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10016-20-3
futurechem
10016-20-3
Alpha-Cyclodextrin, also known as cyclodextrin, cyclohexaamylose, cyclomaltohexaose, cyclohexapentylose, alpha-Schardinger dextrin, Alfadex, Cavamax W6, has the chemical formula C36H60O30, a molecular weight of 972.84, CAS number 10016-20-3, EINECS 233-007-4, UNII Z1LH97KTRM, and international food additive number E457 (EU)/INS 457. It is a cyclic oligosaccharide composed of six D-glucanose units linked end-to-end by α-1,4 glycosidic bonds. It belongs to the cyclodextrin family (one of the three common α, β, and γ cyclodextrins) and is the smallest cyclodextrin variety in the family. It is a natural source molecule obtained by enzymatic hydrolysis and cyclization of starch using cyclodextrin glucosyltransferase (CGTase): the molecule is hollow truncated cone-shaped, with a hydrophilic outer wall and a hydrophobic inner cavity. The inner diameter of the cavity is about 0.47-0.53 nm, which can just accommodate small hydrophobic molecules such as menthol, cinnamaldehyde, fatty acids, and small molecule fragrances.
Basic information : Chemical formula C36H60O30 (composed of 6 glucose units, hence also known as cyclomaltohexaose); Molecular weight 972.84; CAS number 10016-20-3; EINECS 233-007-4; UNII Z1LH97KTRM; DSSTox DTXSID7030698; Synonyms: α-cyclodextrin, cyclodextrin, cyclohexaamylose, cyclomaltohexaose, hexaglucosylcyclodextrin, α-cyclomaltohexaose, cyclohexaamylose, cyclohexaamylose, cyclohexaamylose, cyclohexaamylose, cyclohexaamylose, cyclohexaamylose, cyclohexaamylose, cyclohexaamylose, cyclohexaamylose, cyclohexaamylose, cyclohexaamylose, cyclohexaamylose, cyclohexaamylose, cyclohexaamylose, alpha-Cycloamylose, alpha-Dextrin, alpha-Schardinger dextrin, Alfadex, Cavamax W6, etc.
Structurally , α-cyclodextrin molecules consist of 6 D-glucanyl units linked end-to-end by α-1,4 glycosidic bonds to form a ring. The entire molecule is hollow and truncated pyramidal (frustum) in shape. The primary and secondary hydroxyl groups on the outer ring of the glucose units form a hydrophilic outer wall, while the CH bonds pointing into the cavity and the ether oxygen bonds form a hydrophobic inner cavity. The inner diameter of the cavity is about 0.47-0.53 nm, which is the smallest among the three common α, β, and γ cyclodextrins. It is suitable for encapsulating small hydrophobic molecules such as menthol, cinnamaldehyde, fatty acids, and small molecule essential oils, but it is not easy to accommodate large molecules.
Physically , α-cyclodextrin is a white or nearly white crystalline solid, almost odorless and tasteless, often appearing as hexagonal plate-like or blade-shaped needle crystals; its melting point is approximately 278℃ (decomposes); its solubility in water at room temperature (25℃) is approximately 14.5 g/100 mL, making it the most water-soluble of the three common α, β, and γ cyclodextrins (significantly higher than β-cyclodextrin's 1.85 g/100 mL); it is readily soluble in hot water and soluble in some organic solvents; it has no reducing properties and its aqueous solution is neutral; it has low bulk density, large specific surface area, low hygroscopicity, and good powder flowability.
Chemically , α-cyclodextrin is a non-reducing cyclic oligosaccharide (without reducing ends in the molecule, and does not react with Fehling's reagent, etc.): it is stable to acids, alkalis, and heat, and is not easily decomposed under conventional food processing (sterilization, baking, boiling); its hydrophobic cavity can form a host-guest inclusion complex with various size-matched hydrophobic or amphiphilic guest molecules (small molecule flavorings, menthol, cinnamaldehyde, essential oils, flavor substances, bitter substances, pesticide active ingredients, etc.) through non-covalent interactions. After inclusion, the guest molecule is "trapped" in the cavity, and its volatility, oxidation sensitivity, irritating odor, bitterness, and toxicity are shielded, while the entire outer wall of the molecule remains hydrophilic, and the overall water solubility of the guest is improved; the inclusion process is a reversible equilibrium, and the guest can be slowly released when conditions change (temperature, pH, dilution, competing molecules); it has good biocompatibility and high safety.
Why do α-cyclodextrins play these roles in various fields such as food, cosmetics, industry, and scientific research? Their mechanisms of action mainly include the following:
Inclusion (molecular cage) mechanism : Small-sized hydrophobic cavities encapsulate guest molecules of matching size, such as menthol, cinnamaldehyde, fatty acids, small-molecule flavorings, flavor substances, and bitter components, forming inclusion complexes. This is the basis of all the functions of α-cyclodextrin. After inclusion, the guest molecules are isolated from the external environment (oxygen, light, heat, and moisture), while the whole remains hydrophilic and soluble, allowing oil-soluble components to exist stably in the water-based system in a "molecular-level dispersion" state.
Stability and anti-volatility mechanism : After the flavoring and easily oxidized components are encapsulated, their volatility and oxidation sensitivity are significantly reduced, making them less prone to loss and deterioration during drying, baking, sterilization, and storage, thus extending the retention time and improving batch stability; this is the core mechanism by which it acts as a flavor carrier, fixative, and nutritional protectant.
Mechanism of masking and flavor regulation : The cavity selectively encapsulates bitter substances, off-flavor substances (beany smell, fishy smell) and irritating components, reducing their release in the oral cavity, thereby masking bitterness and unpleasant odors and improving taste; it has little effect on normal flavor substances, which is the mechanism by which it acts as a flavor regulator, masking agent and deodorizing agent for soy milk.
Sustained-release and controlled-release mechanisms : Guest molecules in inclusion complexes are slowly released during oral chewing, dilution, or changes in temperature or pH, achieving sustained release of aroma (chewing gum, candy) and sustained release of pesticides in the field, improving effectiveness and user experience.
Mechanism of dietary fiber : α-Cyclodextrin is not hydrolyzed and absorbed by digestive enzymes in the human upper digestive tract. It reaches the large intestine in its intact form and is slowly fermented by intestinal microorganisms. It has the characteristics of soluble dietary fiber , which is its characteristic function as a dietary fiber component in health foods.
Adsorption and molecular recognition mechanism : The cavity is selective for different molecules in terms of size and hydrophobicity, and can adsorb and enrich specific small organic molecules (odor molecules, organic pollutants). It can also be used as a chromatographic stationary phase and a molecular recognition material to distinguish isomers from similar small molecules. This is the basis for its use in industrial deodorization, environmental adsorption and scientific research separation.
In summary , α-cyclodextrin, with its core small-sized cavity structure of "internal hydrophobicity and external hydrophilicity," integrates functions such as inclusion, solubilization, stabilization, flavor masking, sustained release, dietary fiber, adsorption, and molecular recognition. It is a versatile small molecule cage material that spans five major fields: food (flavor carrier, flavor protection, dietary fiber, health food), industry (pesticide sustained release, deodorization, detergent additives), and scientific research (chromatographic separation, molecular recognition). Food-grade applications are characterized by flavor carrier and dietary fiber applications.
Corresponding products: powdered flavorings, microcapsule flavorings, menthol inclusion complexes, cinnamaldehyde inclusion complexes, essential oil inclusion complexes, flavor carriers, flavor protectants, flavor stabilizers, flavor sustained-release agents, etc.
Why it can be used in this way: The small cavity of α-cyclodextrin matches the size of small molecule flavorings such as menthol, cinnamaldehyde, and citrus essential oil, encapsulating liquid, volatile, and easily oxidized flavorings into stable powdery inclusion complexes. This achieves anti-volatilization, anti-oxidation, sustained release, and precise dosage control. It is a classic application of flavoring carriers and stabilizers, and is used by downstream food companies such as beverage, confectionery, and baking companies.
Corresponding products: chewing gum, bubble gum, hard candy, mints, soft candy, compressed candy, throat lozenges, filled candy, fruit-flavored candy, compressed candy, etc.
Why it works for this purpose: The menthol and fruit flavorings in candy are encapsulated by α-cyclodextrin for slow release, resulting in a longer-lasting cooling sensation and aroma; at the same time, α-cyclodextrin acts as a candy absorbent, absorbing excess moisture and volatile components, preventing moisture absorption and clumping, and aroma loss, thus improving texture and shelf life. This is a classic application of candy absorbents.
Corresponding products: carbonated beverages, fruit juice beverages, fruit-flavored soft drinks, sports drinks, functional beverages, tea beverages, plant-based beverages, flavored water, concentrated beverages, etc.
Why it can be used in this way: The stability of flavoring and aroma components in beverages is improved and the aroma is longer-lasting after being encapsulated by α-cyclodextrin. Oil-soluble flavors are evenly dispersed in beverages without becoming cloudy or separated. The FDA has approved its use in some beverages (up to 1.05%), where it serves as a flavor carrier and stabilizer for beverage systems.
Corresponding products: solid beverages, powdered beverages, dry beverage mixes, instant coffee, fruit juice powder, instant tea powder, protein powder beverages, meal replacement powders, effervescent tablet beverages, etc.
Why it can be used for this purpose: During the storage and preparation of solid beverages, the flavorings are easily volatilized and lost. α-Cyclodextrin transforms liquid small-molecule flavorings into stable powdered inclusion complexes, realizing the powdering of flavorings, preventing volatilization and clumping, and ensuring the full release of aroma after preparation. It is the core application of flavor carrier in solid beverage systems.
Corresponding products: soy milk, soy milk beverages, plant protein beverages, oat milk, nut milk, compound plant-based beverages, etc.
Why it works for this purpose: Legumes and plant-based ingredients have a distinct beany and raw taste. Alpha-cyclodextrin selectively encapsulates and masks the beany and off-flavors, improving the taste and flavor acceptance. It is the core application of soy milk flavor modifiers and is also suitable for other plant protein drinks.
Corresponding products: bread, cakes, biscuits, breakfast cereals, oatmeal, baking dry mixes, cookies, mooncakes, pastry premixes, waffle mixes, etc.
Why it can be used for this purpose: Baking is a high-temperature process and flavorings are volatile. Alpha-cyclodextrin encapsulates the flavorings, which significantly reduces the loss of volatilization and makes the aroma of the finished product last longer during baking, packaging and shelf life. At the same time, it acts as a stabilizer to improve the texture of the batter and the finished product, and can also be used in conjunction with dietary fiber for healthy baked products.
Corresponding products: yogurt, ice cream, cheese, dairy beverages, flavored milk, cream, condensed milk, sour cream, dairy-containing desserts, lactic acid bacteria drinks, etc.
Why it can be used for this purpose: dairy products have a delicate flavor and easily absorb off-odors. α-Cyclodextrin acts as a flavor stabilizer and masking component, encapsulating and protecting the aroma of frankincense and added flavorings, masking the oxidative and fishy smells that occur during storage, and at the same time, its encapsulation effect with lipids helps stabilize the emulsification system and improve texture and taste.
Corresponding products: meal replacement powders, fiber supplements, sugar-controlled foods, low-GI foods, filling meal replacement bars, dietary fiber drinks, prebiotic foods, etc.
Why it can be used for this purpose: Alpha-cyclodextrin is not digested and absorbed in the human upper digestive tract, but can be fermented by intestinal microorganisms. It is an FDA-approved source of soluble dietary fiber.
Corresponding products: MCT medium-chain triglyceride powder, DHA/EPA algal oil powder, conjugated linoleic acid preparations, flaxseed oil powder, fish oil powder, oil-soluble nutrient beverages, oil-powder solid beverages, etc.
Why it can be used for this purpose: Fatty acids and functional oils have poor water solubility. Alpha-cyclodextrin achieves water solubility and powdering of fatty acids and oils through inclusion, transforming liquid oils into stable soluble powders and improving their dispersibility in beverages and foods. This is the core application of fatty acid water solubilizers and is widely used in functional oil products.
Corresponding products: sausages, ham, luncheon meat, meatballs, fish balls, surimi products, smoked fish, pickled aquatic products, ready-to-eat seafood, meat-flavored seasonings, etc.
Why it can be used for this purpose: Meat and aquatic products are prone to fishy smells, oxidized oil smells and unpleasant odors. α-Cyclodextrin encapsulates and masks fishy smells and odors, while also encapsulating and protecting the flavors of meat spices and flavorings, prolonging flavor retention time and improving product flavor stability.
Corresponding products: soy sauce, vinegar, oyster sauce, salad dressing, ketchup, compound seasoning sauce, chili sauce, hot pot base, seasoning powder, chicken essence, broth powder, etc.
Why it can be used for this purpose: Fermented condiments often have pungent and unpleasant odors. Alpha-cyclodextrin masks fermentation off-flavors and bitterness, improves the salty and umami balance, and at the same time encapsulates and protects spices and flavor enhancers, stabilizes the flavor of the sauce, and prevents the aroma from dissipating during storage.
Corresponding products: dry soup mix, soup powder, instant noodle seasoning packets, instant porridge, instant soup, broth cubes, flavored powder packets, instant noodle seasoning, instant soup mix, etc.
Why it can be used for this purpose: The flavorings in dry soup mixes and seasoning packets are easily volatile during processing and storage. α-Cyclodextrin encapsulates the flavorings into powder, preventing volatilization and oxidation, and quickly releases the aroma when mixed or cooked. It is used as a flavor carrier and protectant in dry soup mix systems.
Corresponding products: fresh fruit preservation coatings, fruit and vegetable preservatives, fresh-cut fruit and vegetable treatment agents, ethylene absorbent/encapsulating materials, preservation packaging materials, post-harvest treatment agents, etc.
Why can it be used for this purpose? Ethylene and other ripening gases produced by the respiration of fruits and vegetables after harvest accelerate ripening and aging. The small cavity of α-cyclodextrin can encapsulate small-molecule ripening gases such as ethylene and release them slowly or isolate them, thus delaying the ripening, softening and rotting of fruits and vegetables. At the same time, it can encapsulate antibacterial and preservative components to achieve slow release and extend the shelf life of fruits and vegetables.
Corresponding products: skin care products, lotions, creams, serums, perfumes, deodorants, makeup, face masks, toothpaste, mouthwash, sunscreens, etc.
Why it can be used for this purpose: Fragrances and active ingredients (plant extracts, whitening/anti-aging ingredients) in cosmetics are prone to volatility, oxidation, or skin irritation. After being encapsulated by α-cyclodextrin, they can achieve slow-release and fragrance retention of fragrances, stabilize and slow-release active ingredients, reduce irritation, and at the same time act as an adsorbent to improve the stability of the formula.
Corresponding products: indoor deodorizers, refrigerator deodorizer boxes, shoe cabinet deodorizers, bathroom deodorizers, garbage deodorizers, textile deodorizing and finishing agents, pet product deodorizers, car deodorizers, etc.
Why it works for this purpose: Odor molecules in the environment (ammonia, hydrogen sulfide, aldehydes, smoke, musty smell, etc.) are small in size and can be encapsulated and adsorbed by the cavities of α-cyclodextrin, achieving continuous deodorization rather than masking. It is highly safe and can be used for textile finishing and home cleaning.
Corresponding products: laundry detergent, laundry powder, fabric softener, dishwashing liquid, multi-purpose cleaner, aromatherapy cleaner, laundry fragrance beads, surface cleaning wipes, etc.
Why it works for this purpose: Fragrances, active enzymes, and bleaching ingredients in detergent formulas are easily volatile or interfere with each other. α-Cyclodextrin encapsulates fragrances to achieve slow-release fragrance retention during washing and wearing, while encapsulating dirt and odor molecules to enhance the cleaning and deodorizing effect and stabilize the active ingredients in the formula.
Corresponding products: chromatographic stationary phases, chiral separation column packing materials, gas/liquid chromatography columns, molecular recognition materials, chemical sensors, analytical reagents, chiral resolution materials, etc.
Why it can be used for this purpose: The selective recognition ability of α-cyclodextrin cavities for different small molecules and enantiomers makes it a classic chiral chromatographic stationary phase and molecular recognition material, used for enantiomer resolution, isomer separation and sensing detection, and is an important tool in analytical chemistry and scientific research.
Alpha-cyclodextrin (E457/alfadex) is a cyclic oligosaccharide composed of six glucose units. Its core structure features a small cavity with an internal hydrophobic and external hydrophilic appearance, enabling it to perform functions such as inclusion, solubilization, stabilization, flavor masking, sustained release, dietary fiber, adsorption, and molecular recognition. It spans five major fields: food, cosmetics, industry, and scientific research. In food, it serves as a flavor carrier and stabilizer, a flavor modifier for soy milk, and an absorbent for candies, masking beany and bitter tastes. In cosmetics, it encapsulates flavors and active ingredients, achieving fragrance retention and stability. In industry, it acts as a pesticide sustained-release carrier, deodorant, and detergent additive. In scientific research, it is a classic carrier for chromatographic chiral separation and supramolecular chemistry. Understanding its small cavity inclusion principle helps explain its effectiveness in handling small molecules such as menthol and fatty acids.
