D-Ribose, Cas: 50-69-1

D-Ribose
D-ribose (Rib) is an aldopentose, a component of RNA and a constituent of numerous cofactors, and certain vitamins. (Collins, 2006). Ribose is a component of bacterial polysaccharides found in Salmonella (Lindberg, 1990). Ribosylation leads to the production of significant amounts of advanced glycation end products, both extracellularly and intracellularly, it may be involved in cell dysfunction and subsequent cognitive impairments.Title:?D-RiboseCAS Registry Number:?50-69-1Molecular Formula:?C5H10O5Molecular Weight:?150.13Percent Composition:?C 40.00%, H 6.71%, O 53.29%Literature References:?Prepd by hydrolysis of yeast-nucleic acid: Levene, Jacobs,?Ber.?42,?1201, 3247 (1909); Levene, Clark,?J. Biol. Chem.?46,?19 (1921); Bredereck,?Ber.?71,?408 (1938); Bredereck?et al.,?ibid.?73,?956 (1940); Phelps,?US?2152662?(1939 to U.S. Gov’t); by ion-exchange resin chromatography: Cohn,?Science?109,?377 (1949);?J. Am. Chem. Soc.?71,?2275 (1949);?72,?1471 (1950). From glucose: Karrer,?Helv. Chim. Acta?18,?1435 (1935); Austin, Humoller,?J. Am. Chem. Soc.?56,?1152 (1934); Kuhn?et al.,?Ber.?68,?1765 (1935); from nucleosides: Laufer, Charney,?US?2379913;?US?2379914?(both 1945 to Schwarz Labs.); from?D-erythrose: Sowden,?J. Am. Chem. Soc.?72,?808 (1950); from?L-glutamic acid: Koga?et al.,?Tetrahedron Lett.?1971,?263. Reduction of?D-ribonic acid: van Ekenstein, Blanksma,?Chem. Zentralbl.?1913, II,?1562; Steiger,?Helv. Chim. Acta?19,?189 (1936).?Review:?Overend, Stacey, in?Nucleic Acids?vol. I,?E. Chargaff, J. N. Davidson, Eds. (Academic Press, New York, 1955) pp 1-80.Properties:?Plates from abs alcohol, mp 87?. Shows complex mutarotation: Phelps?et al.,?J. Am. Chem. Soc.?56,?748 (1934). Final [a]D24?-25? (water). Sol in water, slightly sol in alc.Melting point:?mp 87?Optical Rotation:?[a]D24?-25? (water)?Derivative Type:?PhenylosazoneMolecular Formula:?C17H20N4O3Molecular Weight:?328.37Percent Composition:?C 62.18%, H 6.14%, N 17.06%, O 14.62%Properties:?Yellow needles from pyridine + water, mp 163-164?.Melting point:?mp 163-164??Derivative Type:?Methyl-D-ribosideProperties:?Crystals from ethyl acetate, mp 83-84?. [a]D20?-113.6? (p = 3), Minsaas,?Ann.?512,?286 (1934).Melting point:?mp 83-84?Optical Rotation:?[a]D20?-113.6? (p = 3), Minsaas,?Ann.?512,?286 (1934)CAS Number50-69-1Product Name(2R,3R,4R)-2,3,4,5-tetrahydroxypentanalIUPAC Name(2R,3R,4R)-2,3,4,5-tetrahydroxypentanalMolecular FormulaC5H10O2Molecular Weight150.13 g/molInChIInChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4+,5-/m0/s1InChI KeyPYMYPHUHKUWMLA-LMVFSUKVSA-NSMILESO=C[C@@H]([C@@H]([C@@H](CO)O)O)OSolubilitySoluble in DMSOSynonymsD Ribose, D-Ribose, RiboseCanonical SMILESC(C(C(C(C=O)O)O)O)OIsomeric SMILESC([C@H]([C@H]([C@H](C=O)O)O)O)O
CAS No: 50-69-1 Synonyms: (2R,3R,4R)-2,3,4,5-Tetrahydroxypentanal MDL No: MFCD00135453 Chemical Formula: C5H10O5 Molecular Weight: 150.13References: 1. Salerno C, D’Eufemia P, Finocchiaro R, Celli M, Spalice A, Iannetti P, Crifo C, Giardini O, Biochim. Biophys. Acta 1999, Jan 6, 1453(1), 135-402. Berezovskii VM, Rodionova EP, Chem. Abstr. 1955, Vol49, p6838