Record Information
Version1.0
Creation date2011-09-21 00:26:06 UTC
Update date2015-10-09 22:33:12 UTC
Primary IDFDB023194
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSalicin
DescriptionSalicin, also known as salicoside or delta-salicin, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Salicin is an extremely weak basic (essentially neutral) compound (based on its pKa). Salicin exists in all living organisms, ranging from bacteria to humans. Salicin is a bitter tasting compound.
CAS Number138-52-3
Structure
Thumb
Synonyms
SynonymSource
2(Hydroxymethyl)phenyl-beta-D-glucopyranosideChEBI
2-(Hydroxymethyl)phenyl-beta-D-glucopyranosideChEBI
2-(Hydroxymethyl)phenyl-O-beta-D-glucopyranosideChEBI
D-(-)-SalicinChEBI
O-(Hydroxymethyl)phenyl beta-D-glucopyranosideChEBI
SalicosideChEBI
Salicyl alcohol glucosideChEBI
Saligenin beta-D-glucopyranosideChEBI
2(Hydroxymethyl)phenyl-b-D-glucopyranosideGenerator
2(Hydroxymethyl)phenyl-β-D-glucopyranosideGenerator
2-(Hydroxymethyl)phenyl-b-D-glucopyranosideGenerator
2-(Hydroxymethyl)phenyl-β-D-glucopyranosideGenerator
2-(Hydroxymethyl)phenyl-O-b-D-glucopyranosideGenerator
2-(Hydroxymethyl)phenyl-O-β-D-glucopyranosideGenerator
O-(Hydroxymethyl)phenyl b-D-glucopyranosideGenerator
O-(Hydroxymethyl)phenyl β-D-glucopyranosideGenerator
Saligenin b-D-glucopyranosideGenerator
Saligenin β-D-glucopyranosideGenerator
2-(Hydroxymethyl)phenyl hexopyranosideHMDB
D-SalicinHMDB
delta-SalicinHMDB
SalicineHMDB
Saligenin beta-delta-glucopyranosideHMDB
Saligenin-b-D-glucopyranosideHMDB
Saligenin-beta-D-glucopyranosideHMDB
Saligenin-beta-delta-glucopyranosideHMDB
Salicinhmdb
Predicted Properties
PropertyValueSource
Water Solubility24.9 g/LALOGPS
logP-1.1ALOGPS
logP-1.4ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area119.61 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67 m³·mol⁻¹ChemAxon
Polarizability27.89 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC13H18O7
IUPAC name(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
InChI IdentifierInChI=1S/C13H18O7/c14-5-7-3-1-2-4-8(7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1
InChI KeyNGFMICBWJRZIBI-UJPOAAIJSA-N
Isomeric SMILESOC[C@H]1O[C@@H](OC2=C(CO)C=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight286.2778
Monoisotopic Molecular Weight286.10525293
Classification
Description belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • O-glycosyl compound
  • Phenoxy compound
  • Benzyl alcohol
  • Phenol ether
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Aromatic alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-016s-0931000000-d7cfab7dda5ba5b8cb8dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-016s-0931000000-d7cfab7dda5ba5b8cb8dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-6970000000-4a3fc41bdfdcae61270aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-001i-1111149000-413e4462b838237eb990JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0920000000-dd9147181f57af043933JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-0900000000-5f01886cdb3b1b83482dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a6r-6900000000-60990058ed2008115d3cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0aor-0970000000-b0ab03332dc31197e24dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0aor-0970000000-1eff788038412eafc6e0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0920000000-e1a9ed30eb900b2d13f5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0930000000-53b80e6d9343986fce22JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0479000000-e3d1fa41cebd0db517ecJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0469000000-7bd2e826ca0d8c4e246bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05r9-0970000000-300143a83a460b0b8de6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-d56d227c3ed2911b275eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-da1f6546fa4860684208JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-0790000000-705ce708dcc235d02e31JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fu-3940000000-1b35dca166815881ea11JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-45d5d35d6bc2783638e4JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID388601
ChEMBL IDCHEMBL462997
KEGG Compound IDC01451
Pubchem Compound ID439503
Pubchem Substance IDNot Available
ChEBI ID17814
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03546
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDSA0
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSalicin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference