Spiraeoside

Spiraeoside
Names

IUPAC name 4′-(β-D-Glucopyranosyloxy)-3,3′,5,7-tetrahydroxyflavone
Systematic IUPAC name 3,5,7-Trihydroxy-2-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]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	20229-56-5^Y
3D model (JSmol)	Interactive image
Beilstein Reference	68011
ChEBI	CHEBI:75839^N
ChEMBL	ChEMBL402947^N
ChemSpider	4478811^N
ECHA InfoCard	100.039.634
EC Number	243-614-6
PubChem CID	5320844
UNII	K2B74751XI^N
CompTox Dashboard (EPA)	DTXSID00174078
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/s1^N Key: OIUBYZLTFSLSBY-HMGRVEAOSA-N^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/s1 Key: OIUBYZLTFSLSBY-HMGRVEAOBO
SMILES c1cc(c(cc1c2c(c(=O)c3c(cc(cc3o2)O)O)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](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 [77 °F], 100 kPa). N verify (what is ^YN ?) 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).^[1]^[2]

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

References

^ 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.
^ 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	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Conjugates

Glycosides of herbacetin

Rhodionin
Rhodiosin

Glycosides of kaempferol

Afzelin (Kaempferol 3-rhamnoside)
Astragalin (kaempferol 3-O-glucoside)
Kaempferitrin (kaempferol 3,7-dirhamnoside)
Juglanin (Kaempferol 3-O-arabinoside)
Kaempferol 3-alpha-L-arabinopyranoside
Kaempferol 3-alpha-D-arabinopyranoside
Kaempferol 7-alpha-L-arabinoside
Kaempferol 7-O-glucoside
Kaempferol 3-lathyroside
Kaempferol 4'-rhamnoside
Kaempferol 5-rhamnoside
Kaempferol 7-rhamnoside
Kaempferol 7-O-alpha-L-rhamnofuranoside
Kaempferol 3-xyloside
Kaempferol 7-xyloside
Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
Kaempferol 3-O-rutinoside
Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Trifolin (Kaempferol 3-O-beta-D-galactoside)

Glycosides of myricetin

Betmidin (Myricetin 3-O-arabinoside)
Myricetin 3-O-rutinoside
Myricetin-3-O-neohesperidoside
Myricitrin (Myricetin 3-O-rhamnoside)

Conjugates of quercetin

Sulfates

Quercetin 3-O-sulfate
Quercetin 3,3'-bissulfate
Quercetin 3,4'-bissulfate

Glycosides

Avicularin (quercetin-3-O-α-L-arabinofuranoside)
CTN-986
Guaijaverin (quercetin 3-O-arabinoside)
Heliosin (quercetin 3-digalactoside)
Hyperoside (quercetin 3-O-galactoside)
Isoquercetin (quercetin 3-O-glucoside)
Miquelianin (quercetin 3-O-glucuronide)
Quercetin 3,4'-diglucoside
Quercetin-3-sophorodide
Quercitrin (quercetin 3-O-rhamnoside)
Rutin (quercetin rutinoside)
Reinutrin (quercetin-3-D-xyloside)
Spiraeoside (quercetin 4'-O-glucoside)
Taxillusin (galloylated 3-O-glucoside of quercetin°

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside
other	Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside)