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Trehalose, Mycose, Tremalose, E963, 99-20-7

Trehalose, Mycose, Tremalose, E963, 99-20-7

TREHALOSE

1. PRODUCT DEFINITION AND CHEMICAL IDENTITY

Parameter Description
Chemical Name (IUPAC) α-D-Glucopyranosyl-α-D-glucopyranoside
Common Name Trehalose
Other Names Mycose, Tremalose
CAS Number 99-20-7 (anhydrous) / 6138-23-4 (dihydrate)
E Code E963
Molecular Formula C₁₂H₂₂O₁₁ (anhydrous); C₁₂H₂₂O₁₁·2H₂O (dihydrate)
Molecular Weight 342.30 g/mol (anhydrous); 378.33 g/mol (dihydrate)
Appearance White crystalline powder
Taste Mildly sweet (approximately 45% of sucrose)

Note: Trehalose is a non-reducing disaccharide formed by two glucose molecules linked by an α,α-1,1-glycosidic bond. It occurs naturally in many plants, fungi, yeasts, and invertebrates. It is renowned for its exceptional cell protection and stabilization properties; its ability to protect biological structures against desiccation, freezing, and osmotic stress (anhydrobiosis) makes it widely used in the food, cosmetic, pharmaceutical, and biotechnology industries.

2. PHYSICAL AND CHEMICAL PROPERTIES

Property Value / Description
Physical form White crystalline powder
Melting point ~97 °C (dihydrate); ~203 °C (anhydrous)
Boiling point Decomposes before boiling
Solubility in water (20 °C) ~69 g/100 mL (high solubility)
Solubility in ethanol Practically insoluble
Sweetness ~45% of sucrose
pH (10% aqueous solution) 5.0 – 6.7
Optical rotation ([α]D²⁰) +178° (c=1, water)
Stability Highly resistant to heat and acidic pH; its non-reducing nature prevents it from undergoing the Maillard (browning) reaction
Hygroscopy Low; the dihydrate form is non-hygroscopic

3. FUNCTIONAL PROPERTIES

  • Bioprotective (Anhydrobiosis): The most significant property of trehalose is its ability to protect biological membranes, proteins, and cells against extreme environmental stresses such as desiccation, freezing, and high osmotic pressure. It maintains structural integrity by replacing water during dehydration (water replacement hypothesis) and forming a glassy (vitreous) matrix within the cell.

  • Protein and Enzyme Stabilizer: Protects proteins from thermal denaturation and aggregation. This property is critical, especially in liquid or lyophilized (freeze-dried) formulations of vaccines, antibodies, and other biopharmaceuticals.

  • Moisturizer: Enhances the skin's water retention capacity in cosmetic formulations, helping to reduce transepidermal water loss (TEWL).

  • Low Sweetness and Low Glycemic Index: Offers lower sweetness and a lower glycemic index compared to sucrose, making it suitable for calorie-reduced and diabetic-friendly products.

  • Resistance to Maillard Reaction: Thanks to its non-reducing structure, it does not undergo browning (Maillard) reactions with amino acids during heat treatment. This is an important advantage for maintaining the colour and flavour stability of products.

  • Odour and Taste Masking: Possesses the ability to mask undesirable bitter tastes and odours in some food and pharmaceutical formulations.

4. APPLICATION AREAS AND TYPICAL DOSAGES

Sector Application Typical Usage Rate / Notes
Food Industry Bakery products, confectionery, beverages, frozen foods 0.5 – 10%; used as a humectant, sweetener, texture improver, flavour stabilizer
Pharma & Biotechnology Stabilization of proteins, vaccines, antibodies, and enzymes; cell/tissue preservation 5 – 20% (in lyophilized formulations); mM levels in cell culture media
Cosmetics & Personal Care Skincare creams, lotions, hair conditioners, anti-aging products 1 – 5%; as a moisturizing and cell-protective agent
Medical Research Neuroprotective effect studies (Alzheimer's, Parkinson's, Huntington's models); ophthalmic solutions Research stage; 3 – 5% solution for dry eye treatment

5. HEALTH BENEFITS AND MECHANISM OF ACTION

  • Cell Protection: Trehalose protects cells from damage caused by dehydration, freezing, and osmotic stress. It acts by preserving the integrity of biological membranes and the native three-dimensional structure (conformation) of proteins.

  • Autophagy Induction: Trehalose has been shown to induce autophagy, a natural mechanism that clears damaged cellular components (misfolded proteins, damaged mitochondria). This property is the subject of intense research, particularly in the context of neurodegenerative diseases.

  • Antioxidant Properties: Helps protect cells from free radical damage by reducing oxidative stress.

  • Neuroprotective Effects: In animal models of neurodegenerative disorders characterized by protein aggregation, such as Alzheimer's, Parkinson's, and Huntington's disease, trehalose has been found to exert neuroprotective effects by promoting the clearance of toxic protein aggregates. These applications are still under research.

6. ALTERNATIVES AND COMPARISON

Alternative Comparison
Sucrose (Table Sugar) Higher sweetness and glycemic index; undergoes Maillard reaction; its bioprotective properties are not as strong as trehalose.
Maltose A reducing sugar, undergoes Maillard reaction; not as effective a bioprotectant as trehalose.
Mannitol Lower solubility; has an osmotic diuretic effect; its cell protection mechanism is different.
Sorbitol High hygroscopy; used as a humectant but its bioprotective properties are not as pronounced as trehalose.
Glycerol A common cryoprotectant; penetrates into the cell; unlike trehalose, it does not form a vitreous matrix.

Summary: The most important differences of trehalose from its alternatives are its non-reducing structure (does not undergo Maillard reaction) and its superior bioprotective (water replacement and vitrification) properties.

7. REGULATORY STATUS, SAFETY, AND STORAGE

  • Food Additive (E963): Approved as a food additive in the European Union under the code E963. Holds GRAS (Generally Recognized As Safe) status by the FDA in the USA.

  • Safety Profile: Toxicologically considered very safe. Its acute oral toxicity is very low (LD50 > 5000 mg/kg). Consumption of large amounts (>50 g/day) may cause temporary digestive discomfort (osmotic diarrhoea) in some sensitive individuals. Trehalose intolerance is a very rare condition due to trehalase enzyme deficiency.

  • Storage: Store in a cool (<25 °C), dry, and well-ventilated area in tightly sealed packaging. The dihydrate form is non-hygroscopic, but protection from moisture is recommended to prevent caking.

  • Shelf Life: At least 24 months under proper storage conditions.

  • Packaging: Typically 1–25 kg cardboard or kraft bags with PE inner liner.

8. QUICK REFERENCE TABLE

Property Value
CAS 99-20-7
Formula C₁₂H₂₂O₁₁
Molecular Weight 342.30 g/mol
Appearance White crystalline powder
Taste Mildly sweet (~45% of sucrose)
E Code E963
Main Uses Food humectant, protein/vaccine stabilizer, cosmetic moisturizer
Key Benefit Superior bioprotective and stabilization properties

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