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Spiraeoside

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Spiraeoside
Spiraeoside structure
Spiraeoside structure
Names
IUPAC name 4′-(β-D-Glucopyranosyloxy)-3,3′,5,7-tetrahydroxyflavone
Systematic IUPAC name 3,5,7-Trihydroxy-2-(3-hydroxy-4-{oxy}phenyl)-4H-1-benzopyran-4-one
Other names Spiraeosid
Spiraein
Quercetin-4'-glucoside
Quercetin 4'-O-glucoside
Quercetin-4-O-β-D-glucoside
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 68011
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.039.634 Edit this at Wikidata
EC Number
  • 243-614-6
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)32-11-2-1-7(3-9(11)24)20-18(29)16(27)14-10(25)4-8(23)5-12(14)31-20/h1-5,13,15,17,19,21-26,28-30H,6H2/t13-,15-,17+,19-,21-/m1/s1Key: OIUBYZLTFSLSBY-HMGRVEAOSA-N
  • InChI=1/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)32-11-2-1-7(3-9(11)24)20-18(29)16(27)14-10(25)4-8(23)5-12(14)31-20/h1-5,13,15,17,19,21-26,28-30H,6H2/t13-,15-,17+,19-,21-/m1/s1Key: OIUBYZLTFSLSBY-HMGRVEAOBO
SMILES
  • c1cc(c(cc1c2c(c(=O)c3c(cc(cc3o2)O)O)O)O)O4((((O4)CO)O)O)O
Properties
Chemical formula C21H20O12
Molar mass 464.37 g/mol
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

Spiraeoside is a chemical compound. It can be isolated from flowers of Filipendula ulmaria (L.) (a.k.a. Spiraea ulmaria or meadowsweet) or from the garden onion (Allium cepa).

Spiraeoside is the 4'-O-glucoside of quercetin.

References

  1. Williamson, Gary; Plumb, Geoff W.; Uda, Yasushi; Price, Keith R.; Rhodes, Michael J.C. (1996). "Dietary quercetin glycosides: Antioxidant activity and induction of the anticarcinogenic phase II marker enzyme quinone reductase in Hepalclc7 cells". Carcinogenesis. 17 (11): 2385–7. doi:10.1093/carcin/17.11.2385. PMID 8968052.
  2. Olsson, Marie E.; Gustavsson, Karl-Erik; Vågen, Ingunn M. (2010). "Quercetin and Isorhamnetin in Sweet and Red Cultivars of Onion (Allium cepaL.) at Harvest, after Field Curing, Heat Treatment, and Storage". Journal of Agricultural and Food Chemistry. 58 (4): 2323–30. doi:10.1021/jf9027014. PMID 20099844.
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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