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332593

Sigma-Aldrich

(2-Hydroxypropyl)-β-cyclodextrin

average Mw ~1,380

Synonym(s):

(2-Hydroxypropyl)-beta-cyclodextrin

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About This Item

CAS Number:
128446-35-5
EC Number:
420-920-1
UNSPSC Code:
12352302
PubChem Substance ID:
24859909
NACRES:
NA.22
Pricing and availability is not currently available.

form

powder

optical activity

[α]26/D +139°, c = 1 in H2O

mol wt

average Mw ~1,380

extent of labeling

0.6 molar substitution

mp

278 °C (dec.)

solubility

water: 180 g/L

SMILES string

CC(O)COCC1OC2OC3C(COCC(C)O)OC(OC4C(COCC(C)O)OC(OC5C(COCC(C)O)OC(OC6C(COCC(C)O)OC(OC7C(COCC(C)O)OC(OC8C(COCC(C)O)OC(OC1C(OCC(C)O)C2OCC(C)O)C(OCC(C)O)C8OCC(C)O)C(OCC(C)O)C7OCC(C)O)C(OCC(C)O)C6OCC(C)O)C(OCC(C)O)C5OCC(C)O)C(OCC(C)O)C4OCC(C)O)C(OCC(C)O)C3OCC(C)O

InChI

1S/C63H112O42/c1-22(64)8-85-15-29-50-36(71)43(78)57(92-29)100-51-30(16-86-9-23(2)65)94-59(45(80)38(51)73)102-53-32(18-88-11-25(4)67)96-61(47(82)40(53)75)104-55-34(20-90-13-27(6)69)98-63(49(84)42(55)77)105-56-35(21-91-14-28(7)70)97-62(48(83)41(56)76)103-54-33(19-89-12-26(5)68)95-60(46(81)39(54)74)101-52-31(17-87-10-24(3)66)93-58(99-50)44(79)37(52)72/h22-84H,8-21H2,1-7H3/t22?,23?,24?,25?,26?,27?,28?,29-,30-,31?,32?,33?,34?,35?,36?,37-,38?,39-,40+,41+,42+,43?,44+,45?,46+,47+,48+,49+,50+,51+,52-,53-,54-,55-,56-,57+,58-,59+,60-,61-,62-,63-/m1/s1

InChI key

ODLHGICHYURWBS-RYJYQAAZSA-N

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General description

(2-Hydroxypropyl)-β-cyclodextrin (HP-β-CD) is a beta-cyclodextrin and hydroxyalkyl derivative and is widely used as a chiral solvent, phase transfer catalyst, and host molecule in organic synthesis. HP-β-CD can form inclusion complexes with guest molecules, which can help enhance the solubility, stability, and bioavailability of the guest molecule. It is an alternative to α-, β- and γ-cyclodextrin and exhibits a higher water solubility. HP-β-CD is commonly used as a drug solubilizer. [1]

Application

HP-β-CD can be used:
  • As an additive in the separation of amino acids and lactic acids based on the coordination interactions between Cu2+ ions and analytes. [2]
  • As a chiral selector in capillary electrophoresis, enabling the robust separation of diastereomeric derivatives of aspartic acid for analysis. [3]
  • As a reagent to improve water solubility and anti-proliferative activity of pyrazolo[3,4-d] pyrimidines. [4]
  • As formulation vehicle. It increases water solubility of the drug for successful delivery of medical agents to a biological system.[1]
  • To increase the solubility of ropivacaine (RVC) upon complexation, which in turn enhances the pharmacological activity of RVC.[5]
  • To increase the aqueous solubility of naproxen (NAP) in presence of polyvinylpyrrolidone (PVP).[6]
  • As a template in the synthesis of hollow spherical copper sulfide nanoparticle assemblies.[7]
The solubility of lipophilic drugs increases linearly with the concentration of hydroxypropyl-β-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. Solutions may be lyophilized to produce freely soluble powders. Non-toxic in rabbits and mice.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 1

Flash Point(F)

>752.0 °F

Flash Point(C)

> 400 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF5095V
WXBF3316V
WXBF0225V
MKCT5635
WXBF1789V

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The influence of polyvinylpyrrolidone on naproxen complexation with hydroxypropyl- β -cyclodextrin
Mura P, et al.
European Journal of Pharmaceutical Sciences, 13(2), 187-194 (2001)
The fabrication of hollow spherical copper sulfide nanoparticle assemblies with 2-hydroxypropyl- β -cyclodextrin as a template under sonication
Xu J-Z, et al.
Ultrasonics Sonochemistry, 13(5), 451-454 (2006)
Dobrin Draganov et al.
NPJ breast cancer, 7(1), 22-22 (2021-03-04)
We show that treatment with the FDA-approved anti-parasitic drug ivermectin induces immunogenic cancer cell death (ICD) and robust T cell infiltration into breast tumors. As an allosteric modulator of the ATP/P2X4/P2X7 axis which operates in both cancer and immune cells
Development and pharmacological evaluation of ropivacaine-2-hydroxypropyl- β -cyclodextrin inclusion complex
de Araujo DR, et al.
European Journal of Pharmaceutical Sciences, 33(1), 60-71 (2008)
Magdalena Koziczak-Holbro et al.
The Journal of pharmacology and experimental therapeutics, 369(2), 188-199 (2019-03-02)
The anabolic effects of β2-adrenoceptor (β2-AR) agonists on skeletal muscle have been demonstrated in various species. However, the clinical use of β2-AR agonists for skeletal muscle wasting conditions has been limited by their undesired cardiovascular effects. Here, we describe the
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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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