332593

(2-Hydroxypropyl)-β-cyclodextrin

average M_w ~1,380

• Synonym(s): (2-Hydroxypropyl)-beta-cyclodextrin
• CAS Number: 128446-35-5
• EC Number: 420-920-1
• UNSPSC Code: 12352302
• PubChem Substance ID: 24859909
• NACRES: NA.22

Properties

• form: powder
• optical activity: [α]26/D +139°, c = 1 in H₂O
• mol wt: average M_w ~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

Description

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.

Safety Information

• 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