Luteolin

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Luteolin
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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
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3D model (JSmol)
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  • 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 checkY
    Key: IQPNAANSBPBGFQ-UHFFFAOYSA-N checkY
  • 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).

Template:Chembox Footer/trackingTemplate:Short description

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

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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  1. ^ a b Page Module:Citation/CS1/styles.css has no content.Mann, John (1992). Secondary Metabolism (2nd ed.). Oxford, UK: Oxford University Press. pp. 279–280. ISBN 978-0-19-855529-2.
  2. ^ Page Module:Citation/CS1/styles.css has no content.Chevreul, M.E. (1829). "30e Leçon, Chapitre XI. De la Gaude. [30th lesson. Chapter 11. On Weld (i.e., the plant Reseda luteola, which provides a yellow dye)]". Leçons de Chimie Appliquée à la Teinture [Lessons on Chemistry Applied to Dyeing] (in French). Paris, France: Pichon et Didier. pp. 143–148.{{cite book}}: CS1 maint: unrecognized language (link) Chevreul named luteolin on p. 144: "J'ai fait des recherches sur la composition de la gaude, j'ai obtenu le principe colorant critalisé par sublimation; je l'ai nommé lutéolin." (I have done some research on the composition of weld; I obtained the principal colorant [which I] crystallized via sublimation; I have called it "luteolin".)
  3. ^ Page Module:Citation/CS1/styles.css has no content.Thomson, Thomas (1838). Chemistry of Organic Bodies. Vegetables. London, England: J.B. Baillière. pp. 415–416.
  4. ^ However, Perkin claimed (without citing a source) that Chevreul had isolated luteolin as early as 1814–1815. See: Page Module:Citation/CS1/styles.css has no content.Perkin, Arthur George; Everest, Arthur Ernest (1918). The Natural Organic Colouring Matters. London, England: Longmans, Green and Co. p. 4.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Hlasiwetz, H.; Pfaundler, L. (1864). "Über das Morin, Maclurin und Quercitrin". Sitzungsberichte der Kaiserlichen Akademie der Wissenschaften. Mathematisch-Naturwissenschaftliche Classe. (Part 2) (in German). 50: 6–59.{{cite journal}}: CS1 maint: unrecognized language (link) ; see pp. 44–45.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Hlasiwetz, H.; Pfaundler, L. (1865). "Ueber das Morin, Maclurin und Quercitrin". Journal für praktische Chemie (in German). 94: 65–106. doi:10.1002/prac.18650940112.{{cite journal}}: CS1 maint: unrecognized language (link) Hlasiwetz and Pfaundler melted quercitrin with potassium carbonate. Among the reaction's products, they found paradatiscetin, whose empirical formula they determined to be C15H10O6 (p. 94). They concluded that although luteolin and paradatiscetin were isomeric (i.e., had the same empirical formula), they were distinct compounds. From p. 94: "Das Luteolin scheint demnach wohl als isomer oder metamer mit unserer Substanz betrachtet werden zu können. Eine Identität beider liegt jedoch nicht vor, denn an einer Probe Luteolin fanden wir die charakteristischen Farben-reactionen nicht, welche das Paradatiscetin kaum verwechseln lassen." (Luteolin thus seems to be able to be regarded perhaps as an isomer or metamer of our substance [viz, paradatiscetin]. However, the two are evidently not identical, for upon a test of luteolin, we did not find the characteristic color reactions, which hardly allows paradatiscetin to be confused [with it].)
  7. ^ Page Module:Citation/CS1/styles.css has no content.Perkin, A. G. (1896). "Luteolin. Part II" (PDF). Journal of the Chemical Society. 69: 799–803. doi:10.1039/CT8966900799. See p. 803.
  8. ^ Page Module:Citation/CS1/styles.css has no content.Kostanecki, St. v.; Róžycki, A.; Tambor, J. (1900). "Synthese des Luteolins" (PDF). Berichte der Deutschen Chemischen Gesellschaft (in German). 33 (3): 3410–3417. doi:10.1002/cber.190003303121.{{cite journal}}: CS1 maint: unrecognized language (link)
  9. ^ Page Module:Citation/CS1/styles.css has no content.Thorpe, Edward, ed. (1913). A Dictionary of Applied Chemistry. Vol. 5. London, England: Longmans, Green, and Co. pp. 747–748.
  10. ^ Page Module:Citation/CS1/styles.css has no content.A. Ulubelen; M. Miski; P. Neuman; T. J. Mabry (1979). "Flavonoids of Salvia tomentosa (Labiatae)". Journal of Natural Products. 42 (4): 261–63. Bibcode:1979JNAtP..42..261U. doi:10.1021/np50003a002.
  11. ^ a b Page Module:Citation/CS1/styles.css has no content."Flavonoids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2025. Retrieved 22 October 2025.
  12. ^ Page Module:Citation/CS1/styles.css has no content.López-Lázaro M. (2009). "Distribution and biological activities of the flavonoid luteolin". Mini Rev Med Chem. 9 (1): 31–59. doi:10.2174/138955709787001712. PMID 19149659.
  13. ^ Page Module:Citation/CS1/styles.css has no content.Lee, D; Cuendet, M; Vigo, JS; et al. (2001). "A novel cyclooxygenase-inhibitory stilbenolignan from the seeds of Aiphanes aculeata". Organic Letters. 3 (14): 2169–71. doi:10.1021/ol015985j. PMID 11440571.
  • Page Template:Sister-inline/styles.css has no content.Script error: No such module "Sister project logo". Media related to Script error: No such module "Commons link". at Wikimedia Commons

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