Isosakuranetin

Isosakuranetin

Isosakuranetin
Names
IUPAC name (2S)-5,7-Dihydroxy-4′-methoxyflavan-4-one
Systematic IUPAC name (2S)-5,7-Dihydroxy-2-(4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
Other names 4'-Methylnaringenin
Identifiers
CAS Number	480-43-3  Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL470266  N
ChemSpider	141023  N
ECHA InfoCard	100.006.866
PubChem CID	160481
UNII	U02X7TF8UA  Y
CompTox Dashboard (EPA)	DTXSID60963980
InChI 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
SMILES COC1=CC=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O
Properties
Chemical formula	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). N  verify  (what is  YN ?) Infobox references

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]

Glycosides

• Poncirin is the 7-O-neohesperidoside of isosakuranetin.
• Didymin is the 7-O-rutinoside of isosakuranetin

References

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.