Naringenin
Synonym(s):(±)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;(±)-Naringenin;4′,5,7-Trihydroxyflavanone
- CAS NO.：480-41-1
- Empirical Formula: C15H12O5
- Molecular Weight: 272.25
- MDL number: MFCD00870553
- EINECS: 207-550-2
- SAFETY DATA SHEET (SDS)
- Update Date: 2025-12-17 09:49:52
What is Naringenin?
Chemical properties
beige-brown powder
The Uses of Naringenin
The aglucon of Naringin. Inhibitory mechanism of Naringenin against carcinogenic acrylamide formation and nonenzymic browning in Maillard model reactions
The Uses of Naringenin
antiulcer, antioxidant, immunomodulator, cholesterol lowering
The Uses of Naringenin
(S)-Naringenin, an active flavanone, maintains antioxidative, anti-inflammatory and antitumorigenic activities. Used in the treatment of praquat (PQ)-induced oxidative stress.
What are the applications of Application
Naringenin is the aglucon of naringin
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).
Properties of Naringenin
| 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 |
| 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 for Naringenin
| Signal word | Warning |
| Pictogram(s) |
 Exclamation Mark Irritant GHS07 |
| GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
| Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Naringenin
| InChIKey | FTVWIRXFELQLPI-ZDUSSCGKSA-N |
| SMILES | [C@H]1(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C2C(=O)C1 |
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