3811-75-4

Basic information

• Product Name: HEXAMIDINE
• Synonyms: Hexcarbacholine bromide;4,4'-(1,6-Hexanediyl)bis(oxy)bisbenzamidine;4,4'-(Hexamethylenebisoxy)bis(benzamidine);4,4'-(Hexamethylenedioxy)bis(benzamidine);4,4'-[1,6-Hexanediylbis(oxy)]bis[benzamidine];4,4'-[1,6-Hexanediylbis(oxy)]bisbenzamidine;Hexamidine【antipeptic】;4-[6-(4-amidinophenoxy)hexoxy]benzamidine
• CAS NO: 3811-75-4
• Molecular Formula: C₂₀H₂₆N₄O₂
• Molecular Weight: 354.45
• EINECS: 211-533-5
• Mol File: 3811-75-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 548.6°C at 760 mmHg
• Flash Point: 285.6°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 4.35E-12mmHg at 25°C
• Refractive Index: 1.587
• PKA: 12.80±0.50(Predicted)
• CAS DataBase Reference: HEXAMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: HEXAMIDINE(3811-75-4)
• EPA Substance Registry System: HEXAMIDINE(3811-75-4)

Safety Data

• Hazardous Substances Data: 3811-75-4(Hazardous Substances Data)

Usage

Description

HEXAMIDINE, also known as bis(4-guanidinophenyl) ether of hexane-1,6-diol, is a polyether compound with significant biocide and preservative properties. It is widely recognized for its ability to inhibit the growth of microorganisms, making it a valuable asset in various applications.

Uses

Used in Biocide and Preservative Applications:
HEXAMIDINE is used as a biocide and preservative for its ability to inhibit the growth of microorganisms, providing protection against bacterial, fungal, and other microbial contamination in different industries.
Used in Skin Care Industry:
HEXAMIDINE is used as a skin care ingredient for its potential to increase the production of skin lipids, such as cholesterol, sphingolipids, and fatty acids. This, in turn, may help improve skin moisture content, providing benefits for skin health and hydration. However, further evidence is required to confirm these effects.

Contact allergens

Hexamidine is an antiseptic active against Grampositive bacteria and fungi, used as a disinfectant and a preservative in cosmetics. It induces papulo-vesicular and diffuse allergic contact dermatitis.

InChI:InChI=1/C20H26N4O2/c21-19(22)15-5-9-17(10-6-15)25-13-3-1-2-4-14-26-18-11-7-16(8-12-18)20(23)24/h5-12H,1-4,13-14H2,(H3,21,22)(H3,23,24)

Upstream product

• 629-03-8 1 ,6-dibromohexane 
• 767-00-0 4-cyanophenol 
• 1448-62-0 4,4'-iminoethyl-1,6-diphenoxyhexane 
• 94291-61-9 4,4'-(hexane-1,6-diylbis(oxy))dibenzonitrile 

Relevant articles and documents

Discovery of decamidine as a new and potent PRMT1 inhibitor

Protein arginine methyltransferase 1 (PRMT1) is a key player for the dynamic regulation of arginine methylation. Its dysregulation and aberrant expression are implicated in various pathological conditions, and a plethora of evidence suggests that PRMT1 inhibition is of significant therapeutic value. Herein, we reported the modification of a series of diamidine compounds with varied lengths in the middle alkyl linker for PRMT1 inhibition. Decamidine (2j), which possesses the longest linker in the series, displayed 2- and 4-fold increase in PRMT1 inhibition (IC50 = 13 μM), compared with furamidine and stilbamidine. The inhibitory activity toward PRMT1 was validated by secondary orthogonal assays. Docking studies showed that the increased activity is due to the extra interaction of the amidine group with the SAM binding pocket, which is absent when the linker is not long enough. These results provide structural insights into developing the amidine type of PRMT1 inhibitors.

Hexanoic the trunk decides method for the synthesis of

The invention discloses a synthetic method of hexamidine. Hexamidine is a key raw material for producing antibiotic medicines hexamidine salts (such as dihydrochloride and dihydroxyethyl sulfonate). The synthetic method of hexamidine comprises the following steps: 1, reacting p-cyanophenol with 1,6-dibromohexane in an ethanol-water solution of sodium hydroxide to prepare 1,6-(p-cyanophenyl)hexyl diether (an intermediate I); 2, carrying out alcoholysis on the intermediate I in ethanol-toluene under the catalysis of trifluoroacetic acid or methanesulfonic acid to prepare 1,6-(p-ethyl iminoformate phenyl)hexyl diether (an intermediate II); and 3, carrying out aminolysis on the intermediate II in a methanol-ammonia solution to prepare hexamidine. The total yield of three-step synthesis is greater than 72%, and a nuclear magnetism identification result shows that the above obtained product is a preconceived structure product. The method is suitable for large-scale industrial production.

Analogues of 1,5-bis(4-amidinophenoxy)pentane (pentamidine) in the treatment of experimental Pneumocystis carinii pneumonia

A series of 33 analogues of the anti-Pneumocystis carinii drug 1,5-bis(4-amidinophenoxy)pentane (pentamidine) was synthesized for screening against a rat model of P. carinii pneumonia (PCP). Twenty-five of the compounds showed efficacy against PCP when compared to a saline-treated control group. Two compounds, 1,4-bis(4-amidinophenoxy)butane (butamidine, 6) and 1,3-bis(4-amidino-2-methoxyphenoxy)propane (DAMP, 16), were statistically more effective than the parent drug in treating PCP in the rat model of infection. In addition to their activity against PCP, the compounds were also evaluated for antitrypsin activity, ability to inhibit thymidylate synthetase, affinity for DNA, and toxicity. No correlation was observed between the tested molecular interactions of the diamidines and their effectiveness against PCP.