Naringenin

Naringenin Property

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

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29329990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Naringenin Chemical Properties,Usage,Production

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.

Synthesis

The general procedure for synthesizing naringin from naringin is as follows: 1. 52g of naringin was mixed with 5% (w/v) hydrochloric acid solution at a solid-liquid ratio of 1:100 (g/mL) and hydrolyzed at 100°C for 1 hour. After completion of the reaction it was rapidly cooled to room temperature and left to settle for 12 hours to allow the solids to precipitate. The solids were collected by filtration and washed with purified water to neutrality to obtain 24.5 g of wet crude naringenin with 25% water content. 2. The crude naringenin obtained in step (1) was added to a 30% (w/v) acetic acid solution with a solid-liquid ratio of 1:7 (g/mL) and stirred for 30 minutes at room temperature. Subsequently, the same concentration of acetic acid solution was added and treated for 15 minutes, filtered and the solids were washed with water to neutrality. 3. The treated solid was dissolved in 95% (v/v) ethanol at a solid-liquid ratio of 1:10 (g/mL) and purified by passing through a neutral alumina column. 100 mL of 95% (v/v) ethanol eluate was collected and the solutions after column chromatography were combined. 4. Activated carbon equal to 10% by volume of the solution was added to the combined solution, stirred for 30 minutes at room temperature and filtered. Repeat this activated carbon treatment step once. 5. Concentrate the filtrate to 1/3 of the original volume, add an equal volume of distilled water, cool to room temperature and place in a refrigerator at 5°C for 24 hours to precipitate white mother-of-pearl-like crystals. The crystals were collected by filtration, and naringenin wet product was obtained. 6. Naringenin wet good to 1:6 (g/mL) solid-liquid ratio of heating dissolved in 95% ethanol, add an equal volume of distilled water for a recrystallization. The precipitated white needle-like crystals were collected by filtration and dried to obtain 14 g of naringenin. Under this condition, the purity of naringenin was 99.92% and the yield was 26.9%.

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).

References

[1] Patent: CN103467428, 2016, B. Location in patent: Paragraph 0017-0020
[2] Phytochemistry, 2005, vol. 66, # 14, p. 1698 - 1706
[3] Journal of Agricultural and Food Chemistry, 2013, vol. 61, # 4, p. 931 - 938
[4] Patent: CN103772337, 2017, B. Location in patent: Paragraph 0030-0033