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Showing Compound Gein (FDB001162)

Record Information
Version1.0
Creation date2010-04-08 22:04:51 UTC
Update date2021-01-13 18:20:31 UTC
Primary IDFDB001162
Secondary Accession Numbers
  • FDB020784
Chemical Information
FooDB NameGein
DescriptionGein, also known as geoside or eugenol vicianoside, is classified as a phenylpropanoid glycoside. Gein is the glycosylated derivative of eugenol on its free hydroxyl group. More precisely, the glycoside present in the structure of gein is known as vicianose, a disaccharide composed of glucose and arabinose. Gein was first isolated from herb Bennet (Geum urbanum), a perennial plant native from Europe and the Middle East, but that has been introduced to North America and other continents. Since its isolation and identification from G. urbanum, gein has been isolated from several plant sources, including Stevia rebaudiana. The phenolic moiety of gein, eugenol, is widespread in nature and exists in all eukaryotes, from yeast to humans. It is biosynthesized from tyrosine. It is a clear to pale yellow oily liquid extracted from clove oil, nutmeg, cinnamon, basil and bay leaf. It has a pleasant, spicy, clove-like odor with a spicy pungent taste. Eugenol is found in highest concentrations in cloves, allspices, and carrots and in lower concentrations in walnuts, ceylon cinnamons, and wild carrots. Eugenol has also been detected in shea tree, passion fruits, winged beans, fireweeds, and gingers, making it a potential biomarker for the consumption of these foods. Gein is less volatile then eugenol due to the presence of the vicianoside moiety.
CAS Number585-90-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility6.85 g/LALOGPS
logP-0.53ALOGPS
logP-0.8ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)11.92ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area167.53 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity107.38 m³·mol⁻¹ChemAxon
Polarizability46.06 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H30O11
IUPAC name2-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol
InChI IdentifierInChI=1S/C21H30O11/c1-3-4-10-5-6-12(13(7-10)28-2)31-21-19(27)17(25)16(24)14(32-21)9-30-20-18(26)15(23)11(22)8-29-20/h3,5-7,11,14-27H,1,4,8-9H2,2H3
InChI KeyFSCNUJMKSQHQSY-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC2OC(COC3OCC(O)C(O)C3O)C(O)C(O)C2O)C=CC(CC=C)=C1
Average Molecular Weight458.4563
Monoisotopic Molecular Weight458.178811802
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
  • Disaccharide
  • O-glycosyl compound
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Oxane
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Polyol
  • Ether
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01oy-4586900000-250014060847faef5d6fSpectrum
Predicted GC-MSGein, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0bta-3233219000-277675539b8c0b7db716Spectrum
Predicted GC-MSGein, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGein, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066u-0901500000-100838ec2d480fa707532015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0901000000-446e16cec3a480e682612015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-2900000000-b7f06d168ba046afd03c2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08fr-1922600000-d0c473b49bbd64ffdf042015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03ea-0900100000-84bd55d596a54f7a272b2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-2900000000-e0c04600ea5548a42cef2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0513900000-5a763d7ae727c57c80622021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05o0-0901100000-370d47beb94572e7148c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-1901000000-3aae5354806919f8eade2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0btj-0902500000-913b0ead288934c9a8372021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-1509000000-b37ff1c22ebbfff89adf2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bta-2900200000-72d28f63a33d8e862fa92021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC17058
Pubchem Compound ID99562
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHDW90-Y:BTZ99-Q
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00030363
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGein
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference