structure of alpha-CYCLODEXTRIN

alpha-CYCLODEXTRIN

CAS No.: 10016-20-3
M. Wt: 972.844
M. Fa: C36H60O30
InChI Key: HFHDHCJBZVLPGP-RWMJIURBSA-N
Appearance: White Solid

Names and Identifiers of alpha-CYCLODEXTRIN

CAS Number

10016-20-3

EC Number

233-007-4

MDL Number

MFCD00078207

IUPAC Name

(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

InChI

InChI=1S/C36H60O30/c37-1-7-25-13(43)19(49)31(55-7)62-26-8(2-38)57-33(21(51)15(26)45)64-28-10(4-40)59-35(23(53)17(28)47)66-30-12(6-42)60-36(24(54)18(30)48)65-29-11(5-41)58-34(22(52)16(29)46)63-27-9(3-39)56-32(61-25)20(50)14(27)44/h7-54H,1-6H2/t7-,8-,9-,10-,11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-,26-,27-,28-,29-,30-,31-,32-,33-,34-,35-,36-/m1/s1

InChIKey

HFHDHCJBZVLPGP-RWMJIURBSA-N

Canonical SMILES

C(C1C2C(C(C(O1)OC3C(OC(C(C3O)O)OC4C(OC(C(C4O)O)OC5C(OC(C(C5O)O)OC6C(OC(C(C6O)O)OC7C(OC(O2)C(C7O)O)CO)CO)CO)CO)CO)O)O)O

Isomeric 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

UNII

Z1LH97KTRM

UNSPSC Code

12352100

Physical and chemical properties of alpha-CYCLODEXTRIN

Acidity coefficient

11.77±0.70(Predicted)

Boiling Point

1410.8±60.0 °C at 760 mmHg

BRN

4227442

Density

1.6±0.1 g/cm3

Exact Mass

972.316956

Flash Point

807.1±32.9 °C

H Bond Acceptors

30

H Bond Donors

18

Index of Refraction

1.591

LogP

-6.55

Melting Point

532 °F (decomposes) (NTP, 1992)

Merck

14,2718

Molecular Formula

C36H60O30

Molecular Weight

972.844

optical activity

[α]20/D +136±3°, c = 10% in H2O

pH

5.0-8.0 (1% in solution)

PSA

474.90000

Solubility

H2O: 50 mg/mL

Specific rotation

[α]D25 +146～+151° (c=1, H2O) (After Drying)

Stability

Stable. Combustible. Incompatible with strong oxidizing agents.

Storage condition

Store at RT.

Vapour Pressure

0.0±0.6 mmHg at 25°C

Water Solubility

H2O: 50 mg/mL

Solubility of alpha-CYCLODEXTRIN

Solvent Dissolution Behavior Temperature Effect pH Effect
Water Soluble, solubility approximately 14.5% (w/w) Solubility increases significantly with rising temperature Stable under neutral to weakly acidic conditions; may hydrolyze under strong alkaline conditions
Ethanol Slightly soluble (approximately 0.1–0.3%) Solubility improves slightly with increasing temperature, but remains low overall Insensitive to pH changes, but high ethanol concentrations may reduce solubility
Methanol Slightly soluble Modest improvement with temperature, but still limited Similar to ethanol; stability is minimally affected by environmental conditions
Acetone Practically insoluble No significant improvement No notable effect
Acetonitrile Very slightly soluble Virtually no improvement No significant effect
Dimethyl sulfoxide (DMSO) Freely soluble (>20%) Solubility increases with rising temperature Stable over a wide pH range, but may degrade under strongly acidic or basic conditions
Glycerol Soluble (solubility slightly lower than in water) Increased temperature promotes dissolution Stable under neutral conditions; side reactions may occur under strong acidic conditions

Safety Information of alpha-CYCLODEXTRIN

Pictograms

Signal Word

 Warning

Safety Data Sheet
Supports customized editing of SDS information and downloading in PDF documents.

Key Milestone of alpha-CYCLODEXTRIN

Year Event Description
1891 First Discovery French scientist Villiers first isolated a crystalline substance from the fermentation products of starch using Bacillus amylobacter. This substance was later confirmed to be a mixture of cyclodextrins, including α-cyclodextrin.
1903–1911 Initial Structural Elucidation German chemist Franz Schardinger further studied this compound, isolating two major components (later named α- and β-cyclodextrins), and confirmed they were composed of glucose units. As a result, cyclodextrins were initially referred to as "Schardinger dextrins."
1930s–1950s Chemical Structure Confirmation Through chemical degradation and X-ray diffraction analyses, scientists confirmed that α-cyclodextrin consists of six D-glucopyranose units linked by α-1,4-glycosidic bonds, forming a cyclic oligosaccharide.
1950s–1970s Process Optimization for Production Methods utilizing cyclodextrin glucanotransferase (CGTase) to efficiently produce α-cyclodextrin from starch were developed, significantly improving yield and purity, laying the foundation for industrial-scale production.
1970s–1980s Deepened Research on Inclusion Properties It was discovered that α-cyclodextrin has a hydrophobic cavity and a hydrophilic outer surface, enabling it to form inclusion complexes with various small molecules. This property enhances solubility, stability, and bioavailability, driving its exploration in drug delivery systems.
1980s–1990s Applications in Food and Cosmetics Due to its high safety profile (GRAS status), α-cyclodextrin was widely used in the food industry (e.g., stabilizing flavors, removing off-flavors) and cosmetics (e.g., controlled release of active ingredients, improved stability).
1990s–2000s Development as Pharmaceutical Excipients α-Cyclodextrin and its derivatives were employed to enhance the solubility and stability of poorly water-soluble drugs; some formulations entered clinical research. Systematic toxicological and pharmacokinetic evaluations were also conducted.
2000s–2010s Expansion into Functional Materials Applications expanded into environmental remediation (e.g., adsorption of organic pollutants), analytical chemistry (chiral separation), and nanotechnology (construction of supramolecular assemblies).
2010s – Present Emerging Applications and Regulatory Approval Approved by the EU, FDA, and other regulatory bodies as a food additive (E459) and pharmaceutical excipient. Active research continues in frontier areas such as precision medicine, targeted delivery, and smart responsive materials.

Applications of alpha-CYCLODEXTRIN

Alpha-Cyclodextrin6SmallModerateDrug delivery, food stabilizationBeta-Cyclodextrin7MediumHighDrug delivery, chromatographyGamma-Cyclodextrin8LargeVery highDrug delivery, flavor encapsulation

Interaction Studies of alpha-CYCLODEXTRIN

Studies on interaction dynamics between alpha-cyclodextrin and various guest molecules reveal that the size and polarity of the guest significantly influence complex formation. The binding strength varies based on the compatibility of the guest molecule with the hydrophobic cavity of alpha-cyclodextrin. Research indicates that smaller, less polar molecules tend to form more stable complexes compared to larger or more polar ones. Additionally, pH and temperature can affect the stability of these complexes.

Biological Activity of alpha-CYCLODEXTRIN

Alpha-cyclodextrin exhibits notable biological activities, including enhancing the solubility and bioavailability of poorly soluble drugs. Its hydrophilic exterior and hydrophobic cavity allow it to interact with various biological molecules, which can improve drug delivery systems. Furthermore, alpha-cyclodextrin has been studied for its potential use in encapsulating flavors and fragrances in the food industry, thereby improving product stability and sensory properties.

Physical sample testing spectrum (NMR) of alpha-CYCLODEXTRIN

Physical sample testing spectrum (NMR) of alpha-CYCLODEXTRIN