1.0 2010-04-08 22:10:13 UTC 2020-09-17 15:31:51 UTC FDB012526 L-Quebrachitol L-Quebrachitol belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. L-Quebrachitol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, L-Quebrachitol is found, on average, in the highest concentration within sea-buckthornberries. L-Quebrachitol has also been detected, but not quantified in, mugworts. This could make L-quebrachitol a potential biomarker for the consumption of these foods. It is also found in Cannabis sativa, in Paullinia pinnata and in seabuckthorn. For example, its conversion into antifungal (E)-β-methoxyacrylate, oudemansin X has been made. It shows a sweetening property half of that of sucrose but induces colic or diarrhoea at concentration used to render the food palatable. Quebrachitol is a versatile building block in the construction of naturally occurring bioactive materials. It can be found in Allophylus edulis and in the serum left after the coagulation of the Hevea brasiliensis latex in the operation of rubber tapping. It was first isolated by Tanret in 1887 from the bark of Aspidosperma quebracho. The substance was tested as a sweetening agent for diabetics in 1933. Quebrachitol is a naturally occurring optically active cyclitol, a cyclic polyol. (-)-Quebrachitol 1L-2-O-methyl-chiro-inositol 2-O-Methyl-L-chiro-inositol Inositol, 2-O-methyl-, L-chiro- L-chiro-Inositol, 2-O-methyl- L-Quebrachitol Quebrachitol Quebrachitol, (-)- C7H14O6 194.1825 194.07903818 (1R,2S,3S,4S,5R,6R)-6-methoxycyclohexane-1,2,3,4,5-pentol (-)-quebrachitol 642-38-6 CO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5+,6+,7-/m0/s1 DSCFFEYYQKSRSV-FIZWYUIZSA-N belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Cyclohexanols Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aliphatic homomonocyclic compounds Cyclitols and derivatives Dialkyl ethers Hydrocarbon derivatives Polyols Aliphatic homomonocyclic compound Cyclic alcohol Cyclitol or derivatives Cyclohexanol Dialkyl ether Ether Hydrocarbon derivative Polyol cyclitol logp -2.67 ALOGPS logs 0.45 ALOGPS solubility 5.44e+02 g/l ALOGPS melting_point Mp 191° logp -3.1 ChemAxon pka_strongest_acidic 12.36 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (1R,2S,3S,4S,5R,6R)-6-methoxycyclohexane-1,2,3,4,5-pentol ChemAxon average_mass 194.1825 ChemAxon mono_mass 194.07903818 ChemAxon smiles CO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O ChemAxon formula C7H14O6 ChemAxon inchi InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5+,6+,7-/m0/s1 ChemAxon inchikey DSCFFEYYQKSRSV-FIZWYUIZSA-N ChemAxon polar_surface_area 110.38 ChemAxon refractivity 40.53 ChemAxon polarizability 17.96 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsIr 6490 Specdb::MsIr 6491 Specdb::MsIr 6492 Specdb::CMs 1569 Specdb::CMs 26358 Specdb::CMs 31640 Specdb::CMs 43771 Specdb::CMs 133664 Specdb::CMs 141398 Specdb::NmrOneD 124918 Specdb::NmrOneD 124919 Specdb::NmrOneD 124920 Specdb::NmrOneD 124921 Specdb::NmrOneD 124922 Specdb::NmrOneD 124923 Specdb::NmrOneD 124924 Specdb::NmrOneD 124925 Specdb::NmrOneD 124926 Specdb::NmrOneD 124927 Specdb::NmrOneD 124928 Specdb::NmrOneD 124929 Specdb::NmrOneD 124930 Specdb::NmrOneD 124931 Specdb::NmrOneD 124932 Specdb::NmrOneD 124933 Specdb::NmrOneD 124934 Specdb::NmrOneD 124935 Specdb::NmrOneD 124936 Specdb::NmrOneD 124937 Specdb::MsMs 101769 Specdb::MsMs 101770 Specdb::MsMs 101771 Specdb::MsMs 167451 Specdb::MsMs 167452 Specdb::MsMs 167453 Specdb::MsMs 1478437 Specdb::MsMs 1478438 Specdb::MsMs 1478439 Specdb::MsMs 1478440 Specdb::MsMs 1478441 Specdb::MsMs 1478442 Specdb::MsMs 1478443 Specdb::MsMs 1478444 Specdb::MsMs 1478445 Specdb::MsMs 1478446 Specdb::MsMs 1478447 Specdb::MsMs 1478448 Specdb::MsMs 1478449 Specdb::MsMs 1478450 Specdb::MsMs 1478451 Specdb::MsMs 1478452 Specdb::MsMs 1478453 Specdb::MsMs 1478454 Specdb::MsMs 1478455 HMDB34221 #<Reference:0x000055ce2f71b508> Mugwort Type 1 specific Artemisia vulgaris 4220 Sea-buckthornberry Type 1 specific Hippophae rhamnoides 193516 350.0 350.0 350.0 mg/100 g