{{Use dmy dates|date=February 2026}} {{Chembox | ImageFile = Luteolin.svg | ImageSize = 220px | ImageName = The chemical structure of luteolin | ImageFile1 = Luteolin molecule ball.png | ImageSize1 = 220 | ImageAlt1 = Ball-and-stick model of Luteolin | IUPACName = 3′,4′,5,7-Tetrahydroxyflavone | SystematicName = 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4''H''-1-benzopyran-4-one | OtherNames = Luteolol<br>Digitoflavone<br>Flacitran<br>Luteoline |Section1={{Chembox Identifiers | IUPHAR_ligand = 5215 | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 491-70-3 | PubChem = 5280445 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 15864 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 151 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = KUX1ZNC9J2 | KEGG = C01514 | SMILES = C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4444102 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = IQPNAANSBPBGFQ-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=15 | H=10 | O=6 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Luteolin''' is a flavone, a type of flavonoid, with a yellow crystalline appearance.<ref name=MannSecondaryMetabolism>{{cite book |last=Mann |first=John |title=Secondary Metabolism |edition=2nd |publisher=Oxford University Press |year=1992 |location=Oxford, UK |pages=[https://archive.org/details/secondarymetabol00mann/page/279 279–280] |isbn=978-0-19-855529-2 |url-access=registration |url=https://archive.org/details/secondarymetabol00mann/page/279 }}</ref>
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.<ref>{{cite book |last1=Chevreul |first1=M.E. |title=Leçons de Chimie Appliquée à la Teinture |trans-title=Lessons on Chemistry Applied to Dyeing |date=1829 |publisher=Pichon et Didier |location=Paris, France |pages=143–148 |url=https://books.google.com/books?id=-McPAAAAQAAJ&pg=PA143 |language=French |chapter=30<sup>e</sup> Leçon, Chapitre XI. De la Gaude. [30th lesson. Chapter 11. On Weld (i.e., the plant ''Reseda luteola'', which provides a yellow dye)]}} 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".)</ref><ref>{{cite book |last1=Thomson |first1=Thomas |title=Chemistry of Organic Bodies. Vegetables |date=1838 |publisher=J.B. Baillière |location=London, England |pages=415–416 |url=https://books.google.com/books?id=Wq45AAAAcAAJ&pg=PA415 }}</ref><ref>However, Perkin claimed (without citing a source) that Chevreul had isolated luteolin as early as 1814–1815. See: {{cite book |last1=Perkin |first1=Arthur George |last2=Everest |first2=Arthur Ernest |title=The Natural Organic Colouring Matters |date=1918 |publisher=Longmans, Green and Co. |location=London, England |page=[https://archive.org/details/naturalorganicc00evergoog/page/n79 4] |url=https://archive.org/details/naturalorganicc00evergoog }}</ref>
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.<ref>{{cite journal |last1=Hlasiwetz |first1=H. |last2=Pfaundler |first2=L. |title=Über das Morin, Maclurin und Quercitrin |journal=Sitzungsberichte der Kaiserlichen Akademie der Wissenschaften. Mathematisch-Naturwissenschaftliche Classe. (Part 2) |date=1864 |volume=50 |pages=6–59 |url=https://babel.hathitrust.org/cgi/pt?id=mdp.39015073681051&view=1up&seq=18 |language=German}} ; see pp. 44–45.</ref><ref>{{cite journal |last1=Hlasiwetz |first1=H. |last2=Pfaundler |first2=L. |title=Ueber das Morin, Maclurin und Quercitrin |journal=Journal für praktische Chemie |year=1865 |volume=94 |pages=65–106 |doi=10.1002/prac.18650940112 |url=https://zenodo.org/record/2030398 |language=German}} Hlasiwetz and Pfaundler melted quercitrin with potassium carbonate. Among the reaction's products, they found paradatiscetin, whose empirical formula they determined to be C<sub>15</sub>H<sub>10</sub>O<sub>6</sub> (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].)</ref> In 1896, the English chemist Arthur George Perkin proposed the correct structure for luteolin.<ref>{{cite journal |last1=Perkin |first1=A. G. |title=Luteolin. Part II. |journal=Journal of the Chemical Society |date=1896 |volume=69 |pages=799–803 |doi=10.1039/CT8966900799 |url=https://zenodo.org/records/2057511/files/article.pdf}} See p. 803.</ref> 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.<ref>{{cite journal |last1=Kostanecki |first1=St. v. |last2=Róžycki |first2=A. |last3=Tambor |first3=J. |title=Synthese des Luteolins |journal=Berichte der Deutschen Chemischen Gesellschaft |date=1900 |volume=33 |issue=3 |pages=3410–3417 |doi=10.1002/cber.190003303121 |url=https://zenodo.org/records/2400108/files/article.pdf |language=German }}</ref><ref>{{cite book |editor1-last=Thorpe |editor1-first=Edward |title=A Dictionary of Applied Chemistry |date=1913 |publisher=Longmans, Green, and Co. |location=London, England |volume=5 |pages=747–748 |url=https://books.google.com/books?id=YWxbAAAAcAAJ&pg=PA747 }}</ref>
== Natural occurrences == Luteolin is most often found in leaves, but it is also present in rinds, barks, clover blossoms, and ragweed pollen.<ref name="MannSecondaryMetabolism"/> It has also been isolated from the aromatic flowering plant, ''Salvia tomentosa'' in the mint family, ''Lamiaceae''.<ref>{{cite journal |author1=A. Ulubelen |authorlink1=Ayhan Ulubelen |author2=M. Miski |author3=P. Neuman |author4=T. J. Mabry |title=Flavonoids of ''Salvia tomentosa'' (Labiatae) |journal=Journal of Natural Products |volume=42 |year=1979 |issue=4 |pages=261–63 |doi=10.1021/np50003a002 |bibcode=1979JNAtP..42..261U }}</ref> It is present in raw peppermint and thyme.<ref name=lpi/>
Other dietary sources include celery, broccoli, artichoke, green pepper, parsley, dandelion, perilla, chamomile tea, carrots, olive oil, rosemary, navel oranges, and oregano.<ref name="lopez">{{cite journal |author=López-Lázaro M. |title=Distribution and biological activities of the flavonoid luteolin |journal=Mini Rev Med Chem |volume=9 |issue=1 |pages=31–59 |year=2009 |pmid=19149659 |doi=10.2174/138955709787001712 }}</ref> It is present in the seeds of the palm ''Aiphanes aculeata''.<ref>{{Cite journal |pmid=11440571 |year=2001 |last1=Lee |first1=D |last2=Cuendet |first2=M |last3=Vigo |first3=JS |last4=Graham |first4=JG |last5=Cabieses |first5=F |last6=Fong |first6=HH |last7=Pezzuto |first7=JM |last8=Kinghorn |first8=AD |display-authors=3 |title=A novel cyclooxygenase-inhibitory stilbenolignan from the seeds of ''Aiphanes aculeata'' |volume=3 |issue=14 |pages=2169–71 |journal=Organic Letters |doi=10.1021/ol015985j }}</ref>
== 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.<ref name="lpi">{{cite web |title=Flavonoids |url=https://lpi.oregonstate.edu/mic/dietary-factors/phytochemicals/flavonoids |publisher=Micronutrient Information Center, Linus Pauling Institute, Oregon State University |access-date=22 October 2025 |date=2025 }}</ref>
==References== {{Reflist}}
==External links== *{{Commons category-inline}}
{{Flavones}} Category:Flavones