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  • 480-41-1 Structure
  • Basic information

    1. Product Name: Naringenin
    2. 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
    3. CAS NO:480-41-1
    4. Molecular Formula: C15H12O5
    5. Molecular Weight: 272.25
    6. EINECS: 266-769-1
    7. 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
    8. Mol File: 480-41-1.mol
    9. Article Data: 57
  • Chemical Properties

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

    1. Hazard Codes: Xi,Xn
    2. Statements: 36/37/38-22
    3. Safety Statements: 26-36-37/39
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 480-41-1(Hazardous Substances Data)

480-41-1 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).

Check Digit Verification of cas no

The CAS Registry Mumber 480-41-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 0 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 480-41:
(5*4)+(4*8)+(3*0)+(2*4)+(1*1)=61
61 % 10 = 1
So 480-41-1 is a valid CAS Registry Number.
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

480-41-1Synthetic route

(2S)-naringenin 5,4'-di-O-β-D-glucopyranoside
1160434-47-8

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

A

D-glucose
50-99-7

D-glucose

B

naringenin
480-41-1

naringenin

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

naringin

naringenin
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

naringin

naringenin
480-41-1

naringenin

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

naringin

A

naringenin
480-41-1

naringenin

B

5,6,7,4′-tetrahydroxyflavanone

5,6,7,4′-tetrahydroxyflavanone

C

5,7,8,4′-tetrahydroxyflavanone

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

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

naringenin
480-41-1

naringenin

Conditions
ConditionsYield
With formic acid; ethylene glycol
4,2',4',6'-tetrahydroxychalchone 4'-glucoside
112294-87-8

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

naringenin
480-41-1

naringenin

Conditions
ConditionsYield
acid and enzymatic hydrolysis;
naringenin 7-O-(6-O-((E)-p-coumaroyl)-β-D-glucopyranoside)

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

naringenin
480-41-1

naringenin

Conditions
ConditionsYield
With hydrogenchloride for 4h; Heating;
2''-O-p-coumaroylprunin

2''-O-p-coumaroylprunin

naringenin
480-41-1

naringenin

Conditions
ConditionsYield
With hydrogenchloride for 4h; Heating;

A

naringenin
480-41-1

naringenin

B

(2S)-naringenin 4′-O-sulphate

(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
5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on
480-41-1

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

A

naringenin
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;
Conditions
ConditionsYield
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

naringin

A

β-D-glucose
492-61-5

β-D-glucose

B

L-rhamnose
6014-42-2

L-rhamnose

D

naringenin
480-41-1

naringenin

Conditions
ConditionsYield
With naringinase In tetrahydrofuran at 45℃; pH=4; Kinetics; Solvent; Concentration; aq. acetate buffer;
naringin
10236-47-2

naringin

A

D-Glucose
2280-44-6

D-Glucose

B

L-rhamnose
73-34-7

L-rhamnose

D

naringenin
480-41-1

naringenin

Conditions
ConditionsYield
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 chalcone

naringenin
480-41-1

naringenin

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

A

alpha-D-glucopyranose
492-62-6

alpha-D-glucopyranose

B

naringenin
480-41-1

naringenin

Conditions
ConditionsYield
With β-D-glucosidase In aq. buffer at 50 - 100℃; for 0.166667h; pH=5; Enzymatic reaction;
naringin
10236-47-2

naringin

A

β-D-glucose
492-61-5

β-D-glucose

B

L-rhamnose
6014-42-2

L-rhamnose

C

naringenin
480-41-1

naringenin

Conditions
ConditionsYield
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

naringin

A

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

2-O-α-L-rhamnopyranosyl-β-D-glucopyranose

B

naringenin
480-41-1

naringenin

Conditions
ConditionsYield
With sulfuric acid In methanol; water for 6h; Reflux;
Conditions
ConditionsYield
With β-D-glucosidase In aq. buffer at 50 - 100℃; for 0.583333h; pH=4; Kinetics; Enzymatic reaction;
L-tyrosine
60-18-4

L-tyrosine

A

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

isoliquirtigenin

B

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

C

liquiritigenin
578-86-9

liquiritigenin

D

naringenin
480-41-1

naringenin

Conditions
ConditionsYield
With isopropyl β-D-thiogalactopyranoside at 30℃; for 24h; Reagent/catalyst; Microbiological reaction;
L-tyrosine
60-18-4

L-tyrosine

A

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

B

naringenin
480-41-1

naringenin

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

A

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

7-methoxy-3',4',5-trihydroxyflavanone

B

eriodictyol
552-58-9

eriodictyol

C

7-methoxyflavanone
21785-09-1

7-methoxyflavanone

D

naringenin
480-41-1

naringenin

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

A

eriodictyol
552-58-9

eriodictyol

B

naringenin
480-41-1

naringenin

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

1-deoxy-1-fluoro-α-D-glucose

naringenin
480-41-1

naringenin

naringenin 7-α-O-glucoside

naringenin 7-α-O-glucoside

Conditions
ConditionsYield
With α-glucosidase from sulfolobus solfataricus In dimethyl sulfoxide at 45℃; for 2h; pH=9; Enzymatic reaction;99%
naringenin
480-41-1

naringenin

7,4'-di-O-hexylnaringenin oxime

7,4'-di-O-hexylnaringenin oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In ethanol at 40 - 50℃; for 25h;98.6%
water
7732-18-5

water

copper diacetate
142-71-2

copper diacetate

naringenin
480-41-1

naringenin

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

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

Conditions
ConditionsYield
In ethanol at 60 - 65℃; for 1h; pH=7;95%
benzyl bromide
100-39-0

benzyl bromide

naringenin
480-41-1

naringenin

7,4'-O,O-dibenzyl naringenin

7,4'-O,O-dibenzyl naringenin

Conditions
ConditionsYield
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

Hexanoyl chloride

naringenin
480-41-1

naringenin

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

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

Conditions
ConditionsYield
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

naringenin oxime

naringenin oxime

Conditions
ConditionsYield
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

ethylenediamine

naringenin
480-41-1

naringenin

1,2-di(4-iminenaringenin)ethane

1,2-di(4-iminenaringenin)ethane

Conditions
ConditionsYield
With acetic acid In ethanol for 5h; Inert atmosphere; Reflux;87%
naringenin
480-41-1

naringenin

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

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

Conditions
ConditionsYield
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
Conditions
ConditionsYield
With quinoline; silver (II) carbonate at 20℃; for 3h; Koenigs-Knorr Glycosidation;86%
ethylenediamine
107-15-3

ethylenediamine

naringenin
480-41-1

naringenin

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

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

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

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

Conditions
ConditionsYield
In dimethyl sulfoxide for 168h; Microbiological reaction; regioselective reaction;82%
benzyl bromide
100-39-0

benzyl bromide

naringenin
480-41-1

naringenin

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

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

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;81%
With potassium carbonate In acetone Heating / reflux;81%
copper diacetate
142-71-2

copper diacetate

naringenin
480-41-1

naringenin

Cu(naringenin)2

Cu(naringenin)2

Conditions
ConditionsYield
With triethylamine In methanol; water at 20℃; for 3h;80%
naringenin
480-41-1

naringenin

7-O-hexylnaringenin oxime

7-O-hexylnaringenin oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In ethanol at 40 - 50℃; for 5h;79.1%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

copper(II) perchlorate

copper(II) perchlorate

naringenin
480-41-1

naringenin

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

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

Conditions
ConditionsYield
In methanol for 8h; Reflux;79%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

copper(II) choride dihydrate

copper(II) choride dihydrate

naringenin
480-41-1

naringenin

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

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

Conditions
ConditionsYield
With triethylamine In methanol; water at 20℃; for 6h;79%
formaldehyd
50-00-0

formaldehyd

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

naringenin
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

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
ConditionsYield
In toluene at 100℃; for 3h;79%
1-iodo-butane
542-69-8

1-iodo-butane

naringenin
480-41-1

naringenin

7-O-butylnaringenin

7-O-butylnaringenin

Conditions
ConditionsYield
With potassium carbonate In acetone at 40 - 45℃; regioselective reaction;78.7%
2,3,4,5-tetrahydropyridine
505-18-0

2,3,4,5-tetrahydropyridine

naringenin
480-41-1

naringenin

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

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

Conditions
ConditionsYield
at 80℃; Mannich Aminomethylation; Inert atmosphere; regioselective reaction;78%
naringenin
480-41-1

naringenin

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

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

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

Conditions
ConditionsYield
In methanol; hexane; dichloromethane at 20℃; for 12h;77%
morpholine
110-91-8

morpholine

formaldehyd
50-00-0

formaldehyd

naringenin
480-41-1

naringenin

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

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

Conditions
ConditionsYield
In methanol at 65℃; Mannich Aminomethylation; regioselective reaction;76%
formaldehyd
50-00-0

formaldehyd

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

ethyl 4-(piperazin-1-yl)benzoate

naringenin
480-41-1

naringenin

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

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

Conditions
ConditionsYield
In methanol at 65℃; Mannich Aminomethylation; regioselective reaction;76%
formaldehyd
50-00-0

formaldehyd

aniline
62-53-3

aniline

naringenin
480-41-1

naringenin

C31H26N2O5

C31H26N2O5

Conditions
ConditionsYield
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

dimethyl sulfate

naringenin
480-41-1

naringenin

Conditions
ConditionsYield
With potassium carbonate In acetone at 50℃; for 12h;76%
naringenin
480-41-1

naringenin

Absidia coerulea AM 93 grown on a sabouraud medium

Absidia coerulea AM 93 grown on a sabouraud medium

Conditions
ConditionsYield
In dimethyl sulfoxide for 168h; Microbiological reaction; regioselective reaction;73%
benzyl bromide
100-39-0

benzyl bromide

naringenin
480-41-1

naringenin

C22H18O5
88607-75-4

C22H18O5

Conditions
ConditionsYield
With tertamethylammonium iodide In N,N-dimethyl-formamide at 20℃; for 48h;72%
Iododecane
2050-77-3

Iododecane

naringenin
480-41-1

naringenin

7-O-decylnaringenin

7-O-decylnaringenin

Conditions
ConditionsYield
With potassium carbonate In acetone at 40 - 45℃; regioselective reaction;70.8%
2-(bromomethyl)-3,5,6-trimethylpyrazine
79074-45-6

2-(bromomethyl)-3,5,6-trimethylpyrazine

naringenin
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

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

480-41-1Relevant articles and documents

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

Celiz, Gustavo,Suarez, Sebastián A.,Arias, Analía,Molina, José,Brondino, Carlos D.,Doctorovich, Fabio

, p. 595 - 610 (2019)

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

Ibrahim, Abdel-Rahim S.

, p. 209 - 212 (2000)

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

Gujer, Rene,Magnolato, Daniele,Self, Ron

, p. 1431 - 1436 (1986)

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

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Paragraph 0202-0205, (2021/04/17)

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.

Novel chromenone derivatives having substituted biphenyl group and a pharmaceutical composition for prevention or treatment of allergic diseases compring the same

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Paragraph 0157-0164; 0166-0170, (2020/11/26)

The present invention relates to: a novel chromenone derivative compound capable of effectively suppressing an allergic immune response by inhibiting signal transduction mediated by thymic stromal lymphopoietin (TSLP); and a pharmaceutical composition capable of fundamentally preventing or treating various allergic diseases by using the same.COPYRIGHT KIPO 2021

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