Glucose pentaacetate

Product Details

CasNo： 604-68-2

MF： C16H22O11

Appearance： powder

Delivery Time： 15 days

Packing： 25kg/drum

Purity： 99%

1. Basic Information

• Chinese Name: α-D - 葡萄糖五乙酸酯；α- 五乙酰葡萄糖；ALPHA 五乙酰葡萄糖
• English Name: Alpha-D-Glucose Pentaacetate (α-GPA); 1,2,3,4,6-Penta-O-acetyl-alpha-D-glucopyranose
• CAS Number: 604-68-2
• Molecular Formula: C16​H22​O11​
• Molecular Weight: 390.34
• Chemical Structure: Formed by acetylating all five hydroxyl groups (-OH) on the alpha-D-glucopyranose ring with acetyl groups (-COCH₃). The alpha configuration (at the C1 anomeric carbon) and fully acetylated structure confer high chemical stability and lipophilicity, enabling compatibility with various non-polar to weakly polar systems.

2. Physicochemical Properties

• Appearance: Colorless to white needle-like crystals or crystalline powder, odorless or with a faint characteristic ester scent, free of visible impurities.
• Melting Point: 109–113°C (a narrow melting range indicates high purity; deviations typically reflect impurity content).
• Solubility: Insoluble in water but highly soluble in organic solvents such as chloroform, dichloromethane, acetone, ethyl acetate, and ethanol. It disperses uniformly in oil-based or mixed solvent systems (e.g., ethanol-water) and shows excellent compatibility with most non-polar to weakly polar raw materials.
• Stability: Exhibits outstanding stability under normal storage conditions—resistant to hydrolysis (especially in neutral to weakly acidic environments), oxidation, and light. It remains intact below 80°C and only undergoes thermal decomposition above 180°C, yielding acetic acid and glucose derivatives. Avoid contact with strong bases (e.g., sodium hydroxide) or strong nucleophiles to prevent deacetylation.
• Optical Activity: As an alpha-glucose derivative, it possesses specific optical rotation. The specific rotation [α]₂₀ᴰ (c=1, chloroform) ranges from +100° to +105°, a key indicator for identifying its configuration and purity.

3. Quality Indicators

4. Core Efficacy & Mechanisms

Alpha-D-glucose pentaacetate exerts its functions through its structural features (fully acetylated groups) and biotransformation capabilities, with key effects including:

1. Stabilizer & Protective Agent: In pharmaceutical and cosmetic applications, its lipophilic acetyl groups form a "protective film" around sensitive active ingredients (e.g., fat-soluble vitamins, polyphenols), isolating them from oxygen and light to slow oxidation and degradation, thus extending product shelf life.
2. Active Ingredient Precursor: In biological systems (e.g., human skin, intestinal tract), it is gradually deacetylated by esterases to release alpha-D-glucose and acetic acid. Glucose provides energy for cell metabolism (e.g., promoting skin cell repair), while trace amounts of acetic acid exhibit mild antibacterial activity without tissue irritation.
3. Solubility Enhancer & Dispersant: For water-insoluble active ingredients (e.g., certain pharmaceutical APIs, plant extracts), it acts as a co-solvent or dispersant in organic solvent systems, improving the solubility and bioavailability of target substances and ensuring uniform distribution in formulations.

5. Application Fields

5.1 Pharmaceutical Industry

• Intermediate for carbohydrate-based drug synthesis: Provides a stable alpha-glucose skeleton for modifying antiviral, hypoglycemic, and other carbohydrate drugs, enhancing their activity and metabolic stability.
• Formulation excipient: Added to oral solid dosages (tablets, capsules) or topical ointments, serving as both a stabilizer (protecting active ingredients from degradation) and a plasticizer (improving formulation moldability and skin permeability).

5.2 Cosmetics Industry

• Active ingredient protectant: Used in skincare products with high-potency ingredients (e.g., retinol serums, antioxidant creams) to prevent oxidation during storage and use, maintaining product efficacy.
• Skin feel regulator: Adding 0.1%–0.5% to lotions and creams improves spreadability, reduces stickiness, and enhances user experience.

5.3 Food Additives

• Precursor for food fragrances: During food processing, it releases acetic acid and glucose through heating or enzymatic hydrolysis, imparting a subtle fruity aroma and sweetness. Its stability exceeds that of small-molecule fragrances, making it suitable for baked goods, candies, etc.
• Preservation aid: Added to fruit and vegetable 保鲜 coatings, it inhibits surface microbial growth by slowly releasing trace acetic acid while glucose maintains cell viability, extending shelf life.

5.4 Organic Synthesis

• Chiral synthesis raw material: Its alpha-configured glucose skeleton is used to synthesize chiral catalysts and ligands for asymmetric organic reactions, ensuring product optical purity.

6. Usage Recommendations

• Addition Timing: In oil-based or organic solvent formulations, add when the system temperature drops below 60°C and stir until fully dissolved. For water-based systems, dissolve it in ethanol or ethyl acetate first, then gradually incorporate into the water phase to avoid precipitation.
• Recommended Dosage: Adjust as needed for pharmaceutical intermediates (typically 1.0–1.2 equivalents of the reactant). In cosmetics and food, the dosage is generally 0.1%–0.5%, customizable based on efficacy requirements.
• Compatibility: Compatible with most organic raw materials (alcohols, esters, hydrocarbons) and pharmaceutical excipients. Avoid mixing with strong alkalis (e.g., excessive triethanolamine) or strong reducing agents to prevent deacetylation or decomposition.

7. Packaging & Storage

• Packaging: Double-sealed packaging with an inner food-grade polyethylene plastic bag (moisture isolation) and an outer brown glass bottle or aluminum foil bag (light protection). Common specifications include 100 g/bottle, 500 g/bag, 1 kg/bag, and 25 kg/cardboard drum (lined with moisture-proof film). Custom pharmaceutical-grade small-batch packaging (10 g/20 g) is available.
• Storage: Store sealed in a cool, dry place (temperature ≤25°C, relative humidity ≤60%), away from light, heat sources, and strongly corrosive substances. The shelf life is 24 months when unopened; after opening, use promptly (recommended within 1 month) and reseal to prevent moisture absorption and caking.