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2-Hydroxypropyl-β-cyclodextrin

Structure

CAS No.128446-35-5
Chemical Name:2-Hydroxypropyl-β-cyclodextrin
CBNumber:CB6204503
Molecular Formula:C63H112O42
Formula Weight:1541.54
MOL File:128446-35-5.mol

2-Hydroxypropyl-β-cyclodextrin Property

Melting point 278 °C (dec.)
Boiling point 400℃
Density 1.05 at 20.3℃
refractive index 125 ° (C=1, H2O)
storage temp. room temp
solubility H₂O: 45 % (w/v)
form solution (clear, colorless)
color White to slightly yellow
PH 5.0-7.0 (20g/L in H2O)
biological source synthetic (organic)
optical activity [α]26/D +139°, c = 1 in H2O
Water Solubility Soluble in water.
InChIKey ODLHGICHYURWBS-FOSILIAISA-N
LogP -4 at 20℃
Surface tension 63.6-65mN/m at 1g/L and 22℃
FDA UNII HYDROXYPROPYL BETADEX (1I96OHX6EK)
ADRABETADEX (8W6Q67R6NX)
EPA Substance Registry System .beta.-Cyclodextrin, 2-hydroxypropyl ethers (128446-35-5)
UNSPSC Code 41116107
NACRES NA.77

Safety

Safety Statements :24/25
WGK Germany :3
RTECS :GU2293332
TSCA :Yes
HS Code :29400090
Toxicity :mouse,LD,intravenous,> 5gm/kg (5000mg/kg),Journal of Pharmaceutical Sciences. Vol. 84, Pg. 1223, 1995.

NFPA 704:

	1
1		1

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H315-H319-H335
Precautionary statements P280-P261

2-Hydroxypropyl-β-cyclodextrin Price More Price(36)

Brand: Sigma-Aldrich(India)
Product number: H107
Product name : (2-Hydroxypropyl)-β-cyclodextrin
Purity: powder
Packaging: 5G
Price: ₹12892.58
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: PHR1440
Product name : Hydroxypropyl Beta Cyclodextrin
Purity: Pharmaceutical Secondary Standard; Certified Reference Material
Packaging: 1G
Price: ₹8919.8
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: H107
Product name : (2-Hydroxypropyl)-β-cyclodextrin
Purity: powder
Packaging: 5X5G
Price: ₹53594.58
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: H107
Product name : (2-Hydroxypropyl)-β-cyclodextrin
Purity: powder
Packaging: 100G
Price: ₹104612.8
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: C0926
Product name : (2-Hydroxypropyl)-β-cyclodextrin
Purity: powder, BioReagent, suitable for cell culture
Packaging: 5G
Price: ₹35733.33
Updated: 2022/06/14
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2-Hydroxypropyl-β-cyclodextrin Chemical Properties,Usage,Production

Structure 2-Hydroxypropyl-β-cyclodextrins (HPβCDs) are synthesized by condensation between β-cyclo-dextrin (βCD) and propylene oxide. Structure of 2-hydroxypropyl-β-cyclodextrin (HPβCD) where R = H or CH2-CHOH-CH3 is shown below. There are 21 (red) hydroxyl groups on βCD, which are potential substitution sites for the condensation reaction with propylene oxide to yield various species of HPβCD with different degrees of substitution depending upon how many sites are substituted[3].
Chemical Properties Hydroxypropyl betadex occurs as a white or almost white, amorphous or crystalline powder.
Chemical Properties White to slightly yellow powder
Uses enteric coating, sustained release formulations, buccal and transdermal drug delivery
Uses 2-Hydroxypropyl-β-cyclodextrin can be used as selective estrogen receptor modulator for the prevention of osteoporosis
Uses 2-Hydroxypropyl-β-cyclodextrin (HBC) is a widely used modified cyclodextrin, the lipophilic cavity formed by 7 glucose units. Drug solubility in water is greatly enhanced by complexing with 2-Hydroxypropyl-β-cyclodextrin.
Production Methods Hydroxypropyl betadex is prepared by the treatment of an alkaline solution of b-cyclodextrin with propylene oxide. The substitution pattern can be influenced by varying the pH. Formation of O-6 and O-2 substituted products is favored by high and low alkali concentration, respectively. The mixture of products produced may be refined by preparative chromatography.
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.
Pharmaceutical Applications Hydroxypropyl betadex has been widely investigated in pharmaceutics and has principally been used as a solubilizer for hydrophobic molecules in oral liquids,oral solids, parenterals, pressurized metered dose inhalers, dry powder inhalers, and topical formulations. It has also been shown to act as a stabilizer during processing and storage of formulations.
Hydroxypropyl betadex inclusion complexes have been reported to show mechanical properties distinct from the pure materials. The reported advantage of hydroxypropyl betadex over unsubstituted b-cyclodextrin is its greater water solubility.
Biological Activity Cell treatment with HPβCD results in the activation of the transcription factor EB, a master regulator of lysosomal function and autophagy, and in the enhancement of the cellular autophagic clearance capacity. HPβCD administration promotes transcription factor EB-mediated clearance of proteolipid aggregates that accumulate due to inefficient activity of the lysosome-autophagy system in cells derived from a patient with a lysosomal storage disorder. Interestingly, HPβCD-mediated activation of autophagy was found not to be associated with activation of apoptotic pathways[2].
Side effects 2-Hydroxypropyl-β-cyclodextrin (HP-beta-CD) has been shown to be well tolerated in humans, with the main adverse event being diarrhoea and there have been no adverse events on kidney function, documented to date[1].
Safety The pharmaceutical toxicology of hydroxypropyl betadex has been reviewed, and in general, the material was found to be of low toxicity. It has been suggested that hydroxypropyl betadex may have a synergistic toxic effect with, for example, carcinogens, by increasing their solubility and thus bioavailability.
storage Store in well-closed containers.
Regulatory Status Included in oral and parenteral medicinal products. Included in an injectable preparation licensed in the UK for intramuscular or intravenous administration.
References [1] Sarah Gould, Robert C. Scott. “2-Hydroxypropyl-β-cyclodextrin (HP-β-CD): A toxicology review.” Food and Chemical Toxicology 43 10 (2005): Pages 1451-1459.
[2] Wensi Song. “2-Hydroxypropyl-β-cyclodextrin promotes transcription factor EB-mediated activation of autophagy: implications for therapy.” The Journal of Biological Chemistry (2014): 10211–22.
[3] Alfred L Yergey. “Correction: Characterization of hydroxypropyl-beta-cyclodextrins used in the treatment of Niemann-Pick Disease type C1.” PLoS ONE (2018): e0192424.