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480-41-1

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Identification

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

Appearance
beige-brown powder
Melting point 
247-250 °C(lit.)

mp 
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
form 
Powder
pka
7.52±0.40(Predicted)
color 
Beige-brown
Usage
The aglucon of naringin
CAS DataBase Reference
480-41-1(CAS DataBase Reference)
EPA Substance Registry System
480-41-1(EPA Substance)

Safety Data

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

Material Safety Data Sheet(MSDS)

Questions And Answer

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

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
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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