Acacetin

{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477237550 | Name = Acacetin | ImageFile = Acacetin.svg | ImageSize = 230px | ImageName = Chemical structure of acacetin | ImageAlt = Chemical structure of acacetin | ImageFile1 = Acacetin molecule ball.png | ImageSize1 = 220 | ImageAlt1 = Ball-and-stick model of acacetin | IUPACName = 5,7-Dihydroxy-4′-methoxyflavone | SystematicName = 5,7-Dihydroxy-2-(4-methoxyphenyl)-4''H''-1-benzopyran-4-one | OtherNames = 5,7-Dihydroxy-2-(4-methoxyphenyl)-4''H''-chromen-4-one Linarigenin Acacetine Buddleoflavonol Linarisenin 4′-Methoxyapigenin Apigenin 4′-methyl ether 5,7-Dioxy-4′-methoxyflavone |Section1={{Chembox Identifiers | SMILES1 = O=C\1c3c(O/C(=C/1)c2ccc(OC)cc2)cc(O)cc3O | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 480-44-4 | CASNoOther = | UNII_Ref = {{fdacite|correct|FDA}} | UNII = KWI7J0A2CC | PubChem = 5280442 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4444099 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 243664 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C16H12O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-8,17-18H,1H3 | InChI = 1/C16H12O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-8,17-18H,1H3 | InChIKey = DANYIYRPLHHOCZ-UHFFFAOYAN | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = DANYIYRPLHHOCZ-UHFFFAOYSA-N | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 15335 | SMILES = COC1=CC=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O | MeSHName = }} |Section2={{Chembox Properties | Formula = | C=16 | H=12 | O=5 | MolarMass = 284.26 g/mol | Appearance = | Density = | MeltingPtC = | BoilingPtC = | Solubility = }} }}

'''Acacetin''' is a 4′-''O''-methylated flavone of the parent compound apigenin, found in ''Robinia pseudoacacia'' (black locust), ''Turnera diffusa'' (damiana), ''Betula pendula'' (silver birch),<ref>{{cite journal | last1=Valkama | first1=E | last2=Salminen | first2=J-P | last3=Koricheva | first3=J | last4=Pihlaja | first4=K | title=Changes in leaf trichomes and epicuticular flavonoids during leaf development in three birch taxa | journal=Annals of Botany| year=2004 | volume=94 | issue=2 | pages=233–242 | doi=10.1093/aob/mch131 | pmid=15238348 | pmc=4242156}}</ref> and in the fern ''Asplenium normale''.<ref>{{cite journal | title=Flavonoid distribution in asplenioid ferns | first1=Yusuf | last1=UmiKalsom | first2=Jeffrey B. | last2=Harborne | journal=Pertanika | year=1991 | volume=14 | issue=3 | pages=297–300}}</ref>

In plant synthesis the enzyme apigenin 4′-''O''-methyltransferase uses ''S''-adenosyl methionine and 5,7,4′-trihydroxyflavone (apigenin) to produce ''S''-adenosylhomocysteine and 4′-methoxy-5,7-dihydroxyflavone (acacetin).<ref>{{cite journal | vauthors = Kuroki G, Poulton JE | date = 1981 | title = The para-O-methylation of apigenin to acacetin by cell-free extracts of Robinia pseudoacacia L | journal = Z. Naturforsch. C: Biosci. | volume = 36 | issue = 11–12 | pages = 916–920 | doi = 10.1515/znc-1981-11-1202 | doi-access = free }}</ref>

It shows moderate aromatase inhibition.<ref>{{cite journal | last1=Zhao | first1=J | last2=Dasmahapatra | first2=AK | last3=Khan | first3=SI | last4=Khan | first4=IA | title=Anti-aromatase activity of the constituents from damiana (''Turnera diffusa'') | journal=Journal of Ethnopharmacology |date=December 2008 | volume=120 | issue=3 | pages=387–393 | pmid=18948180| doi=10.1016/j.jep.2008.09.016}}</ref>

== See also == * Genkwanin (methoxylated apigenin) * Thevetiaflavone (methoxylated apigenin)

== References == {{reflist}}

Category:Aromatase inhibitors Category:O-methylated flavones Category:Diols