1.0 2010-04-08 22:04:44 UTC 2019-11-26 02:55:33 UTC FDB000867 (+)-Asarinin (+)-sesamin, also known as episesamin or asarinin, is a member of the class of compounds known as furanoid lignans. Furanoid lignans are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units (+)-sesamin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (+)-sesamin can be found in a number of food items such as flaxseed, fats and oils, ucuhuba, and sesame, which makes (+)-sesamin a potential biomarker for the consumption of these food products. (+)-Asarinin (+)-Episesamin 1-Asarinine Episesamin Isosesamin L-asarinin Xanthoxylin S C20H18O6 354.3533 354.110338308 5-[(1S,3aS,4R,6aS)-4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxole 5-[(1S,3aS,4R,6aS)-4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxole 133-03-9 C1OC2=C(O1)C=C(C=C2)C1OCC2C1COC2C1=CC2=C(OCO2)C=C1 InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2 PEYUIKBAABKQKQ-UHFFFAOYSA-N belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units. Furanoid lignans Organic compounds Lignans, neolignans and related compounds Furanoid lignans Aromatic heteropolycyclic compounds Acetals Benzenoids Benzodioxoles Dialkyl ethers Furofuran lignans Furofurans Hydrocarbon derivatives Oxacyclic compounds Oxolanes Acetal Aromatic heteropolycyclic compound Benzenoid Benzodioxole Dialkyl ether Ether Furanoid lignan Furofuran Furofuran lignan skeleton Hydrocarbon derivative Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxolane melting_point Mp 121-122° logp 2.45 ChemAxon pka_strongest_basic -3.8 ChemAxon iupac 5-[(1S,3aS,4R,6aS)-4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxole ChemAxon average_mass 354.3533 ChemAxon mono_mass 354.110338308 ChemAxon smiles C1OC2=C(O1)C=C(C=C2)C1OCC2C1COC2C1=CC2=C(OCO2)C=C1 ChemAxon formula C20H18O6 ChemAxon inchi InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2 ChemAxon inchikey PEYUIKBAABKQKQ-UHFFFAOYSA-N ChemAxon polar_surface_area 55.38 ChemAxon refractivity 89.75 ChemAxon polarizability 36.5 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 6 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Sesame Type 1 specific Sesamum orientale 4182 192.600006 192.600006104 192.600006104 mg/100 g