Amurensin (flavonol)
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
ChemSpider
UNII
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
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
C26 H30 O12
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).
Chemical compound
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]
6"'-O-acetyl amurensin is found in the leaves of Phellodendron japonicum .[ 2]
References
^ 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
^ 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
Flavonols and their conjugates
Backbone
Flavonols
O -Methylated flavonols
Derivative flavonols
Pyranoflavonols
Furanoflavonols
Semisynthetic