Luteolin

Chemical compound From Wikipedia, the free encyclopedia

Luteolin is a flavone, a type of flavonoid, with a yellow crystalline appearance.[1]

Quick facts Names, Identifiers ...
Luteolin
The chemical structure of luteolin
The chemical structure of luteolin
Ball-and-stick model of Luteolin
Names
IUPAC name
3′,4′,5,7-Tetrahydroxyflavone
Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
Other names
Luteolol
Digitoflavone
Flacitran
Luteoline
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.038 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H ☒N
    Key: IQPNAANSBPBGFQ-UHFFFAOYSA-N ☒N
  • InChI=1/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H
    Key: IQPNAANSBPBGFQ-UHFFFAOYAY
  • C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O
Properties
C15H10O6
Molar mass 286.239 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Luteolin is the main yellow dye from the Reseda luteola plant, used for dyeing since at least the first millennium B.C. Luteolin was first isolated in pure form, and was named in 1829 by the French chemist, Michel Eugène Chevreul.[2][3][4]

Luteolin is a phytochemical present in leaves, bark, flower blossoms, pollens, various vegetables, and herbs.

History of discovery

The luteolin empirical formula was determined by the Austrian chemists Heinrich Hlasiwetz and Leopold Pfaundler in 1864.[5][6] In 1896, the English chemist Arthur George Perkin proposed the correct structure for luteolin.[7] Perkin's proposed structure for luteolin was confirmed in 1900 when the Polish-Swiss chemist Stanisław Kostanecki (1860–1910) and his students A. Różycki and J. Tambor synthesized luteolin.[8][9]

Natural occurrences

Luteolin is most often found in leaves, but it is also present in rinds, barks, clover blossoms, and ragweed pollen.[1] It has also been isolated from the aromatic flowering plant, Salvia tomentosa in the mint family, Lamiaceae.[10] It is present in raw peppermint and thyme.[11]

Other dietary sources include celery, broccoli, artichoke, green pepper, parsley, dandelion, perilla, chamomile tea, carrots, olive oil, rosemary, navel oranges, and oregano.[12] It is present in the seeds of the palm Aiphanes aculeata.[13]

Research

Although preliminary laboratory research has been conducted on luteolin, there is no clinical evidence to indicate that its presence in consumed plant foods has any effect on human health or diseases.[11]

References

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