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3615-37-0 , D-Fucose, CAS:3615-37-0

3615-37-0 , D-Fucose,
CAS: 3615-37-0
C6H12O5 / 164.16

D-Fucose, D-岩藻糖

D-Fucose is a sugar that can be synthesized in vitro. It is a component of the xanthurenic acid pathway, which is involved in the synthesis of l-arabinose. D-Fucose has been found to have anti-leukemic effects and to inhibit enzyme activities in vitro. It has also been shown to bind to the toll-like receptor, α1-acid glycoprotein, and surface membranes. A hydroxyl group at position 1 on the fucose molecule may be important for this binding. D-Fucose's biological properties are related to its structural analysis and the cell receptors it binds with. D-Fucose has an optimum pH level of 7, so it cannot survive outside of a neutral environment. It does not need any biological cofactors or enzymes for its synthesis, so it is classified as a nonessential nutrient.

(2R,3S,4S,5R)-2,3,4,5-tetrahydroxyhexanal, commonly known as threose, is a four-carbon sugar that is found in nature and synthesized in the laboratory. Threose is an important molecule in biochemistry and has various applications in different fields of research and industry. This paper provides an in-depth analysis of threose, including its definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions.

Definition and Background

Threose is one of the three ketotetroses, which are monosaccharides with four carbon atoms and a ketone functional group. The other two ketotetroses are erythrulose and xylulose. Threose is a chiral molecule with four stereoisomers: (2R,3R)-threose, (2S,3S)-threose, (2S,3R)-threose, and (2R,3S)-threose. The most common stereoisomer is (2R,3S)-threose, which occurs naturally in some bacteria and is synthesized in the laboratory.

Physical and Chemical Properties

Threose is a white crystalline solid that is soluble in water and slightly soluble in ethanol and acetone. It has a melting point of 102-104°C and a specific rotation of -22.5°. Threose is a reducing sugar, which means it can react with other compounds to form a variety of products, including alcohols, acids, and glycosides. Threose can undergo oxidation, reduction, and glycosylation reactions, which make it a versatile molecule with various applications in different fields.

Synthesis and Characterization

Threose can be synthesized in the laboratory from dihydroxyacetone, an intermediate in the glycolysis pathway. The conversion of dihydroxyacetone to threose involves a series of chemical reactions, including a keto-enol tautomerization, an aldol-type condensation, and a dehydration. Threose can be purified and characterized by various analytical techniques, such as high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS).

Analytical Methods

HPLC is a commonly used method to analyze the purity and concentration of threose. NMR spectroscopy can provide structural information about threose and its derivatives, such as the configuration of the chiral centers and the bond distances and angles. MS can confirm the molecular weight of threose and its fragments and detect impurities and contaminants in the sample.

Biological Properties

Threose has various biological properties, such as antimicrobial, antitumor, and immunostimulatory activities. Some studies have shown that threose and its derivatives can inhibit the growth of certain bacteria and fungi and induce apoptosis in cancer cells. Threose can also enhance the immune response in animals and humans by stimulating the production of interleukin-12 and other cytokines.

Toxicity and Safety in Scientific Experiments

Threose is generally considered safe and non-toxic when used in scientific experiments at low concentrations. However, some studies have reported adverse effects of threose in cell cultures and animal models, such as cytotoxicity, genotoxicity, and teratogenicity. These effects may depend on the dose, route of administration, and duration of exposure, as well as the biological system and experimental conditions.

Applications in Scientific Experiments

Threose has various applications in different fields of research, such as biochemistry, microbiology, immunology, and drug discovery. Threose can be used as a substrate or inhibitor of enzymes, such as aldolases, dehydrogenases, and glycosidases, which play important roles in metabolic pathways and disease processes. Threose can also be incorporated into oligosaccharides, glycopeptides, and glycolipids, which are important biomolecules with various functions in cells and tissues. Moreover, threose and its derivatives can be used as lead compounds or pharmacophores for developing new drugs or biologics that target specific diseases or pathogens.

Current State of Research

Threose has been the subject of numerous research studies in recent years, focusing on its synthesis, characterization, biological properties, and applications. Some of the key findings include the discovery of new enzymatic and chemical reactions for threose synthesis, the development of novel analytical methods for threose detection and quantification, the identification of new targets and mechanisms of threose action in cells and organisms, and the exploration of threose-based drugs and biologics for various diseases and infections.

Potential Implications in Various Fields of Research and Industry

Threose has the potential to impact various fields of research and industry, such as biotechnology, agriculture, and medicine. Threose can be used to synthesize novel biomolecules with enhanced properties and functions, such as stability, solubility, and specificity. Threose-based compounds can be used as diagnostic tools or therapeutic agents for various diseases, such as cancer, infections, and autoimmune disorders. Threose can also be used as a renewable and sustainable feedstock for producing biofuels and other high-value chemicals.

Limitations and Future Directions

Despite the promising applications of threose, there are still some limitations and challenges that need to be addressed in future research and development. For example, threose is not widely available or commercially produced, and its synthesis can be challenging and costly. Threose-based compounds may also have limited bioavailability, stability, or efficacy in vivo, which may affect their clinical or agricultural applications. Therefore, future research should focus on developing more efficient and sustainable methods for threose synthesis, improving the properties and performance of threose-based compounds, and exploring new applications and markets for threose-derived products.

Future Directions

1. Optimization of threose synthesis using novel enzymes or chemical catalysts

2. Development of threose-based biosensors for detecting pathogens or toxins

3. Formulation of threose-based drugs or vaccines for infectious diseases or cancer

4. Investigation of threose metabolism and transport in cells and tissues

5. Development of threose analogs or derivatives with improved properties or activities

6. Application of threose in biocatalysis or bioprocessing for producing chemicals or fuels

7. Exploration of threose-based materials for electronic or optical devices

8. Integration of threose into gene editing or gene therapy platforms for precision medicine

9. Investigation of the ecological and environmental impacts of threose production and use

10. Collaboration between academia and industry to accelerate the translation of threose discoveries into practical applications.

Title: D-Fucose

CAS Registry Number: 3615-37-0

CAS Name: 6-Deoxy-D-galactose

Additional Names: D-galactomethylose; rhodeose

Molecular Formula: C6H12O5

Molecular Weight: 164.16

Percent Composition: C 43.90%, H 7.37%, O 48.73%

Literature References: Obtained from glucosides found in various species of Convolvulaceae, e.g., convolvulin, jalapin, b-turpethein. Isoln: Votocek, Z. Zuckerind. Böhmen 24, 249; Chem. Zentralbl. 1901, I, 1042; 1902, II, 1361; 1905, II, 1528. Isoln from jalap resin: Votocek, Bulir, ibid. 1906, I, 1818. Prepn by acid hydrolysis of chartreusin: Sternbach et al., J. Am. Chem. Soc. 80, 1639 (1958).

Properties: a-Form, needles from alc. Sweet taste. mp 144°. Shows mutarotation, [a]D19 +127.0° (7 min) ® +89.4° (31 min) ® +77.2° (71 min) ® +76.0° (final value 146 min, c = 10). Soluble in water; moderately sol in alcohol.

Melting point: mp 144°

Optical Rotation: [a]D19 +127.0° (7 min) ® +89.4° (31 min) ® +77.2° (71 min) ® +76.0° (final value 146 min, c = 10)


Derivative Type: Pentaacetate

Molecular Formula: C16H22O10

Molecular Weight: 374.34

Percent Composition: C 51.34%, H 5.92%, O 42.74%

Properties: mp 115.5°.

Melting point: mp 115.5°


Derivative Type: Oxime

Molecular Formula: C6H13NO5

Molecular Weight: 179.17

Percent Composition: C 40.22%, H 7.31%, N 7.82%, O 44.65%

Properties: mp 188.5°.

Melting point: mp 188.5°


Derivative Type: Phenylhydrazone

Molecular Formula: C12H18N2O4

Molecular Weight: 254.28

Percent Composition: C 56.68%, H 7.14%, N 11.02%, O 25.17%

Properties: mp 172°.

Melting point: mp 172°


Derivative Type: Phenylosazone

Molecular Formula: C18H22N4O3

Molecular Weight: 342.39

Percent Composition: C 63.14%, H 6.48%, N 16.36%, O 14.02%

Properties: mp 176.5°.

Melting point: mp 176.5°

CAS Number


Product Name




Molecular Formula


Molecular Weight

164.16 g/mol



InChI Key





6-Deoxy-D-galactose; (+)-Fucose; 6-Deoxy-D-galactose; 6-Deoxygalactose; D-(+)-Fucose; D-6-Deoxygalactose; Rhodeose

Canonical SMILES


Isomeric SMILES


CAS No: 3615-37-0 Synonyms: 6-Deoxy-D-galactoseRhodeose MDL No: MFCD00135603 Chemical Formula: C6H12O5 Molecular Weight: 164.16

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Name: D-Fucose     M.F.: C6H12O5      M.W.: 164.16       CAS: 3615-37-0





White crystalline powder



Readily soluble in water and

insoluble in ether


NMR and MS

Should comply



IR and TLC


Specific rotation

+74°  to  +77°


Loss Weight On Dryness

Max. 1%



One spot


Assay (HPLC)

Min. 95%



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