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Sigma-Aldrich

(2-Hydroxypropyl)-β-cyclodextrin

average Mw ~1,460

Synonym(s):

(2-Hydroxypropyl)-beta-cyclodextrin, HP-β-CD

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$167.00
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$362.00
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5 G
$63.70
25 G
$167.00
100 G
$362.00
500 G
$1,160.00

About This Item

CAS Number:
128446-35-5
EC Number:
420-920-1
UNSPSC Code:
12352201
PubChem Substance ID:
24859911
NACRES:
NA.22
form:
powder

$63.70

In StockDetails

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form

powder

Quality Level

200

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.[1]

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.[2]
  • 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.[3]
  • As a mobile phase additive for the effective separation of β-carbolines by HPLC.[4]
  • In cyclodextrin-modified micellar electrokinetic chromatography (CD-modified MEKC) for the determination of sertraline hydrochloride and the synthesis-related products.[5]

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.[1][6] HP-β-CD can be used to prepare an inclusion complex with ropivacaine (RVC) to increase the solubility of RVC for efficient drug delivery.[7]
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.

Storage Class

13 - Non Combustible Solids

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCM4393
BCCL3259
BCCL9564
WXBF1726V
WXBD9912V

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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)
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
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
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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Questions

1–5 of 5 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. I purchased this material which lists the "molar substitution" as 0.8-1.0 with a MW of ~1460. The C of A specifies the molar substitution as 0.9, does this correspond to MW of 1500? And what is the distribution of MW?

    1 answer

    1. Yes, the molar substitution is used to determine the 1500 MW. The following example calculations may be helpful:
      Molecular Substitution = (1460 -1135.12) / 7 / 58.09 09 = 0.80 (# of substituted units per ring)
      Where 1460 is the average molecular weight
      Where 1135.12 is the molecular weight of the material if it had no substitution (if all R were H and not C3OH7)
      Where 7 is the number of repeating glucopyranose units for this compound
      Where 58.09 is the molecular weight of one substitution - C3OH7

      Please see the image below for an image of this cyclodextrin molecule.
      Please see the link below to review additional information regarding cyclodextrins:
      https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/cell-culture-and-cell-culture-analysis/mammalian-cell-culture/cyclodextrins

      Helpful?

  4. How can I make a stock solution for this chemical? Is there a protocol? Thank you!

    1 answer

    1. This material is freely soluble in water and is often used to enhance the solubility of lipophilic compounds. Please see the link below to review the datasheet for C0926, the cell culture tested version of this cyclodextrin, which applies to this item as well:
      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/944/233/c0926pis.pdf

      Please see the following link to review additional information regarding general cyclodextrin properties and applications:
      https://www.sigmaaldrich.com/technical-documents/technical-article/cell-culture-and-cell-culture-analysis/mammalian-cell-culture/cyclodextrins

      Helpful?

  5. Hi, I would like to know if this product is USP/NF grade. In other words, does it meet the USP/NF monograph test requirements? Thank you!

    1 answer

    1. This product is not a USP/NF tested product. Please see the link below to reivew product 1.42020, which is an NF grade product option.
      https://www.sigmaaldrich.com/US/en/product/mm/142020

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