Isosakuranetin

Isosakuranetin, an O-methylated flavonoid, is the 4'-methoxy derivative of naringenin, a flavanone. Didymin, a disaccharide of isosakuranetin, occur e.g. in sweet orange, blood orange and mandarin.[1] Isosakuranetin is a potent inhibitor of TRPM3 channels.[2]

Isosakuranetin
Isosakuranetin
Names
IUPAC name
(2S)-5,7-Dihydroxy-4′-methoxyflavan-4-one
Preferred IUPAC name
(2S)-5,7-Dihydroxy-2-(4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
Other names
4'-Methylnaringenin
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.006.866 Edit this at Wikidata
UNII
  • InChI=1S/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1 ☒N
    Key: HMUJXQRRKBLVOO-AWEZNQCLSA-N ☒N
  • InChI=1/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1
    Key: HMUJXQRRKBLVOO-AWEZNQCLBJ
  • COC1=CC=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O
Properties
C16H14O5
Molar mass 286.27 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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GlycosidesEdit

ReferencesEdit

  1. ^ "Polyphenols in Human Health and Disease" ISBN 9780123984562
  2. ^ Straub, Isabelle; Krügel, Ute; Mohr, Florian; Teichert, Jens; Rizun, Oleksandr; Konrad, Maik; Oberwinkler, Johannes; Schaefer, Michael (November 2013). "Flavanones that selectively inhibit TRPM3 attenuate thermal nociception in vivo". Molecular Pharmacology. 84 (5): 736–750. doi:10.1124/mol.113.086843. ISSN 1521-0111. PMID 24006495.