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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:04:10 UTC
Update Date2022-03-07 02:56:37 UTC
HMDB IDHMDB0040513
Secondary Accession Numbers
  • HMDB40513
Metabolite Identification
Common Name2,3-Dehydrosilybin
Description2,3-Dehydrosilybin belongs to the class of organic compounds known as flavonolignans. These are non-conventional lignans that derived from flavonoids. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to the B-ring of the 2-phenylchromene moiety. 2,3-Dehydrosilybin has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, green vegetables, and robusta coffees (Coffea canephora). This could make 2,3-dehydrosilybin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2,3-Dehydrosilybin.
Structure
Thumb
Synonyms
Chemical FormulaC25H20O10
Average Molecular Weight480.4203
Monoisotopic Molecular Weight480.10564686
IUPAC Name3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-4H-chromen-4-one
Traditional Name3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chromen-4-one
CAS Registry Number25166-14-7
SMILES
COC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=CC(=C2)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1
InChI Identifier
InChI=1S/C25H20O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,24,26-29,31H,10H2,1H3
InChI KeyBVKQRAYKLBRNIK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonolignans. These are non-conventional lignans that derived from flavonoids. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to the B-ring of the 2-phenylchromene moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFlavonolignans
Sub ClassNot Available
Direct ParentFlavonolignans
Alternative Parents
Substituents
  • Flavonolignan
  • 3-hydroxyflavone
  • 3-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • 2-phenylbenzo-1,4-dioxane
  • Phenylbenzodioxane
  • Chromone
  • Benzo-1,4-dioxane
  • Benzodioxane
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Phenol
  • Pyranone
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Para-dioxin
  • Pyran
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point254 - 255 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility45.29 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane
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 IDNot Available
FooDB IDFDB020279
KNApSAcK IDC00054112
Chemspider ID4578204
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5467200
PDB IDNot Available
ChEBI ID172705
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1884031
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.. .