259886-51-6

Basic information

• Product Name: CUCURBIT(8)URIL
• Synonyms: Cucurbit[8]uril;Curcubit[8]uril;Cucurbit[8]uril (CB[8]) hydrate, 99+%;Cucurbit[8]uril hydrate contains acid of crystalization;Cucurbit[8]uril hydrate ;2,20:3,19-Dimethano-2,3,4a,5a,6a,7a,8a,9a,10a,11a,12a,13a,14a,15a,16a,17a,19,20,21a,22a,23a,24a,25a,26a,27a,28a,29a,30a,31a,32a,33a,34a-dotriacontaazabispentaleno[1''''',6''''':5'''',6'''',7'''']cycloocta[1'''',2'''',3'''':3''',4''']pentaleno[1''',6''':5'
• CAS NO: 259886-51-6
• Molecular Formula: C₄₈H₄₈N₃₂O₁₆
• Molecular Weight: 1329.1
• Product Categories: Amine-Functional Polymers;Hydrophilic Polymers;Polymer Science
• Mol File: 259886-51-6.mol
• Article Data: 6

Chemical Properties

• Appearance: white/solid
• Density: 2.71
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: CUCURBIT(8)URIL(CAS DataBase Reference)
• NIST Chemistry Reference: CUCURBIT(8)URIL(259886-51-6)
• EPA Substance Registry System: CUCURBIT(8)URIL(259886-51-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 259886-51-6(Hazardous Substances Data)

Usage

Description

Cucurbit(8)uril is a macrocyclic compound composed of eight glycoluril units connected by methylene bridges, forming a basket-shaped structure. It is a host molecule known for its ability to encapsulate various guest molecules within its cavity through non-covalent interactions. Its unique structure and high binding affinity make it a promising material for a wide range of scientific and technological applications. Cucurbit(8)uril is notable for its stability, water solubility, and biocompatibility, further enhancing its potential for use in various biological and medical settings.

Uses

Used in Molecular Recognition:
Cucurbit(8)uril is used as a molecular recognition agent for its ability to selectively bind and encapsulate guest molecules within its cavity. This property allows for the development of sensors, diagnostic tools, and other applications that rely on the specific recognition of target molecules.
Used in Drug Delivery Systems:
Cucurbit(8)uril is used as a drug delivery carrier for its ability to encapsulate and release therapeutic agents. Its high binding affinity and biocompatibility make it an ideal candidate for the development of targeted drug delivery systems, improving the efficacy and reducing the side effects of various medications.
Used in Catalysis:
Cucurbit(8)uril is used as a catalyst in various chemical reactions due to its ability to stabilize and orient reactive intermediates within its cavity. This property allows for the acceleration of reaction rates and the enhancement of selectivity in a range of catalytic processes.
Used in Supramolecular Chemistry:
Cucurbit(8)uril is used as a building block in supramolecular chemistry for the construction of complex molecular architectures. Its ability to form non-covalent interactions with other molecules allows for the assembly of larger structures with unique properties and functions.
Used in Environmental Applications:
Cucurbit(8)uril is used in environmental applications for the selective capture and removal of pollutants and contaminants from water and air. Its high binding affinity and selectivity make it a promising material for the development of advanced environmental remediation technologies.
Used in Biomedical Applications:
Cucurbit(8)uril is used in biomedical applications for its potential in diagnostics, imaging, and therapeutics. Its biocompatibility and ability to encapsulate biologically relevant molecules make it a valuable tool for the development of new medical technologies and treatments.

Upstream product

• 50-00-0 formaldehyd 
• 950526-89-3 glycoluril tetramer 
• 950526-90-6 C₂₈H₃₀N₂₀O₁₀ 
• 848440-50-6 glycoluril dimer 
• 496-46-8 glycouril 
• 496-46-8 glycoluril 
• 462-95-3 formaldehyde diethyl acetal 

Relevant articles and documents

SERS multiplexing of methylxanthine drug isomersviahost-guest size matching and machine learning

Multiplexed detection and quantification of structurally similar drug molecules, methylxanthine MeX, incl. theobromine TBR, theophylline TPH and caffeine CAF, have been demonstratedviasolution-based surface-enhanced Raman spectroscopy (SERS), achieving highly reproducible SERS signals with detection limits down to ～50 nM for TBR and TPH, and ～1 μM for CAF. Our SERS substrates are formed by aqueous self-assembly of gold nanoparticles (Au NPs) and supramolecular host molecules, cucurbit[n]urils (CBn,n= 7, 8). We demonstrate that the binding constants can be significantly increased using a host-guest size matching approach, which enables effective enrichment of analyte molecules in close proximity to the plasmonic hotspots. The dynamic range and the robustness of the sensing scheme can be extended using machine learning algorithms, which shows promise for potential applications in therapeutic drug monitoring, food processing, forensics and veterinary science.

PROCESS FOR THE PREPARATION OF CUCURBITURIL DERIVATIVES

This invention relates to cucurbituril and/or one or more derivatives thereof with low formaldehyde content, to a process of manufacturing said cucurbituril and/or one or more derivatives thereof and to the use of said cucurbituril and/or one or more derivatives thereof, in particular in consumer and industrial products, and in industrial processes.

Cucurbit[n]uril formation proceeds by step-growth cyclo-oligomerization

In contrast to the high yield formation of cucurbit[n]uril (CB[n]) from a 1:2 ratio of glycoluril to formaldehyde, the condensation of glycoluril with less than 2 equiv of formaldehyde delivers a reaction mixture that contains glycoluril oligomers (2-6) and CB[n] compounds that lack one or more methylene bridges known as nor-seco-cucurbit[n]urils (ns-CB[n]). In this paper we report the chromatographic purification of C-shaped glycoluril oligomers (dimer-hexamer), their characterization in solution, and their X-ray crystal structures. Quite interestingly, despite being acyclic glycoluril pentamer 5 and hexamer 6 retain the ability to bind to guests typical of CB[6] but are also able to expand their cavity to accommodate larger guests like cationic adamantane derivatives. We performed product resubmission experiments with glycoluril oligomers 2-6 and found preferences for the formation of specific ring sizes during CB[n] formation. A comprehensive mechanistic scheme is proposed that accounts for the observed formation of 2-6 and ns-CB[n]. Overall, the experiments establish that a step-growth cyclo-oligomerization process operates during CB[n] formation.