Rutinose, CAS:90-74-4

Rutinose is a naturally occurring polyphenol found in many plants, including the leaves and bark of rue plants. It is a glycoside derivative that has been shown to inhibit human colorectal adenocarcinoma cells (HL-60) by binding to DNA and inhibiting RNA synthesis. Rutinose also has been shown to have anti-inflammatory effects and has been used in the treatment of metabolic disorders such as diabetes mellitus. Rutinose is a bioactive compound with antioxidant properties that may be related to its ability to bind metal ions, including calcium ions at physiological pH levels. Rutinose also has been shown to have a signal peptide sequence that targets it for secretion into the blood stream, where it may act on brain functions.Title:?RutinoseCAS Registry Number:?90-74-4CAS Name:?6-O-(6-Deoxy-a-L-mannopyranosyl)-D-glucoseAdditional Names:?6-O-a-L-rhamnosyl-D-glucoseMolecular Formula:?C12H22O10Molecular Weight:?326.30Percent Composition:?C 44.17%, H 6.80%, O 49.03%Literature References:?A disaccharide present in glycosides. Prepn from rutin by enzymatic hydrolysis using rhamnodiastase: Charaux,?Compt. Rend.?178,?1312 (1924);?Bull. Soc. Chim. Biol.?6,?634 (1924); Zempl?n, Gerecs,?Ber.?68B,?1320 (1935). Synthesis:?eidem,?Ber.?67B,?2049 (1934);?68B,?1318 (1935). Structure: Gorin, Perlin,?Can. J. Chem.?37,?1930 (1959).Properties:?Very hygroscopic powder from alcohol and ether turning into a syrup on exposure to air. The freshly pptd material loses about 6% of its wt at 100?. The dried rutinose softens around 140?, dec 189-192?. [a]D20?+3.2????+0.8? (c = 4 in water). [a]D20?-10? (95% alc). Very sol in water. Sol in alc. Hydrolysis with dil HCl yields 1 mol?L-rhamnose and 1 mol?D-glucose.Optical Rotation:?[a]D20?+3.2????+0.8? (c = 4 in water); [a]D20?-10? (95% alc)?Derivative Type:?HeptaacetylrutinoseProperties:?mp 169-170?. [a]D20?-27.7? (chloroform).Melting point:?mp 169-170?Optical Rotation:?[a]D20?-27.7? (chloroform)CAS Number90-74-4Product NameRutinoseIUPAC Name(2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyhexanalMolecular FormulaC12H22O10Molecular Weight326.3 g/molInChIInChI=1S/C12H22O10/c1-4-7(16)10(19)11(20)12(22-4)21-3-6(15)9(18)8(17)5(14)2-13/h2,4-12,14-20H,3H2,1H3/t4-,5-,6+,7-,8+,9+,10+,11+,12+/m0/s1InChI KeyCPYCUQCIDSHOHI-IFLAJBTPSA-NSMILESCC1C(C(C(C(O1)OCC(C(C(C(C=O)O)O)O)O)O)O)OSynonyms6-O-(6-deoxy-alpha-L-mannopyranosyl)-D-glucose, rutinoseCanonical SMILESCC1C(C(C(C(O1)OCC(C(C(C(C=O)O)O)O)O)O)O)OIsomeric SMILESC[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@H]([C@H]([C@@H]([C@H](C=O)O)O)O)O)O)O)O
CAS No: 90-74-4 Synonyms: 6-O-(Deoxy-a-L-mannopyranosyl)-D-glucopyranose6-O-(a-L-Rhamnopyranosyl)-D-glucopyranose MDL No: MFCD00161473 Chemical Formula: C12H22O10 Molecular Weight: 326.3References: 1. Kamiya S, Esaki S, Tanaka R, Ag. Biolog. Chem., 1985, 49, p55