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L-Fucose, also known as L-(+)-fucose or 6-deoxy-L-galactose, is a deoxyhexose monosaccharide that is found in various biological niches, including Nand O-linked glycans and glycolipids of a wide variety of organisms. It plays a crucial role in the determination of A and B blood group antigen substructures, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions in humans. L-Fucose exists as a white crystalline powder and is soluble in methanol, ethanol, DMSO, and other organic solvents.

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  • 2438-80-4 Structure
  • Basic information

    1. Product Name: L-FUCOSE
    2. Synonyms: 6-DEOXY-BETA-GALACTOSE;6-DEOXY-L-GALACTOSE;6-DESOXY-L-GALACTOSE;L-(-)-RHODEOSE;L-(-)-FUCOSE;L-FUCOSE;FUCOSE, L-;6-deoxy-l-galactos
    3. CAS NO:2438-80-4
    4. Molecular Formula: C6H12O5
    5. Molecular Weight: 164.16
    6. EINECS: 219-452-7
    7. Product Categories: 13C & 2H Sugars;Biochemistry;Deoxysugars;Fucose;Sugars;Dextrins、Sugar & Carbohydrates;Carbohydrates & Derivatives
    8. Mol File: 2438-80-4.mol
  • Chemical Properties

    1. Melting Point: 150-153 °C(lit.)
    2. Boiling Point: 211.61°C (rough estimate)
    3. Flash Point: 209.3 °C
    4. Appearance: Beige to light brown to purple-grayish/Powder
    5. Density: 1.1738 (rough estimate)
    6. Vapor Pressure: 5E-08mmHg at 25°C
    7. Refractive Index: -75.5 ° (C=10, H2O)
    8. Storage Temp.: -20°C Freezer
    9. Solubility: H2O: 0.1 g/mL, clear, colorless
    10. PKA: 12.50±0.20(Predicted)
    11. Water Solubility: Soluble in water.
    12. Sensitive: Hygroscopic
    13. Stability: Stable. Incompatible with strong oxidizing agents.
    14. Merck: 14,4279
    15. BRN: 1723321
    16. CAS DataBase Reference: L-FUCOSE(CAS DataBase Reference)
    17. NIST Chemistry Reference: L-FUCOSE(2438-80-4)
    18. EPA Substance Registry System: L-FUCOSE(2438-80-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 24/25
    4. WGK Germany: 3
    5. RTECS:
    6. F: 3-10
    7. TSCA: Yes
    8. HazardClass: N/A
    9. PackingGroup: N/A
    10. Hazardous Substances Data: 2438-80-4(Hazardous Substances Data)

2438-80-4 Usage

Uses

Used in Cosmetics:
L-Fucose is used as an ingredient in anti-aging creams for its potential benefits in promoting skin health and reducing the appearance of aging.
Used in Pharmaceuticals:
L-Fucose is used as a component in the determination of antigen in A and B blood groups, aiding in the identification and classification of blood types.
Used in Dietary Supplements:
L-Fucose is used as a supplement to support various health functions, including immune system support and gut health.
Used in Wound Healing:
L-Fucose is used as a component in products that promote the accelerated healing of wounds, potentially due to its role in cell adhesion and host-microbe interactions.
Used in Allergy Reduction:
L-Fucose is used in products aimed at reducing allergy symptoms, possibly through its involvement in immune system regulation.
Used in the Selection-Mediated Leukocyte-Endothelial Adhesion:
L-Fucose is used in the study and manipulation of leukocyte-endothelial adhesion, which is crucial for various immune system functions and the body's response to inflammation.
Used in Host-Microbe Interactions:
L-Fucose is used in research and applications related to host-microbe interactions, which are essential for understanding the complex relationships between the human body and its microbial inhabitants.
Used in the Determination of Blood Group Antigens:
L-Fucose is used in the identification and classification of blood group antigens, particularly in the A and B blood groups, which is vital for safe blood transfusions and organ transplants.

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 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.

Check Digit Verification of cas no

The CAS Registry Mumber 2438-80-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,4,3 and 8 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 2438-80:
(6*2)+(5*4)+(4*3)+(3*8)+(2*8)+(1*0)=84
84 % 10 = 4
So 2438-80-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4+,5+,6-/m0/s1

2438-80-4 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (A16789)  L-(-)-Fucose, 99%   

  • 2438-80-4

  • 1g

  • 260.0CNY

  • Detail
  • Alfa Aesar

  • (A16789)  L-(-)-Fucose, 99%   

  • 2438-80-4

  • 5g

  • 1004.0CNY

  • Detail
  • Sigma

  • (F2252)  L-(−)-Fucose  ≥99%

  • 2438-80-4

  • F2252-5G-9

  • 1,771.38CNY

  • Detail

2438-80-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name L-fucopyranose

1.2 Other means of identification

Product number -
Other names L-(-)-Fucose

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2438-80-4 SDS

2438-80-4Relevant articles and documents

Composition, structural characteristics, and antitumor properties of polysaccharides from the brown algae Dictyopteris polypodioides and Sargassum sp.

Sokolova,Ermakova,Awada,Zvyagintseva,Kanaan

, p. 329 - 334 (2011)

The polysaccharide compositions of the brown algae Dictyopteris polypodioides and Sargassum sp. from the Mediterranean Sea were determined. The principal polysaccharide of the studied algae (about 12% of the dry alga weight) was alginic acid. The content of water-soluble polysaccharides was low. The amount of fucoidan was less than 1% of the dry alga weight; of neutral polysaccharides, less than 0.25%. The monosaccharide compositions of fucoidans and neutral polysaccharides were investigated. Experiments on soft agar-agar models showed that fucoidans from D. polypodioides and Sargassum sp. exhibited antitumor activity against RPMI-7951 human melanoma cells.

Polysaccharides from Sargassum tenerrimum: Structural features, chemical modification and anti-viral activity

Sinha, Sharmistha,Astani, Akram,Ghosh, Tuhin,Schnitzler, Paul,Ray, Bimalendu

, p. 235 - 242 (2010)

Herpes simplex viruses (HSVs) display affinity for cell-surface heparan sulfate proteoglycans with biological relevance in virus entry. Here, we exploit an approach to inhibiting HSV infection by using a sulfated fucoidan, and a guluronic acid-rich alginate derived from Sargassum tenerrimum, mimicking the active domain of the entry receptor. These macromolecules have apparent molecular masses of 30 ± 5 and 26 ± 5 kDa, respectively. They and their chemically sulfated derivatives showed activity against herpes simplex virus type 1 (HSV-1). Their inhibitory concentration 50% (IC50) values were in the range 0.5-15 μg/ml and they lacked cytotoxicity at concentrations up to 1000 μg/ml. The anti-HSV activity increased with increasing sulfate ester content. Our results suggest the feasibility of inhibiting HSV infection by blocking viral entry with polysaccharide having specific structure.

Two new compounds from the fruits of Buddleja lindleyana with neuroprotective effect

Wu, De-Ling,Wang, Yang-Kui,Liu, Jing-Song,Wang, Xun-Cui,Zhang, Wei

, p. 342 - 347 (2012)

Two new triterpenoid glycosides, mimengosides H (1) and I (2), were isolated from the fruits of Buddleja lindleyana Fort. Their structures were determined by extensive spectroscopic methods. Neuroprotective effects of these isolates against 1-methyl-4- phenylpyridinium ion-induced neurotoxicity in PC12 cells were evaluated. Pretreatment with compound 1 had potential protective effect in a concentration range from 0.1 to 1μmol l-1.

Heteroglycan of an edible mushroom Termitomyces clypeatus: Structure elucidation and antioxidant properties

Pattanayak, Manabendra,Samanta, Surajit,Maity, Prasenjit,Sen, Ipsita K.,Nandi, Ashis K.,Manna, Dilip K.,Mitra, Payel,Acharya, Krishnendu,Islam, Syed S.

, p. 30 - 36 (2015)

A water-soluble heteroglycan (PS) of an average molecular weight ~1.98 ×105 Da was isolated from the aqueous extract of an edible mushroom Termitomyces clypeatus (R. Heim). The structure of the polysaccharide (PS) was established using total hydrolysis, methylation analysis, Smith degradation, and 1D/2D NMR experiments. Total hydrolysis indicated the presence of d-glucose, d-galactose, d-mannose, and l-fucose in a molar ratio of 4.10:1.95:1.0:0.95, respectively. The chemical and NMR analysis indicated the presence of a repeating unit with a backbone consisting of one each of the residues (1→3)-α-d-galactopyranosyl, (1→3)-α-d-mannopyranosyl, (1→3)-α-d-glucopyranosyl, (1→3)-β-d-glucopyranosyl, (1→6)-β-d-glucopyranosyl, and (1→6)-α-d-galactopyranosyl, respectively. The (1→3)-α-d-mannopyranosyl residue was found branched at O-2 with terminal α-l-fucopyranosyl moiety and (1→3)-β-d-glucopyranosyl residue was branched at O-6 with terminal α-d-glucopyranosyl residue. The PS exhibited antioxidant properties.

Biological activities of fucose-containing polysaccharide ascophyllan isolated from the brown alga Ascophyllum nodosum

Nakayasu, Seiichirou,Soegima, Ryo,Yamaguchi, Kenichi,Oda, Tatsuya

, p. 961 - 964 (2009)

A fucose-containing, sulfated polysaccharide ascophyllan was isolated from the brown alga Ascophyllum nodosum. Composition analysis demonstrated that ascophyllan mainly contains uronic acid, xylose, fucose, and sulfate half ester in approximately equimole

Two new noroleanane-type triterpenoid saponins from the stems of Stauntonia chinensis

Feng, Tong-Tong,Fu, Hui-Zheng,Yang, Yi-Sheng,Zhou, Zhi-Qiang,Dai, Mian,Bi, Hong-Yu,Wang, Dong

, p. 1269 - 1276 (2019)

Two new noroleanane-type triterpenoid saponins, 3β,20α,24-trihydroxy-29-norolean-12-en-28-oic acid 24-O-β-L-fucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranoside (1) and 3β,20α,24-trihydroxy-29-norolean-12-en-28-oic acid 24-O-β-D-glucopyranosyl-(1→2)-[α-L-arabinopyranosyl-(1→3)]-β-D-glucopyranoside (2) were isolated from the stems of Stauntonia chinensis DC., together with three known compounds, brachyantheraoside B2 (3), eupteleasaponin Ⅷ (4) and fargoside B (5). Their structures were elucidated by spectroscopic and chemical methods. The cytotoxic activities of compounds 1 and 2 were evaluated against five human tumor cell lines (HCT-116, HepG2, BGC-823, NCI-H1650, and A2780). Compounds 1 and 2 showed moderate cytotoxic activities toward the tested cell lines with IC50 values ranging from 12.71 to 32.04?μM.

Two new flavonol glycosides from the leaves of Elaeagnus pungens

Ge, Yue-Bin,Li, Meng-Shun,Mei, Zhi-Nan,Yang, Guang-Zhong

, p. 1073 - 1079 (2013)

The leaves of Elaeagnus pungens were extracted with 70% ethanol and successively purified by column chromatography. Seven constituents were obtained and characterized, all of which belong to the class of flavonol glycosides. Their structures were elucidat

Potential anti-gout constituents as xanthine oxidase inhibitor from the fruits of Stauntonia brachyanthera

Liu, Dan,Wang, Dandan,Yang, Wei,Meng, Dali

, p. 3562 - 3566 (2017)

With the aim of finding a better xanthine oxidase inhibitor with potential anti-gout properties, the studies on the fruit of Stauntonia brachyanthera were carried out, which led to the isolation of 12 glycosides, including 4 new nor-oleanane triterpenoids. Their structures were determined by comprehensive spectroscopic (NMR and HR MS) analysis. Two compounds (4 and 11) exhibited significant inhibitory activities on xanthine oxidase with IC50 values of 5.22 and 1.60?μM, respectively. Another five compounds (1, 2, 3, 8 and 10) showed qualified activities. The results suggested that the existences of nor-oleanane triterpenoids and flavonoids in the fruits were responsible for the inhibitory activity on xanthine oxidase that could cut off the production of uric acid. Nor-oleanane triterpenoids, a new leading XO inhibitor, is worthy of further studies on molecular biology level for its mechanisms.

Structure and gene cluster of the O-antigen of Escherichia coli O41

Zhu, Hongfei,Perepelov, Andrei V.,Senchenkova, Sof'Ya N.,Shashkov, Alexander S.,Wang, Lei,Knirel, Yuriy A.

, p. 86 - 89 (2012)

The acidic O-polysaccharide (O-antigen) of Escherichia coli O41 was studied by sugar analysis along with 1D and 2D 1H and 13C NMR spectroscopy, and the following structure of the branched hexasaccharide repeating unit was established: This structure is unique among the known structures of bacterial polysaccharides. The O-antigen gene cluster of E. coli O41 was sequenced. The gene functions were tentatively assigned by a comparison with sequences in the available databases and found to be in full agreement with the E. coli O41 O-polysaccharide structure.

Studies on isolation, characterization of fucoidan from brown algae Turbinaria decurrens and evaluation of it's in vivo and in vitro anti-inflammatory activities

Manikandan, Ramar,Parimalanandhini, Duraisamy,Mahalakshmi, Krishnan,Beulaja, Manikandan,Arumugam, Munuswamy,Janarthanan, Sundaram,Palanisamy, Subramanian,You, SangGuan,Prabhu, Narayanasamy Marimuthu

, p. 1263 - 1276 (2020)

In the present study, the anti-nociception and anti-inflammatory activity of fucoidan isolated from T. decurrens on formalin induced paw-edema in mice model were investigated. The extracted fucoidan contain 54.86% of total sugar, 23.51% of sulfate and 3.4% of protein. The monosaccharide composition analysis revealed that fucoidan encompassed of fucose (59.3%), galactose (12.6%), mannose (9.6%), rhamnose (6.4%) and xylose (11.4%). Further, the structural characterization was done by UV–visible spectroscopy, X-ray diffraction, FT-IR and 1HNMR analysis. The fucoidan reduced the licking time thereby suggesting anti-nociceptive effect and decreased the size of paw swelling in the formalin induced inflammatory edema condition. The isolated fucoidan could significantly decreased the MDA and also increase the SOD, CAT, GPx, GST and GSH activity in paw edema tissue of formalin injected mice. Furthermore, fucoidan administration retained p65/NF-κB transcription factor in the cytosol thereby showing down regulation of the gene expression of pro-inflammatory mediators such as IL-1β, COX-2 and MMP-9 in fucoidan treated mice. The anti-inflammatory effect of fucoidan was attributed to its capacity on modulating the levels of enzymatic antioxidants, master regulator NF-κB and pro-inflammatory cytokines. The fucoidan has reduced LPS induced cytotoxicity in IC-21 macrophage at a dose depended on manner.

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