2,6-Di-O-methyl-β-cyclodextrin (DM-β-CD) - ≥98% , CAS No.51166-71-3

CAS: 51166-71-3 Cat. No.: D100520 Molecular Weight: 1331.36 Beilstein Registry Number: 1679140

GRADE & PURITY ≥98%

Synonyms

Heptakis(2,6-di-O-methyl)-beta-cyclodextrin | 2,6-Dimethyl--cyclodextrin | 5FJP73E35O | DTXSID501311203 | STK350629 | W-202928 | NSC 91541 | beta-Cyclodextrin, 2A,2B,2C,2D,2E,2F,2G,6A,6B,6C,6D,6E,6F,6G-tetradeca-O-methyl- | 2,6-Dimethyl-b-cyclodextrin | A

Storage

Room temperature,Argon charged

Shipped In

Normal

Overview

 Solubility in water: 800 g / L (25 ° C), dissolved in methanol, ethanol, acetone, pyridine, DMSO, and THF.

Heptakis(2,6-di-O-methyl)-β-cyclodextrin is a hydrophilic derivative of cyclodextrin that possesses the ability to effectively dissolve lipophilic drugs like steroid hormones, vitamins A, E, and K, etc. It can be utilized to increase the dissolution and bioavailability of weakly water-soluble pharmaceutical compounds.

Complexes are more soluble in aqueous solution than the corresponding complexes of β-cyclodextrin; Stimulation of fatty acid synthesis

Reactant involved in:

• Physicochemical studies of inclusion complexes

• Probing diffusion and single molecule interactions with reconstituted membrane proteins

• Interactions with micelles causing micellar rupture

• Studying cellular transport, used as a cell penetration enhancer

• Physicochemical and biopharmaceutical improvement of drugs particularly with solubilization and stability

• Interactions with cholesterol

Heptakis(2,6-di-O-methyl)-β-cyclodextrin may be used:

• To measure the equilibrium constant of its complexes with various enantiomeric pairs of chiral nitroxides by electron paramagnetic resonance (EPR) spectroscopy.

• To study the crystal structure of its complex with n-butyl acrylate and isobornyl acrylate using X-ray diffraction (XRD).

• As a chiral selector to resolve amphetamine related drugs by capillary zone electrophoresis.

Specifications

Synonyms

Heptakis(2, 6-di-O-methyl)-beta-cyclodextrin | 2, 6-Dimethyl--cyclodextrin | 5FJP73E35O | DTXSID501311203 | STK350629 | W-202928 | NSC 91541 | beta-Cyclodextrin, 2A, 2B, 2C, 2D, 2E, 2F, 2G, 6A, 6B, 6C, 6D, 6E, 6F, 6G-tetradeca-O-methyl- | 2, 6-Dimethyl-b-cyclodextrin | A

Specifications & Purity

≥98%

Storage

Room temperature, Argon charged

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488196563
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488196563
• Canonical Smiles: COCC1C2C(C(C(O1)OC3C(OC(C(C3O)OC)OC4C(OC(C(C4O)OC)OC5C(OC(C(C5O)OC)OC6C(OC(C(C6O)OC)OC7C(OC(C(C7O)OC)OC8C(OC(O2)C(C8O)OC)COC)COC)COC)COC)COC)COC)OC)O
• IUPAC Name: (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36S,37R,38S,39R,40S,41R,42S,43R,44S,45R,46S,47R,48S,49R)-37,39,41,43,45,47,49-heptamethoxy-5,10,15,20,25,30,35-heptakis(methoxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,38,40,42,44,46,48-heptol
• InChIKey: QGKBSGBYSPTPKJ-UZMKXNTCSA-N
• INCHI: 1S/C56H98O35/c1-64-15-22-36-29(57)43(71-8)50(78-22)86-37-23(16-65-2)80-52(45(73-10)30(37)58)88-39-25(18-67-4)82-54(47(75-12)32(39)60)90-41-27(20-69-6)84-56(49(77-14)34(41)62)91-42-28(21-70-7)83-55(48(76-13)35(42)63)89-40-26(19-68-5)81-53(46(74-11)33(40)61)87-38-24(17-66-3)79-51(85-36)44(72-9)31(38)59/h22-63H,15-21H2,1-14H3/t22-,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-,49-,50-,51-,52-,53-,54-,55-,56-/m1/s1
• Isomeric SMILES: COC[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)OC)O[C@@H]4[C@H](O[C@@H]([C@@H]([C@H]4O)OC)O[C@@H]5[C@H](O[C@@H]([C@@H]([C@H]5O)OC)O[C@@H]6[C@H](O[C@@H]([C@@H]([C@H]6O)OC)O[C@@H]7[C@H](O[C@@H]([C@@H]([C@H]7O)OC)O[C@@H]8[C@H](O[C@H](O2)[C@@H]([C@H]8O)OC)COC)COC)COC)COC)COC)COC)OC)O
• WGK Germany: 3
• Molecular Weight: 1331.36
• Beilstein: 1679140
• Reaxy-Rn: 16858380
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=16858380&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Not available
• Direct Parent: Oligosaccharides
• Alternative Parents: Oxanes Secondary alcohols Polyols Oxacyclic compounds Dialkyl ethers Acetals Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Oligosaccharide - Oxane - Secondary alcohol - Oxacycle - Organoheterocyclic compound - Polyol - Ether - Dialkyl ether - Acetal - Hydrocarbon derivative - Alcohol - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: moisture sensitive
• Flash Point(°C): 187°C
• Melt Point(°C): 180-182°C
• Molecular Weight: 1331.400 g/mol
• XLogP3: -7.500
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 35
• Rotatable Bond Count: 21
• Exact Mass: 1330.59 Da
• Monoisotopic Mass: 1330.59 Da
• Topological Polar Surface Area: 400.000 Ų
• Heavy Atom Count: 91
• Formal Charge: 0
• Complexity: 1690.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 35
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Hang Li, Qing-Sheng Zhao, Li-Wei Wang, Sen-Lin Chang, Pei-Dong Wang, Bing Zhao.  (2022)  Optimization of cyclodextrin-assisted green extraction of cannabidiol from industrial hemp leaves: Release behavior, permeability, bioactivity, and stability.  INDUSTRIAL CROPS AND PRODUCTS,      [PMID:] [10.1016/j.indcrop.2022.115709]

2. Hang Li, Qing-Sheng Zhao, Sen-Lin Chang, Tan-Ran Chang, Ming-Hui Tan, Bing Zhao.  (2021)  Development of cannabidiol full-spectrum oil/2,6-di-O-methyl-β-cyclodextrin inclusion complex with enhanced water solubility, bioactivity, and thermal stability.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2021.118318]

3. Liyuan Chen, Waixiang Yang, Chuanzhu Gao, Xiali Liao, Jing Yang, Bo Yang.  (2021)  The complexes of cannabidiol mediated by bridged cyclodextrins dimers with high solubilization, in vitro antioxidant activity and cytotoxicity.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2021.117017]

4. Hang Li, Sen-Lin Chang, Tan-Ran Chang, Ying You, Xiao-Dong Wang, Li-Wei Wang, Xiao-Fan Yuan, Ming-Hui Tan, Pei-Dong Wang, Peng-Wei Xu, Wei-Bo Gao, Qing-Sheng Zhao, Bing Zhao.  (2021)  Inclusion complexes of cannabidiol with β-cyclodextrin and its derivative: Physicochemical properties, water solubility, and antioxidant activity.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2021.116070]

5. Ying Chen, Yongchao Yao, Xueying Zhou, Chunyan Liao, Xin Dai, Jie Liu, Yunlong Yu, Shiyong Zhang.  (2019)  Cascade-Reaction-Based Nanodrug for Combined Chemo/Starvation/Chemodynamic Therapy against Multidrug-Resistant Tumors.  ACS Applied Materials & Interfaces,      [PMID:31722522] [10.1021/acsami.9b15848]

6. Xiaoxu Du, Nan Song, Ying-Wei Yang, Guolin Wu, Jianbiao Ma, Hui Gao.  (2014)  Reverse micelles based on β-cyclodextrin-incorporated amphiphilic polyurethane copolymers for protein delivery.  Polymer Chemistry,  5  (18): (5300-5309).  [PMID:] [10.1039/C4PY00278D]

7. Pu Zheng, Xinru Chen, Chunyang Zhao, Jialong Wang, Jianhong Zhang, Xiong Hu, Wenchao Geng, Qianqian Zhao.  (2024)  Integrating strategy to investigate the formation and stabilization mechanisms of Curcumin-Cyclodextrin inclusion complexes: Experimental characterizations and multi-scale computational simulations.  FOOD HYDROCOLLOIDS,      [PMID:] [10.1016/j.foodhyd.2024.110679]