Rhamnose

Rhamnose (Rha, 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[1]

Names
IUPAC name 6-Deoxy-L-mannopyranose
Systematic 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 L-Rhamnopyranose
Identifiers
CAS Number	3615-41-6 N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16055 Y
ChemSpider	18150 Y
DrugBank	DB01869 Y
ECHA InfoCard	100.020.722
KEGG	C00507 Y
PubChem CID	19233
UNII	QN34XC755A Y
CompTox Dashboard (EPA)	DTXSID7042647
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
SMILES O=C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C
Properties
Chemical formula	C6H12O5
Molar mass	164.157 g·mol−1
Density	1.41 g/mL
Melting point	91 to 93 °C (196 to 199 °F; 364 to 366 K) (monohydrate)
Magnetic susceptibility (χ)	-99.20·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Rhamnose can be isolated from Buckthorn (Rhamnus), poison sumac, and plants in the genus Uncaria. Rhamnose is also produced by microalgae belonging to class Bacillariophyceae (diatoms).[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]