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