L-Gulose, CAS:6027-89-0

L-Gulose
L-Gulose is a carbohydrate that is used in biochemical research. It can be found in plant sources such as sugar cane, sugar beet, and fruit, but it is not naturally present in mammals. L-Gulose has antioxidant properties and can act as an antiviral agent. It also has some structural similarities to vitamin C. L-Gulose can be synthesized from D-glucose by oxidation of the hydroxyl group with sodium hypochlorite or hydrogen peroxide. L-Gulose is a structural analog of D-mannitol, which has been shown to have transcriptional regulation activity. L-Gulose has been shown to inhibit the growth of tumor cells and induce apoptosis in vitro by increasing intracellular reactive oxygen species (ROS) levels.Title:?L-GuloseCAS Registry Number:?6027-89-0Molecular Formula:?C6H12O6Molecular Weight:?180.16Percent Composition:?C 40.00%, H 6.71%, O 53.28%Literature References:?Prepd by sodium amalgam reduction of an acid soln of the?g-lactone of?L-gulonic acid: Fischer, Piloty,?Ber.?24,?526 (1891).?See also?van Ekenstein, Blanksma,?Rec. Trav. Chim.?27,?3 (1908); Levene, LaForge,?J. Biol. Chem.?20,?430 (1915); Talen,?Rec. Trav. Chim.?44,?891 (1925); Isbell,?J. Am. Chem. Soc.?55,?2167 (1933). Synthesis from?D-mannose: Evans, Parrish,?Carbohydr. Res.?28,?359 (1973); from?D-glucose: D. K. Minster, S. M. Hecht,?J. Org. Chem.?43,?3987 (1978).Properties:?Syrup. [a]D20?+61.6?. [a]D?+21.3? (c = 4.58) (Evans, Parrish). Freely sol in water; slightly sol in alcohol. Not fermentable by yeast.Optical Rotation:?[a]D20?+61.6?; [a]D?+21.3? (c = 4.58) (Evans, Parrish)CAS Number6027-89-0Product NameL-GuloseIUPAC Name(2S,3S,4R,5S)-2,3,4,5,6-pentahydroxyhexanalMolecular FormulaC6H12O6Molecular Weight180.16 g/molInChIInChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4+,5-,6-/m1/s1InChI KeyGZCGUPFRVQAUEE-JGWLITMVSA-NSMILESC(C(C(C(C(C=O)O)O)O)O)OSynonymsL-(+)-Gulose;Canonical SMILESC(C1C(C(C(C(O1)O)O)O)O)OIsomeric SMILESC([C@H]1[C@H]([C@@H]([C@@H](C(O1)O)O)O)O)O
CAS No: 6027-89-0 MDL No: MFCD00136022 Chemical Formula: C6H12O6 Molecular Weight: 180.16References: 1. Beil.1, IV, 4334