Rhamnose

Rhamnose[1]
Names
IUPAC name
(2R,3R,4R,5R,6S)-6-Methyloxane-2,3,4,5-tetrol
Other names
Isodulcit
α-L-Rhamnose
L-Rhamnose
L-Mannomethylose
α-L-Rha
α-L-Rhamnoside
α-L-Mannomethylose
6-Deoxy-L-mannose
Rhamnopyranose
Rhamnopyranoside
Identifiers
10485-94-6 
ChEBI CHEBI:16055 Yes
ChemSpider 18150 Yes
DrugBank DB01869 Yes
Jmol-3D images Image
KEGG C00507 Yes
PubChem 19233
UNII QN34XC755A Yes
Properties
Molecular formula
 C6H12O5
Molar mass 164.16 g·mol−1
Density 1.41 g/mL
Melting point 91 to 93 °C (196 to 199 °F; 364 to 366 K) (monohydrate)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Rhamnose (Rham) is a naturally occurring deoxy sugar. It can be classified as either a methyl-pentose or a 6-deoxy-hexose. Rhamnose occurs in nature in its L-form as L-rhamnose (6-deoxy-L-mannose). This is unusual, since most of the naturally occurring sugars are in D-form. Exceptions are the methyl pentoses L-fucose and L-rhamnose and the pentose L-arabinose.

Rhamnose can be isolated from Buckthorn (Rhamnus), poison sumac, and plants in the genus Uncaria. High-rhamnose extracts from the latter have found use in anti-wrinkle creams.[2]

Rhamnose is commonly bound to other sugars in nature. It is a common glycone component of glycosides from many plants. Rhamnose is also a component of the outer cell membrane of acid-fast bacteria in the Mycobacterium genus, which includes the organism that causes tuberculosis.[3]

References

  1. ↑ Merck Index, 11th Edition, 8171.
  2. ↑ "Chemical from tropical flower latest weapon against wrinkles". The Daily Telegraph. February 6, 2011. Retrieved January 7, 2011.
  3. ↑ Golan, David E., ed. (2005). "Chapter 35 - Pharmacology of the Bacterial Cell Wall". Principles of Pharmacology: The Pathophysiologic Basis of Drug Therapy. Armen H. Tashjian Jr., Ehrin J. Armstrong, Joshua N. Galanter, April Wang Armstrong, Ramy A. Arnaout, Harris S. Rose. Lippincott Williams and Wilkins. p. 569. ISBN 0-7817-4678-7.

External links