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Sigma-Aldrich

(2-Hydroxypropyl)-β-cyclodextrin

average Mw ~1,460

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Synonym(s):
(2-Hydroxypropyl)-beta-cyclodextrin, HP-β-CD
CAS Number:
EC Number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.22

form

powder

optical activity

[α]25/D +135°, c = 1 in H2O (typical)

mol wt

average Mw ~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

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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.

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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Daniele R de Araujo et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 33(1), 60-71 (2007-11-27)
Ropivacaine (RVC) is an enantiomerically pure local anesthetic (LA) largely used in surgical procedures, which presents physico-chemical and therapeutic properties similar to those of bupivacaine (BPV), but associated to less systemic toxicity. This study focuses on the development and pharmacological
Chromatographic Separation and Purification of Novel Drug Excipient 2-Hydroxypropyl-beta-Cyclodextrin [J]
Yimin Z, et al.
Chinese Journal of Analytical Chemistry, 5 (2006)
Björn-Hendrik Peters et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 95, 72-81 (2016-05-26)
Microscale freeze-drying makes rapid process cycles possible for early-stage formulation development. To investigate the effects of equipment scale and cooling rate on the solid state properties and the protein's secondary structure of a sample, three binary formulations of catalase were
K Miyake et al.
Pharmaceutical development and technology, 5(3), 399-407 (2000-08-10)
The object of this study was to enhance the solubility, dissolution rate, and oral bioavailability of rutin by complexation with 2-hydroxypropyl-beta-cyclodextrin (HP-beta-CyD). The interaction of rutin with cyclodextrins (CyDs) was evaluated by the solubility, and ultraviolet (UV) and circular dichroism
S E Lucangioli et al.
Journal of chromatography. A, 871(1-2), 207-215 (2000-03-29)
In this work development, optimization and validation of a cyclodextrin-modified micellar electrokinetic chromatography (CD-modified MEKC) method is proposed to resolve separation of the sertraline hydrochloride and synthesis-related substances. Sertraline hydrochloride, the cis-(1S,4S) enantiomer form, is used as an antidepressant therapeutic

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