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3615-41-6, L-Rhamnose, 6-Deoxy-L-mannose, CAS:3615-41-6

3615-41-6, L-Rhamnose, 6-Deoxy-L-mannose,
CAS:3615-41-6
C6H12O5.H2O / 182.17
MFCD00149363

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: 3615-41-6

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)

CAS Number3615-41-6
Product Name(2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal
IUPAC Name(2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal
Molecular FormulaC6H12O5
Molecular Weight164.16 g/mol
InChIInChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4-,5-,6-/m0/s1
InChI KeyPNNNRSAQSRJVSB-BXKVDMCESA-N
SMILESCC(C(C(C(C=O)O)O)O)O
SolubilitySoluble in DMSO
SynonymsRhamnose; L-Rhamnose; NSC 2056; NSC-2056; NSC2056; Isodulcitol; Isodulcit; Locaose; Mannomethylose, L-;
Canonical SMILESCC(C(C(C(C=O)O)O)O)O
Isomeric SMILESC[C@@H]([C@@H]([C@H]([C@H](C=O)O)O)O)O
CAS No: 10030-85-0,6155-35-7,3615-41-6 Synonyms: 6-Deoxy-L-mannosea-L-Rhamnose monohydrate MDL No: MFCD00149363 Chemical Formula: C6H12O5·H2O Molecular Weight: 182.17

In Stock.

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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

Items

Standards

Results

Appearance

Crystal powder

Complies

Solubility

Readily soluble in water

Complies

Identification

IR and TLC

Complies

Melting point

90 ~  94°C

90 ~92 

Specific rotation

+8.8~  +9.2o

+8.9o

Loss weight on dryness

Max.10%

7.4%

Heavy metal

Max. 50ppm

Complies

Residue on ignition

Max. 0.1%

0.01%

TLC

One spot

One spot

Assay

Min. 99%

99.5 %

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


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