Luteolin

Luteolin
Compound Structure:
Synonyms: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one; luteolin; 491-70-3; Digitoflavone; Luteolol; 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one; 3',4',5,7-Tetrahydroxyflavone; Flacitran; Luteoline; 5,7,3',4'-Tetrahydroxyflavone
Compound ID: NMPC-1220
PubChem ID:

5280445

Molecular Formula: C15H10O6
Canonical SMILES: C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O
InChIKey: IQPNAANSBPBGFQ-UHFFFAOYSA-N
About the compound:

Luteolin has been known since ancient times, primarily as a yellow dye obtained from the plant Reseda luteola.

   - It was first isolated in its pure form and named in 1829 by the French chemist Michel EugèneChevreul.

   - The empirical formula of luteolin was determined in 1864 by Austrian chemists Heinrich Hlasiwetz and Leopold Pfaundler.

   - The correct structure of luteolin was proposed by English chemist Arthur George Perkin in 1896 and later confirmed in 1900 by Polish-Swiss chemist Stanislaw Kostanecki and his students.

   - Luteolin is classified as a tetrahydroxyflavone, with hydroxy groups located at positions 3', 4', 5, and 7.

   - It is a 3'-hydroxyflavonoid and a tetrahydroxyflavone, and it is the conjugate acid of a luteolin-7-olate.

Biological Roles and Activities:

   - Luteolin is known for its antioxidant properties, acting as a free radical scavenger.

   - It serves as an anti-inflammatory agent and an immune system modulator.

   - Luteolin has shown activity against several cancers and is known as an antineoplastic agent.

   - It functions as an inhibitor of fatty acid synthase (EC 2.3.1.85), a vascular endothelial growth factor receptor antagonist, and an angiogenesis inhibitor.

   - It is also recognized as a nephroprotective agent, a c-Jun N-terminal kinase inhibitor, an apoptosis inducer, and an immunomodulator.

Luteolin's multifaceted roles, particularly in health and medicine, make it a compound of interest for further research and application in various therapeutic areas. Its historical use as a dye also underscores its significance in cultural and scientific contexts.

GHS Hazard Statements

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

286.24 g/mol

XLogP3

1.4

Hydrogen Bond Donor Count

4

Hydrogen Bond Acceptor Count

6

Rotatable Bond Count

1

Exact Mass

286.04773803 g/mol

Monoisotopic Mass

286.04773803 g/mol

Topological Polar Surface Area

107Ų

Heavy Atom Count

21

Formal Charge

0

Complexity

447

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

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

329.5 °C

Source: PubChem            

Source Species: Caesalpinia bonduc
Raphia hookeri
Solenostemon monostachyus
Struchium sparganophora
Vernonia perrottetii
Talinum triangulare
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