2-Hydroxypropyl-β-cyclodextrin CAS 128446-35-5

Introduction：Basic information about 2-Hydroxypropyl-β-cyclodextrin CAS 128446-35-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

2-Hydroxypropyl-β-cyclodextrin Basic information

• Product Name: 2-Hydroxypropyl-β-cyclodextrin
• Synonyms: beta-cyclodextrin,2-hydroxypropylether;(2-Hydroxypropyl)-^b-cyclodextrin, avge. MW ca 1340;(2-Hydroxypropyl)-^b-cyclodextrin, avge. MW ca 1400;Hydroxypropyl-beta-cyclodextrin,97%;(2-Hydroxypropyl)-beta-cyclode;(2-Hydroxypropyl)-beta-cyclodextrin, avge. MW ca 1400;(2-Hydroxypropyl)-beta-cyclodextrin, MW ca 1250-1480;(2-Hydroxypropyl)-β-cyclodextrin ,97%
• CAS: 128446-35-5
• MF: C63H112O42
• MW: 1541.54
• EINECS: 420-920-1
• Product Categories: Other APIs;Carbohydrates & Derivatives;CyclodextrinsSynthetic Reagents;Cell Signaling and Neuroscience;Lipids and Lipid Carriers;Reagents and Supplements;Signal Transduction Research Tools;Biochemistry;Cyclodextrins;Functional Materials;Macrocycles for Host-Guest Chemistry;Oligosaccharides;Sugars;Chelation/Complexation Compounds;Synthetic Reagents;CyclodextrinsCell Culture;128446-35-5
• Mol File: 128446-35-5.mol

2-Hydroxypropyl-β-cyclodextrin Chemical Properties

• 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)
• Optical Rotation: [α]26/D +139°, c = 1 in H2O
• biological source: synthetic (organic)
• Water Solubility: Soluble in water.
• Major Application: pharmaceutical (small molecule)
• Cosmetics Ingredients Functions: SKIN CONDITIONING FRAGRANCE
• InChIKey: ODLHGICHYURWBS-FOSILIAISA-N
• LogP: -4 at 20℃
• Surface tension: 63.6-65mN/m at 1g/L and 22℃
• EPA Substance Registry System: .beta.-Cyclodextrin, 2-hydroxypropyl ethers (128446-35-5)

Safety Information

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: GU2293332
• TSCA: TSCA listed
• HS Code: 29400090
• Storage Class: 11 - Combustible Solids
• Toxicity: mouse,LD,intravenous,> 5gm/kg (5000mg/kg),Journal of Pharmaceutical Sciences. Vol. 84, Pg. 1223, 1995.

2-Hydroxypropyl-β-cyclodextrin Usage And Synthesis

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

White to slightly yellow powder

Chemical Properties

Hydroxypropyl betadex occurs as a white or almost white,amorphous or crystalline powder.

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.

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

Production Methods

Hydroxypropyl betadex is prepared by the treatment of an alkalinesolution of b-cyclodextrin with propylene oxide. The substitutionpattern can be influenced by varying the pH. Formation of O-6 andO-2 substituted products is favored by high and low alkaliconcentration, respectively. The mixture of products producedmay 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 pharmaceuticsand has principally been used as a solubilizer forhydrophobic 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 astabilizer during processing and storage of formulations.
Hydroxypropyl betadex inclusion complexes have been reportedto show mechanical properties distinct from the pure materials.The reported advantage of hydroxypropyl betadex over unsubstitutedb-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 beenreviewed, and in general, the material was found to be of lowtoxicity. It has been suggested that hydroxypropyl betadex mayhave a synergistic toxic effect with, for example, carcinogens, byincreasing their solubility and thus bioavailability.

storage

Store in well-closed containers.

Regulatory Status

Included in oral and parenteral medicinal products. Included in aninjectable preparation licensed in the UK for intramuscular orintravenous 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.

2-Hydroxypropyl-β-cyclodextrin Preparation Products And Raw materials

• Raw materials: β-Cyclodextrin-->Propylene oxide