15894-70-9

Basic information

• Product Name: 1,6-Bis(cyano-guanidino)hexane
• Synonyms: HMBCG;1,6-HEXAMETHYLENE-BIS-CYANOGUANIDINE;N,N'''-1,6-hexanediylbis[N'-cyanoguanidine];1,6-Bis(cyano-guanidino)-hexane;Guanidine, N,N-1,6-hexanediylbisN-cyano-;1,6-Hexamethylenebis-(dicyanamide);NN-Dicyano-N,Nhexanediyl-di-guanidine;1,6-Bis(3-cyanoguanidino)hexane
• CAS NO: 15894-70-9
• Molecular Formula: C₁₀H₁₈N₈
• Molecular Weight: 250.3
• EINECS: 240-032-4
• Product Categories: Small molecule;Aliphatics;Metabolites & Impurities
• Mol File: 15894-70-9.mol

Chemical Properties

• Melting Point: >2950C
• Boiling Point: 437.7 °C at 760 mmHg
• Flash Point: 218.5 °C
• Appearance: White Solid
• Density: 1.25 g/cm³
• Vapor Pressure: 0Pa at 95℃
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Very Slightly), Water (Very Slightly, Heated)
• PKA: 3.21±0.70(Predicted)
• Water Solubility: 7.05mg/L at 25℃
• CAS DataBase Reference: 1,6-Bis(cyano-guanidino)hexane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-Bis(cyano-guanidino)hexane(15894-70-9)
• EPA Substance Registry System: 1,6-Bis(cyano-guanidino)hexane(15894-70-9)

Safety Data

• Hazardous Substances Data: 15894-70-9(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Flammability and Explosibility

Nonflammable

Upstream product

• 6055-52-3 hexane-1,6-diamine dihydrochloride 
• 1934-75-4 sodium dicyanamide 
• 124-09-4 1,6-Hexanediamine 

Downstream Products

• 50765-39-4 5,5'-dicyclohexyl-1,1'-hexanediyl-bis-biguanide; dihydrochloride 
• 111937-02-1 5,5'-bis-(3-chloro-phenyl)-1,1'-hexanediyl-bis-biguanide; dihydrochloride 
• 120176-57-0 5,5'-diphenethyl-1,1'-hexanediyl-bis-biguanide 
• 114398-73-1 5,5'-bis-(4-methyl-benzyl)-1,1'-hexanediyl-bis-biguanide; dihydrochloride 
• 65568-72-1 5,5'-bis-(4-carboxy-phenyl)-1,1'-hexanediyl-bis-biguanide; dihydrochloride 
• 123936-96-9 5,5'-bis-(2,6-dichloro-benzyl)-1,1'-hexanediyl-bis-biguanide; dihydrochloride 
• 124106-36-1 5,5'-bis-(2,4-dichloro-benzyl)-1,1'-hexanediyl-bis-biguanide; tetrahydrochloride 
• 114278-67-0 5,5'-bis-(3,4-dichloro-phenyl)-1,1'-hexanediyl-bis-biguanide; dihydrochloride 
• 22573-93-9 alexidine 
• 55-56-1 chlorhexidine 
• 53416-52-7 C₂₂H₃₀F₂N₁₀ 
• 59470-54-1 C₂₂H₃₀Br₂N₁₀ 

Relevant articles and documents

Synthesis and biochemical evaluation of highly enantiomerically pure (R,R)- and (S,S)-alexidine

Alexidine is in everyday human use as oral disinfectant and contact lens disinfectant. It is used as a mixture of stereoisomers. Since all of alexidine's known biological targets are chiral, the biological activity of any of its chiral stereoisomers could be significantly higher than that of the mixture of stereoisomers. This makes a synthetic methodology for obtaining the individual enantiomers of the chiral diastereoisomer highly desirable. Here, we describe the first synthesis of both enantiomers of alexidine in high enantiomeric purity, and demonstrate their activity against the protein-protein interaction between the anti-apoptotic protein Bcl-xL and the pro-apoptotic protein Bak.

Preparation method of chlorhexidine

The invention discloses a preparation method of chlorhexidine. The preparation method comprises the following steps: mixing n-butyl alcohol, hexanediamine and hydrochloric acid, adding triethylamine and sodium dicyandiamide, carrying out a primary condensation reaction, adding parachloroaniline, water and hydrochloric acid after the primary condensation reaction is finished, carrying out a secondary condensation reaction, adding liquid caustic soda after the secondary condensation reaction is finished, alkalizing, crystallizing, and carrying out centrifugal filtration to obtain a chlorhexidinecrude product; and washing, carrying out centrifugal filtration, and drying to obtain chlorhexidine. According to the method, chlorhexidine is prepared by adopting a one-pot boiling principle, so that the reaction steps and the wastewater amount are reduced, the operation is simplified, and the quality and the yield are remarkably improved.

Discovery of Novel Inhibitors Targeting Human O-GlcNAcase: Docking-Based Virtual Screening, Biological Evaluation, Structural Modification, and Molecular Dynamics Simulation

β-N-Acetylhexosaminidases have emerged as promising targets for drug and pesticide discovery due to their critical physiological functions in various cellular processes. In particular, human O-GlcNAcase (hOGA) from the glycoside hydrolase family 84 (GH84) has gained significant attention. This enzyme was found to be linked to various diseases such as diabetes, cancer, and Alzheimer's disease (AD). In this study, to develop novel hOGA inhibitors with suitable pharmaceutical properties, virtual screening of the Drugbank database was performed using a docking-based approach targeting hOGA. Chlorhexidine (4, Ki = 4.0 μM) was identified as a potent hOGA inhibitor with excellent selectivity (Ki > 200 μM against human β-N-acetylhexosaminidase B) and subjected to structural modifications and SAR studies. Furthermore, molecular dynamics simulations as well as binding free energy and free energy decomposition calculations were carried out to investigate the basis for the efficiency of potent inhibitors against hOGA. This present work revealed the new application of the disinfectant chlorhexidine and provided useful information for the future design of hOGA inhibitors.

COMPOUNDS, COMPOSITONS AND METHODS RELATED TO ANTIMICROBIAL APPLICATIONS

The present disclosure is in the field of polymers and pharmaceuticals/antimicrobials. The disclosure provides compounds based on SNAP (synthetic novel antimicrobial polymer) technology, compositions and methods of managing microbial infections including surgical site infections (SSIs). The present compounds are used as a management/therapeutic strategy to target microbial infections and have advantages including excellent antimicrobial potency, biofilm disruption ability, broad spectrum activity against various organisms covering both gram negative and gram positive bacteria as well as fungal pathogens, and low toxicity profile to ensure a healthy therapeutic window for use in humans.

Oral disinfectants inhibit protein-protein interactions mediated by the anti-apoptotic protein Bcl-xL and induce apoptosis in human oral tumor cells

Chlorhexidine and alexidine have long been used as oral disinfectants by humans. Both compounds inhibit protein-protein interactions mediated by the anti-apoptotic protein Bcl-xL at physiologically relevant concentrations and induce apoptosis in a series of tumor cell lines derived from the tongue and pharynx (see picture). Inhibition of protein-protein interactions is a potential mode of action of drugs in current human use. Copyright