alpha-Cyclodextrin
Alfadex
CAS: 10016-20-3
Molecular Formula: C36 H60 O30
alpha-Cyclodextrin - Names and Identifiers
| Name | Alfadex |
| Synonyms | Alfadex alpha-dextrin CYCLOHEXAAMYLOSE cyclomaltohexose CYCLOMALTOHEXOSE CYCLOMALTOHEXAOSE alpha-Cycloamylose Cyclohexapentylose alpha-Cyclodextrin alpha-cycloamylose ALPHA-CYCLODEXTRIN Cyclohexaamylose hydrate SCHARDINGER ALPHA-DEXTRIN 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, 5,10,15,20,25,30-hexakis(hydroxymethyl)- 5,10,15,20,25,30-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29-dodecaoxaheptacyclo[26.2.2.2~3,6~.2~8,11~.2~13,16~.2~18,21~.2~23,26~]dotetracontane-31,32,33,34,35,36,37,38,39,40,41,42-dodecol (non-preferred name) (1S,3R,6S,8R,11S,13R,16S,18R,21S,23R,26S,28R)-5,10,15,20,25,30-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29-dodecaoxaheptacyclo[26.2.2.2~3,6~.2~8,11~.2~13,16~.2~18,21~.2~23,26~]dotetracontane-31,32,33,34,35,36,37,38,39,40,41,42-dodecol (non-preferred 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[26.2.2.2~3,6~.2~8,11~.2~13,16~.2~18,21~.2~23,26~]dotetracontane-31,32,33,34,35,36,37,38,39,40,41,42-dodecol (non-preferred name) |
| CAS | 10016-20-3 |
| EINECS | 233-007-4 |
| InChI | InChI=1/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 |
alpha-Cyclodextrin - Physico-chemical Properties
| Molecular Formula | C36 H60 O30 |
| Molar Mass | 972.84 |
| Density | 1.2580 (rough estimate) |
| Melting Point | >278 °C (dec.) (lit.) |
| Boling Point | 784.04°C (rough estimate) |
| Specific Rotation(α) | [α]D25 +146～+151° (c=1, H2O) (After Drying) |
| Flash Point | 807.051°C |
| Water Solubility | Soluble in water at 1%(w/v) |
| Solubility | Soluble in water (145 mg/ml at 20 °C). Insoluble in ethanol, and acetone. |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | White powder |
| Color | White |
| Merck | 14,2718 |
| BRN | 4227442 |
| pKa | 11.77±0.70(Predicted) |
| PH | 5.0-8.0 (1% in solution) |
| Storage Condition | 2-8°C |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Refractive Index | 1.7500 (estimate) |
| MDL | MFCD00078207 |
| Physical and Chemical Properties | Appearance: white crystal powder Melting Point: 278 ℃ water solubility: 145G/L (25 ℃) |
| Use | Suitable for high-grade flavors, spices, cosmetics and pharmaceutical industries. |
alpha-Cyclodextrin - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36 - Irritating to the eyes R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | GU2292000 |
| TSCA | Yes |
| HS Code | 29400090 |
alpha-Cyclodextrin - Reference
| Reference Show more | 1. Liu Chaoyue Jia Lihua Guo Xiangfeng. Fluorescence Spectra of 1-Bromopyrene in Cyclodextrin Aqueous Solution [J]. Journal of Qiqihar University (Natural Science Edition) 2015 31(003):13-15. 2. Xu Yang, Hou Zhanqun, Xu Duoxia, et al. Effects of Starch Derivatives on Physical Properties of Spray Drying Monascus Pigment [J]. Food and Fermentation Industry, 2018, 044(007):82-88. 3. Liu Zhongbo. Construction of Food Grade Pickering Emulsion Based on Cyclodextrin [D]. Henan Institute of Science and Technology, 2021. 4. Yang Dan, Feng Liang, Liu Jun, Zhao Jing, Li Chao, Zhu Fagen, Shao Jianguo, Jia Xiaobin, Sun E. Study on Improvement of Drug Compliance of Pudilan Anti-inflammatory Oral Liquid for Children Based on Material Property Characterization Technology [J]. World Chinese Medicine, 2020,15(15):2221-2227. 5. Han Dongxu, Li Tianle, Miao Ruidan, Wang Yao, Liu Liyan, Yu Zhan. Solubilization of seven-(2, 6-dimethyl)-β-cyclodextrin to luteolin [J]. Modern Chinese Applied Pharmacy, 2020,37(22):2747-2751. 6. Yanping Wu, Yue Xiao, Yuxi Yue, Kai Zhong, Yinglan Zhao, Hong Gao, A deep insight into mechanism for inclusion of 2R,3R-dihydromyricetin with cyclodextrins and the effect of complexation on antioxidant and lipid-lowering activities, Food Hydrocolloids, Vol 7. Zhao, Qian, et al. "Design and fabrication of bilayer hydrogel system with self-healing and detachment properties achieved by near-infrared irradiation." Polymers 9.6 (2017): 237. https://doi.org/10.3390/polym9060237 8. [IF = 9.381] Qiuna Zhou et al. "Preparation and characterization of inclusion complexes formed between baicalein and cyclodextrins." Carbohyd Polym. 2013 Jun;95:733 9. [IF = 4.329] Qian Zhao et al. "Design and Fabrication of Bilayer Hydrogel System with Self-Healing and Detachment Properties Achieved by Near-Infrared Irradiation." Polymers-Basel. 2017 Jun;9(6): 237 10. [IF = 4.24] Hui-da Wan et al. "Preparation, characterization and evaluation of an inclusion complex of steviolbioside with γ-cyclodextrin." Food Biosci. 2018 Dec;26:65 11. [IF = 1.633] Wan Hui-da et al. "Enzymatic production of steviol using a commercial beta-glucose and preparation of its inclusion complex with γ-CD." J Incl Phenom Macro. 2019 Apr;93(3):193-201 12. [IF = 9.147] Yanping Wu et al. "A deep insight into mechanism for inclusion of 2R, 3R-dihydroricetin with cyclodextrins and the effect of complexation on antioxidant and lipid-lowering activities." Food Hydrocolloid. 2020 Jun;103:105718 13. [IF = 4.35] Jianjun Zhou et al. "The Addition of α-cyclodextrin and γ-cyclodextrin Effect Quality of Dough and Prebaked Bread During Frozen Storage." Foods. 2019 May;8(5):174 14. [IF = 1.633] Wan Hui-da et al. "Isosteviol preparation and inclusion complexation of it with γ-cyclodextrin." J Incl Phenom Macro. 2019 Jun;94(1):65-73 |
alpha-Cyclodextrin - Introduction
The water solubility is 14-5g /100ml, insoluble in ethanol, ether and other organic solvents. It starts to decompose when melting and is a natural encapsulation agent.
Last Update：2022-10-16 17:11:20
alpha-Cyclodextrin - Reference Information
| introduction | cyclodextrin (Cyclodextrins, usually referred to as CD), is a class of starch or polysaccharides produced by cyclodextrin glucosyltransferase The general term for the cyclic compound that is connected end to end by the D-glucopyranose unit through the alpha-1,4-glycosidic bond, common molecules with 6, 7 and 8 glucose units are called α-cyclodextrin, β-cyclodextrin and γ-cyclodextrin respectively. Because α-cyclodextrin can form inclusion complexes with many guest molecules, thus changing the physical and chemical properties of guest molecules, such as solubility and stability, it has been widely used in food, medicine, agriculture, textile, environmental protection, cosmetics, biotechnology and analytical chemistry. |
| cyclodextrin | cyclodextrin (CD,Cyclodextrin) is a general term for a class of cyclic oligosaccharides obtained by decomposing starch by cyclodextrin glucosyltransferase secreted by Bacillus, usually containing 6-12 D-( )-glucopyranose units, among them, α-cyclodextrin, β-cyclodextrin and γ-cyclodextrin are the most studied and have practical significance, with six, seven and eight glucose molecular structures respectively. 1891-2030s: Cyclodextrin was discovered, and α cyclodextrin and β cyclodextrin were successfully separated. From the 1970s to the present, the chemical research of cyclodextrin has entered its heyday. Using chemical modification or enzymatic modification, substituents are introduced into cyclodextrin molecules to improve their physical and chemical properties, and the research of cyclodextrin in the fields of medicine, food, cosmetics and analytical chemistry is vigorously carried out. At present, many modified cyclodextrins have been commercialized and put on the market. β-cyclodextrin is currently widely produced and widely used in industry. In recent years, α-cyclodextrin has attracted more and more attention due to its excellent physical and chemical properties and various effects. In addition to the characteristics and uses of other cyclodextrins, α-cyclodextrins are more suitable for inclusions of small molecules due to their inner cavity size smaller than β-cyclodextrins, and applications require higher solubility of cyclodextrins. Alpha-cyclodextrin is also used as a material for soluble food fiber or improving metabolic syndrome in the field of functional foods and drug excipients. Its efficacy of reducing blood sugar concentration and weight loss have also been authoritative certification and market recognition. |
| use | as a new pharmaceutical excipient, betacyclodextrin is mainly used to increase the stability of drugs, prevent oxidation and decomposition of drugs, improve the solubility and bioavailability of drugs, reduce the toxicity and side effects of drugs, and cover up the peculiar smell and odor of drugs. In food manufacturing, it is mainly used to eliminate peculiar smell and odor, improve the stability of spices, flavors and pigments, enhance emulsification and moisture-proof ability to improve the taste of food. It is a good stabilizer, emulsifier and flavoring agent for pharmaceutical, food and cosmetic manufacturing. Cyclodextrin has holes in the center of the ring structure, and there are-CH-oxygen atoms bound to glucosides inside, which are sulfur-water, and the-OH groups in the 2, 3 and 6 positions of glucose are hydrophilic. Other molecules can be complexed into an inclusion through weak van der Waals force. There are many substances that can be encapsulated by cyclodextrins, including rare gases, halogens, dyes, spices, medicines, foods, pesticides and preservatives. After encapsulation, its stability, volatility, solubility and reactivity are improved. This special function of cyclodextrin makes it a wrapping material with wide application value. 1. Use in the pharmaceutical industry The use of cyclodextrin can form an encapsulation (encapsulation) with drugs, which can stabilize (1) unstable drugs;(2) deliquescence, adhesion or liquid drug powdering;(3) insoluble or insoluble drugs are soluble (solubilized), etc. 2. Use in pesticide industry Cyclodextrin package stabilization, some pesticides can withstand storage and improve insecticidal efficiency. 3. Use in the food industry Cyclodextrin is used in the food industry and has the following effects:(1) elimination and masking of specific odors;(2) improvement and improvement of food tissue structure;(3) reduction and removal of bitter taste;(4) Antioxidant effect;(5) Maintaining and improving flavor. 4. Use in daily chemical industry Cyclodextrin can also be used as emulsifier and quality improver in cosmetic manufacturing. It also has deodorization (such as bad breath) and antiseptic effects, and can be used in the manufacture of toothpaste and tooth powder. 5. Other uses can be used as a treatment agent for oily sewage in environmental protection. The aqueous solution of cyclodextrin is used to clean the oil tank, and the waste liquid can be recycled to obtain fuel oil. 6. Use of Cyclodextrin in Chemistry Cyclodextrin is a valuable chemical reagent. When it exists, the fluorescence intensity of the fluorescent pigment will increase significantly, so it can be used for the analysis of proteins and amino acids; it can also be used to separate long-chain organic compounds, racemates, etc. In addition, the adsorbent made of cyclodextrin can be used as adsorption for chromatographic analysis. Biochemical research Cyclodextrin is an ideal host molecule similar to enzymes discovered so far, and it has the characteristics of an enzyme model. Therefore, cyclodextrins have received great attention and been widely used in the fields of catalysis, separation, food and medicine. In addition to the characteristics and uses of other CDs, α-CD is more suitable for inclusion of small molecules because the inner cavity size of α-CD is smaller than β-CD, and applications require high CD solubility. Suitable for high-grade flavors, fragrances, cosmetics and pharmaceutical industries. |
| function and application of α-cyclodextrin | 1) adjust gastrointestinal function and improve constipation α-cyclodextrin will be decomposed by some normally parasitic bacteria in intestinal tract and converted into a series of short-chain fatty acids such as acetic acid, propionic acid and butyric acid. These short-chain fatty acids can inhibit the growth of harmful bacteria in the intestine and help the growth of probiotics such as bifidobacteria. The increase in the number of probiotics in the human body can in turn improve human immunity and prevent enteritis, Intestinal cancer, dysentery and constipation, etc. Alpha-cyclodextrin is widely used in functional foods as an additional material for food fiber or improvement of metabolic syndrome. 2) Prevention and improvement of diabetes α-cyclodextrin can prevent the absorption of sugars in the intestine, promote the excretion of sugars after being wrapped, reduce the peak blood sugar after high starch diet, and achieve the effect of inhibiting the rise of postprandial blood sugar. α-cyclodextrin has a good effect on preventing and improving diabetes, and can be used as an effective hypoglycemic health food raw material for patients with hyperglycemia and patients with type II diabetes to prevent postprandial hyperglycemia. EU Regulation No. 536 of 2013 confirmed in the statement on food nutrition and health that alpha cyclodextrin has been scientifically proven to have the effect of regulating blood sugar. "Eating starch-containing meals containing alpha cyclodextrin can reduce the increase in blood sugar after a meal." If it is noted that a meal of food contains at least 5 grams of alpha cyclodextrin per 50 grams of starch, the manufacturer will allow the product to be marked on the package with hypoglycemic effect. 3) Improve the stability of additives α-cyclodextrin and vitamin E, natural pigments (β-carotene, chlorophyll, etc.), edible flavors (such as rose oil, anethole, etc.) and other additives can be used in combination to improve the stability of additives and facilitate long-term storage or maintenance in food. |
| preparation | 1. cassava starch and distilled water are mixed into pulp according to the concentration of 15%, and stirred at 85 ℃ for 15 minutes to fully swell and dissolve the starch particles. 2. The PH value is adjusted to 5, CGT enzyme is added according to the proportion of 200 units per gram of starch, and then n-decanol with volume accounting for 8% of starch mass is added to react for 6 hours. 3. The n-decanol in the reaction solution is separated by steam distillation. 4. The temperature is adjusted to 50 ℃, and then CGT enzyme is added to make the ratio reach 400 units per gram of starch. Add ethanol accounting for 20% of starch volume, and then react for 10 hours. 5. Filter the reaction liquid directly to collect the filter cake, including the precipitation of the complex formed by ethanol and α-cyclodextrin and the starch without reaction; re-dissolve the filter cake, use the vacuum distillation method to remove the ethanol, and wait for the distillation After finishing, filter the distillate to remove the unreacted starch to obtain an aqueous solution of α-cyclodextrin; evaporate and concentrate the aqueous solution, the crystallization of α-cyclodextrin was obtained by placing it in a low temperature environment of 2 ℃. |
| Chemical properties | Cyclodextrin is a cyclic oligomeric glucose. It is usually composed of 6, 7 or 8 glucose units through α,1-→ 4 bond cyclic phase to the connected crystal. They are called α-, β or γ-cyclodextrin [α-Cyclodex-trinak Cyclohexaamylose,β-Cyclodextrin or Cyclo-heptaamylose,γ-Cyclodextrin or Cyclooctaamylose]. Cyclodextrins do not have reducing ends and have certain stability to acids. Ordinary starch acids are difficult to hydrolyze them. The properties of various cyclodextrins are shown in the following table: α-glucose number 6 molecular weight 972.86 space diameter (× 10-8m) 6 hole depth (× 10-8m) 7-8 crystal shape (anhydrous) needle specific rotation [α]D25 water 150.5 solubility 14.5(g/100g water, 25 ℃) color reaction with iodine green |
| production method | cyclodextrin was discovered by Villers in 1891, and α and β cyclodextrin were successfully separated at the beginning of this century. In 1972-1973, the discovery of bacteria that produced cyclodextrin enzyme (cyclodextrin glucose translocation enzyme, abbreviated as CGT-ase), especially the basophilic bacteria, was of great significance for the large-scale production of cyclodextrin. Using potato, corn, wheat and other processed starch as raw materials, cyclodextrin can be obtained through the following processes: starch suspension [70-80 ℃ liquefaction][60 ℃ reaction with ethanol], heating deactivation, filtration, concentration and drying. |
| NIST chemical information | The information is: webbook.nist.gov provides (external link) |
| EPA chemical information | The information is: offered by ofmpub.epa.gov (external link) |
Last Update：2024-04-09 20:52:54
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