Naringenin
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
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)
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
- Language:English Provider:5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
- Language:English Provider:ACROS
- Language:English Provider:SigmaAldrich
- Language:English Provider:ALFA
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).
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- Product Name:Naringenin
CAS:480-41-1
Purity:HPLC:98% Package:1起订量你定/RMB 100
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- Products Intro
- Product Name:4',5,7-Trihydroxyflavanone, 96%
CAS:480-41-1
Purity:96% Package:100G;1G;25G;5G
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- Products Intro
- Product Name:4',5,7-Trihydroxyflavanone
CAS:480-41-1
Purity:97% Remarks:13982
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- Products Intro
- 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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CAS:480-41-1
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Naringenin(480-41-1)Related Product Information
- FLAVONE
- Isoflavone
- Naringin dihydrochalcone
- Chrysin
- Dihydromyrcenol
- 7-HYDROXYFLAVONE
- Naringin
- Prunin
- NARINGENIN
- Naringenin 7-O-β-D-Glucuronide (Mixture of Diastereomers)
- Naringin D4
- NARINGENIN CHALCONE,NARINGENIN CHALCONE
- ISOFLAVONES
- 6,8-DIMETHYL-4',5,7-TRIHYDROXYFLAVANONE
- 5,7-DIHYDROXY-3',4',5'-TRIMETHOXYFLAVANONE
- NARINGENIN-7-RUTINOSIDE,NARINGENIN-7-O-RUTINOSIDE,NARINGENIN-7-RUTINOSIDE,NARINGENIN-7-O-RUTINOSIDE
- ERIOCITRIN
- ERIODICTYOL