Naringenin

Naringenin Basic information
Pharmacological effects Application
Product Name:Naringenin
Synonyms:naringenine;naringetol;4’,5,7-trihydroxy-flavanon;S-Dihydrogenistein;NSC 34875;NSC 11855;(S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-ben;4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (S)-
CAS:480-41-1
MF:C15H12O5
MW:272.25
EINECS:207-550-2
Product Categories:Natural Plant Extract;natural product;chemical reagent;pharmaceutical intermediate;phytochemical;CITRIMORE;Flavanones;Inhibitors;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
Mol File:480-41-1.mol
Naringenin Structure
Naringenin Chemical Properties
Melting point 247-250 °C(lit.)
Boiling point 335.31°C (rough estimate)
density 1.2066 (rough estimate)
FEMA 4797 | (+/-)-NARINGENIN
refractive index 1.6000 (estimate)
storage temp. Inert atmosphere,Room Temperature
solubility DMSO (Slightly), Methanol (Slightly, Sonicated)
form Powder
pka7.52±0.40(Predicted)
color Beige-brown
LogP2.520
CAS DataBase Reference480-41-1(CAS DataBase Reference)
EPA Substance Registry System4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)- (480-41-1)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/37/38-22
Safety Statements 26-36-37/39
WGK Germany 3
HazardClass IRRITANT
HS Code 29329990
MSDS Information
Naringenin Usage And Synthesis
Pharmacological effectsNaringenin 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.





ApplicationIt has anti-bacterial, anti-inflammatory, anti-cancer, antispasmodic and choleretic effects.
Chemical Propertiesbeige-brown powder
UsesThe aglucon of Naringin. Inhibitory mechanism of Naringenin against carcinogenic acrylamide formation and nonenzymic browning in Maillard model reactions
Usesantiulcer, antioxidant, immunomodulator, cholesterol lowering
Uses(S)-Naringenin, an active flavanone, maintains antioxidative, anti-inflammatory and antitumorigenic activities. Used in the treatment of praquat (PQ)-induced oxidative stress.
DefinitionChEBI: (S)-naringenin is the (S)-enantiomer of naringenin. It has a role as an expectorant and a plant metabolite. It is a naringenin and a (2S)-flavan-4-one. It is a conjugate acid of a (S)-naringenin(1-). It is an enantiomer of a (R)-naringenin.
Purification MethodsCrystallise 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).
Naringenin Preparation Products And Raw materials
Preparation Products2,3-Dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-(phenylmethoxy)-4H-1-benzopyran-4-one
Naringin dihydrochalcone Naringin TAXIFOLIN HOMOERIODICTYOL HESPERETIN Hesperidin Isoflavone 6,8-DIMETHYL-4',5,7-TRIHYDROXYFLAVANONE Naringenin ERIODICTYOL SAKURANETIN Chrysin (+)-TAXIFOLIN FLAVONE NEOERIOCITRIN Dihydromyrcenol 7-HYDROXYFLAVONE ISOFLAVONES

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