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Sigma-Aldrich

(2-Hydroxypropyl)-β-cyclodextrin

produced by Wacker Chemie AG, Burghausen, Germany

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Synonym(s):
(2-Hydroxypropyl)-beta-cyclodextrin, Cavasol® W7 HP, HP-β-CD
CAS Number:
128446-35-5
EC Number:
420-920-1
NACRES:
NA.22

grade

produced by Wacker Chemie AG, Burghausen, Germany

Quality Level

100

form

powder

extent of labeling

molar substitution per 0.60

impurities

≤1.0% unsubstituted cyclodextrin
≤5.0% polypropylene glycol

ign. residue

≤2.5%

loss

≤7.0% loss on drying

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 (HP-β-CD), is a macrocyclic oligosaccharide with a hydrophobic inner cavity and a hydrophilic outer surface, that allows it to incorporate hydrophobic drugs into the cavities, thus enhancing water solubility and bioavailability of poorly water-soluble drugs. It also possesses high surface activity and stabilizing performance.

Application

2-Hydroxypropyl)-β-cyclodextrin is used as a:
  • Macromolecular additive in the synthesis of single-phasetetragonal zirconium oxides.
  • Precursor in the synthesis of polyrotaxane.
  • Solubilizer and stabilizer in pharmaceutical formulations. HP-β-CD also shows potent anticancer activity.
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.

Legal Information

Cavasol is a registered trademark of Wacker Chemie AG

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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?Back to the future?: a new look at hydroxypropyl beta-cyclodextrins.
Malanga M, et al.
Journal of Pharmaceutical Sciences, 105(9), 2921-2931 (2016)
Synthesis of 2-hydroxypropyl-$\beta$-cyclodextrin/pluronic-based polyrotaxanes via heterogeneous reaction as potential Niemann-Pick type C therapeutics
Yawo MA,et al.
Biomacromolecules, 14, 4189-4197 (2013)
2-Hydroxypropyl-?-cyclodextrin acts as a novel anticancer agent.
Yokoo M, et al.
PLoS ONE, 10(11), e0141946-e0141946 (2015)
Hydroxypropyl-$\beta$-cyclodextrin as a versatile additive for the formation of metastable tetragonal zirconia exhibiting high thermal stability
Lei B,et al.
CrystEngComm, 15, 2076-2083 (2013)
Hydroxypropyl-$\beta$-cyclodextrin-based solid dispersed granules: A prospective alternative to conventional solid dispersion
Jung Suk K,et al.
International Journal of Pharmaceutics, 628, 122286-122286 (2022)
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