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Merck

390690

(2-Hydroxypropyl)-α-cyclodextrin

average Mw ~1,180

Synonym(s):

α‐HPCD, 2OHpαCD, 2‐hydroxypropyl‐α‐CD, HPαCD, HP-α-CD

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About This Item

CAS Number:
128446-33-3
UNSPSC Code:
12352201
NACRES:
NA.22
MDL number:
MFCD00197866

Product Name

(2-Hydroxypropyl)-α-cyclodextrin, average Mw ~1,180

SMILES string

O1[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@@H]([C@@H](O[C@H]4O[C@@H]([C@@H](O[C@H]5O[C@@H]([C@@H](O[C@H]6O[C@@H]([C@@H](O[C@H]7O[C@@H]([C@@H]1[C@H]([C@@H]7O)O)COCC(O)C)[C@H]([C@@H]6O)O)COCC(O)C)[C@H]([C@@H]5O)O)COCC(O)C)[C@H]([C@@H]4O)O)COCC(O)C)[C@H]([C@@H]3O)O)C

InChI

1S/C54H96O36/c1-19(55)7-73-13-25-43-31(61)37(67)49(79-25)86-44-26(14-74-8-20(2)56)81-51(39(69)33(44)63)88-46-28(16-76-10-22(4)58)83-53(41(71)35(46)65)90-48-30(18-78-12-24(6)60)84-54(42(72)36(48)66)89-47-29(17-77-11-23(5)59)82-52(40(70)34(47)64)87-45-27(15

InChI key

PMPYGZCSMCXHTA-WABPNHHRSA-N

form

powder

optical activity

[α]20/D +125°, c = 1 in H2O

mol wt

average Mw ~1,180

extent of labeling

0.6 molar substitution

mp

245 °C (dec.) (lit.)

Quality Level

100

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Application

  • (2-Hydroxypropyl)-α-cyclodextrin can be used as a chiral selector to resolve tryptophan racemate by capillary electrophoresis.
  • It can be used to synthesize biodegradable polyrotaxanes for fabricating blood-contacting devices.
  • Co-polymer based on (2-hydroxypropyl)-α-cyclodextrin cross-linked with polyethylenimine can be used as a gene delivery vector.
  • It can also be used as stabilizer for antibacterial iodine formulations, as it forms a stable inclusion complex with iodine and improves aqueous solubility.

General description

(2-Hydroxypropyl)-α-cyclodextrin is a hydroxyalkyl derivative of cyclodextrin, which is generally used as a substitute of α-cyclodextrin for potential application in food, cosmetics and pharmaceutical industries. It may be used as a parenteral drug carrier on account of its attractive characteristics such as: a greater extent of solubility in water, high dissolution capacity for weakly soluble analytes, and low toxicity.

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB3753
SDBB0379
STBL0616
STBK8576
STBK7541

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A novel co-polymer based on hydroxypropyl α-cyclodextrin conjugated to low molecular weight polyethylenimine as an in vitro gene delivery vector.
Huang H, et al.
International Journal of Molecular Sciences, 9(11), 2278-2289 (2008)
Effect of biodegradable polyrotaxanes on platelet activation.
Yui N, et al.
Bioconjugate Chemistry, 9(1), 118-125 (1998)
2-Hydroxypropylated cyclodextrins as a sustained-release carrier for fragrance materials
TANAKA M, et al.
Chemical & Pharmaceutical Bulletin, 44(2), 416-420 (1996)
Interaction of iodine with 2-hydroxypropyl-α-cyclodextrin and its bactericidal activity.
Tomono K, et al.
Drug Development and Industrial Pharmacy, 28(10), 1303-1309 (2002)
Benguo Liu et al.
Food chemistry, 134(2), 926-932 (2012-10-31)
The inclusion complexation of (2-hydroxypropyl)-cyclodextrins with flavanones was investigated by phase solubility measurements, as well as thermodynamic and quantum chemical methods. Inclusion complexes were formed between (2-hydroxypropyl)-α-cyclodextrin (HP-α-CD), (2-hydroxypropyl)-β-cyclodextrin (HP-β-CD), (2-hydroxypropyl)-γ-cyclodextrin (HP-γ-CD) and β-cyclodextrin (β-CD) and four flavanones (naringenin, naringin
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