1.0 2010-04-08 22:04:51 UTC 2025-11-18 22:28:35 UTC FDB001162 Gein Gein, 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. 3,7-Dimethyl-1-(2-propynyl)xanthine 3,7-dimethyl-1-propargylxanthine 3,7-Dimethyl-I-propargylxanthine DMPX Eugenol vicanoside Gein Geoside C21H30O11 458.4563 458.178811802 2-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol 2-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol 585-90-0 COC1=C(OC2OC(COC3OCC(O)C(O)C3O)C(O)C(O)C2O)C=CC(CC=C)=C1 InChI=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 FSCNUJMKSQHQSY-UHFFFAOYSA-N 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. Phenolic glycosides Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aromatic heteromonocyclic compounds Acetals Alkyl aryl ethers Anisoles Disaccharides Hydrocarbon derivatives Methoxybenzenes O-glycosyl compounds Oxacyclic compounds Oxanes Phenoxy compounds Polyols Secondary alcohols Acetal Alcohol Alkyl aryl ether Anisole Aromatic heteromonocyclic compound Benzenoid Disaccharide Ether Hydrocarbon derivative Methoxybenzene Monocyclic benzene moiety O-glycosyl compound Organoheterocyclic compound Oxacycle Oxane Phenol ether Phenolic glycoside Phenoxy compound Polyol Secondary alcohol logp -0.53 ALOGPS logs -1.83 ALOGPS solubility 6.85e+00 g/l ALOGPS melting_point Mp 183-184° (anhyd) logp -0.8 ChemAxon pka_strongest_acidic 11.92 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac 2-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol ChemAxon average_mass 458.4563 ChemAxon mono_mass 458.178811802 ChemAxon smiles COC1=C(OC2OC(COC3OCC(O)C(O)C3O)C(O)C(O)C2O)C=CC(CC=C)=C1 ChemAxon formula C21H30O11 ChemAxon inchi InChI=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 ChemAxon inchikey FSCNUJMKSQHQSY-UHFFFAOYSA-N ChemAxon polar_surface_area 167.53 ChemAxon refractivity 107.38 ChemAxon polarizability 46.06 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 11 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 21784 Specdb::CMs 41630 Specdb::CMs 133785 Specdb::CMs 141519 Specdb::MsMs 13151 Specdb::MsMs 13152 Specdb::MsMs 13153 Specdb::MsMs 19823 Specdb::MsMs 19824 Specdb::MsMs 19825 Specdb::MsMs 2802430 Specdb::MsMs 2802431 Specdb::MsMs 2802432 Specdb::MsMs 2880314 Specdb::MsMs 2880315 Specdb::MsMs 2880316 Specdb::NmrOneD 16542 Specdb::NmrOneD 16543 Specdb::NmrOneD 16544 Specdb::NmrOneD 16545 Specdb::NmrOneD 16546 Specdb::NmrOneD 16547 Specdb::NmrOneD 16548 Specdb::NmrOneD 16549 Specdb::NmrOneD 16550 Specdb::NmrOneD 16551 Specdb::NmrOneD 16552 Specdb::NmrOneD 16553 Specdb::NmrOneD 16554 Specdb::NmrOneD 16555 Specdb::NmrOneD 16556 Specdb::NmrOneD 16557 Specdb::NmrOneD 16558 Specdb::NmrOneD 16559 Specdb::NmrOneD 16560 Specdb::NmrOneD 16561 HMDB0029909 Herbs and Spices Unknown generic