51166-72-4

Basic information

• Product Name: 2,6-DI-O-METHYL-ALPHA-CYCLODEXTRIN
• Synonyms: METHYL ALPHA-CYCLODEXTRIN;2,6-DI-O-METHYL-ALPHA-CYCLODEXTRIN;Methyl a-cyclodextrin
• CAS NO: 51166-72-4
• Molecular Formula: C₄₈H₈₄O₃₀
• Molecular Weight: 1033.07
• Mol File: 51166-72-4.mol

Chemical Properties

• Boiling Point: 1099.2°Cat760mmHg
• Flash Point: 618.5°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.549
• CAS DataBase Reference: 2,6-DI-O-METHYL-ALPHA-CYCLODEXTRIN(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DI-O-METHYL-ALPHA-CYCLODEXTRIN(51166-72-4)
• EPA Substance Registry System: 2,6-DI-O-METHYL-ALPHA-CYCLODEXTRIN(51166-72-4)

Safety Data

• Hazardous Substances Data: 51166-72-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Di-O-Methyl-Alpha-Cyclodextrin is used as a drug delivery system for improving the solubility, stability, and bioavailability of pharmaceutical compounds. Its ability to form inclusion complexes with guest molecules makes it an effective carrier for drugs, enhancing their therapeutic outcomes.
Used in Analytical Chemistry:
2,6-Di-O-Methyl-Alpha-Cyclodextrin is used as a chiral selector for enantiomeric separations. Its unique structure allows for the differentiation and separation of enantiomers, which is crucial in the analysis and purification of chiral compounds.
Used in Food Industry:
2,6-Di-O-Methyl-Alpha-Cyclodextrin is used for encapsulating and solubilizing flavors, fragrances, and other bioactive compounds in the food industry. Its ability to form inclusion complexes helps in stabilizing and protecting these compounds, improving their shelf life and sensory properties.

InChI:InChI=1/C48H84O30/c1-55-13-19-31-25(49)37(61-7)43(67-19)74-32-20(14-56-2)69-45(39(63-9)26(32)50)76-34-22(16-58-4)71-47(41(65-11)28(34)52)78-36-24(18-60-6)72-48(42(66-12)30(36)54)77-35-23(17-59-5)70-46(40(64-10)29(35)53)75-33-21(15-57-3)68-44(73-31)38(62-8)27(33)51/h19-54H,13-18H2,1-12H3/t19-,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

Upstream product

• 129371-86-4 hexakis(3-O-benzyl-2,6-di-O-methyl)-α-cyclodextrin 
• 123154-96-1 hexakis(3-O-allyl-2,6-di-O-methyl)cyclomaltohexaose 
• 125882-74-8 hexakis(3-O-benzoyl-2,6-di-O-methyl)cyclomaltohexaose 
• 10016-20-3 alpha cyclodextrin 
• 74-88-4 methyl iodide 

Downstream Products

• 1643392-00-0 C₄₈H₈₄O₃₀*C₆H₁₂O 

Relevant articles and documents

Dynamic Aspects in Host-Guest Interactions. 3. Kinetics and Mechanism for Molecular Recognition by Hexakis(2,6-di-O-methyl)-α-cyclodextrin of Some Azo Guest Molecules

The inclusion reactions of some azo guest molecules, 3'-Pr-4'-(OH)Ph-N=N-PhSO3-Na+ (1), 3'-iPr-4'-(OH)Ph-N=N-PhSO3-Na+ (2), and 3'-tBu-4'-(OH)Ph-N=N-PhSO3-Na+ (3), with hexakis(2,6-di-O-methyl)-α-cyclodextrin (DM-αCDx) were investigated.The rates and mechanism for the inclusion reactions of 1, 2, and 3 with DM-αCDx have been determined.Enhanced binding ability with the guest and a threestep inclusion mechanism by DM-αCDx were found.

CHARACTERIZATION OF PER-O-ALKYLATED CYCLODEXTRINS BY GC/MS AS O-ALKYLATED GLUCONONITRILE ACETATES

The O-alkyl (C1, C2, n-C3, n-C4, n-C6) groups distribution in per-O-alkylated cyclodextrins has been investigated by GC - MS. The per-O-alkylated cyclodextrins were acid hydrolysed to partially O-alkylated glucose molecules that were treated with hydroxylamine hydrochloride in dimethylacetamide and then with pyridine and acetic anhydride. The mass spectra of O-ethylated glucononitrile acetates obtained from per-O-ethylated alpha-cyclodextrin are presented.

Selective chemical modification of cyclomalto-oligosaccharides via tert-butyldimethylsilylation

Selective reaction of cyclomaltoheptaose and cyclomalto-octaose with tert-butylchlorodimethylsilane in N,N-dimethylformamide in the presence of inidazole gave the heptakis(6-O-tert-butyldimethylsilyl) (21) and octakis(6-O-tert-butyldimethylsilyl) (27) der

SECOND-SPHERE CO-ORDINATION OF CARBOPLATIN AND RHODIUM COMPLEXES BY CYCLODEXTRINS (CYCLOMALTO-OLIGOSACCHARIDES)

The cyclomalto-oligosaccharides and the pure methylated derivatives, hexakis(2,6-di-O-methyl)-αCD (DM-αCD, 4) and heptakis(2,6-di-O-methyl)-βCD (DM-βCD, 5), function as second-sphere ligands towards diammine(η4-cycloocta-1,5-diene)rhodium(I) hexafluorophosphate (8), ethylenediammine(η4-cycloocta-1,5-diene)rhodium(I) hexafluorophosphate (9), and diammine(1,1-cyclobutanedicarboxylato)platinum(II) (11, carboplatin).The transition metal complexes are included inside the cavities of the CDs both in aqueous solution (1H-n.m.r. data) and in the solid state (X-ray data).In the crystals of the 1:1 adducts 8-αCD and 11-αCD, the transition metal complexes have their organic ligands inserted into the cavity of 1 and their ammine ligands hydrogen-bonded to secondary hydroxyl groups on the rim.The ammine ligands of 8 are displaced in the presence of either αCD or DM-αCD, but 9 is stable.Although 8 and 9 also form adducts with βCD, 11 is specific in forming a 1:1 adduct with αCD in aqueous solution.The standard enthalpy (-25.3 kJ.mol-1) and entropy (-42 J.K-1.mol-1) changes for the "reaction" between 11 and αCD indicate that adduct formation is an enthalpy driven process.The greatly increased solubility (from 50 to 240 mM) of 11 in aqueous solutions of αCD, and its encapsulation by αCD in solid state, could find applications in the use of carboplatin in cancer chemotherapy.