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C4555 Sigma

Methyl-β-cyclodextrin

powder, BioReagent, suitable for cell culture

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Properties

Related Categories Cell Biology, Cell Culture, Cell Signaling and Neuroscience, Chelation/Complexation Compounds, Chemical Synthesis,
product line   BioReagent
form   powder
extent of labeling   1.5-2.1 methyl per mol glucose
mp   180-182 °C(lit.)
solubility   H2O: 50 mg/mL
suitability   suitable for cell culture

Description

Frequently Asked Questions

Frequently Asked Questions are available for this Product.

Application

Use to increase the solubility of non-polar substances such as fatty acids, lipids, vitamins and cholesterol for use in cell culture applications.

Packaging

1, 5, 10 g in poly bottle

Reconstitution

Solutions may be obtained by stirring 30 min at room temperature. Alternatively, sonication with cooling may be employed. Solutions may be stored for several months at 4°C. Solid should be stored tightly sealed at room temperature.

General description

Cyclodextrins are cyclic oligosaccharides consisting of 6, 7, or 8 glucopyranose units, usually referred to as α-, β-, or γ-cyclodextrins, respectively. These compounds have rigid doughnut-shaped structures making them natural complexing agents. The unique structures of these compounds owe their stability to intramolecular hydrogen bonding between the C2- and C3-hydroxyl groups of neighboring glucopyranose units. The molecule 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 C6-hydroxyls 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 cyclodextrins is very poor. In the late 1960’s, it 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 β-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, β-cyclodextrin is most commonly used as a complexing agent.

Price and Availability


All labs need water
Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
Flash Point(F) 
368.6 °F
Flash Point(C) 
187 °C

Frequently Asked Questions

What is the molecular weight of Methyl-?-cyclodextrin, Product No. C4555?
The approximate molecular weight is 1320 g/mol. The molecular weight can vary from lot to lot due to variation in the methyl content of the product. The molecular weight of this product is dependent on the average number of methyl groups per glucose residue (reported on the lot specific Certificate of Analysis).  To view a specification sheet click on the following link:http://www.sigmaaldrich.com/catalog/search/SpecificationSheetPage/SIGMA/C4555
How can I make a solution of Methyl-ß-cyclodextrin, Product C4555?
This product is tested and found soluble at 50 mg/ml in 1 M NaOH yielding a clear, colorless solution.  This product is also soluble in water (150 mg/ml), yielding a clear, colorless solution. Aqueous solutions may be obtained by stirring 30 minutes at room temperature. Alternatively, sonication with cooling may be employed.
How should a solution of Methyl-ß-cyclodextrin, Product C4555, be sterilized?
Solutions can be sterile filtered using a 0.2 µm membrane.  We do not recommend autoclaving the solution.  The product as supplied is not sterile.
How does Methyl-ß-cyclodextrin, Product C4555, work to solubilize products that have minimal solubility in aqueous solutions for use in cell culture?
The cavity diameter of ß -cyclodextrins 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, ß-cyclodextrin is most commonly used as a complexing agent.  Hydrophobic molecules are incorporated into the cavity of cyclodextrins by displacing water. This reaction is favored by the repulsion of the molecule by water. This effectively encapsulates the molecule of interest within the cyclodextrin, rendering the molecule water soluble. When the water soluble complex is diluted in a much larger volume of aqueous solvent, the process is reversed, thereby releasing the molecule of interest into the solution. To view this information in C4555 General Information Sheet, click on the following link:http://www.sigmaaldrich.com/sigma/general%20information/c4555inf.pdf
What concentration of Methyl-ß-cyclodextrin, Product C4555, do I use to remove cholesterol from cell membranes?
This product has been used to reduce the cholesterol content of cell membranes at 10 - 50 mM.References:Eur J Cell Biol. 1999 Jul, 78(7): 473-84.Lipids. 1996 Aug, 31(8): 817-28.
Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis. These documents are located on the product detail page under Useful Links & Tools. Click on the following link to search for a Certificate of Analysis. Please click the following link to see the details on our Product Dating Information.
How do I get lot-specific information or a Certificate of Analysis?
A Certificate of Analysis is available by lot number and can be obtained through our Advanced Search Option: http://www.sigmaaldrich.com/catalog/AdvancedSearchPage.do
What is Product C4555, Methyl-ß-cyclodextrin?
Methyl-ß-cyclodextrin is used as a "carrier" molecule to facilitate the dissolution of compounds with low solubility in water.  More information can be found on the Product Information Sheet for product C4555: http://www.sigmaaldrich.com/etc/medialib/docs/Sigma/General_Information/1/c4555inf.Par.0001.File.tmp/c4555inf.pdf
How do I find price and availability?
There are several ways to find pricing and availability for our products.  Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers. 
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS. To access the shipping information for this material, use the link on the product detail page for the product, or search here. 
My question is not addressed here, how can I contact Technical Service for assistance?
Use the option to the right to "Ask a Question" by email of a Technical Service Scientist.
  What kind of solution is the A5955 - Antibiotic Antimycotic Solution (100×), Stabilized product suspended in?
A5955 - Antibiotic Antimycotic Solution (100×), Stabilized is supsended in a sodium citrate buffer solution. Source: Israel production group
Show more questions
Protocols & Articles

Articles

Cyclodextrins

Many metabolically important compounds, such as lipid-soluble vitamins and hormones, have very low solubilities in aqueous solutions. Various techniques have been used to solubilize these compounds i...
Vicki Caligur
BioFiles 2008, 3.3, 32.
Keywords: Cell culture, Hormones, Nuclear magnetic resonance spectroscopy, Substitutions, Vitamins

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Peer-Reviewed Papers
15

References

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