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D(+)-trehalose dihydrate is a stable non reducing disaccharide composed of two molecules of glucose in an alpha, α, Composed of 1,1-glycoside bonds. Originally extracted from ergot fungus in rye, it was later found to be widely present in animals, plants, and microorganisms in nature, especially in fungi, algae, mosses, and invertebrates with high levels. Molecular formula C12H22O11 · 2H2O, CAS 6138-23-4, It is a white crystal, and one molecule of D (+) - trehalose dihydrate contains two molecules of crystal water. It is soluble in water, glacial acetic acid, and hot ethanol, but insoluble in ether and acetone. When heated to 130 ℃, trehalose loses its crystalline water and becomes amorphous. In the vast field of biochemistry, carbohydrates play a crucial role as essential energy sources and structural components for life activities. Among them, this seemingly ordinary yet mysterious compound, with its unique properties and functions, has shown a wide range of application prospects in scientific research, food industry, and even pharmaceutical fields.
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Chemical Formula |
C12H26O13 |
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Exact Mass |
378.14 |
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Molecular Weight |
378.33 |
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m/z |
378.14 (100.0%), 379.14 (13.0%), 380.14 (2.7%) |
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Elemental Analysis |
C, 38.10; H, 6.93; O, 54.98 |
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D(+)-trehalose dihydrate, chemically known as α - D-glucopyranosyl - (1 → 1) - α - D-glucopyranosyl dihydrate, is a substance composed of two glucose molecules that pass through an alpha, α-1, A non reducing disaccharide formed by the connection of 1-glycosidic bonds. Its molecular formula is usually C12H22O11 · 2H2O, with a molecular weight of approximately 342.30 (some data also shows it as 378.3, possibly due to differences in the calculation method of moisture content in different data). It has a stable molecular structure and can protect other biomolecules in the organism from damage under extreme conditions such as high temperature, cold, dryness, high osmotic pressure, etc. This characteristic makes it known as the "sugar of life".
(1) Cell membrane and protection of biomolecules: In nature, many organisms are able to survive in extreme environments largely due to the accumulation of D - (+) - trehalose in the body. It can effectively protect biological macromolecules such as cell membranes, proteins, and DNA from damage, and is one of the important mechanisms for organisms to cope with adversity. This protective mechanism makes D - (+) - trehalose have broad application prospects in the biomedical field.
(2) Blood products and vaccine protection: It has been successfully used in medicine as a stabilizer for bioactive substances such as blood products, vaccines, and cell tissues. This not only extends the storage time at room temperature, but also prevents blood contamination. Meanwhile, as a freeze-drying protectant, it is also widely used in biological products. Compared with sucrose, it can provide better protection for proteins.
(3) Energy reserve substance: Although trehalose is not the main source of energy, it serves as an energy reserve substance in certain organisms, such as certain fungi and insects, and can be rapidly broken down into glucose for energy supply during food shortages. This characteristic has potential application value in the fields of agriculture and horticulture. By spraying or soaking, the drought resistance, cold resistance, and disease resistance of crops can be significantly improved.
(4) Enhancing body resistance: Recent studies have shown that D - (+) - trehalose also has the function of regulating immune responses, enhancing the body's resistance to pathogens, promoting wound healing, and demonstrating potential value in the field of medicine. This immune regulatory effect may be related to its ability to protect immune cells from damage.
(1) Sweeteness and calories: As a natural sweetener, it has moderate sweetness, low calories, and will not cause sharp fluctuations in blood sugar. It is an ideal choice for patients with diabetes and people pursuing healthy diet.
(2) Baked goods and candies: Its excellent moisturizing and stability make D(+)-trehalose dihydrate increasingly widely used in baked goods, candies, beverages, and other fields.
(3) Eye drops and vaccine preservation: Adding trehalose to eye drops can effectively protect corneal cells and reduce drug irritation; In vaccine preservation, trehalose can significantly enhance the stability and effectiveness of vaccines.
3. Application in the cosmetics industry
(1) Moisturizing function: The moisturizing function of trehalose makes it an important ingredient in high-end cosmetics. It can effectively lock in skin moisture, reduce external environmental damage to the skin, and promote skin health.
(2) Antioxidant and skin barrier repair: In addition to moisturizing function, trehalose also has antioxidant and skin barrier repair functions. These characteristics make trehalose have broad application prospects in cosmetics such as anti-aging and anti sensitivity.
4. Agricultural and Horticultural Applications
(1) Drought resistance, cold resistance, and disease resistance: Through spraying or soaking treatment, D - (+) - trehalose can significantly improve the drought resistance, cold resistance, and disease resistance of crops. This stress resistance enhancement effect helps crops maintain growth and yield in harsh environments.
(2) Flower preservation: In terms of flower preservation, D - (+) - trehalose also shows great potential. By spraying or soaking, the viewing period of flowers can be extended, maintaining their brightness and freshness.
5. Other applications
(1) Chemical raw materials: They are also widely used in the field of fine chemicals. It can be used as a chemical raw material for synthesizing other compounds, providing raw material support for the production of fine chemical products.
(2) Preservation of enzymes and cell membranes: It can also be used to preserve research biological products, such as genetically engineered enzymes and other enzymes, cell membranes, antibodies, antigens, organelles, etc. These biological products play an important role in scientific research and industrial production, and their protective effect helps to extend their shelf life and maintain their activity.
There are various production methods for D(+)-trehalose dihydrate, mainly including natural extraction, chemical synthesis, and biotransformation.
Raw material source:
Natural extraction method mainly extracts from plants (such as kelp and seaweed) or microorganisms (such as yeast and mold) rich in trehalose. These raw materials are rich in trehalose, making them an ideal source for extracting trehalose.
Extraction process:
The extraction process usually includes steps such as raw material processing, extraction, separation, and purification. Through a series of chemical reactions and physical operations, high-purity products can be extracted from the raw materials.
Advantages and disadvantages:
The natural extraction method has the advantages of a wide range of raw material sources and a relatively simple extraction process; The disadvantage is that the output is limited and the cost is high, making it difficult to meet the needs of large-scale production.
Synthesis principle:
The chemical synthesis method directly synthesizes the substance through chemical means. This method utilizes chemical reactions to convert substrates such as glucose into trehalose.
Synthesis process:
The synthesis process usually includes steps such as substrate selection, catalyst selection, and optimization of reaction conditions. By adjusting reaction conditions and catalyst types, synthesis efficiency and product purity can be improved.
Advantages and disadvantages:
The advantages of chemical synthesis method are high efficiency and high product purity; The disadvantage is that it may introduce harmful substances and affect product safety. Therefore, when using chemical synthesis to produce this substance, it is necessary to strictly control the reaction conditions and product quality.
Conversion principle:
The biotransformation method utilizes microorganisms or enzymes to catalyze the production of trehalose from substrates such as glucose. This method utilizes the enzyme system within the organism for catalytic reactions, and has the characteristics of being environmentally friendly, safe, and efficient.
Conversion process:
The conversion process usually includes steps such as microbial cultivation, enzyme extraction, catalytic reaction, etc. By optimizing the microbial culture conditions and enzyme catalytic conditions, the conversion efficiency and product purity can be improved.
Advantages and disadvantages:
The advantages of biotransformation method are green, environmentally friendly, safe and efficient; The disadvantage is that the production cost is relatively high, requiring complex fermentation and extraction processes. However, with the continuous development of biotechnology, biotransformation has gradually become the mainstream production method and has broad application prospects.
Raw Material Sources and Pre-treatment
The production of D(+)-trehalose dihydrate is based on the liquefaction of starch as the core raw material. Commonly used are renewable resources such as corn starch and cassava starch. The starch needs to undergo liquefaction treatment: under high temperature (90-100℃) and acidic conditions, the starch granules absorb water, expand and rupture, forming a dextrin solution; subsequently, enzymatic hydrolysis (such as α-amylase) is carried out to further degrade it into oligosaccharides, providing suitable substrates for subsequent enzymatic reactions.
Core Manufacturing Process: Multi-enzyme Synergistic Catalysis
The synthesis of trehalose is achieved through a multi-enzyme cascade reaction. The key enzymes include:
Maltotriose-based trehalose synthase (MTSase)
This enzyme cuts two glucose units from the non-reducing end of maltotriose, forming a trehalose intermediate with the remaining oligosaccharide.
Maltotriose-based trehalose hydrolase (MTHase)
Further hydrolyzes the intermediate to release free trehalose.
Starch glucosidase (AMG)
Breaks down the remaining oligosaccharide into glucose, increasing the purity of trehalose.
Typical process flow:
Liquefy starch solution (DE value 10-15) → Adjust pH to 6.0-6.5 → Add MTSase and MTHase (ratio 1:1) → React at 50-60℃ for 12-24 hours → Heat up to 80℃ to inactivate enzymes → Add AMG for further reaction for 4-6 hours → Terminate the reaction and cool down.
Purification and Crystallization: From crude product to high-purity crystals
Initial purification
Activated carbon decolorization: Remove pigments and organic impurities from the reaction solution.
Ion exchange chromatography: Through a series of cation exchange resins (such as H⁺ type) and anion exchange resins (such as OH⁻ type), remove salts, proteins, and small molecule impurities.
Membrane filtration: Use ultrafiltration membranes (with a molecular weight cut-off of 10-30 kDa) to further concentrate and remove large molecule impurities.
Concentration and crystallization
Vacuum evaporation concentration: Concentrate the purified solution to a seaweed sugar content of ≥ 60% (w/v).
Induced crystallization:
Cooling crystallization method: Slowly cool the concentrated solution to 10-15°C, add seed crystals (dihydrate microcrystals of seaweed sugar) to induce crystallization.
Evaporation crystallization method: Evaporate water continuously at 50-60°C until the solution reaches the critical supersaturation value, and naturally crystallize.
Crystal type control: Adjust the crystallization temperature, stirring speed, and seed crystal addition amount to ensure the formation of uniform rhombic dihydrate crystals (melting point 97°C, containing 2 molecules of crystalline water).
Centrifugation and drying
Centrifugal separation: Use a horizontal centrifuge (rotational speed 3000-4000 rpm) to separate crystals from the mother liquor, with a recovery rate of up to 95%.
Fluidized bed drying: Dry the crystals in a hot air at 40-50°C, controlling the moisture content ≤ 1.5% (avoiding dehydration to obtain anhydrous seaweed sugar).
Screening and packaging: Grade by vibrating screen (mesh size 200-400) and the final product is white crystalline powder with a purity of ≥ 98%.
Quality Control and Standards
Purity testing
High performance liquid chromatography (HPLC): Use an amino column as the stationary phase, acetonitrile-water as the mobile phase, and detect the proportion of the seaweed sugar peak area.
Optical rotation meter: Determine the specific rotation [α]²⁰ᴰ = +199° (5% aqueous solution) to confirm the purity of D-configuration.
Impurity control
Heavy metals: Use atomic absorption spectrometry (AAS) to detect lead and arsenic content, with a limit of ≤ 1 mg/kg.
Microorganisms: Test total bacterial count (≤ 1000 CFU/g) and pathogenic bacteria (not detectable) according to the Chinese Pharmacopoeia method.
Stability test
Accelerated test: Place at 40°C and 75% humidity for 6 months, detect the purity change (≤ 0.5%) and crystalline water content (stabilized at 10-11%).
Technological Innovation and Industry Trends
Enzyme immobilization technology
Fix MTsase and MTHase on magnetic nanoparticles or resin carriers to achieve repeated use of enzymes (cycling times ≥ 50 times), reducing production costs.
Continuous production
Develop membrane bioreactor (MBR), couple enzyme catalytic reaction with membrane separation to achieve continuous synthesis and purification of seaweed sugar, increasing production efficiency by 3 times.
Green manufacturing
Use organic solvent-water dual-phase crystallization to reduce water resource consumption; use microbial fermentation method to produce enzyme preparations, replacing chemical synthesis enzymes, and reducing carbon emissions.
Application Areas and Market Prospects
D(+)-Trehalose Dihydrate is widely used in:
Food Industry: As a low-calorie sweetener (with 45% of the calories of sucrose) and a humectant, it is used in baked goods, candies, and frozen beverages.
Biomedical: As a protein stabilizer (such as vaccines, antibody drugs) and a cell freeze-drying protective agent, it increases the survival rate of biological products.
Cosmetics: It inhibits the evaporation of moisture from the skin's stratum corneum and is used in high-end skin care products and sunscreen products.
According to market research institutions, the global trehalose market size will grow at an annual rate of 6.2% and is expected to exceed 500 million US dollars by 2027.
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