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5-hydroxymethylfurfural, molecular formula C6H6O3, CAS 67-47-0, typically appears as a white to light yellow crystalline or powdery solid at room temperature. Its structure consists of a furan ring (a five membered oxygen-containing heterocyclic ring) and a hydroxyl (- OH) and a hydroxymethyl (- CH ₂ OH) group. This structure makes it both hydrophilic and polar, soluble in water, alcohol, ethyl acetate, acetone, dimethylformamide, benzene, ether, and chloroform. The 5-hydroxymethylfurfural synthesis content can be used to evaluate the freshness or processing level of honey. The HMF content in fresh honey is extremely low, and heating or long-term storage can lead to an increase in its concentration. It can be used as a precursor for synthesizing biobased materials such as polyester and plastics, or converted into high-value compounds such as 2,5-furandicarboxylic acid (FDCA) through oxidation, hydrogenation, and other reactions.
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Chemical Formula |
C6H6O3 |
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Exact Mass |
126.03 |
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Molecular Weight |
126.11 |
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m/z |
126.03 (100.0%), 127.04 (6.5%) |
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Elemental Analysis |
C, 57.14; H, 4.80; O, 38.06 |
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Melting point |
28-34 °C (lit.) |
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Boiling point |
114-116 °C/1 mmHg (lit.) |
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Density |
1.082 ± 0.06 g / cm3 (predicted) |
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Acidity coefficient ( pKa ) |
15.03 ± 0.70 (predicted) |
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Flash point |
175 °F |
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Vapor density |
5.21 (vs air) |
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Refractive index |
20/D 1.562(lit.) |
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Additional information of chemical compound:
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5-hydroxymethylfurfural synthesis (5-HMF) is an important organic compound with multiple applications, widely used in various fields such as medicine, chemical industry, food, energy, etc.
Active ingredients of drugs
5-HMF itself has pharmacological activity and can be used to prepare various drugs. Research has shown that 5-HMF has various pharmacological effects such as anti-inflammatory, antioxidant, anti allergic, protecting nerve cells, and improving memory. It can be used to prepare anti cerebral ischemia drugs, antiviral drugs, anti cerebral hypoxia drugs, etc. For example, 5-HMF is used in the treatment of endotoxemia and the reduction of mortality caused by multiple organ failure. In addition, 5-HMF can also be used to prepare drugs for the treatment of sepsis, acute pneumonia, acute liver failure, acute DIC, severe shock, and other conditions.
New anti-cancer infusion and oral supplements
5-HMF is used as a substance called Karal due to its antioxidant properties ® The active agents in the new anti-cancer infusion and oral supplements. After oral and intravenous administration, the substance is completely broken down into its metabolites, such as 5-hydroxymethylfuranic acid, 2,5-furandicarboxylic acid, and N - (hydroxymethyl) furanylglycine. These metabolites may have anti-cancer or other biological activities, providing new ideas for cancer treatment.
Treatment of sickle cell anemia
Due to its structure, 5-HMF has the ability to bind to hemoglobin and have a positive impact on its ability to bind to oxygen, making it suitable for treating sickle cell anemia. This discovery provides new possibilities for the treatment of sickle cell anemia and is expected to improve the quality of life of patients.
Improve exercise efficiency
Research has shown that both amateur and professional athletes can improve training efficiency when using 5-HMF as a supplement. This discovery provides a new way for athletes to improve their competitive level, and also indicates the potential application value of 5-HMF in the field of sports medicine.
Organic chemical intermediates
5-HMF is an important organic chemical intermediate that can be used for the synthesis of polymer materials, pharmaceutical products, and other high value-added fine chemicals. It contains active functional groups such as aldehyde and hydroxymethyl, which can be synthesized through various chemical reactions such as hydrogenation, oxidative dehydrogenation, esterification, halogenation, polymerization, hydrolysis, etc., and used to synthesize many useful compounds and new polymer materials.
Preparation of polymer materials
Based on 5-HMF, various polymer materials can be prepared. For example, 5-HMF can be converted into 2,5-furandicarboxylic acid (FDCA), which can then polymerize into biobased polyester PEF (polyethylene furan ester). PEF has excellent mechanical properties and thermal stability, and can replace traditional petroleum based polyester PET (polyethylene terephthalate). It has broad application prospects in packaging, fiber, film and other fields.
Preparation of fine chemicals
5-hydroxymethylfurfural can also be used to prepare various fine chemicals. For example, it can be converted into high value-added chemicals such as acetic acid, 2,5-dimethylfuran, gamma valerolactone, 5-aminoacetic acid, etc. These chemicals can be further applied as fuel additives, solvents, pharmaceutical intermediates, etc.
Replace formaldehyde and benzene containing compounds
In chemical synthesis, 5-HMF can be used as a substitute for formaldehyde and benzene containing compounds. For example, in the synthesis of phenolic resin (PF), melamine resin (MF), and urea resin (UF), 5-HMF is being studied as a possible alternative to formaldehyde. This application helps to reduce the use of toxic and harmful substances and promote the green development of the chemical industry.
Production of resins and adhesives
5-HMF can be used to produce advanced materials such as resins and adhesives. It can form a cross-linked network, therefore it has important value in developing high-performance resins with enhanced mechanical properties. These resins can be used in coatings, composite materials, and various industrial applications, with durability and resistance to environmental factors.
Edible spices
5-HMF can be used as an edible spice in the production of fried and spicy foods. It endows food with unique aroma and flavor, enhancing its sensory quality. However, it should be noted that during high-temperature processing, reducing sugars (carbohydrates) in food may undergo Maillard reaction, generating 5-HMF. Although 5-HMF has a certain aroma contribution in food, excessive intake may have adverse effects on human health.
Food processing and preservation
5-HMF is widely present in foods such as raisins, dairy products, honey, cakes, etc. During food processing, it may exist as a natural ingredient or processing byproduct. In addition, 5-HMF also has certain antibacterial effects, which may help extend the shelf life of food. However, further research is needed on its specific mechanism of action and safety in food.
Heat treatment indicators
5-HMF is formed during the heat treatment of carbohydrate containing foods, especially during the frying process. Therefore, it is commonly used as an indicator for heat treatment. By monitoring the content of 5-HMF in food, the degree of heat treatment and quality changes of the food can be evaluated. This is of great significance for ensuring the safety and quality of food.
Energy sector
Biofuel additive
5-hydroxymethylfurfural synthesis can be used to manufacture biofuel additives, which can effectively improve the storage stability and combustion performance of biofuels. For example, converting 5-HMF into biofuels such as 2,5-dimethylfuran has high energy density and good combustion performance, and can be used as a substitute or additive for gasoline.
Replace traditional petrochemical products
5-HMF, as a biomass based platform compound, has the potential to replace traditional petrochemical products. It mainly comes from biomass sources such as starch, sucrose, fructose, etc., and has the advantages of being renewable and biodegradable. By converting it into valuable chemicals and fuels, reliance on traditional petrochemical products can be reduced, promoting the sustainable development of the energy industry.
Environmental monitoring markers
5-HMF is a byproduct of biomass thermal degradation and can be used as a marker to track the degradation process. By monitoring the content and distribution of 5-HMF in the environment, the efficiency of biomass conversion process can be evaluated and the environmental impact can be monitored. This is of great significance for understanding the mechanism of biomass degradation and optimizing biomass utilization processes.
Biobased environmentally friendly materials
Polymer materials and fine chemicals prepared based on 5-HMF, such as biobased polyester PEF and biobased adhesives, have advantages such as biodegradability and environmental friendliness. The application of these materials helps to reduce the use of traditional petrochemical based materials, lower environmental pollution and ecological damage risks.
Research field
Experiment and analysis
5-HMF is widely used in scientific research for experimentation and analysis. It can be used as a model compound or reaction intermediate for studying organic chemical reaction mechanisms, polymer material synthesis pathways, etc. In addition, 5-HMF can also be used to prepare high-purity chemical reagents and standards, providing accurate and reliable experimental materials for scientific research.
New drug development
In the process of drug development, 5-HMF can be used as a lead compound or drug intermediate for structural modification and optimization. By introducing different functional groups or changing the molecular structure, new drug candidates with better efficacy and lower toxicity can be developed. This is of great significance for promoting innovation and development in the pharmaceutical industry.
Functional food and feed
5-HMF is considered a promising substance due to its various biological activities, which can be used in a range of innovative functional food and feed applications. For example, adding it to functional foods may have health benefits such as antioxidant, anti-inflammatory, and immune enhancement; Adding it to feed may help improve the growth performance and health level of animals.
Cosmetics and personal care products
Although there is currently limited research on the application of 5-hydroxymethylfurfural synthesis in cosmetics and personal care products, considering its antioxidant, anti-inflammatory and other biological activities, it may be developed into a cosmetic ingredient with skincare, beauty and other effects in the future. For example, adding it to skin care products such as face cream and essence may help to resist free radical damage and delay the skin aging process.
In the field of agriculture
Feed additives
Research has shown that 5-HMF can theoretically replace antibiotics as feed additives. It has antibacterial, antioxidant and other effects, which may help improve animal immunity and growth performance. However, due to the long feed certification cycle and the need for toxicology experiments, there are currently no feed products based on 5-HMF available on the market. But with the deepening of research and the advancement of technology, the future application prospects of 5-HMF in the agricultural field are worth looking forward to.
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