L-(-)-Fucose
Basic information
- CAS
2438-80-4- Standard SMILES
C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C=O- InChIKey
PNNNRSAQSRJVSB-KCDKBNATSA-N- Molecular formula
- C6H12O5
- Average molar mass
- 164.16 g/mol
- Monoisotopic mass
- 164.06847348
Overview
Aldehydo-L-fucose is a L-fucose and an aldehydo-fucose. It is an enantiomer of an aldehydo-D-fucose.
Names & identifiers
- Preferred name
- L-(-)-Fucose
- IUPAC
- (2S,3R,4R,5S)-2,3,4,5-tetrahydroxyhexanal
- English name
- L-Fucose
- Molecular formula
- C6H12O5
- Molecular weight
- 164.16
Names & synonyms
L-(-)-Fucose(2S,3R,4R,5S)-2,3,4,5-tetrahydroxyhexanalaldehydo-L-fucoseL-(-)-Rhodeose3h-fucoseFucose, L-MFCD00135607L-FUCOSE [MI]DTXSID50883845AKOS015919077DB15236AC-34938
Show more names
Fucose6-DEOXY-L-GALACTOSEL-Galactose, 6-deoxy-L-fucopyranoseL-(-)-Fucose ,99%6-DEOXY-BETA-GALACTOSEFuoseL-FUCOSE
DS-10931CS-0016990L-(-)-FlucoseUNII-28RYY2IV3Felfucose [INN]EINECS 219-452-7Elfucose [WHO-DD](-)-Fucose (Standard)
Database identifiers
- CAS
2438-80-4- PubChem CID
- 3034656
- DTXSID
DTXSID50883845- ChEMBL
CHEMBL6067643- ChEBI
CHEBI:48204- UNII
- 28RYY2IV3F
- Nikkaji
- J92.797J
Properties
Computed structural properties
- XLogP
- -2.4
- Topological polar surface area
- 98 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 126
Physicochemical properties
- Melting point
- 150 · 150-153 °C(lit.)
- Boiling point
- 211.61 °C · 211.61°C (rough estimate)
- alpha
- -73 · -73~-77°(D/20℃)(c=4,H2O,24hr)
- Density
- 1.1738 · 1.1738 (rough estimate)
- refractive index
- -75.5 ° · -75.5 ° (C=10, H2O)
- storage temp.
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- solubility
- 2 O: · H2O: 0.1 g/mL, clear, colorless
- form
- Powder
- pka
- 12.5 · 12.50±0.20(Predicted)
- color
- Beige to light brown to purple-grayish
- Water Solubility
- Soluble in water.
- Sensitive
- Hygroscopic
- Merck
- 14 · 14,4279
- BRN
- 1723321 · 1723321
- Stability
- Stable. Incompatible with strong oxidizing agents.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 3-10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29400090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
DescriptionL-(−)-Fucose is a deoxyhexose monosaccharide found on N- and O-linked glycans and glycolipids of a wide variety of organisms. It can exist as a terminal modification of glycan structures or serve as a point of attachment for adding other sugars. In humans, L-(−)-fucose plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions.
OccurrenceL-Fucose exists in nature in various biological niches. A major natural source of L-fucose is the brown algal polysaccharide fucoidan. It is also present in the polysaccharides of tragacanth, potatoes, kiwi, soybeans, varieties of wing peas, canola and other plants.L-Fucose is a minor component in plant cell wall polysaccharides, specifically rhamnogalacturonan, xyloglucan and also arabinogalactan proteins that are involved in plant cell elongation.
UsesL-Fucose was isolated from seaweed. It finds application in cosmetics, pharmaceuticals and dietary supplements. It is used in the determination of antigen in A and B blood group. It is also used in the selection-mediated leukocyte-endothelial adhesion and host-microbe interactions. L-Fucose is also used in anti aging creams as well as to promote the accelerated healing of wounds and to reduce allergy.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: L-fucopyranose is the pyranose form of L-fucose. It has a role as an Escherichia coli metabolite and a mouse metabolite. It is a L-fucose and a fucopyranose.
Related reactions
35 records
Compound notes
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