Cyclohexapentylose
[CAS# 10016-20-3]

Identification

• Classification: Biochemical >> Carbohydrate >> Oligosaccharide
• Name: Cyclohexapentylose
• Synonyms: alpha-Cyclodextrin; Cyclohexaamylose;(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31R,32R,33R,34R,35R,36R,37R,38R,39R,40R,41R,42R)-5,10,15,20,25,30-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29-dodecaoxaheptacyclo[26.2.2.23,6.28,11.213,16.218,21.223,26]dotetracontane-31,32,33,34,35,36,37,38,39,40,41,42-dodecol
• Molecular Formula: C₃₆H₆₀O₃₀
• Molecular Weight: 972.84
• CAS Registry Number: 10016-20-3
• EC Number: 233-007-4
• SMILES: C([C@@H]1[C@@H]2[C@@H]([C@H]([C@H](O1)O[C@@H]3[C@H](O[C@@H]([C@@H]([C@H]3O)O)O[C@@H]4[C@H](O[C@@H]([C@@H]([C@H]4O)O)O[C@@H]5[C@H](O[C@@H]([C@@H]([C@H]5O)O)O[C@@H]6[C@H](O[C@@H]([C@@H]([C@H]6O)O)O[C@@H]7[C@H](O[C@H](O2)[C@@H]([C@H]7O)O)CO)CO)CO)CO)CO)O)O)O

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.591, Calc.^*
• Melting Point: 278 °C
• Boiling Point: 1410.8±60.0 °C (760 mmHg), Calc.^*
• Flash Point: 807.1±32.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H319
• Safety Statements: P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Cyclohexapentylose, also known as α-cyclodextrin, is a cyclic oligosaccharide composed of six glucose units linked by α(1→4) glycosidic bonds. It is a member of the cyclodextrin family, which also includes β-cyclodextrin (seven glucose units) and γ-cyclodextrin (eight glucose units). Cyclohexapentylose is produced through the enzymatic degradation of starch using cyclodextrin glucanotransferase (CGTase), a process that selectively forms cyclic structures from linear polysaccharides.

Cyclohexapentylose is widely used as a solubilizing agent due to its ability to form inclusion complexes with hydrophobic molecules. Its toroidal structure features a hydrophobic internal cavity and a hydrophilic outer surface, enabling it to encapsulate poorly water-soluble compounds and improve their solubility and stability. This property is particularly valuable in pharmaceutical applications, where it is employed to enhance the bioavailability of certain drugs. By forming non-covalent host-guest complexes, cyclohexapentylose can protect active pharmaceutical ingredients from degradation and facilitate their controlled release.

In the food industry, cyclohexapentylose functions as a stabilizer, emulsifier, and flavor carrier. It can encapsulate volatile compounds, protecting them from oxidation and extending the shelf life of food products. Additionally, it is used to mask undesirable tastes and odors in certain formulations. Regulatory authorities in various regions have approved its use as a food additive, considering it safe for human consumption within specified limits.

Cyclohexapentylose also plays a role in cosmetics and personal care products, where it is used to enhance the solubility of active ingredients in formulations such as creams and lotions. Its ability to modulate the release of encapsulated compounds makes it a useful component in skincare applications.

Beyond pharmaceutical and consumer product applications, cyclohexapentylose is utilized in analytical chemistry, biotechnology, and environmental science. It can be employed in chromatography as a chiral selector for enantiomeric separation, as well as in enzymatic research to study carbohydrate interactions. Additionally, its complexation properties have been explored for removing contaminants from water and stabilizing reactive substances in industrial processes.

Cyclohexapentylose is biodegradable and generally regarded as non-toxic. It is excreted largely unchanged by the human body, as digestive enzymes have limited capacity to hydrolyze the cyclic structure. Due to its functional versatility and favorable safety profile, cyclohexapentylose remains a key material in numerous scientific and industrial applications.

References

2025. Ratio type nanoprobe with boric acid as recognition unit for imaging intracellular H2O2 with SERS. Talanta, 281.
DOI: 10.1016/j.talanta.2024.127224

2025. Modulating room temperature phosphorescence of acrylamide by stepwise rigidification for its detection in potato crisps. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 328.
DOI: 10.1016/j.saa.2024.125372