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 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL470266 ;
ChemSpider	141023 ;
ECHA InfoCard	100.006.866
PubChem CID	160481;
UNII	U02X7TF8UA ;
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 Key: HMUJXQRRKBLVOO-AWEZNQCLSA-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). verify (what is ?) 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

^ "Polyphenols in Human Health and Disease" ISBN 9780123984562
^ 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.

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[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.

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