Acacetin

Acacetin
Chemical structure of acacetin
Ball-and-stick model of 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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.867 Edit this at Wikidata
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 checkY
    Key: DANYIYRPLHHOCZ-UHFFFAOYSA-N checkY
  • 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
C16H12O5
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).
☒N verify (what is checkY☒N ?)

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

  1. ^ 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.
  2. ^ UmiKalsom, Yusuf; Harborne, Jeffrey B. (1991). "Flavonoid distribution in asplenioid ferns". Pertanika. 14 (3): 297–300.
  3. ^ 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.


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