Amurensin (flavonol)

Amurensin is a flavonol, a type of flavonoid. It is the tert-amyl alcohol derivative of kaempferol 7-O-glucoside. It can be found in Phellodendron amurense.^[1]

Amurensin

Names
IUPAC name 7-(β-D-Glucopyranosyloxy)-3,4′,5-trihydroxy-8-(3-hydroxy-3-methylbutyl)flavone
Systematic IUPAC name 3,5-Dihydroxy-8-(3-hydroxy-3-methylbutyl)-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one
Identifiers
CAS Number	641-94-1 N
3D model (JSmol)	Interactive image
ChemSpider	20120043 N
PubChem CID	5318156
UNII	F3862WT2AZ Y
CompTox Dashboard (EPA)	DTXSID40982614
InChI InChI=1S/C26H30O12/c1-26(2,35)8-7-13-15(36-25-22(34)20(32)18(30)16(10-27)37-25)9-14(29)17-19(31)21(33)23(38-24(13)17)11-3-5-12(28)6-4-11/h3-6,9,16,18,20,22,25,27-30,32-35H,7-8,10H2,1-2H3/t16-,18-,20+,22-,25-/m1/s1 N Key: UNHHWEHQUUGKEE-MLLLWRCASA-N N InChI=1/C26H30O12/c1-26(2,35)8-7-13-15(36-25-22(34)20(32)18(30)16(10-27)37-25)9-14(29)17-19(31)21(33)23(38-24(13)17)11-3-5-12(28)6-4-11/h3-6,9,16,18,20,22,25,27-30,32-35H,7-8,10H2,1-2H3/t16-,18-,20+,22-,25-/m1/s1 Key: UNHHWEHQUUGKEE-MLLLWRCABA
SMILES CC(C)(CCC1=C(C=C(C2=C1OC(=C(C2=O)O)C3=CC=C(C=C3)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
Properties
Chemical formula	C26H30O12
Molar mass	534.50 g/mol
Density	1.581 g/mL
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

Related compounds

6"'-O-acetyl amurensin is found in the leaves of Phellodendron japonicum.^[2]

References

1. Two New Flavonoid Glycosides from the Leaves of Phellodendron amurense Ruprecht. Masao Hasegawa and Teruo Shirato, J. Am. Chem. Soc., 1953, 75 (22), pages 5507–5511, doi:10.1021/ja01118a013
2. Constituents of Leaves of Phellodendron japonicum MAXIM. and Their Antioxidant Activity, Chih-Yang Chiu, Chia-Ying Li, Chao-Chen Chiu, Masatake Niwa, Susumu Kitanaka, Amooru Gangaiah Damu, E-Jian Lee and Tian-Shung Wu, Chem. Pharm. Bull., Vol. 53, pages 1118-1121 (2005), doi:10.1248/cpb.53.1118