin-2-yl)chroman-4-one

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

naringenin (480-41-1) + diazomethyl-trimethyl-silane (18107-18-1) → (S)-5-hydroxy-2-(4-methoxyphenyl)-7-methoxy-2,3-dihydro chromen-4-one

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

morpholine (110-91-8) + formaldehyd (50-00-0) + naringenin (480-41-1) → 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(morpholinomethyl)chroman-4-one

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

formaldehyd (50-00-0) + ethyl 4-(piperazin-1-yl)benzoate (80518-57-6) + naringenin (480-41-1) → ethyl 4-(4-((5, 7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochroman-6-yl)methyl) piperazin-1-yl)benzoate

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

formaldehyd (50-00-0) + aniline (62-53-3) + naringenin (480-41-1) → C31H26N2O5

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%

dimethyl sulfate (77-78-1) + naringenin (480-41-1) → (-)-(S)-sakuranetin (520-29-6, 2957-21-3, 17784-36-0, 118244-13-6)

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

naringenin (480-41-1) + Absidia coerulea AM 93 grown on a sabouraud medium → prunin (529-55-5, 88275-21-2, 127469-97-0)

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

benzyl bromide (100-39-0) + naringenin (480-41-1) → C22H18O5 (88607-75-4)

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

Iododecane (2050-77-3) + naringenin (480-41-1) → 7-O-decylnaringenin

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

2-(bromomethyl)-3,5,6-trimethylpyrazine (79074-45-6) + naringenin (480-41-1) → (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	Yield
With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide; acetone for 2h; Inert atmosphere;	70%

Upstream product

• 529-41-9 (2S)-(-)-naringenin-5-O-β-D-glucopyranoside 
• 10236-47-2 naringin 
• 529-55-5 prunin 
• 23711-00-4 naringenin-5-O-glucoside 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 10236-47-2 naringin 
• 25515-46-2 naringenin chalcone 
• 1160434-44-5 (2S)-naringenin 5-O-β-D-glucopyranosyl(1->6)-β-D-glucopyranoside 
• 520-29-6 (-)-(S)-sakuranetin 
• 1160434-47-8 (2S)-naringenin 5,4'-di-O-β-D-glucopyranoside 
• 94392-49-1 naringenin 7-O-(6-O-((E)-p-coumaroyl)-β-D-glucopyranoside) 
• 112294-87-8 4,2',4',6'-tetrahydroxychalchone 4'-glucoside 
• 3420-72-2 flavokawain A 
• 60-18-4 L-tyrosine 

Downstream Products

• 68682-02-0 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-8-(3-methyl-but-2-enyl)-chroman-4-one 
• 68682-00-8 (+/-)-6,8-Diprenylnaringenin 
• 68682-01-9 5,7,4'-trihydroxy-6-prenylflavanone 
• 29424-96-2 naringenin-4',7-dimethyl ether 
• 520-29-6 5,4'-dihydroxy-7-methoxyflavanone 
• 4049-38-1 eriodictyol 
• 189299-03-4 3'-Geranylchalconaringenin 
• 128374-01-6 Acetic acid 3,5-dihydroxy-4-[3-(4-hydroxy-phenyl)-propyl]-phenyl ester 
• 252881-05-3 4',5,7-trihydroxy-8-(tricarbonyl[(1'',2'',3'',4''-η)-1'',3''-cyclohexadien-5''α-yl]iron(0))flavanone 
• 220433-57-8 4',5,7-trihydroxy-6-(tricarbonyl[(1'',2'',3'',4''-η)-1'',3''-cyclohexadien-5''α-yl]iron(0))flavanone 
• 220433-67-0 4',5,7-trihydroxy-6,8-bis-(tricarbonyl[(1'',2'',3'',4''-η)-1'',3''-cyclohexadien-5''α-yl]iron(0))flavanone 
• 220433-69-2 4',5,7-trihydroxy-6-(tricarbonyl[(1'',2'',3'',4''-η)-2''-methoxy-1'',3''-cyclohexadien-5''α-yl]iron(0))flavanone 
• 252881-06-4 4',5,7-trihydroxy-8-(tricarbonyl[(1'',2'',3'',4''-η)-2''-methoxy-1'',3''-cyclohexadien-5''α-yl]iron(0))flavanone 
• 220433-71-6 4',5,7-trihydroxy-6,8-bis-(tricarbonyl[(1'',2'',3'',4''-η)-2''-methoxy-1'',3''-cyclohexadien-5''α-yl]iron(0))flavanone 

Relevant articles and documents

Synthesis, structural elucidation and antiradical activity of a copper (II) naringenin complex

Coupling the extraction and derivatization of flavonoids to the Citrus processing industry is attractive from both the environmental and economic points of view. In the present work, the flavonoid naringin, obtained by “green” extraction with a water:ethanol mixture from waste grapefruit industry, was hydrolyzed to obtain naringenin. This flavonoid was used to synthesize the complex trans-di(aqua) bis(7-hydroxy-2-(4-hydroxyphenyl)-4-oxo-5-chromanolato) copper (II). This compound was characterized by spectroscopic techniques (UV/Vis, IR, Raman, NMR and EPR), and by thermal analysis (TG and DSC). Then, a monocrystal of the complex obtained by dissolution and recrystallization in DMF was analyzed by single crystal X-ray diffraction. This is the first report of the crystal structure of a Citrus flavonoid complex. Additionally, its antiradical activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) was determined and compared with that for naringenin, demonstrating that coordination to copper enhances the antiradicalar activity of naringenin. According to the Mulliken population analysis conducted, by copper favors the delocalization and stabilization of the produced radical, since it acts as an electronic density acceptor.

Sulfation of naringenin by Cunninghamella elegans

A new flavonoid sulfate, naringenin-7-sulfate, was obtained by fermentation of naringenin using the fungus Cunninghamella elegans NRRL 1392 in 23% yield. Structural elucidation of the metabolite was achieved using EIMS, UV, IR, 1D and 2D NMR spectroscopy beside acid and enzyme hydrolyses. (C) 2000 Elsevier Science Ltd.

GLUCOSYLATED FLAVONOIDS AND OTHER PHENOLIC COMPOUNDS FROM SORGHUM

The principal tannin constituents of sorghum are proanthocyanidins or condensed tannins.Analysis of the methanolic extract of a Hungarian sorghum (szegedi toerpe) containing 6percent catechin equivalents of tannins resulted in the separation and purification of 4 procyanidins having the basic formula epicatechin-(epicatechin)n-catechin and one procyanidin trimer corresponding to epicatechin-catechin-epicatechin.Apart from these procyanidins, the monomeric flavonoids eriodictyol 5-glucoside and (+)-taxifolin 7 glucoside together with their aglycones eriodictyol and taxifolin were found.Glucosylated dimeric and trimeric flavanoids with eriodictyol or eriodictyol 5-glucoside as the lower unit were also identified with the help of negative ion FABMS.Polymeric flavonoids formed between a chalcone and a flavonoid, as yet not identified, are also present in the grain. Key Word Index - Sorghum; Gramineae; flavanoids; glycosides; new oligomer glucosides; procyanidins; chalchone identification.

Flavanone compound as well as preparation method and application thereof

The invention belongs to the technical field of medicines, and particularly relates to a flavanone compound as well as a preparation method and application thereof. Specifically disclosed is a compound represented by formula (I) or a pharmaceutically acceptable salt thereof. The compound shown in the formula (I) can target hURAT1 and/or GLUT9, so that uric acid excretion is promoted, and the effect of reducing uric acid is achieved. The compound can be used for preparing medicines for treating and/or preventing and/or delaying and/or adjunctively treating and/or treating diseases related to hURAT1/GLUT9 activity, and has a good application prospect in preventing or treating diseases (such as gout, gouty arthritis, uric acid kidney stone and the like) related to hyperuricemia.

Covalent Immobilization of Naringinase over Two-Dimensional 2D Zeolites and its Applications in a Continuous Process to Produce Citrus Flavonoids and for Debittering of Juices

The crude naringinase from Penicillium decumbens and a purified naringinase with high α-L-rhamnosidase activity could be covalently immobilized on two-dimensional zeolite ITQ-2 after surface modification with glutaraldehyde. The influence of pH and temperature on the enzyme activity (in free and immobilized forms) as well as the thermal stability were determined using the specific substrate: p-nitrophenyl-alpha-L-rhamnopyranoside (Rha-pNP). The crude and purified naringinase supported on ITQ-2 were applied in the hydrolysis of naringin, giving the flavonoids naringenin and prunin respectively with a conversion '90 percent and excellent selectivity. The supported enzymes showed long term stability, being possible to perform up to 25 consecutive cycles without loss of activity, showing its high potential to produce the valuable citrus flavonoids prunin and naringenin. We have also succeeded in the application of the immobilized crude naringinase on ITQ-2 for debittering grapefruit juices in a continuous process that was maintained operating for 300 h, with excellent results.