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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:11:51 UTC
Update Date2022-03-07 02:55:34 UTC
HMDB IDHMDB0037932
Secondary Accession Numbers
  • HMDB37932
Metabolite Identification
Common NameQuercetin 4'-glucoside
DescriptionQuercetin 4'-glucoside, also known as spiraein or spiraeoside, belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Quercetin 4'-glucoside is found, on average, in the highest concentration within a few different foods, such as garden onions (Allium cepa), shallots (Allium ascalonicum), and garden onion (var.). Quercetin 4'-glucoside has also been detected, but not quantified in, sweet cherries (Prunus avium) and yali pears (Pyrus × bretschneideri). This could make quercetin 4'-glucoside a potential biomarker for the consumption of these foods. Quercetin 4'-glucoside is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Quercetin 4'-glucoside.
Structure
Thumb
Synonyms
ValueSource
SpiraeinChEBI
SpiraeosideChEBI
Quercetin-4'-glucosideMeSH
Quercetin 4'-O-beta-D-glucopyranosideHMDB
Quercetin 4'-O-beta-D-glucosideHMDB
Quercetin 4'-O-glucosideHMDB
SpiraeosidHMDB
Spireoside (6ci,7ci,8ci)HMDB
Quercetin 4'-O-b-D-glucopyranosideGenerator
Quercetin 4'-O-β-D-glucopyranosideGenerator
Chemical FormulaC21H20O12
Average Molecular Weight464.3763
Monoisotopic Molecular Weight464.095476104
IUPAC Name3,5,7-trihydroxy-2-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4H-chromen-4-one
Traditional Namespiraeoside
CAS Registry Number20229-56-5
SMILES
OC[C@H]1O[C@@H](OC2=CC=C(C=C2O)C2=C(O)C(=O)C3=C(O2)C=C(O)C=C3O)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
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
InChI KeyOIUBYZLTFSLSBY-HMGRVEAOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glycosides
Alternative Parents
Substituents
  • Flavonoid o-glycoside
  • Flavonoid-4p-o-glycoside
  • 3-hydroxyflavone
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Phenol ether
  • Phenoxy compound
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point240 - 241 °CNot Available
Boiling Point835.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility21590 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.380 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID335
FooDB IDFDB017095
KNApSAcK IDC00005387
Chemspider ID4478811
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSpiraeoside
METLIN IDNot Available
PubChem Compound5320844
PDB IDNot Available
ChEBI ID75839
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1698731
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .