Rhamnose

Rhamnose[1]
IUPAC name (2R,3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol
Other names isodulcit alpha-L-Rhamnose L-rhamnose L-mannomethylose alpha-L-Rha alpha-L-Rhamnoside alpha-L-rhamnosides alpha-L-Mannomethylose 6-deoxy-L-mannose
Identifiers
CAS number	10485-94-6 Y
PubChem	19233
ChemSpider	18150 Y
UNII	QN34XC755A Y
DrugBank	DB01869
KEGG	C00507 Y
ChEBI	CHEBI:16055 Y
Jmol-3D images	Image 1
SMILES O=C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C
InChI InChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4-,5-,6-/m0/s1 Y Key: PNNNRSAQSRJVSB-BXKVDMCESA-N Y InChI=1/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4-,5-,6-/m0/s1 Key: PNNNRSAQSRJVSB-BXKVDMCEBH
Properties
Molecular formula	C6H12O5
Molar mass	164.16 g/mol
Exact mass	164.068473
Melting point	91-93 °C (monohydrate)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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. http://www.telegraph.co.uk/health/healthnews/8306768/Chemical-from-tropical-flower-latest-weapon-against-wrinkles.html. 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

• Use of L-rhamnose to Study Irreversible Adsorption of Bacteriophage PL-1 to a Strain of Lactobacillus casei Journal of General Virology