389145

Sigma-Aldrich

(2-Hydroxypropyl)-β-cyclodextrin

average Mw ~1,540

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

Quality Level

optical activity

[α]23/D +125°, c = 1 in H2O

mol wt

average Mw ~1,540

extent of labeling

1.0 molar substitution dextrin

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, is mainly used as a formulation vehicle to increase the dissolution of drugs in water for the successful delivery of medicinal agents to biological systems. It is commonly utilized 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 as well as nanoparticle formulations by thin layer chromatography (TLC) and high performance liquid chromatography (HPLC), respectively.
  • To study the host-guest interaction with organic low molecular mass compounds prior to their quantification using reversed phase 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.
  • As a chiral selector to resolve pantothenic acid by capillary electrophoresis.

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.

Packaging

5, 25 g in poly bottle

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Chromatographic Separation and Purification of Novel Drug Excipient 2-Hydroxypropyl-beta-Cyclodextrin [J]
Yimin Z, et al.
Chinese Journal of Analytical Chemistry, 5 (2006)
Direct chiral resolution of pantothenic acid using 2-hydroxypropyl-beta-cyclodextrin in capillary electrophoresis
Kodama S, et al.
Journal of Chromatography A, 811(1-2), 269-273 (1998)
M Agüeros et al.
Journal of pharmaceutical and biomedical analysis, 39(3-4), 495-502 (2005-06-11)
A rapid and simple HPLC method with evaporative scattering detection (ELSD) has been developed for the separation and quantitation of beta-cyclodextrin (beta-CD), 2-hydroxypropyl-beta-cyclodextrin (2-HP-beta-CD) and poly(methyl vinyl ether-co-maleic anhydride) (Gantrez). Separation was carried out on a Zorbax Eclipse XDB-Phenyl narrow...
The role of beta-cyclodextrin and hydroxypropyl beta-cyclodextrin in the secondary chemical equilibria associated to the separation of beta-carbolines by HPLC
Leon AG, et al.
Journal of Inclusion Phenomena and Macrocyclic Chemistry, 57(1-4), 577-583 (2007)
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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