THC Science

Vitexin
Names
	IUPAC name 8-(β-D-Glucopyranosyl)-4′,5,7-trihydroxyflavone
	Systematic IUPAC name 5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-1-benzopyran-4-one
	Other names Apigenin-8-C-glucoside
Identifiers
CAS Number	3681-93-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16954 ;
ChEMBL	ChEMBL487417 ;
ChemSpider	4444098 ;
ECHA InfoCard	100.020.876
KEGG	C01460 ;
PubChem CID	5280441;
UNII	9VP70K75OK ;
CompTox Dashboard (EPA)	DTXSID90190287 ;
	InChI InChI=1S/C21H20O10/c22-7-14-17(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2/t14-,17-,18+,19-,21+/m1/s1 Key: SGEWCQFRYRRZDC-VPRICQMDSA-N ; InChI=1/C21H20O10/c22-7-14-17(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2/t14-,17-,18+,19-,21+/m1/s1 Key: SGEWCQFRYRRZDC-VPRICQMDBU;
	SMILES O=C2\C=C(/Oc1c(c(O)cc(O)c12)[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)CO)c4ccc(O)cc4;
Properties
Chemical formula	C21H20O10
Molar mass	432.38 g/mol
Appearance	Light yellow powder
Melting point	203 to 204 °C (397 to 399 °F; 476 to 477 K)
Supplementary data page
	Vitexin (data page)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Vitexin is an apigenin flavone glucoside, a chemical compound found in the passion flower, Vitex agnus-castus (chaste tree or chasteberry), in the Phyllostachys nigra bamboo leaves,^[1] in the pearl millet (Pennisetum millet),^[2] and in Hawthorn.^[3]

Metabolism[edit]

Goitrogenicity of millet flavones : Vitexin inhibits thyroid peroxidase thus contributing to goiter.^[4]^[5]

^ Zhang Y, Jiao J, Liu C, Wu X, Zhang Y (2007). "Isolation and purification of four flavone C-glycosides from antioxidant of bamboo leaves by macroporous resin column chromatography and preparative high-performance liquid chromatography". Food Chemistry. doi:10.1016/j.foodchem.2007.09.037. Archived from the original on 2012-09-10.
^ J.O. AKINGBALA (1991). "Effect of Processing on Flavonoids in Millet (Pennisetum americanum) Flour" (PDF). Cereal Chem. 68 (2): 180–183. Archived from the original (PDF) on 2009-05-14. Retrieved 2009-08-21.
^ Scholz H (1995). Gustav Hegi. Illustrierte Flora von Mitteleuropa IV(2B). Spermatophyta: Angiospermae: Dicotyledones 2(3). Rosaceae 2 (2nd ed.). Berlin: Blackwell Wissenschafts-Verlag. p. 431. ISBN 978-3-8263-2533-5.
^ Gaitan E (1990). "Goitrogens in food and water". Annual Review of Nutrition. 10: 21–39. doi:10.1146/annurev.nu.10.070190.000321. PMID 1696490.
^ Birzer DM, Klopfenstein CF, Leipold HW (1987). "Goitre causing compounds found in pearl millet". Nutr. Rep. Int. 36: 131–141. ISSN 0029-6635.