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R3875

Sigma-Aldrich

L-Rhamnose monohydrate

≥99%

Synonym(s):

6-Deoxy-L-mannose, L(+)Rhamnopyranose

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About This Item

Empirical Formula (Hill Notation):
C6H12O5 · H2O
CAS Number:
10030-85-0
Molecular Weight:
182.17
Beilstein/REAXYS Number:
3912643
EC Number:
222-793-4
MDL number:
MFCD00071591
UNSPSC Code:
12352201
PubChem Substance ID:
24899364
NACRES:
NA.25

biological source

oranges

Quality Level

200

assay

≥99%

form

powder

technique(s)

gas chromatography (GC): suitable

color

white to off-white

mp

90 °C

solubility

water: 50 mg/mL, clear, colorless

storage temp.

room temp

SMILES string

O.C[C@@H]1O[C@@H](O)[C@H](O)[C@H](O)[C@H]1O

InChI

1S/C6H12O5.H2O/c1-2-3(7)4(8)5(9)6(10)11-2;/h2-10H,1H3;1H2/t2-,3-,4+,5+,6+;/m0./s1

InChI key

BNRKZHXOBMEUGK-NRBMBCGPSA-N

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General description

L-Rhamnose is a part of plant cell wall polysaccharides, rhamnogalacturonan I and rhamnogalacturonan. It is also present in bacterial cell walland a major antigenic determinant contributing to its pathogenicity. L-rhamnose is non-absorbable in humans but is fermented by intestinal microbes. Supplementation of L-rhamnose slows down gastric emptying. L-rhamnose monosaccharide conjugated immunogens have applications in cancer immunotherapies. Intake of L-rhamnose elevates serum propionate levels.

Application

L-Rhamnose monohydrate has been used:
  • in biofilm enhancement assay in S.pneumonia
  • as a sugar drink in humans undergoing intestinal barrier permeability test
  • for the standard curve generation in high performance liquid chromatography(HPLC)

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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L-rhamnose antigen: a promising alternative to alpha-gal for cancer immunotherapies
Chen W, et al.
ACS Chemical Biology, 6(2), 185-191 (2010)
The effect of L-rhamnose on intestinal transit time, short chain fatty acids and appetite regulation: a pilot human study using combined 13CO2/H2 breath tests
Byrne CS, et al.
Journal of Breath Research, 12(4), 046006-046006 (2018)
Effects of oral glutamine supplementation on exercise-induced gastrointestinal permeability and tight junction protein expression
Zuhl MN, et al.
Journal of Applied Physiology, 116(2), 183-191 (2013)
L-Rhamnose increases serum propionate in humans
Vogt JA, et al.
American Journal of Clinical Nutrition, 80(1), 89-94 (2004)
Bacterial glycobiology: rhamnose-containing cell wall polysaccharides in Gram-positive bacteria
Mistou MY, et al.
FEMS Microbiology Reviews, 40(4), 464-479 (2016)
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