1.0 2010-04-08 22:11:53 UTC 2018-05-29 01:19:24 UTC FDB015499 Quassin Bitter constituent of Quassia amara (Surinam quassia) and Picrasma excelsa (Jamaican quassiawood) Quassin is a white bitter, crystalline substance extracted from the quassia tree. It is the bitterest substance found in nature with a bitter threshold of 0.08ppm and it is 50 times more bitter than quinine. Nigakilactone D C22H28O6 388.4541 388.188588628 4,15-dimethoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-4,14-diene-3,11,16-trione quassin 76-78-8 COC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(=O)C(C34C)C2(C)C1=O InChI=1S/C22H28O6/c1-10-7-14(26-5)20(25)22(4)12(10)8-15-21(3)13(9-16(23)28-15)11(2)18(27-6)17(24)19(21)22/h7,10,12-13,15,19H,8-9H2,1-6H3 IOSXSVZRTUWBHC-UHFFFAOYSA-N belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. Quassinoids Organic compounds Lipids and lipid-like molecules Prenol lipids Terpene lactones Aliphatic heteropolycyclic compounds Carboxylic acid esters Cyclohexenones Delta valerolactones Hydrocarbon derivatives Monocarboxylic acids and derivatives Naphthalenes Naphthopyrans Organic oxides Oxacyclic compounds Oxanes Pyrans Aliphatic heteropolycyclic compound C-20 quassinoid skeleton Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cyclohexenone Delta valerolactone Delta_valerolactone Hydrocarbon derivative Ketone Lactone Monocarboxylic acid or derivatives Naphthalene Naphthopyran Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Pyran Quassinoid logp 2.73 ALOGPS logs -3.96 ALOGPS solubility 4.30e-02 g/l ALOGPS melting_point Mp 221-222° logp 2.24 ChemAxon pka_strongest_acidic 18.08 ChemAxon pka_strongest_basic -4.6 ChemAxon iupac 4,15-dimethoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-4,14-diene-3,11,16-trione ChemAxon average_mass 388.4541 ChemAxon mono_mass 388.188588628 ChemAxon smiles COC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(=O)C(C34C)C2(C)C1=O ChemAxon formula C22H28O6 ChemAxon inchi InChI=1S/C22H28O6/c1-10-7-14(26-5)20(25)22(4)12(10)8-15-21(3)13(9-16(23)28-15)11(2)18(27-6)17(24)19(21)22/h7,10,12-13,15,19H,8-9H2,1-6H3 ChemAxon inchikey IOSXSVZRTUWBHC-UHFFFAOYSA-N ChemAxon polar_surface_area 78.9 ChemAxon refractivity 104.2 ChemAxon polarizability 41 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 5 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 11943 Specdb::CMs 153183 Specdb::MsMs 8660 Specdb::MsMs 8661 Specdb::MsMs 8662 Specdb::MsMs 15332 Specdb::MsMs 15333 Specdb::MsMs 15334 Specdb::MsMs 2340231 Specdb::MsMs 2340232 Specdb::MsMs 2340233 Specdb::MsMs 2624993 Specdb::MsMs 2624994 Specdb::MsMs 2624995 HMDB36587 #<Reference:0x00007f093c19a5e0> bitter