L-Fucose

ChemicalBook > CAS DataBase List > L-Fucose

Product Name: L-Fucose
CAS No.: 2438-80-4
Chemical Name: L-Fucose
Synonyms: L-(-)-FUCOSE;6-DEOXY-L-GALACTOSE;L-Galactose, 6-deoxy-;L-fucopyranose;(2S,3R,4R,5S)-2,3,4,5-tetrahydroxyhexanal;L-(-)-Fucose ,99%;6-DEOXY-BETA-GALACTOSE;Fuose;L-FUCOSE;L-FUCOSE
CBNumber: CB1448036
Molecular Formula: C6H12O5
Formula Weight: 164.16
MOL File: 2438-80-4.mol

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L-Fucose Property

Melting point:: 150-153 °C(lit.)
Boiling point:: 211.61°C (rough estimate)
alpha: -73～-77°(D/20℃)(c=4,H2O,24hr)
Density: 1.1738 (rough estimate)
refractive index: -75.5 ° (C=10, H2O)
storage temp.: Inert atmosphere,Store in freezer, under -20°C
solubility: H₂O: 0.1 g/mL, clear, colorless
form: Powder
pka: 12.50±0.20(Predicted)
color: Beige to light brown to purple-grayish
Water Solubility: Soluble in water.
Sensitive: Hygroscopic
Merck: 14,4279
BRN: 1723321
Stability:: Stable. Incompatible with strong oxidizing agents.
InChIKey: SHZGCJCMOBCMKK-DLABPRKASA-N
LogP: -0.340 (est)
CAS DataBase Reference: 2438-80-4(CAS DataBase Reference)
EPA Substance Registry System: L-Galactose, 6-deoxy- (2438-80-4)

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Safety

Safety Statements: 24/25
WGK Germany: 3
F: 3-10
TSCA: Yes
HS Code: 29400090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: F2252
Product name: L-(?)-Fucose
Purity: ≥99%
Packaging: 5g
Price: $212
Updated: 2024/03/01

Sigma-Aldrich

Product number: 1286606
Product name: L-(?)-Fucose
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 200mg
Price: $536
Updated: 2024/03/01

TCI Chemical

Product number: F0065
Product name: L-(-)-Fucose
Purity: >97.0%(HPLC)
Packaging: 1g
Price: $42
Updated: 2024/03/01

TCI Chemical

Product number: F0065
Product name: L-(-)-Fucose
Purity: >97.0%(HPLC)
Packaging: 10g
Price: $233
Updated: 2024/03/01

Alfa Aesar

Product number: A16789
Product name: L-(-)-Fucose, 99%
Packaging: 1g
Price: $44.2
Updated: 2024/03/01

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L-Fucose Chemical Properties,Usage,Production

Description

L-(−)-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.

Chemical Properties

White crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents.

Chemical Properties

l-fucose is a six-carbon sugar also known as 6-deoxy-l-galactose. Its molecular formula is C6H12O5 and its melting point is 150.0–153.0 °C. It is a white crystalline powder that easily absorbs moisture, and its hydrophilicity is weaker than that of other monosaccharides. l-fucose is the main form of fucose found in nature and is also the only levorotatory sugar used by mammals, while d-fucose is found only in some glycosides[1].

Occurrence

L-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.

Uses

L-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.

Definition

ChEBI: 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.

Reactions

L-Fucose is oxidised by the enzyme L-fucose dehydrogenase in the presence of nicotinamide-adenine dinucleotide phosphate (NADP+) to L-fucono-1,5-lactone with the formation of reduced nicotinamideadenine dinucleotide phosphate (NADPH) (1).
(L-fucose dehydrogenase) (1)
L-Fucose + NADP+ --> L-fucono-1,5-lactone + NADPH + H+
The amount of NADPH formed in this reaction is stoichiometric with the amount of L-fucose. It is the NADPH which is measured by the increase in absorbance at 340 nm.

Biological Functions

l-fucose has many biological functions like the antitumor effect and relieving intestinal disease, and exhibits potential as an emulsifier in the food industry. It can be used as a functional food and one of the components of bacteriostatic agents. Moreover, it also has an anti-aging function[1].

Biological Activity

L-Fucose (6-Deoxy-L-galactose) is used in studies of fucoidan polysaccharides containing glycans. It is studied as a glycan modifying carbohydrate that generates antigenic sites recognized by IgE antibodies. It is used as a substrate to identify, differentiate, and characterize enzymes such as fucosidase(s),l-fucose isomerase(s), and L-fucose dehydrogenase(s). It may be used to study organelles, and bacterial microcompartments, involved in the degradation of plant and algal cell wall sugars. L-Fucose may also be used as a reference compound in rare sugar identification and analysis.

References

[1] Yan Wang . “Research progress on the functions, preparation and detection methods of l-fucose.” Food Chemistry 433 (2023): Article 137393.

L-Fucose Preparation Products And Raw materials

Raw materials

Preparation Products

2-Chloro-4-nitrophenyl-alpha-L-fucopyranoside

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View Lastest Price from L-Fucose manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd

Product: L-Fucose 2438-80-4
Price: US $200.00-95.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 20ton
Release date: 2024-04-25

Hebei Zhuanglai Chemical Trading Co.,Ltd

Product: 6-deoxy-L-galactose 2438-80-4
Price: US $70.00/kg
Min. Order: 1kg
Purity: 99
Supply Ability: 5000
Release date: 2024-05-24

Hebei Zhuanglai Chemical Trading Co.,Ltd

Product: 6-deoxy-L-galactopyranose 2438-80-4
Price: US $90.00/kg
Min. Order: 1kg
Purity: 99
Supply Ability: 5000
Release date: 2024-06-04

2438-80-4, L-FucoseRelated Search:

MUCIC ACID D-GALACTURONIC ACID TRIGALACTURONIC ACID METHYL 2,3,4-TRI-O-ACETYL-BETA-D-THIOGALACTOPYRANOSIDURONIC ACID METHYL ESTER L-GALACTONO-1,4-LACTONE L-Fucose ALPHA-D-GALACTURONIC ACID HYDRATE Isometheptene mucate 6-DEOXY-L-GALACTITOL 4-NITROPHENYL-BETA-D-FUCOSE L-(-)-FUCOSE,L-FUCOSE 4-NITROPHENYL-BETA-D-FUCOSE FUCOSE, D-(+)-,D-(+)-FUCOSE,D-FUCOSE P-NITROPHENYL BETA-D-GALACTOPYRANOSIDURONIC ACID ALPHA-L-MANNOHEPTOSE ALPHA-D-GALACTURONIC ACID 1-PHOSPHATE LITHIUM SALT DIGALACTURONIC ACID L-[3-13C]FUCOSE

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