| Identification | More | [Name]
Naringenin | [CAS]
480-41-1 | [Synonyms]
(+/-)-2,3-DIHYDRO-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
(+/-)-4',5,7-TRIHYDROXYFLAVANONE
4',5,7-TRIHYDROXYFLAVANONE
5,7,4'-TRIHYDROXYFLAVANONE
5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)CHROMAN-4-ONE
(+/-)-NARINGENIN
NARINGENIN
TIMTEC-BB SBB006461
(s)-naringenin
3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-(s)-4h-1-benzopyran-4-on
4’,5,7-trihydroxy-flavanon
naringenine
naringetol
salipurol
salipurpol
(S)-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone
4',5,7-Trihydroxyflavanone, Naringetol, Salipurpol,
NARIGENIN
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one
NARINGENIN hplc | [EINECS(EC#)]
266-769-1 | [Molecular Formula]
C15H12O5 | [MDL Number]
MFCD00006844 | [Molecular Weight]
272.25 | [MOL File]
480-41-1.mol |
| Chemical Properties | Back Directory | [Appearance]
beige-brown powder | [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 | [pka]
7.52±0.40(Predicted) | [color ]
Beige-brown | [Usage]
The aglucon of naringin | [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]
480-41-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29329990 |
| Questions And Answer | Back Directory | [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. |
| Hazard Information | Back Directory | [Chemical Properties]
beige-brown powder | [Uses]
antiulcer, antioxidant, immunomodulator, cholesterol lowering | [Uses]
The aglucon of Naringin. Inhibitory mechanism of Naringenin against carcinogenic acrylamide formation and nonenzymic browning in Maillard model reactions | [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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