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Naringenin

Basic information Pharmacological effects Application Safety Supplier Related

Naringenin Basic information

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
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Naringenin Chemical Properties

Melting point:
247-250 °C(lit.)
Boiling point:
335.31°C (rough estimate)
Density 
1.2066 (rough estimate)
refractive index 
1.6000 (estimate)
FEMA 
4797 | (+/-)-NARINGENIN
storage temp. 
Inert atmosphere,Room Temperature
solubility 
DMSO (Slightly), Methanol (Slightly, Sonicated)
form 
Powder
pka
7.52±0.40(Predicted)
color 
Beige-brown
InChI
InChI=1S/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-/m0/s1
InChIKey
FTVWIRXFELQLPI-ZDUSSCGKSA-N
SMILES
[C@H]1(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C2C(=O)C1
LogP
2.520
CAS DataBase Reference
480-41-1(CAS DataBase Reference)
EPA Substance Registry System
4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)- (480-41-1)
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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

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Naringenin Usage And Synthesis

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

The aglucon of Naringin. Inhibitory mechanism of Naringenin against carcinogenic acrylamide formation and nonenzymic browning in Maillard model reactions

Uses

antiulcer, 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.

Definition

ChEBI: (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 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).

NaringeninSupplier

Weifang Huazhi Biological Technology Co., Ltd. Gold
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Products Intro
Product Name:Naringenin
CAS:480-41-1
Purity:HPLC:98% Package:1起订量你定/RMB 100
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Product Name:4',5,7-Trihydroxyflavanone, 96%
CAS:480-41-1
Purity:96% Package:100G;1G;25G;5G
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Product Name:4',5,7-Trihydroxyflavanone
CAS:480-41-1
Purity:97% Remarks:13982
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Product Name:(S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one
CAS:480-41-1
Purity:HPLC>=98% Package:88RMB/ 20mg
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Product Name:Naringenin
CAS:480-41-1
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