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Amurensin (flavonol)

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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-{oxy}-4H-1-benzopyran-4-one
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: UNHHWEHQUUGKEE-MLLLWRCASA-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/s1Key: UNHHWEHQUUGKEE-MLLLWRCABA
SMILES
  • CC(C)(CCC1=C(C=C(C2=C1OC(=C(C2=O)O)C3=CC=C(C=C3)O)O)O4((((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 , 100 kPa). ☒N verify (what is  ?) Infobox references
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.


Related compounds

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

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
Flavonols and their conjugates
Backbone
Aglycones
Flavonols
Aglycones
Conjugates
Glycosides of herbacetin
Glycosides of kaempferol
Glycosides of myricetin
Conjugates of quercetin
Sulfates
Glycosides
O-Methylated flavonols
Aglycones
Glycosides
of isorhamnetin
other
Derivative flavonols
Aglycones
Glycosides
Pyranoflavonols
Aglycones
Furanoflavonols
Aglycones
Glycosides
Semisynthetic
Glycosides
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