332607

(2-Hydroxypropyl)-β-cyclodextrin

average M_w ~1,460

• Synonym(s): (2-Hydroxypropyl)-beta-cyclodextrin, HP-β-CD
• CAS Number: 128446-35-5
• EC Number: 420-920-1
• UNSPSC Code: 12352201
• PubChem Substance ID: 24859911
• NACRES: NA.22

Properties

• form: powder
• optical activity: [α]25/D +135°, c = 1 in H₂O (typical)
• mol wt: average M_w ~1,460
• extent of labeling: 0.8 molar substitution
• mp: 267 °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, a hydroxyalkyl derivative, finds application as a formulation vehicle that is used to enhance the solubility of the drugs in aqueous solutions for the successful delivery of medical agents to biological systems. It is generally employed as a substitute for α-, β- and γ-cyclodextrins.

Application

(2-Hydroxypropyl)-β-cyclodextrin may be used:

• As an analytical standard for the determination of the analyte in pharmaceutical formulations by thin layer chromatography (TLC) method.
• To study the host-guest interaction with organic low molecular mass compounds prior to their quantification using reversed phase-high performance liquid chromatography (RP-HPLC) technique.
• As a mobile phase additive for the effective separation of β-carbolines by HPLC.
• In cyclodextrin-modified micellar electrokinetic chromatography (CD-modified MEKC) for the determination of sertraline hydrochloride and the synthesis-related products.

The solubility of lipophilic drugs increases linearly with the concentration of hydroxypropyl-β-cyclodextrin (HP-β-CD) in aqueous solution because of the complex between HP-β-CD and the drug. This guest-host type complex is formed between the drug and the non-polar cavity in the HP-β-CD that results in enhanced solubility. HP-β-CD can be used to prepare an inclusion complex with ropivacaine (RVC) to increase the solubility of RVC for efficient drug delivery.

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: 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)