Naringenin

Naringenin
Compound Structure:
Synonyms: (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one; naringenin; salipurpol; Salipurol; (S)-Naringenin; (S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one; Naringenine; pelargidanon; (2S)-Naringenin; naringetol; Asahina; 5,7,4'-Trihydroxyflava
Compound ID: NMPC-1290
PubChem ID:

439246

Molecular Formula: C15H12O5
Canonical SMILES: C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
InChIKey: FTVWIRXFELQLPI-ZDUSSCGKSA-N
About the compound:

Naringenin is a flavonoid known for its beneficial health effects, particularly in the context of lipid metabolism and hormonal activities:

Sources and Dietary Occurrence:

Naringenin is primarily found in fruits such as oranges and tomatoes. These fruits contain high amounts of this compound.

Health Benefits:

Naringenin is known for its ability to control body lipids. It possesses hypocholesterolemic and hypolipidemic effects, meaning it can help lower cholesterol levels and reduce lipid content in the body.

It also exhibits anti-estrogenic activities, which could have implications in hormonal balance and related health conditions.

Specific Isomer: (S)-Naringenin:

(S)-Naringenin is the (S)-enantiomer of naringenin, indicating a specific spatial arrangement in its molecular structure.

It functions as an expectorant, aiding in the clearance of mucus from the airways, and is also a natural plant metabolite.

This specific isomer is a type of naringenin and a (2S)-flavan-4-one, and is the conjugate acid of a (S)-naringenin(1-).

It exists as an enantiomer to (R)-naringenin, differing in the spatial orientation of atoms.

Naringenin, including its specific isomers like (S)-naringenin, showcases the diverse biological activities and health benefits of flavonoids, underlining the importance of these compounds in nutrition and potential therapeutic applications.

GHS Hazard Statements

H315 (99.54%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (99.54%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

272.25 g/mol

XLogP3-AA

2.4

Hydrogen Bond Donor Count

3

Hydrogen Bond Acceptor Count

5

Rotatable Bond Count

1

Exact Mass

272.06847348 g/mol

Monoisotopic Mass

272.06847348 g/mol

Topological Polar Surface Area

87Ų

Heavy Atom Count

20

Formal Charge

0

Complexity

363

Isotope Atom Count

0

Defined Atom Stereocenter Count

1

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Solid

Melting Point

251°C

Source: PubChem                        

Source Species: Luffa cylindrica
Talinum triangulare
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