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β-Cyclodextrin

Description References
Product Name
β-Cyclodextrin
CAS No.
7585-39-9
Chemical Name
β-Cyclodextrin
Synonyms
β-Cyclodextrin;betadex;B-Cyclodextrin;Cyclodextrins;CARAWAY;BCD;BETA BYCLODEXTRIN;CYCLOMALTOHEPTAOSE;Β-CycIodextrin;Beta Chitosan
CBNumber
CB8289713
Molecular Formula
C42H70O35
Formula Weight
1134.99
MOL File
7585-39-9.mol
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β-Cyclodextrin Property

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
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)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38-20
Safety Statements 
26-36-24/25
WGK Germany 
2
RTECS 
GU2293000
TSCA 
Yes
HS Code 
29400000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H332Harmful if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
239760
Product name
β-Cyclodextrin - CAS 7585-39-9 - Calbiochem
Packaging
25G
Price
$81.5
Updated
2024/03/01
Sigma-Aldrich
Product number
239760
Product name
β-Cyclodextrin - CAS 7585-39-9 - Calbiochem
Packaging
500G
Price
$755
Updated
2024/03/01
Sigma-Aldrich
Product number
1154569
Product name
Beta Cyclodextrin
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
500mg
Price
$539
Updated
2024/03/01
Sigma-Aldrich
Product number
1154569
Product name
Beta Cyclodextrin
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
30MG
Price
$1810
Updated
2024/03/01
TCI Chemical
Product number
C0777
Product name
Beta Cyclodextrin
Purity
>99.0%(HPLC)
Packaging
25g
Price
$85
Updated
2024/03/01
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β-Cyclodextrin Chemical Properties,Usage,Production

Description

Cyclodextrins refer to a family of compounds consisting of sugar molecules bound together in ring (cyclic oligosaccharides). It is produced from starch through enzymatic conversion. Beta-cyclodextrin is the 7-membered sugar ring molecular form of cyclodextrin. Cyclodextrin has various applications. In the pharmaceutical industry, it can be used as complexing agents for increasing the solubility of poorly soluble drug as well as increasing their bioavailability and stability. It can also alleviate the gastrointestinal drug irritation, and prevent drug-drug and drug-excipient interactions. It can also be used in food, pharmaceutical, drug delivery, and chemical industries, as well as agriculture and environmental engineering.

References

https://en.wikipedia.org/wiki/Cyclodextrin
https://notendur.hi.is/thorstlo/general.pdf

Chemical Properties

white powder

Chemical Properties

Cyclodextrins occur as white, practically odorless, fine crystalline powders, having a slightly sweet taste. Some cyclodextrin derivatives occur as amorphous powders.

Chemical Properties

A biennial herbaceous plant very common in Europe, Asia, Africa and the United States, it 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.

Chemical Properties

beta Cyclodextrin is a virtually odorless, slightly sweet-tasting, white or almost white crystalline solid or fine powder.

Occurrence

A derivative of naturally occurring starch.

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 isomersβ-Cyclodextrin is used with dansyl chloride to form water-soluble complexes for fluorescent labeling of proteins. It is an active ingredient of household odor eliminator. It is also used in personal care products like toothpastes, skin creams and dusting powders. It finds applications in the cosmetic industry for products like detergents and perfumes for the controlled release of fragrances. Further, it is used to produce HPLC columns allowing chiral enantiomers separation. In addition to this, it is used to decrease the level of cholesterol in milk fat.

Uses

β-Cyclodextrin is a cyclic oligosaccharide produced from starch via enzymatic conversion. β-Cyclodextrin is commonly used to produce HPLC columns allowing chiral enantiomers separation.

Production Methods

Cyclodextrins are manufactured by the enzymatic degradation of starch using specialized bacteria. For example, β-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 β-cyclodextrin, and to prevent the growth of microorganisms during the enzymatic reaction. The insoluble complex of β-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 β-cyclodextrin. The β-cyclodextrin is then carbon treated and crystallized from water, dried, and collected.

Definition

ChEBI: Beta-cyclodextrin is a cyclodextrin composed of seven alpha-(1->4) linked D-glucopyranose units.

Preparation

Usually produced commercially from Bacillus macerans or B. circulans fermentation of starch or starch hydrolysate.

Essential oil composition

In addition to carvone, the oil contains d-limonene, carveol, diacetyl furfural, methyl alcohol, acetic aldehyde and other substances. Caraway oil consists of 3.5 to 7% volatile and fatty oils; resin, sugar, tannin, mucilage.

Taste threshold values

Reported to have a taste threshold value lower than that of sucrose with a detection level of 3.9 to 27 ppm and a recognition level of 11 to 52 ppm

General Description

Beta-Cyclodextrin is the most abundant and cheap cyclic oligosaccharide that forms inclusion complexes with several drug molecules. Its 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.

Flammability and Explosibility

Non flammable

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 cyclodextrin to accommodate a guest molecule within the cavity, forming an inclusion complex.
Cyclodextrins 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.
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.
b-Cyclodextrin is the most commonly used cyclodextrin, although it is the least soluble. It 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, b-cyclodextrin is nephrotoxic and should not be used in parenteral formulations. b-Cyclodextrin is primarily used in tablet and capsule formulations.
In oral tablet formulations, b-cyclodextrin may be used in both wet-granulation and direct-compression processes. The physical properties of b-cyclodextrin vary depending on the manufacturer. However, b-cyclodextrin tends to possess poor flow properties and requiresalubricant,such as 0.1% w/w magnesium stearate,when it 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, cyclodextrins 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.
Cyclodextrins have also been used in the formulation of solutions,suppositories, and cosmetics.

Biochem/physiol Actions

β-Cyclodextrin is the cyclic α heptamer of glucose. It 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. It is generally used to solubilize non-polar compounds such a fatty acids, lipids and cholesterol.

Safety

Cyclodextrins are starch derivatives and are mainly used in oral and parenteral pharmaceutical formulations. They are also used in topical and ophthalmic formulations.
Cyclodextrins are also used in cosmetics and food products, and are generally regarded as essentially nontoxic and nonirritant materials. However, when administered parenterally, β-cyclodextrin is not metabolized but accumulates in the kidneys as insoluble cholesterol complexes, resulting in severe nephrotoxicity.
Cyclodextrin administered orally is metabolized by microflora in the colon, forming the metabolites maltodextrin, maltose, and glucose; these are themselves further metabolized before being finally excreted as carbon dioxide and water. Although a study published in 1957 suggested that orally administered cyclodextrins were highly toxic, more recent animal toxicity studies in rats and dogs have shown this not to be the case, and cyclodextrins are now approved for use in food products and orally administered pharmaceuticals in a number of countries.
Cyclodextrins are not irritant to the skin and eyes, or upon inhalation. There is also no evidence to suggest that cyclodextrins are mutagenic or teratogenic.
β-Cyclodextrin
LD50 (mouse, IP): 0.33 g/kg(16)
LD50 (mouse, SC): 0.41 g/kg
LD50 (rat, IP): 0.36 g/kg
LD50 (rat, IV): 1.0 g/kg
LD50 (rat, oral): 18.8 g/kg
LD50 (rat, SC): 3.7 g/kg

storage

Cyclodextrins should be stored in a tightly sealed container, in a cool, dry place.Cyclodextrins are stable in the solid state if protected from high humidity.

Purification Methods

Recrystallise β-cyclodextrin from water and dry it for 12hours in a vacuum at 110o, or 24hours in a vacuum at 70o. The purity is assessed by TLC on cellulose containing a fluorescent indicator. [Taguchi, J Am Chem Soc 108 2705 1986, Tabushi et al. J Am Chem Soc 108 4514 1986, Orstam & Ross J Phys Chem 91 2739 1987.] [Beilstein 19 IV 6287, 19/12 V 801.]

Regulatory Status

Included in the FDA Inactive Ingredients Database: α-cyclodextrin (injection preparations); β-cyclodextrin (oral tablets, topical gels); γ-cyclodextrin (IV injections).
Included in the Canadian List of Acceptable Non-medicinal Ingredients (stabilizing agent; solubilizing agent ); and in oral and rectal pharmaceutical formulations licensed in Europe, Japan, and the USA.

β-Cyclodextrin Preparation Products And Raw materials

Raw materials

Preparation Products

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β-Cyclodextrin Suppliers

Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
400-6206333 18521732826;
Fax
021-50323701
Email
market@aladdin-e.com
Country
China
ProdList
24835
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65
Shandong Xinda Biotechnology Co. Ltd.
Tel
0533-8888698
Email
652317004@qq.com
Country
CHINA
ProdList
5
Advantage
58
Wuxi Jingyao Bio-Technology Co., Ltd.
Tel
0510-88770633 13961738808
Email
jingyaobiotech@126.com
Country
China
ProdList
301
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55
QINGDAO WANYUAN MOUNTAIN BIOTECH CO.,LTD
Tel
0532-0532-66720179 15092119928
Email
cuiningning@bionutrichem.com
Country
China
ProdList
109
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Shandong Zhiyuan Biotechnology Co., Ltd.
Tel
0543-8128041 13562317646
Fax
0543-2605568
Email
2370211093@qq.com
Country
China
ProdList
48
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J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
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Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40241
Advantage
62
future industrial shanghai co., ltd
Tel
400-0066400 13621662912
Fax
021-55660885
Email
sales@jonln.com
Country
China
ProdList
1998
Advantage
65
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24539
Advantage
81
BeiJing Hwrk Chemicals Limted
Tel
0757-86329057 18501085097
Fax
010-89508210
Email
sales3.gd@hwrkchemical.com
Country
China
ProdList
7508
Advantage
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View Lastest Price from β-Cyclodextrin manufacturers

Hebei Yime New Material Technology Co., Ltd.
Product
Beta Cyclodextrin 7585-39-9
Price
US $5.00/kg
Min. Order
1000kg
Purity
99%
Supply Ability
10000kg/month
Release date
2023-11-29
Hebei Yime New Material Technology Co., Ltd.
Product
Beta Cyclodextrin 7585-39-9
Price
US $5.00/kg
Min. Order
1000kg
Purity
99%
Supply Ability
10000kg/month
Release date
2023-11-29
Hebei Yime New Material Technology Co., Ltd.
Product
Beta Cyclodextrin 7585-39-9
Price
US $5.00/kg
Min. Order
1000kg
Purity
99%
Supply Ability
10000kg/month
Release date
2023-11-29

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