Rhamnose (L-Rhamnose) is a naturally occuring methylpentose found in many plant glycosides and some gram-negative bacterial lipopolysaccharides. Rhamnose-conjugated immunogens is used in immunotherapies. Rhamnose crosses the epithelia via the transcellular pathway and acts as a marker of intestinal absorption.

Physicochemical Properties

Molecular Formula	C6H12O5
Molecular Weight	164.1565
Exact Mass	164.068
CAS #	3615-41-6
Related CAS #	Rhamnose monohydrate;10030-85-0
PubChem CID	19233
Appearance	White to off-white solid powder
Density	1.6±0.1 g/cm3
Boiling Point	323.9±42.0 °C at 760 mmHg
Melting Point	91-95°C
Flash Point	149.7±27.9 °C
Vapour Pressure	0.0±1.6 mmHg at 25°C
Index of Refraction	1.593
LogP	-0.34
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Heavy Atom Count	11
Complexity	126
Defined Atom Stereocenter Count	4
SMILES	C[C@@H]([C@@H]([C@H]([C@H](C=O)O)O)O)O
InChi Key	PNNNRSAQSRJVSB-BXKVDMCESA-N
InChi Code	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
Chemical Name	(2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal
Synonyms	L-Rhamnose NSC 2056 NSC-2056 NSC2056 Isodulcitol Isodulcit Locaose L-Mannomethylose
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References

Sheridan RT, Hudon J, Hank JA, Sondel PM, Kiessling LL. Rhamnose glycoconjugates for the recruitment of endogenous anti-carbohydrate antibodies to tumor cells. Chembiochem. 2014 Jul 7;15(10):1393-8. doi: 10.1002/cbic.201402019. Epub 2014 Jun 6. PubMed PMID: 24909955; PubMed Central PMCID: PMC4205123.

Additional Infomation

Aldehydo-L-rhamnose is the acyclic form of L-rhamnose. It is a L-rhamnose and an aldehyde. (2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal has been reported in Codonopsis pilosula, Poa huecu, and other organisms with data available. A methylpentose whose L- isomer is found naturally in many plant glycosides and some gram-negative bacterial lipopolysaccharides. See also: L-Rhamnose (annotation moved to).

Solubility Data

Solubility (In Vitro)

H2O : ~100 mg/mL (~609.16 mM) DMSO : ~100 mg/mL (~609.16 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (15.23 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (15.23 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (15.23 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 50 mg/mL (304.58 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	6.0916 mL	30.4581 mL	60.9162 mL
	5 mM	1.2183 mL	6.0916 mL	12.1832 mL
	10 mM	0.6092 mL	3.0458 mL	6.0916 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.