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)-4H-1-benzopyran-4-one

| OtherNames = 5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-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),{{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}} and in the fern Asplenium normale.{{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}}

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).

It shows moderate aromatase inhibition.{{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}}