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332593

Sigma-Aldrich

(2-Hydroxypropyl)-β-cyclodextrin

average Mw ~1,380

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Synonym(s):
(2-Hydroxypropyl)-beta-cyclodextrin
CAS Number:
EC Number:
PubChem Substance ID:
NACRES:
NA.22

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.)

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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1 of 4

This Item
332607778966389145
vibrant-m

332593

(2-Hydroxypropyl)-β-cyclodextrin

vibrant-m

332607

(2-Hydroxypropyl)-β-cyclodextrin

vibrant-m

778966

(2-Hydroxypropyl)-β-cyclodextrin

vibrant-m

389145

(2-Hydroxypropyl)-β-cyclodextrin

form

powder

form

powder

form

powder

form

powder

mp

278 °C (dec.)

mp

267 °C (dec.)

mp

-

mp

-

optical activity

[α]26/D +139°, c = 1 in H2O

optical activity

[α]25/D +135°, c = 1 in H2O (typical)

optical activity

-

optical activity

[α]23/D +125°, c = 1 in H2O

mol wt

average Mw ~1,380

mol wt

average Mw ~1,460

mol wt

-

mol wt

average Mw ~1,540

extent of labeling

0.6 molar substitution

extent of labeling

0.8 molar substitution

extent of labeling

molar substitution per 0.60

extent of labeling

1.0 molar substitution dextrin

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.

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.
  • As a chiral selector in capillary electrophoresis, enabling the robust separation of diastereomeric derivatives of aspartic acid for analysis.
  • As a reagent to improve water solubility and anti-proliferative activity of pyrazolo[3,4-d] pyrimidines.
  • As formulation vehicle. It increases water solubility of the drug for successful delivery of medical agents to a biological system.
  • To increase the solubility of ropivacaine (RVC) upon complexation, which in turn enhances the pharmacological activity of RVC.
  • To increase the aqueous solubility of naproxen (NAP) in presence of polyvinylpyrrolidone (PVP).
  • As a template in the synthesis of hollow spherical copper sulfide nanoparticle assemblies.
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

13 - Non Combustible Solids

wgk_germany

WGK 1

flash_point_f

752.0 °F

flash_point_c

> 400 °C

ppe

Eyeshields, Gloves, type N95 (US)


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Sigma-Aldrich

C4767

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Sigma-Aldrich

W402826

β-Cyclodextrin

2-Hydroxypropyl-beta-cyclodextrin strongly improves water solubility and anti-proliferative activity of pyrazolo [3, 4-d] pyrimidines Src-Abl dual inhibitors
Elena D,et al.
European Journal of Medicinal Chemistry, 45, 5958-5964 (2010)
Evaluation of enantiomeric purity of magnesium-L-aspartate dihydrate
Oliver W,et al.
Journal of Pharmaceutical and Biomedical Analysis, 102, 100-109 (2015)
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
CE with Cu2+ ions and 2-hydroxypropyl-$\beta$-cyclodextrin additives for the investigation of amino acids composition of the culture medium in a cellular model of non-alcoholic fatty liver disease
Daria M,et al.
Journal of Pharmaceutical and Biomedical Analysis, 213, 114663-114663 (2022)
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)

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