Determine the necessary mass, volume, or concentration for preparing a solution.
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10mM in DMSO for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -80°C Ships Dry ice packs + Cold packs Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 102 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Naringenin is a flavonoid commonly found in grapefruits which functions as an antioxidant, free radical scavenger, anti-inflammatory compound, carbohydrate metabolism promoter, and immune system modulator. Studies indicate that in vitro Naringenin reduces oxidative damage to DNA. In addition, Naringenin potently inhibits the secretion of very-low-density lipoproteins by cells. Furthermore, Naringenin has been shown to reduce cholesterol concentrations in hepatocytes and plasma cells via inhibiting HMGCR (HMG-CoA reductase). Studies conducted on Hepatitis C virus particles demonstrate that Naringenin can inhibit the virus via a PPAR-mediated mechanism by inhibiting the long term assembly of the virus.
The aglucon of naringin.
| Pubchem Sid | 528772165 |
|---|---|
| Canonical Smiles | C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O |
| IUPAC Name | (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one |
| InChIKey | FTVWIRXFELQLPI-ZDUSSCGKSA-N |
| 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 |
| Isomeric SMILES | C1[C@H](OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O |
| Molecular Weight | 272.25 |
| Beilstein | 280888 |
| Reaxy-Rn | 280888 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=280888&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Phenylpropanoids and polyketides |
| Class | Flavonoids |
| Subclass | Flavans |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Flavanones |
| Alternative Parents | 7-hydroxyflavonoids 5-hydroxyflavonoids 4'-hydroxyflavonoids Chromones Aryl alkyl ketones Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Vinylogous acids Oxacyclic compounds Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Flavanone - Hydroxyflavonoid - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Chromone - Benzopyran - Chromane - 1-benzopyran - Aryl alkyl ketone - Aryl ketone - 1-hydroxy-4-unsubstituted benzenoid - Phenol - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Benzenoid - Vinylogous acid - Ketone - Organoheterocyclic compound - Oxacycle - Ether - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as flavanones. These are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. |
| External Descriptors | Flavanones |
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| Boil Point(°C) | 577.5 °C |
|---|---|
| Melt Point(°C) | 247-250°C |
| Molecular Weight | 272.250 g/mol |
| XLogP3 | 2.400 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 1 |
| Exact Mass | 272.068 Da |
| Monoisotopic Mass | 272.068 Da |
| Topological Polar Surface Area | 87.000 Ų |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Complexity | 363.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |