Cyclooctapentylose

• CAS: 17465-86-0
• Catalog Number: ACM17465860
• Category: Main Products
• Molecular Weight: 1297.12
• Molecular Formula: C₄₈H₈₀O₄₀
• Synonyms: SCHARDINGER GAMMA-DEXTRIN;CYCLOFLO(TM) 42;CYCLOOCTAOSE;CYCLOOCTAAMYLOSE;CYCLOMALTOOCTAOSE;GAMMA-CYCLODEXTRIN;cyclooctapentylose;GAMMA-CYCLODEXTRIN CELL CULTURE TESTED
• IUPAC Name: γ-cyclodextrin
• Melting Point: ≥300°C
• Density: 1.624 g/cm³
• Appearance: powder
• Exact Mass: 1296.42000
• Hazard Statements: Xi
• Safety Description: 26-36-24/25-22
• WGK Germany: 2

Case Study

Application of γ-Cyclodextrin in Pharmaceutical, Food and Other Industries

Saokham, Phennapha, et al. International journal of pharmaceutics, 2017, 516(1-2), 278-292.

· γ-Cyclodextrin in Pharmaceutical Applications
γ-Cyclodextrin (γCD) represents a cyclic oligosaccharide obtained from bacterial starch breakdown and functions as both a solubilizing agent and stabilizer within pharmaceutical formulations. With a molecular weight of 1297 Da, γCD is a large, hydrophilic molecule that does not easily cross biological membranes and is swiftly broken down by gut bacteria. In humans, it is metabolized by α-amylase present in saliva, bile, and tears, resulting in negligible bioavailability. After parenteral administration, γCD is promptly excreted unchanged in urine. γCD shares the ability with other cyclodextrins to create water-soluble inclusion complexes with compounds that exhibit poor solubility. Among natural αCD and βCD variants γCD shows superior qualities with the biggest hydrophobic cavity and top water solubility paired with the best toxicological profile.
· γ-Cyclodextrin in Non-Pharmaceutical Applications
As a stabilizer and carrier γCD works to maintain the integrity of flavors, colors, oil-soluble vitamins and polyunsaturated fatty acids in food manufacturing. It serves as an emulsion stabilizer for products including bread spreads, frozen dairy desserts, and ready-to-eat dairy items. The estimated dietary intake of γCD from food is around 9 g per person per day at the 90th percentile, and 4 g per person per day for those consuming meal replacements containing PUFAs.
Due to their complexation capabilities, cyclodextrins have diverse industrial applications. γCD, with its relatively large central cavity and good water solubility, offers advantages over other unsubstituted cyclodextrins. Additional industrial uses of γCD, beyond pharmaceuticals and food, are listed in the table.

Graphene/C60 Nanohybrids via γ-Cyclodextrin Host-Guest Chemistry for Phototherapy

Hu, Zhen, et al. Nanoscale, 2017, 9(25), 8825-8833.

The creation of a versatile carrier involved assembling folic acid-functionalized graphene (GO-FA) with γ-cyclodextrin (γ-CD) on its surface through π-π interactions to produce hybrid structures that combine drug storage and tumor targeting features. Then, the γ-CD-modified graphene structure GO-FA/Py-γ-CD can host pure C60 molecules which enables the creation of the GO-FA/Py-γ-CD/C60 nanohybrid. The combination of GO-FA with γ-CD and C60 prevents C60 aggregation while boosting cellular uptake and light absorption before showing improved phototherapy results in GO-FA/Py-γ-CD/C60.
· Synthesis of Pyrene-Modified γ-CD (Py-γ-CD)
The solution came about when 393.6 mg of amino γ-CD and 172.2 mg of 1-pyrenebutyric acid dissolved together in 100 mL of dimethylformamide (DMF) under ultrasonic conditions. The solution received HOBT (202.2 mg, 1.50 mmol) and DCC (309.0 mg, 1.50 mmol) while an ice bath and nitrogen atmosphere were sustained. The reaction mixture underwent stirring at room temperature over 72 hours. After precipitation, washing and drying, pale yellow powder Py-γ-CD was obtained with a yield of 46.3%.
· Preparation of GO-FA/Py-γ-CD Hybrid
GO-FA (20 mg) underwent dispersion in 50 mL of aqueous NaOH solution (pH 12) through the use of ultrasonic waves. Then, the solution received an addition of 50 mg Py-γ-CD. The mixture underwent stirring for 24 hours under a nitrogen atmosphere which enabled the formation of the GO-FA/Py-γ-CD hybrid through π-π interactions. The product GO-FA/Py-γ-CD Hybrid was obtained after dialysis and centrifugation with a yield of 63.7%.

Synthetic Use

Downstream Synthesis Route 1

• 134-03-2
• 17465-86-0

• 129499-78-1

Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 92, p. 19 - 23

* For details of the synthesis route, please refer to the original source to ensure accuracy.