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Hydroxypropyl 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.
Hydroxypropyl cyclodextrin is generally employed as a substitute for α-, β- and γ-cyclodextrins.
Hydroxypropyl cyclodextrin occurs as a white or almost white, amorphous or crystalline powder.
CAS: 128446-35-5
MF: C63H112O42
MW: 1541.54
EINECS: 420-920-1
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%
Hydroxypropyl cyclodextrin derivative is a functionalized cyclic oligosaccharide composed of seven glucose units, characterized by a hydrophilic exterior and a lipophilic cavity (bigger than α-CD and smaller than γ-CDs), which allows it to encapsulate various guest molecules.
Hydroxypropyl cyclodextrin feature facilitates its use in multiple applications, including pharmaceuticals, food enhancement, and cosmetics.
In the pharmaceutical industry, Hydroxypropyl cyclodextrin enhances the solubility and stability of poorly water-soluble drugs, improving their bioavailability and efficacy while also masking unpleasant tastes.
The food sector utilizes Hydroxypropyl cyclodextrin as a stabilizer for flavors, colors, and nutrients, extending shelf life by protecting sensitive ingredients from degradation.
In cosmetics, Hydroxypropyl cyclodextrin serves as a complexing agent for fragrances and active components, ensuring their stability and controlled release.
Hydroxypropyl cyclodextrin's use expands to many other fields, including nanotechnology for drug delivery systems, environmental remediation for extracting organic pollutants, textiles for slow-release fragrances, and analytical chemistry for chiral separation.
Hydroxypropyl 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)
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℃
EPA Substance Registry System:Hydroxypropyl cyclodextrin (128446-35-5)
Structure
Hydroxypropyl cyclodextrin 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.
Uses
Hydroxypropyl cyclodextrin can be used as selective estrogen receptor modulator for the prevention of osteoporosis.
Hydroxypropyl cyclodextrin 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.
In the pharmaceutical industry, Hydroxypropyl cyclodextrin is an ideal injection solubilizer and drug excipient due to its relatively low relative surface activity and hemolytic activity and no irritation to muscles.
Pharmaceutical Applications
Hydroxypropyl cyclodextrin 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.
Hydroxypropyl cyclodextrin has also been shown to act as a stabilizer during processing and storage of formulations.
Hydroxypropyl cyclodextrin inclusion complexes have been reported to show mechanical properties distinct from the pure materials.
The reported advantage of Hydroxypropyl cyclodextrin over unsubstituted b-cyclodextrin is its greater water solubility.
Production Methods
Hydroxypropyl cyclodextrin 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.
Side effects
Hydroxypropyl cyclodextrin 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.
