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CAS NUMBER: 7585-39-9
EC NUMBER: 231-493-2
MOLECULAR FORMULA: C42H70O35
MOLECULAR WEIGHT: 1134.98
Beta-Cyclodextrin is a cyclic oligosaccharide consisting of seven glucose subunits joined by α-(1,4) glycosidic bonds forming a truncated conical structure.
Beta-Cyclodextrin is widely used in food, pharmaceutical, cosmetics, and chemicals industries.
Beta-Cyclodextrin is a new type of anionic high soluble cyclodextrin derivatives.
Beta-Cyclodextrin could include drug molecules to from covalent compounds so that increase the drug’s stability,solubility,safety.
Beta-Cyclodextrin could reduce the renal toxicity,moderate drug’s hemolysis,control the release rate and cover up the bad smell.
Beta-Cyclodextrin can be used as a solubilizer,wetting agent,chelating agent (complexing agent) and polyvatent masking agent.
Beta-Cyclodextrin has been used in injection,oral,nasal and eye medicines.
Beta-Cyclodextrin could has a special affinity and inclusion for nitrogen drugs.
Beta-Cyclodextrins are cyclic oligosaccharides consisting of 6, 7, or 8 glucopyranose units, usually referred to as α-, β-, or γ-cyclodextrins, respectively.
Beta-Cyclodextrins have rigid doughnut-shaped structures making them natural complexing agents.
The unique structures of Beta-Cyclodextrins owe their stability to intramolecular hydrogen bonding between the C2- and C3-hydroxyl groups of neighboring glucopyranose units.
Beta-Cyclodextrin takes on the shape of a torus with the C2- and C3-hydroxyls located around the larger opening and the more reactive C6-hydroxyl aligned around the smaller opening.
The arrangement of Beta-Cyclodextrinls opposite the hydrogen bonded C2- and C3-hydroxyls forces the oxygen bonds into close proximity within the cavity, leading to an electron rich, hydrophobic interior.
The size of this hydrophobic cavity is a function of the number of glucopyranose units forming the cyclodextrin.
The solubility of natural Beta-Cyclodextrins is very poor.
In the late 1960′s, Beta-Cyclodextrin was discovered that chemical substitutions at the 2, 3, and 6 hydroxyl sites would greatly increase solubility.
Most chemically modified cyclodextrins are able to achieve a 50% (w/v) concentration in water.
Cavity size is the major determinant as to which cyclodextrin is used in complexation.
The cavity diameter of Beta-Cyclodextrins or β-glucopyranose unit compounds is well-suited for use with molecules the size of hormones, vitamins and many compounds frequently used in tissue and cell culture applications.
For this reason, Beta-Cyclodextrin is most commonly used as a complexing agent.
The solubility of lipophilic drugs increases linearly with the concentration of hydroxypropyl-Beta-Cyclodextrin (HBC) in aqueous solution because of the complex between HBC and the drug.
This guest-host type complex is formed between the drug and the non-polar cavity in the HBC that results in enhanced solubility.
Beta-Cyclodextrins may be lyophilized to produce freely soluble powders.
Beta-Cyclodextrin is a high water-soluble anionic cyclodextrin derivative.
Beta-Cyclodextrin,as an excipient,has been used in injection, oral, nasal and eye medication.
Modification by charged functional units can improve the binding affinity of cyclodextrins for oppositely charged guests, so Beta-Cyclodextrin has a special affinity for drugs with nitrogen elements.
Beta-Cyclodextrin is used as a complexing agent in drug delivery because it forms an inclusion complex with a drug molecule.
The complex of cyclodextrin increases the aqueous solubility, dissolution rate and bioavailability of poorly water-soluble drugs, which is useful for the delivery of the medical agent to a biological system.
Beta-Cyclodextrins are a family of cyclic oligosaccharides, consisting of a macrocyclic ring of glucose subunits joined by α-1,4 glycosidic bonds.
Beta-Cyclodextrins are produced from starch by enzymatic conversion.
Beta-Cyclodextrins are used in food, pharmaceutical, drug delivery, and chemical industries, as well as agriculture and environmental engineering.
Beta-Cyclodextrins are composed of 5 or more α-D-glucopyranoside units linked 1->4, as in amylose (a fragment of starch).
The largest Beta-Cyclodextrin contains 32 1,4-anhydroglucopyranoside units, while as a poorly characterized mixture, at least 150-membered cyclic oligosaccharides are also known.
Beta-Cyclodextrins are ingredients in more than 30 different approved medicines.
With a hydrophobic interior and hydrophilic exterior, cyclodextrins form complexes with hydrophobic compounds.
Alpha-, beta-, and gamma-cyclodextrin are all generally recognized as safe by the U.S. FDA.
Beta-Cyclodextrins have been applied for delivery of a variety of drugs, including hydrocortisone, prostaglandin, nitroglycerin, itraconazol, chloramphenicol.
Beta-Cyclodextrin confers solubility and stability to these drugs.
The inclusion compounds of Beta-Cyclodextrins with hydrophobic molecules are able to penetrate body tissues, these can be used to release biologically active compounds under specific conditions.
In most cases the mechanism of controlled degradation of such complexes is based on pH change of water solutions, leading to the loss of hydrogen or ionic bonds between the host and the guest molecules.
Alternative means for the disruption of the complexes take advantage of heating or action of enzymes able to cleave α-1,4 linkages between glucose monomers.
Beta-Cyclodextrins were also shown to enhance mucosal penetration of drugs.
Beta-Cyclodextrins bind fragrances.
Such devices are capable of releasing fragrances during ironing or when heated by human body.
Such a device commonly used is a typical 'dryer sheet'.
The heat from a clothes dryer releases the fragrance into the clothing.
Beta-Cyclodextrins are the main ingredient in Febreze which claims that the β-cyclodextrins "trap" odor causing compounds, thereby reducing the odor.
Beta-Cyclodextrins are also used to produce alcohol powder by encapsulating ethanol.
The powder produces an alcoholic beverage when mixed with water.
Typical Beta-Cyclodextrins are constituted by 6-8 glucopyranoside units.
These subunits are linked by 1,4 glycosidic bonds.
The Beta-Cyclodextrins have toroidal shapes, with the larger and the smaller openings of the toroid exposing to the solvent secondary and primary hydroxyl groups respectively.
Because of this arrangement, the interior of the toroids is not hydrophobic, but considerably less hydrophilic than the aqueous environment and thus able to host other hydrophobic molecules.
In contrast, the exterior is sufficiently hydrophilic to impart cyclodextrins (or their complexes) water solubility.
They are not soluble in typical organic solvents.
Beta-Cyclodextrins are prepared by enzymatic treatment of starch.
Commonly Beta-Cyclodextrin glycosyltransferase (CGTase) is employed along with α-amylase.
First starch is liquified either by heat treatment or using α-amylase, then CGTase is added for the enzymatic conversion.
Beta-Cyclodextrins produce mixtures of cyclodextrins, thus the product of the conversion results in a mixture of the three main types of cyclic molecules, in ratios that are strictly dependent on the enzyme used: each CGTase has its own characteristic α:β:γ synthesis ratio.
Purification of the three types of cyclodextrins takes advantage of the different water solubility of the molecules: β-CD which is poorly water-soluble (18.5 g/l or 16.3mM) (at 25C) can be easily retrieved through crystallization while the more soluble α- and γ-CDs (145 and 232 g/l respectively) are usually purified by means of expensive and time consuming chromatography techniques.
As an alternative a "complexing agent" can be added during the enzymatic conversion step: such agents (usually organic solvents like toluene, acetone or ethanol) form a complex with the desired cyclodextrin which subsequently precipitates.
The complex formation drives the conversion of starch towards the synthesis of the precipitated cyclodextrin, thus enriching its content in the final mixture of products.
Beta-Cyclodextrin uses dedicated enzymes, that can produce alpha-, beta- or gamma-cyclodextrin specifically.
Beta-Cyclodextrin is very valuable especially for the food industry, as only alpha- and gamma-cyclodextrin can be consumed without a daily intake limit.
Interest in cyclodextrins is enhanced because their host–guest behavior can be manipulated by chemical modification of the hydroxyl groups.
Beta-Cyclodextrin and acetylation are typical conversions. Propylene oxide gives hydroxypropylated derivatives.
The primary alcohols can be tosylated.
The degree of derivatization is an adjustable, i.e. full methylation vs partial.
Beta-Cyclodextrins remove cholesterol from cultured cells.
The methylated form Beta-Cyclodextrin was found to be more efficient than β-cyclodextrin.
The water-soluble Beta-Cyclodextrin is known to form soluble inclusion complexes with cholesterol, thereby enhancing its solubility in aqueous solution.
Beta-Cyclodextrin is employed for the preparation of cholesterol-free products: the bulky and hydrophobic cholesterol molecule is easily lodged inside cyclodextrin rings.
Beta-Cyclodextrin is also employed in research to disrupt lipid rafts by removing cholesterol from membranes.
In supramolecular chemistry, Beta-Cyclodextrins are precursors to mechanically interlocked molecular architectures, such as rotaxanes and catenanes.
Illustrative, Beta-Cyclodextrin form second-sphere coordination complex with tetrabromoaurate anion ([AuBr4]-).
Beta-Cyclodextrin complexes with certain carotenoid food colorants have been shown to intensify color, increase water solubility and improve light stability.
Complexes formed between Beta-Cyclodextrin and adamantane derivatives have been used to make self-healing materials, such as hydrogels and low-friction surfaces.
Beta-Cyclodextrin is a cone-shaped molecule.
Beta-Cyclodextrin is hydrophilic at the outer surface of the cavity for many hydroxyl groups, but hydrophobic in the cavity.
So Beta-Cyclodextrin is soluble in water, and a variety of hydrophobic guest molecules can be encapsulated in its non-polar cavity.
Such a characteristic has been widely applied in the fields of drug-controlled release,32 separation33 and adsorption.
Beta-cyclodextrin is a Beta-Cyclodextrin composed of seven alpha-(1->4) linked D-glucopyranose units.
Beta-Cyclodextrin is made of homogeneous cyclic α1,4-linked D-glucopyranose units in a seven member ring.
Forms clathrates and suitable for use with dansyl chloride t
The form water-soluble complexes for fluorescent labeling of proteins.
Beta-Cyclodextrins are ring-shaped oligosaccharides formed in nature by the digestion of cellulose by bacteria.
Beta-Cyclodextrins are composed of varying numbers of glucose units held together by α-1, 4 glycosidic bonds.
The naturally occurring varieties contain at least six glucose units, with the most common having six, seven, or eight (so called, α-, β-, and γ- cyclodextrins, respectively).
Beta-Cyclodextrins with more than eight glucose members are less common in nature and less well characterized, and compounds with five glucose units are only synthetic.
Bountiful research has been poured into α-, β-, and γ- cyclodextrins and their properties are well characterized.
Beta-Cyclodextrin ring these molecules form is often depicted as a cup-shaped toroid.
Beta-Cyclodextrin outside of the cup is hydrophilic, and the inside is more hydrophobic.
Thus, these chemicals are water soluble with the ability to contain hydrophobic guest molecules within them, singly or as dimers.
Beta-Cyclodextrin resulting increase in solubility and stability of the guest compounds is the predominant basis for the vast medical, industrial and scientific uses of cyclodextrins.
Much effort has been expended on improving and tailoring this characteristic by chemical substitution of the hydrogen in the hydroxyl groups, which form the mouths of the toroidal openings, extending from the glucose units.
Some common substitutions at these sites are methyl, hydroxylpropyl and sulfobutylether groups.
Adding these groups occurs with different efficiencies and results in different sets of impurities along with the intended reaction product.
Beta-Cyclodextrin is chemically difficult to achieve substitution of all possible sites, so a reaction process results in a “degree of substitution”, often expressed as the average number of substituted groups present per molecule or per glucose unit.
Different processes produce varied degrees of substitution, and this can have advantages, since both the nature of the substituent group and the degree of substitution influence the performance of the cyclodextrin in ways that can be useful.
Beta-Cyclodextrins are cyclic oligomers of d-(+)-glucopyranose units linked through α-1,4-glycoside bonding.
Beta-Cyclodextrins are produced from starch, not from fossil resources, and are practically nontoxic.
Beta-Cyclodextrins recognize hydrophobic guest compounds, of which shape and size match the cavity, to form inclusion complexes in aqueous media.
Beta-Cyclodextrins have thus been widely used in industry and academia as functional compounds with molecular recognition ability.
This entry overviews Beta-Cyclodextrins; the historical background, basic characteristics and inclusion behavior, industrial applications, and cutting-edge applications.
Beta-Cyclodextrins (CDs) are produced by enzymatic degradation of sugar and starch.
These are cyclic oligosaccharides comprised of glucose units linked by α-1,4-glycosidic bonds.
Beta-Cyclodextrins are available in three forms such as α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin, which comprised of six, seven, and eight α-1,4-glycosidic bonds.
These are lipophilic from inside which can host the guest molecules such as oils, waxes, and fats.
Beta-Cyclodextrin ability to form host-guest complexes is vital for stabilizing and solubilizing hydrophobic compounds in solvents.
Most of the drugs administered through oral route have poor aqueous solubility and dissolution rate.
Beta-Cyclodextrin and its derivates represent as pharmaceutical adjuvants to overcome this challenges and helps in development of stable formulation with enhanced bioavailability.
Beta-Cyclodextrins are unique structure with versatile physicochemical properties which aids the pharmaceutical scientists to overcome drug delivery challenges for poorly aqueous soluble drugs.
Beta-Cyclodextrin and its derivates are widely useful as solubilizers, assisting in preparation of various dosage forms such as liquid oral, solid, and parenteral preparations.
Beta-Cyclodextrins interacts with appropriately sized guest molecules to form inclusion complex and enhance the aqueous solubility, physical chemical stability, and bioavailability of drugs.
Through the various reported literatures, the review highlights the concept of cyclodextrin and Beta-Cyclodextrins derivatives in enhancing solubility and bioavailability of poorly aqueous soluble drugs.
Beta-Cyclodextrins (CDs) represents one of the pharmaceutical excipient in overcoming this challenge.
Beta-Cyclodextrins are molecules of natural origin, discovered earlier by Villiers in 1891.
Beta-Cyclodextrin interest in application of Beta-Cyclodextrins was later on studied in the twentieth century which became the most important topic of interest in pharmaceutical and other fields since from late 1970s to later on.
He described about two crystalline compounds isolated from bacterial digest of potato starch called α-dextrin and β-dextrin which were later and now called as α-CD and β-CD.
Over the span of time, Beta-Cyclodextrins have created a quality platform for various applications like increasing drug solubility and stability, masking odors and tastes,enhancing drug absorption,6 controlling drug release profiles, alleviating local and systemic toxicity, and improving drug permeability across biological barriers.
Beta-Cyclodextrins containing formulations have been delivered through various delivery systems like oral, ocular, nasal, dermal and rectal.
From application point of view, CDs offers various advantages like non-toxic, low cost, safety (recognized by safety health authorities) and easily available.
Various published reports demonstrate wide application of CDs to enhance oral bioavailability of poorly aqueous soluble drugs.
Beta-Cyclodextrin the second half of the 20th century, as the structure and properties of cyclodextrins became known with greater detail, studies were directed towards the exploration of their ability to form inclusion complexes with various molecules.
Beta-Cyclodextrins were found to protect sensitive organic guest molecules from volatilization and from oxidation and their solubilizing action on apolar guests made them attractive for a variety of applications.
When the industrial production of cyclodextrins started to make them available in larger quantities and the toxicological safety was ascertained, applications in the pharmaceutical, cosmetic, and food chemistry have blossomed, and, more recently, applications expanded to (re-)emerging areas as nutraceutics and natural products .
Beta-Cyclodextrin all of these products, cyclodextrins were essentially regarded as excipients or inert materials.
Beta-Cyclodextrins are a family of cyclic oligosaccharides, consisting of a macrocyclic ring of glucose subunits joined by α-1,4 glycosidic bonds.
Beta-Cyclodextrins are produced from starch by enzymatic conversion.
They are used in food, pharmaceutical, drug delivery, and chemical industries, as well as agriculture and environmental engineering.
Beta-Cyclodextrin are composed of or more α-D-glucopyranoside units linked 1->4, as in amylose (a fragment of starch).
The largest Beta-Cyclodextrin contains 1,4-anhydroglucopyranoside units, while as a poorly characterized mixture, at least 150-membered cyclic oligosaccharides are also known.
Typical Beta-Cyclodextrins contain a number of glucose monomers ranging from six to eight units in a ring, creating a cone shape: α (alpha)-cyclodextrin: glucose subunits β (beta)-cyclodextrin: glucose subunits γ (gamma)-cyclodextrin: glucose subunits
USES:
Most of the drugs administered through oral route have poor aqueous solubility and dissolution rate.
Beta-Cyclodextrin and its derivates represent as pharmaceutical adjuvants to overcome this challenges and helps in development of stable formulation with enhanced bioavailability.
Beta-Cyclodextrins are unique structure with versatile physicochemical properties which aids the pharmaceutical scientists to overcome drug delivery challenges for poorly aqueous soluble drugs.
Beta-Cyclodextrin and its derivates are widely useful as solubilizers, assisting in preparation of various dosage forms such as liquid oral, solid, and parenteral preparations.
Beta-Cyclodextrins interacts with appropriately sized guest molecules to form inclusion complex and enhance the aqueous solubility, physical chemical stability, and bioavailability of drugs.
Through the various reported literatures, the review highlights the concept of Beta-Cyclodextrin and Beta-Cyclodextrins derivatives in enhancing solubility and bioavailability of poorly aqueous soluble drugs.
PROPERTIES:
-biological source: corn starch
-Quality Level: 200
-product line: BioReagent
-form: powder
-mol wt: 1396 Da
-extent of labeling: 4-10 (determined by NMR)
-technique(s): cell culture | mammalian: suitable
-solubility: H2O: 100 mg/mL
-shipped in: ambient
-storage temp.: room temp
TECHNICAL INFORMATIONS:
-Appearance: Crystalline powder
-Physical State: Solid
-Solubility: Soluble in water (10 mg/ml), and 1 M NH4OH (50 mg/ml).
-Storage: Store at room temperature
-Melting Point: 290-300° C (lit.)(dec.)
-Boiling Point: ~1541.18° C at 760 mmHg (Predicted)
-Density: 1.44 g/cm3 at 20
-Refractive Index: n20D 1.59 (Predicted)
-Optical Activity: α20/D +162°, c = 1.5 in water
STORAGE:
Beta-Cyclodextrins may be stored for several months at 4°C.
Beta-Cyclodextrin should be stored tightly sealed at room temperature.
SYNONYM:
Cyclomaltoheptaose
Cycloheptaglucan
7585-39-9
Cycloheptaamylose
Cycloheptaglucosan
Kleptose
b-Cyclodextrin
beta-Cycloamylose
Cycloheptapentylose
Kleptose B
Rhodocap N
Ringdex B
Ringdex BL
beta-CD
beta-cyclodextrine
UNII-JV039JZZ3A
Maltodecaose DP10
beta.-Cyclodextrin
JV039JZZ3A
Caraway
beta-Cyclodextrin, homopolymer
CHEBI:495055
Schardinger beta-dextrin
NCGC00090771-01
DSSTox_CID_358
DSSTox_RID_75536
DSSTox_GSID_20358
37331-89-8
beta-Cyclodextrins
79647-56-6
CAS-7585-39-9
Dextrin, beta-cyclo
CCRIS 651
ss-Cyclodextrin
