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BETA-CYCLODEXTRIN

CAS:    7585-39-9
European Community (EC) Number: 231-493-2
Molecular Formula:  (C6H10O5)7
Alternate Names: Cycloheptaamylose; Cyclomaltoheptaose; Betadex
IUPAC Name:    
(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5,10,15,20,25,30,35-heptakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol

DESCRIPTION:
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.
Cyclodextrins are a family of cyclic oligosaccharides, consisting of a macrocyclic ring of glucose subunits joined by α-1,4 glycosidic bonds. 
Cyclodextrins are produced from starch by enzymatic conversion. 
BETA -Cyclodextrin is used in food, pharmaceutical, drug delivery, and chemical industries, as well as agriculture and environmental engineering.
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 to form water-soluble complexes for fluorescent labeling of proteins.

Cyclodextrins are composed of 5 or more α-D-glucopyranoside units linked 1->4, as in amylose (a fragment of starch). 
The largest cyclodextrin contains 32 1,4-anhydroglucopyranoside units, while as a poorly characterized mixture, at least 150-membered cyclic oligosaccharides are also known. 
Typical cyclodextrins contain a number of glucose monomers ranging from six to eight units in a ring, creating a cone shape:
α (alpha)-cyclodextrin: 6 glucose subunits
β (beta)-cyclodextrin: 7 glucose subunits
γ (gamma)-cyclodextrin: 8 glucose subunits

CAS:    7585-39-9
European Community (EC) Number: 231-493-2
Molecular Formula:  (C6H10O5)7

APPLICATIONS OF BETA-CYCLODEXTRIN:
BETA -Cyclodextrin is used as a complexing agent in drug delivery because BETA -Cyclodextrin 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.


Drug delivery:
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. 
They have been applied for delivery of a variety of drugs, including hydrocortisone, prostaglandin, nitroglycerin, itraconazol, chloramphenicol. 
The cyclodextrin confers solubility and stability to these drugs. 
The inclusion compounds of 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. 
Cyclodextrins were also shown to enhance mucosal penetration of drugs.

Chromatography:
BETA -cyclodextrins are used to produce stationary phase media for HPLC separations.

Other:
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. 
They are the main ingredient in Febreze which claims that the BETA -cyclodextrins "trap" odor causing compounds, thereby reducing the odor.

Cyclodextrins are also used to produce alcohol powder by encapsulating ethanol. 
The powder produces an alcoholic beverage when mixed with water.

STRUCTURE OF BETA-CYCLODEXTRIN:

Typical cyclodextrins are constituted by 6-8 glucopyranoside units. 
These subunits are linked by 1,4 glycosidic bonds. 
The 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.

SYNTHESIS OF BETA-CYCLODEXTRIN:
Cyclodextrins are prepared by enzymatic treatment of starch.
Commonly 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. 
CGTases 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: BETA -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. 
Wacker Chemie AG uses dedicated enzymes, that can produce alpha-, beta- or gamma-cyclodextrin specifically. 
This is very valuable especially for the food industry, as only alpha- and gamma-cyclodextrin can be consumed without a daily intake limit.


DERIVATIVES OF BETA-CYCLODEXTRIN:
Interest in cyclodextrins is enhanced because their host–guest behavior can be manipulated by chemical modification of the hydroxyl groups. 
O-Methylation 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.

Both BETA -cyclodextrin and methyl- BETA -cyclodextrin (MβCD) remove cholesterol from cultured cells. 
The methylated form MβCD was found to be more efficient than BETA -cyclodextrin. 
The water-soluble MβCD is known to form soluble inclusion complexes with cholesterol, thereby enhancing its solubility in aqueous solution. 
MβCD is employed for the preparation of cholesterol-free products: the bulky and hydrophobic cholesterol molecule is easily lodged inside cyclodextrin rings. 
MβCD is also employed in research to disrupt lipid rafts by removing cholesterol from membranes.

Research:
In supramolecular chemistry, cyclodextrins are precursors to mechanically interlocked molecular architectures, such as rotaxanes and catenanes. 
Illustrative, α-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.

CAS:    7585-39-9
European Community (EC) Number: 231-493-2
Molecular Formula:  (C6H10O5)7

HISTORY OF BETA-CYCLODEXTRIN:

Cyclodextrins, as they are known today, were called "cellulosine" when first described by A. Villiers in 1891. 
Soon after, F. Schardinger identified the three naturally occurring cyclodextrins -α, -β, and -γ. 
These compounds were therefore referred to as "Schardinger sugars". 
For 25 years, between 1911 and 1935, Pringsheim in Germany was the leading researcher in this area, demonstrating that cyclodextrins formed stable aqueous complexes with many other chemicals. 
By the mid-1970s, each of the natural cyclodextrins had been structurally and chemically characterized and many more complexes had been studied. 
Since the 1970s, extensive work has been conducted by Szejtli and others exploring encapsulation by cyclodextrins and their derivatives for industrial and pharmacologic applications. 
Among the processes used for complexation, the kneading process seems to be one of the best.

Safety:
Cyclodextrins are of wide interest in part because they appear nontoxic in animal studies. 
The LD50 (oral, rats) is on the order of grams per kilogram.
Nevertheless, attempts to use BETA -Cyclodextrin for the prevention of atherosclerosis, age-related lipofuscin accumulation and obesity encounter an obstacle in the form of damage to the auditory nerve and nephrotoxic effect.

CHEMICAL AND PHYSICAL PROPERTIES OF BETA-CYCLODEXTRIN:
Molecular Weight:    1135.0    
XLogP3-AA:     -15    
Hydrogen Bond Donor Count:    21    
Hydrogen Bond Acceptor Count:    35    
Rotatable Bond Count:    7    
Exact Mass:    1134.3697639    
Monoisotopic Mass:    1134.3697639    
Topological Polar Surface Area:    554 Ų    
Heavy Atom Count:    77    
Formal Charge:    0    
Complexity:    1480    
Isotope Atom Count:    0    
Defined Atom Stereocenter Count:    35    
Undefined Atom Stereocenter Count:    0    
Defined Bond Stereocenter Count:    0    
Undefined Bond Stereocenter Count:    0    
Covalently-Bonded Unit Count:    1    
Compound Is Canonicalized:    Yes
biological source: microbial
Quality Level: 200
Assay: ≥97%
Form: powder
optical activity: [α]20/D +162±3°, c = 1.5% in H2O
Mp: 290-300 °C (dec.) (lit.)
Refractive Index :n20D 1.59 (Predicted)
Solubility:  1 M NH4OH: 50 mg/mL
Appearance:    white crystalline powder (est)
Assay:    98.00 to 100.00
Boiling Point:    260.00 °C. @ 760.00 mm Hg
Flash Point:    1627.00 °F. TCC ( 885.90 °C. ) (est)
logP (o/w):    -13.960 (est)
Shelf Life:    24.00 month(s) or longer if stored properly.
Storage:    store in cool, dry place in tightly sealed containers, protected from heat and light.
Soluble in:
 alcohol, slightly
 water, hot
 water, 1e+006 mg/L @ 25 °C (est)
Organoleptic Properties:
Odor Type: odorless
Odor Description:at 100.00 %. odorless
Flavor Type: sweet
Taste Description: slightly sweet

CAS:    7585-39-9
European Community (EC) Number: 231-493-2
Molecular Formula:  (C6H10O5)7


SAFETY INFORMATION ABOUT BETA-CYCLODEXTRIN:
First aid measures:
Description of first aid measures:
If inhaled:
Move the victim into fresh air. 
If breathing is difficult, give oxygen. 
If not breathing, give artificial respiration and consult a doctor immediately. 
Do not use mouth to mouth resuscitation if the victim ingested or inhaled the chemical.

Following skin contact:
Take off contaminated clothing immediately. 
Wash off with soap and plenty of water. 
Consult a doctor.

Following eye contact:
Rinse with pure water for at least 15 minutes. 
Consult a doctor.

Following ingestion:
Rinse mouth with water. 
Do not induce vomiting. 
Never give anything by mouth to an unconscious person. 
Call a doctor or Poison Control Center immediately
Firefighting measures:
Extinguishing media:
Use dry chemical, carbon dioxide or alcohol-resistant foam.

Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.

Accidental release measures:
Personal precautions, protective equipment and emergency procedures:
Avoid dust formation. 
Avoid breathing mist, gas or vapours.
Avoid contacting with skin and eye. 
Use personal protective equipment.
Wear chemical impermeable gloves. 
Ensure adequate ventilation.
Remove all sources of ignition. 
Evacuate personnel to safe areas.
Keep people away from and upwind of spill/leak.

Environmental precautions:
Prevent further spillage or leakage if it is safe to do so.
Do not let the chemical enter drains. 
Discharge into the environment must be avoided.

Methods and materials for containment and cleaning up:
Collect and arrange disposal. 
Keep the chemical in suitable and closed containers for disposal. 
Remove all sources of ignition. 
Use spark-proof tools and explosion-proof equipment. 
Adhered or collected material should be promptly disposed of, in accordance with appropriate laws and regulations.

Handling and storage:

Precautions for safe handling:
Handling in a well ventilated place. 
Wear suitable protective clothing. 
Avoid contact with skin and eyes. 
Avoid formation of dust and aerosols. 
Use non-sparking tools. 
Prevent fire caused by electrostatic discharge steam.

Conditions for safe storage, including any incompatibilities
Store the container tightly closed in a dry, cool and well-ventilated place. 
Store apart from foodstuff containers or incompatible materials.

Exposure controls/personal protection:
Control parameters:
Exposure controls
Ensure adequate ventilation. 
Handle in accordance with good industrial hygiene and safety practice. 
Set up emergency exits and the risk-elimination area.

Individual protection measures:
Eye/face protection:
Wear tightly fitting safety goggles with side-shields conforming to EN 166(EU) or NIOSH (US).

Skin protection:
Wear fire/flame resistant and impervious clothing. 
Handle with gloves. 
Gloves must be inspected prior to use. 
Wash and dry hands. 
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it.

Respiratory protection:
If the exposure limits are exceeded, irritation or other symptoms are experienced, use a full-face respirator.

Disposal considerations:
Disposal methods:
Product:
The material can be disposed of by removal to a licensed chemical destruction plant or by controlled incineration with flue gas scrubbing. 
Do not contaminate water, foodstuffs, feed or seed by storage or disposal. 
Do not discharge to sewer systems.

Contaminated packaging:
Containers can be triply rinsed (or equivalent) and offered for recycling or reconditioning. 
Alternatively, the packaging can be punctured to make it unusable for other purposes and then be disposed of in a sanitary landfill. 
Controlled incineration with flue gas scrubbing is possible for combustible packaging materials.

CAS:    7585-39-9
European Community (EC) Number: 231-493-2
Molecular Formula:  (C6H10O5)7

SYNONYMS OF BETA-CYCLODEXTRIN:
MeSH Entry Terms    
beta-cyclodextrin

betadex

cyclo-epta-amylose

Cycloheptaamylose

Cyclomaltoheptaose

Depositor-Supplied Synonyms:
beta-CYCLODEXTRIN

Betadex

Cycloheptaamylose

Cyclomaltoheptaose

Cycloheptaglucan

7585-39-9

Cycloheptaglucosan

Kleptose

b-Cyclodextrin

beta-Cycloamylose

Cycloheptapentylose

Kleptose B

Rhodocap N

Ringdex B

Ringdex BL

beta-CD

Cyclodextrin B

beta-cyclodextrine

UNII-JV039JZZ3A

Maltodecaose DP10

.beta.-Cyclodextrin

JV039JZZ3A

Caraway

Schardinger beta-dextrin

beta-Cyclodextrin, homopolymer

CHEBI:495055

NCGC00090771-01

DSSTox_CID_358

DSSTox_RID_75536

DSSTox_GSID_20358

37331-89-8

79647-56-6

beta-Cyclodextrins

CAVAMAX W7

CAS-7585-39-9

Dextrin, beta-cyclo

Betacd

CCRIS 651

ss-Cyclodextrin

Oristar bcd

Ringdex-b

Beta cyclodextrin

Betadex [USAN:INN:BAN:NF]

1dmb

2zyn

NSC-269471

beta-cyclo-dextrin

E459

EINECS 231-493-2

Cyclodextrin, beta-

MFCD00078139

Betadex (NF/INN)

NSC 314334

Schardinger A-Dextrin

2y4s

3ck8

3m3r

Beta-schardinger dextrin

AI3-29233

BDBM11

EC 231-493-2

beta-Cyclodextrin, >=97%

SCHEMBL24215

CHEMBL415690

INS NO.459

DTXSID1020358

INS-459

heptakis(hydroxymethyl)[?]tetradecol

Tox21_111017

Tox21_201006

AKOS015900444

Tox21_111017_1

DB03995

NSC 269471

NCGC00090771-02

NCGC00090771-03

NCGC00090771-04

NCGC00258559-01

HY-107201

CS-0027620

E-459

C-9120

D02401

Q27077120

Betadex, European Pharmacopoeia (EP) Reference Standard

D047392000

UNII-7E6SK9QDT8 component WHGYBXFWUBPSRW-FOUAGVGXSA-N

beta-Cyclodextrin, produced by Wacker Chemie AG, Burghausen, Germany

Beta Cyclodextrin, United States Pharmacopeia (USP) Reference Standard

beta-Cyclodextrin, powder, BioReagent, suitable for cell culture, >=97%

Beta-Cyclodextrin, Pharmaceutical Secondary Standard; Certified Reference Material

beta-Cyclodextrin, produced by Wacker Chemie AG, Burghausen, Germany, >=95.0% (HPLC)

beta-Cyclodextrin, Produced by Wacker Chemie AG, Burghausen, Germany, Life Science, >=98.0% (HPLC)

WURCS=2.0/1,7,7/[a2122h-1a_1-5]/1-1-1-1-1-1-1/a1-g4_a4-b1_b4-c1_c4-d1_d4-e1_e4-f1_f4-g1

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