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β-Cyclodextrin sometimes abbreviated as beta-cyclodextrin, is a heptasaccharide derived from glucose.
The α- (alpha), β- (beta), and γ- (gamma) cyclodextrins correspond to six, seven, and eight glucose units, respectively.
beta-cyclodextrin is the most used natural cyclodextrin in marketed medicines.
CAS: 7585-39-9
MF: C42H70O35
MW: 1134.99
EINECS: 231-493-2
Synonyms
BETA BYCLODEXTRIN;SCHARDINGER BETA-DEXTRIN;Schardinger β-Dextrin;b-Cyclodextrin (1.02127);B-cyclodextrin cell culture tested;B-cyclodextrin crystalline;cycloheptapentylose;B-Cyclodextrin
The reason for this lies in the ease of its production and subsequent low price (more than 10,000 tons produced annually with an average bulk price of approximately 5 USD per kg).
Cyclodextrins refer to a family of compounds consisting of sugar molecules bound together in ring (cyclic oligosaccharides).
beta-cyclodextrin is produced from starch through enzymatic conversion.
Beta-cyclodextrin is the 7-membered sugar ring molecular form of cyclodextrin.
beta-cyclodextrin has various applications.
In the pharmaceutical industry, beta-cyclodextrin can be used as complexing agents for increasing the solubility of poorly soluble drug as well as increasing their bioavailability and stability.
beta-cyclodextrin can also alleviate the gastrointestinal drug irritation, and prevent drug-drug and drug-excipient interactions.
beta-cyclodextrin can also be used in food, pharmaceutical, drug delivery, and chemical industries, as well as agriculture and environmental engineering.
beta-cyclodextrin is a cyclodextrin composed of seven alpha-(1->4) linked D-glucopyranose units.
beta-cyclodextrin is the most abundant and cheap cyclic oligosaccharide that forms inclusion complexes with several drug molecules.
beta-cyclodextrin's main application is in tablet and capsule formulations.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
beta-cyclodextrin Chemical Properties
Melting point: 290-300 °C (dec.) (lit.)
Boiling point: 844.96°C (rough estimate)
Alpha: [α]D25 +159～+165° (c=1, H2O) (After Drying)
Density: 1.2296 (rough estimate)
Refractive index: 1.7500 (estimate)
FEMA: 4028 | BETA-CYCLODEXTRIN
Storage temp.: room temp
Solubility: 1 M NaOH: 50 mg/mL
Form: powder
pka: 11.73±0.70(Predicted)
Color: white
PH: 5.0-8.0 (1% in solution, Ph Eur)
Odor: at 100.00 %. odorless
Odor Type: odorless
Biological source: plant
Optical activity: [α]20/D +162±3°, c = 1.5% in H2O
Water Solubility: Soluble in water and ammonium hydroxide.
Merck: 14,2718
BRN: 78623
Stability: Stable. Incompatible with strong oxidizing agents.
LogP: -9.06
EPA Substance Registry System: beta-cyclodextrin (7585-39-9)
Absorption: ≤0.05 at 350-750nm in solution at 1%
≤0.1 at 230-350nm in solution at 1%
A biennial herbaceous plant very common in Europe, Asia, Africa and the United States, beta-cyclodextrin has a tapering fleshy root, furrowed stem, finely cut feathery leaves, umbels of small flower heads in midsummer, and capsules containing two curved narrow seeds. The plant grows to about 60 cm and it blooms from May to July.
The part used is the fruit, containing approximately 15% of fixed oils and 3 to 7% of essential oil.
Caraway has a warm, biting flavor with a strong, fatty, harsh undernote.
beta-cyclodextrin occur as white, practically odorless, fine crystalline powders, having a slightly sweet taste.
Some cyclodextrin derivatives occur as amorphous powders.
Structure
In beta-cyclodextrin, the seven glucose subunits are linked end to end via α-1,4 linkages.
The result has the shape of a tapered cylinder, with seven primary alcohols on one face and fourteen secondary alcohol groups on the other.
The exterior surface of cyclodextrins is somewhat hydrophilic whereas the interior core is hydrophobic.
Physical properties
beta-cyclodextrin exists as a white (colorless) powder or crystals.
The density of its saturated hydrate crystal (βCD·12H2O) is 1.46 g/cm3.
beta-cyclodextrin is moderately soluble in water and glycerin; well soluble in dimethyl sulfoxide, dimethylformamide, pyridine, HFIP, and ethylene glycol; and insoluble in ethanol and acetone.
Uses
Use to solubilize non-polar compounds such as fatty acids, lipids and cholesterol.
Reported useful for the selective precipitation of enantiomeric, positional or structural isomers beta-cyclodextrin is used with dansyl chloride to form water-soluble complexes for fluorescent labeling of proteins.
beta-cyclodextrin is an active ingredient of household odor eliminator.
beta-cyclodextrin is also used in personal care products like toothpastes, skin creams and dusting powders.
beta-cyclodextrin finds applications in the cosmetic industry for products like detergents and perfumes for the controlled release of fragrances.
Further, beta-cyclodextrin is used to produce HPLC columns allowing chiral enantiomers separation.
In addition to this, beta-cyclodextrin is used to decrease the level of cholesterol in milk fat.
beta-cyclodextrin is a cyclic oligosaccharide produced from starch via enzymatic conversion.
beta-cyclodextrin is commonly used to produce HPLC columns allowing chiral enantiomers separation.
beta-cyclodextrin is widely used in medicine, pharmacy, food industry, textiles.
beta-cyclodextrin's molecules can accommodate various biomolecules and hence are also used as a complexing agent.
Hydrophobic forms of beta-cyclodextrin have been used as sustained release drug carriers.
In addition to improving the solubility of compounds, complexation with cyclodextrin has been used to improve the stability of many drugs by inclusion of the compound and protecting certain functional groups from degradation.
Pharmaceutical Applications
Cyclodextrins are ‘bucketlike’ or ‘conelike’ toroid molecules, with a rigid structure and a central cavity, the size of which varies according to the cyclodextrin type.
The internal surface of the cavity is hydrophobic and the outside of the torus is hydrophilic; this is due to the arrangement of hydroxyl groups within the molecule.
This arrangement permits the beta-cyclodextrin to accommodate a guest molecule within the cavity, forming an inclusion complex.
beta-cyclodextrin may be used to form inclusion complexes with a variety of drug molecules, resulting primarily in improvements to dissolution and bioavailability owing to enhanced solubility and improved chemical and physical stability.
beta-cyclodextrin inclusion complexes have also been used to mask the unpleasant taste of active materials and to convert a liquid substance into a solid material.
beta-cyclodextrin is the most commonly used cyclodextrin, although it is the least soluble.
beta-cyclodextrin is the least expensive cyclodextrin; is commercially available from a number of sources; and is able to form inclusion complexes with a number of molecules of pharmaceutical interest.
However, beta-cyclodextrin is nephrotoxic and should not be used in parenteral formulations.
beta-cyclodextrin is primarily used in tablet and capsule formulations.
In oral tablet formulations, beta-cyclodextrin may be used in both wet-granulation and direct-compression processes.
The physical properties of beta-cyclodextrin vary depending on the manufacturer.
However, beta-cyclodextrin tends to possess poor flow properties and requiresalubricant, such as 0.1% w/w magnesium stearate, when beta-cyclodextrin is directly compressed.
In parenteral formulations, cyclodextrins have been used to produce stable and soluble preparations of drugs that would otherwise have been formulated using a nonaqueous solvent.
In eye drop formulations, beta-cyclodextrin form water-soluble complexes with lipophilic drugs such as corticosteroids.
They have been shown to increase the water solubility of the drug; to enhance drug absorption into the eye; to improve aqueous stability; and to reduce local irritation.
beta-cyclodextrin has also been used in the formulation of solutions,suppositories, and cosmetics.
Production Methods
Cyclodextrins are manufactured by the enzymatic degradation of starch using specialized bacteria.
For example, beta-cyclodextrin is produced by the action of the enzyme cyclodextrin glucosyltransferase upon starch or a starch hydrolysate.
An organic solvent is used to direct the reaction that produces beta-cyclodextrin, and to prevent the growth of microorganisms during the enzymatic reaction.
The insoluble complex of beta-cyclodextrin and organic solvent is separated from the noncyclic starch, and the organic solvent is removed in vacuo so that less than 1 ppm of solvent remains in the beta-cyclodextrin.
The beta-cyclodextrin is then carbon treated and crystallized from water, dried, and collected.
Biochem/physiol Actions
beta-cyclodextrin is the cyclic α heptamer of glucose.
beta-cyclodextrin acts as a host to form inclusion compounds with the guests including derivatives of benzene, cyclohexane, adamantane, other alicyclic guests, and also inorganic molecules or ions.
beta-cyclodextrin is generally used to solubilize non-polar compounds such a fatty acids, lipids and cholesterol.
