L-鼠李糖, L-Rhamnose

Rhamnose is a pentose sugar that is naturally found in many different organisms. It can be found in the form of an untreated group, or as part of a metabolic disorder such as sephadex g-100. Rhamnose has been shown to have biological properties that include cell lysis and the activation of toll-like receptor 2. Rhamnose has also been used for the treatment of bowel disease and hyperproliferative disease.

Title: Rhamnose

CAS Registry Number: 10030-85-0

CAS Name: 6-Deoxy-L-mannose

Additional Names: L-rhamnose; L-mannomethylose; isodulcit

Molecular Formula: C6H12O5

Molecular Weight: 164.16

Percent Composition: C 43.90%, H 7.37%, O 48.73%

Literature References: Occurs free in poison sumac (Rhus toxicodendron L., Anacardiaceae), combined in the form of glycosides of many plants. Preparation: Clark, J. Biol. Chem. 38, 255 (1919). Structure and configuration: Fischer, Morrell, Ber. 27, 384 (1894); Fischer, Zach, ibid. 45, 3762 (1912); Hirst, Macbeth, J. Chem. Soc. 1926, 23; Avery, Hirst, ibid. 1929, 2466. Isoln from walls of gram-negative bacteria: Salton, Biochim. Biophys. Acta 45, 364 (1960); from Afraegle paniculata Engl., Rutaceae: Torto, J. Chem. Soc. 1961, 5234; from rabbit skin: Malawista, Davidson, Nature 192, 871 (1961); from leaves of Solanum chacoense Bitter, Solanaceae: Kuhn, Löw, Ber. 94, 1088 (1961).

Derivative Type: a-Form

Properties: Always obtained by crystn from H2O or EtOH. Monohydrate, holohedric rods from water, hemihedric monoclinic columns from alcohol. Loses water of crystn on heating and partially changes to the b-modification. Very sweet taste. mp 82-92°: Ghosh, Proc. R. Soc. Edinburgh 36, 216 (1915/16). Sublimes at 105° and 2 mm Hg. d420 1.4708. Shows mutarotation. [a]D20 -7.7° ® +8.9°: Hudson, Yanovsky, J. Am. Chem. Soc. 39, 1032 (1917).

Melting point: mp 82-92°: Ghosh, Proc. R. Soc. Edinburgh 36, 216 (1915/16)

Optical Rotation: [a]D20 -7.7° ® +8.9°: Hudson, Yanovsky, J. Am. Chem. Soc. 39, 1032 (1917)

Density: d420 1.4708

Derivative Type: b-Form

Properties: Prepd by heating a-rhamnose monohydrate on a steam bath; crystallized from anhydr acetone + alcohol. Needles, mp 122-126° (rapid heating). [a]D20 +31.5° (1 min, p = 10). After a short time the rotation adjusts to the same final value as a-rhamnose. The b-form is hygroscopic and changes into crystals of the a-modification upon exposure to moist air.

Melting point: mp 122-126° (rapid heating)

Optical Rotation: [a]D20 +31.5° (1 min, p = 10)

COA:

Name: L-Rhamnose monohydrate; 6-Deoxy-L-mannosemonohydrate

CAS: 10030-85-0 or 6155-35-7,3615-41-6     M.F.: C₆H₁₂O₅.H₂O       M.W._: 182.17

Batch No: 20140808        Quantity:1.2kg

References:

1. Melo A, Glaser L, J. Biol. Chem. Vol243, No7, p1475-1478
2. Haack T, Haack K, Diederich WE, Blackman B, Roy S, Pusuluri S, Georg GI, J. Org. Chem. 2005, Sep 16, 70(19), 7592-604