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389145

Sigma-Aldrich

(2-Hidroxipropil)-β-ciclodextrina

average Mw ~1,540

Sinónimos:

(2-Hydroxypropyl)-beta-cyclodextrin

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About This Item

Número de CAS:
128446-35-5
EC Number:
420-920-1
UNSPSC Code:
12352201
PubChem Substance ID:
24864264
NACRES:
NA.22

form

powder

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 is a cyclic oligosaccharide and used as a pharmaceutical excipient to improve the stability and bioavailability of drugs.

(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.

La solubilidad de los fármacos lipófilos aumenta linealmente con la concentración de hidroxipropil-β-ciclodextrina (HBC) en disolución acuosa debido al complejo entre la HBC y el fármaco. Este complejo tipo huésped-anfitrión se forma entre el fármaco y la cavidad no polar de la HBC que tiene como consecuencia una mayor solubilidad. Las disoluciones pueden liofilizarse para producir polvos libremente solubles. No tóxico en conejos ni ratones.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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
2-Hydroxypropyl-$\beta$-cyclodextrin acts as a novel anticancer agent
Yokoo, et al.
PLoS ONE, 10, e0141946-e0141946 (2015)
2-Hydroxypropyl-$\beta$-cyclodextrin promotes transcription factor EB-mediated activation of autophagy
Song, et al.
The Journal of Biological Chemistry, 289, 10211-10222 (2014)
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
Chromatographic Separation and Purification of Novel Drug Excipient 2-Hydroxypropyl-beta-Cyclodextrin [J]
Yimin Z, et al.
Chinese Journal of Analytical Chemistry, 5 (2006)
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