L-(-)-Fucose

HCID 3034656CAS 2438-80-4

Basic information

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
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

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

Safety & regulation

Safety data

F
3-10
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
hs_code
29400090
Signal word
Warning

Chemistry & industry

Applications · 3 items

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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海惠诚生物科技有限公司60498804 18930850192 · [email protected]

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

Linked notes

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