-Cyclodextrin
gamma-Cyclodextrin
CAS: 17465-86-0
Molecular Formula: C48H80O40
-Cyclodextrin - Names and Identifiers
| Name | gamma-Cyclodextrin |
| Synonyms | CYCLOOCTAOSE -Cyclodextrin CYCLOFLO(TM) 42 CYCLOOCTAAMYLOSE CYCLOMALTOOCTAOSE Cyclooctapentylose cyclooctapentylose gamma-Cyclodextrin GAMMA-CYCLODEXTRIN gamma-Schardinger dextrin SCHARDINGER GAMMA-DEXTRIN 1,2,3,6-tetra-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-alpha-D-glucopyranose 5,10,15,20,25,30,35,40-octakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34,37,39-hexadecaoxanonacyclo[36.2.2.2~3,6~.2~8,11~.2~13,16~.2~18,21~.2~23,26~.2~28,31~.2~33,36~]hexapentacontane-41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56-hexadecol (non-preferred name) (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36S,38R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R,50R,51R,52R,53R,54R,55R,56R)-5,10,15,20,25,30,35,40-octakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34,37,39-hexadecaoxanonacyclo[36.2.2.2~3,6~.2~8,11~.2~13,16~.2~18,21~.2~23,26~.2~28,31~.2~33,36~]hexapentacontane-41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56-hexadecol (non-preferred name) |
| CAS | 17465-86-0 |
| EINECS | 241-482-4 |
| InChI | InChI=1/C48H80O40/c49-1-9-33-17(57)25(65)41(73-9)82-34-10(2-50)75-43(27(67)19(34)59)84-36-12(4-52)77-45(29(69)21(36)61)86-38-14(6-54)79-47(31(71)23(38)63)88-40-16(8-56)80-48(32(72)24(40)64)87-39-15(7-55)78-46(30(70)22(39)62)85-37-13(5-53)76-44(28(68)20(37)60)83-35-11(3-51)74-42(81-33)26(66)18(35)58/h9-72H,1-8H2/t9-,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-,37-,38-,39-,40-,41-,42-,43-,44-,45-,46-,47-,48-/m1/s1 |
| InChIKey | GDSRMADSINPKSL-HSEONFRVSA-N |
-Cyclodextrin - Physico-chemical Properties
| Molecular Formula | C48H80O40 |
| Molar Mass | 1297.12 |
| Density | 1.2064 (rough estimate) |
| Melting Point | ≥300°C |
| Boling Point | 845.2°C (rough estimate) |
| Specific Rotation(α) | [α]D25 +174～+179° (c=1, H2O) (After Drying) |
| Flash Point | 450℃ |
| Water Solubility | 232g/L(25 ºC) |
| Solubility | 1 M NaOH: 25mg/mL, may be clear to slightly hazy |
| Appearance | White or slightly yellow powder or tetragonal flake or rectangular rod crystals |
| Color | white |
| Maximum wavelength(λmax) | ['λ: 420 nm Amax: ≤0.20'] |
| Merck | 14,2718 |
| BRN | 5725162 |
| pKa | 11.68±0.70(Predicted) |
| Storage Condition | room temp |
| Stability | Hygroscopic |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.7500 (estimate) |
| MDL | MFCD00009595 |
| Physical and Chemical Properties | Appearance: white or off-white crystal powder Melting Point: 267 ℃ water solubility: 22.3G/100ML (25 ℃) |
| Use | Use of cyclodextrin in the field of 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. It can also be used as complexing agent, enzyme activity research, tissue culture agent. This product should be sealed in a dry place. |
-Cyclodextrin - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - 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. S24/25 - Avoid contact with skin and eyes. S22 - Do not breathe dust. |
| WGK Germany | 2 |
| RTECS | GU2293080 |
| FLUKA BRAND F CODES | 3 |
| HS Code | 29400000 |
-Cyclodextrin - Reference
| Reference Show more | 1. Zhang Yang, Zhou Yibin, Cao Shengnan, et al. Preparation and structural characterization of inclusion compounds of β-and γ-cyclodextrin and ethyl butyrate [J]. Food and Fermentation Industry 2014 40(009):34-38. 2. Tian Jiyang, Zou Yuan, Zuo Puyuan, et al. Preparation of apigenin nano-dispersion by subcritical water coupled freeze-drying [J]. Journal of Chemical Engineering 2020 v.71(06):320-331. 3. Zhu Shilong, Li Yong, Lin Hongwei, et al. Optimization of Sinomenine-Cyclodextrin Inclusion Process and Determination of Inclusion Constant [J]. Food Science, 2012(08):54-59. 4. Chen Dizhao, Zhu Shilong, Li Yong, et al. Properties and Spectral Analysis of Sinomenine-γ-Cyclodextrin Inclusion Compound [J]. Food Science, 2013, 34(003):115-118. 5. Liu Chao 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. 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. [IF = 9.381] Qiuna Zhou et al."Preparation and characterization of inclusion complexes formed between baicalein and cyclodextrins." Carbohyd Polym. 2013 Jun;95:733 8. [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 9. [IF = 1.633] Wan Hui-da et al."Enzymatic production of steviol using a commercial β-glucosidase and preparation of its inclusion complex with γ-CD." J Incl Phenom Macro. 2019 Apr;93(3):193-201 10. [IF = 9.147] Yanping Wu et al."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 Hydrocolloid. 2020 Jun;103:105718 11. [IF = 5.923] Dongxu Han et al."Solubility Enhancement of Myricetin by Inclusion Complexation with Heptakis-O-(2-Hydroxypyyl)-β-Cyclodextrin: A Joint Experimental and Theoretical Study." Int J Mol Sci. 2020 Jan;21(3):766 12. [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 13. [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 14. [IF = 6.558] Yuanqing Luo et al."Pd nanoparticles decorated thiol-functionalized MOF as an efficient matrix for differentiation and quantitation of oligosaccharide isomers by laser desorption/ionization mass spectrometry." Anal Chim Acta. 2022 Apr;1202:339665 15. [IF = 3.361] Tao Zhan et al."Enzyme-free glucose sensors with efficient synergistic electro-catalysis based on a ferrocene derivative and two metal nanoparticles." Rsc Adv. 2022 Feb;12(9):5072-5079 |
-Cyclodextrin - Introduction
100ml water at 25 ℃ can dissolve 23.2g. The specific rotation [α]D is 177 · 4. 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. called α-, β or γ-cyclodextrin, respectively
Last Update：2022-10-16 17:14:27
-Cyclodextrin - Reference Information
| LogP | -12.02 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| identification test | dissolution (OT-42) is easily soluble in water and extremely difficult to dissolve in ethanol. Specific rotation [a] D25 +173~+180 (1% solution). Iodine reaction in the test tube into the sample 0.2g, add 0.1mol/L iodine solution 2ml. After heating in a water bath, it should be cooled to room temperature and should be a clear brown solution. Chromatographic analysis is performed under the conditions used in the "Content Analysis" described below. The residence time of the main peak should be similar to the reference sample of γ-cyclodextrin (available from German Consort:fu Elentrochemische Industrie GmbH,Munchen). |
| content analysis | determined by liquid chromatography in GT-10. The column used is 30cm long and 7.8mm in inner diameter, filled with Aminex HPX-42A(Bio-Rad Laboratoties) or similar products with a particle size of 25/μm. The solvent is water. The flow rate was 0.3~1.0 ml/min. Temperature 65 ℃, lO ℃. The injection volume is 20~100/μ 1. The detector is a differential refractometer. Sample liquid 1.0g sample dissolved in 100ml of water. Calculate the content of γ-cyclodextrin/%= the peak area of γ-cyclodextrin/the sum of the recorded peak areas × 100% |
| toxicity | ADI has no special regulations (tentative),FAO/WHO,1998. |
| use | carrier; Spice modifier; Stabilizer. 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 inclusions 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 generate inclusions (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. This reaction can also be carried out in benzene (or acetonitrile). Although potassium cyanide is insoluble in benzene, if 18-crown -6 is added, not only can the reaction occur, but the yield can be as high as 95%. Toxicity of 18-Crown -6: The oral lethal dose of rats is 300mg/kg. It is irritating to eyes and skin. The use of cyclodextrin in the field of 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. It can also be used as complexing agent, enzyme activity research, tissue culture agent. This product should be sealed and stored in a dry place. |
| 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 bacteria that produced cyclodextrin enzyme (cyclodextrin glucose translocation enzyme, abbreviated as CGT-ase) were discovered, especially the basophilic bacteria, which is 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. cyclic maltodextrin glucosyltransferase (CGTase,EC2.4.1.19) acts on the hydrolyzed starch, and then purifies it by one of the following methods: cyclodextrin is precipitated with a complex of a macrocyclic compound, then extracted with n-decane, and then the solvent is strapped; Crystallization is obtained from the purified mother liquor containing cyclodextrin by chromatographic separation method of ion exchange or gel filtration; obtained by membrane separation method of ultrafiltration and reverse osmosis. |
Last Update：2024-04-09 21:04:16
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