From Wikipedia, the free encyclopedia
Acacetin
Names
IUPAC name
5,7-Dihydroxy-4′-methoxyflavone
Systematic IUPAC name
5,7-Dihydroxy-2-(4-methoxyphenyl)-4H -1-benzopyran-4-one
Other names
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
Identifiers
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.006.867
UNII
InChI=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
Y Key: DANYIYRPLHHOCZ-UHFFFAOYSA-N
Y 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
Key: DANYIYRPLHHOCZ-UHFFFAOYAN
COC1=CC=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O
O=C\1c3c(O/C(=C/1)c2ccc(OC)cc2)cc(O)cc3O
Properties
C 16 H 12 O 5
Molar mass
284.26 g/mol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
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),
[1] and in the fern
Asplenium normale .
[2]
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.
[3]
See also
References
^ Valkama, E; Salminen, J-P; Koricheva, J; Pihlaja, K (2004).
"Changes in leaf trichomes and epicuticular flavonoids during leaf development in three birch taxa" . Annals of Botany . 94 (2): 233–242.
doi :
10.1093/aob/mch131 .
PMC
4242156 .
PMID
15238348 .
^ UmiKalsom, Yusuf; Harborne, Jeffrey B. (1991). "Flavonoid distribution in asplenioid ferns". Pertanika . 14 (3): 297–300.
^ Zhao, J; Dasmahapatra, AK; Khan, SI; Khan, IA (December 2008). "Anti-aromatase activity of the constituents from damiana (Turnera diffusa )". Journal of Ethnopharmacology . 120 (3): 387–393.
doi :
10.1016/j.jep.2008.09.016 .
PMID
18948180 .
Aglycones
Monohydroxyflavone Dihydroxyflavones Trihydroxyflavones Tetrahydroxyflavones Pentahydroxyflavones O-methylated flavones
Glycosides
of apigenin of baicalein of hypolaetin of luteolin
Acetylated Sulfated glycosides Polymers Drugs