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C6143

Sigma-Aldrich

Chlorhexidine diacetate salt hydrate

bis(biguanide) antimicrobial

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Synonym(s):
1,6-Bis(N5-[p-chlorophenyl]-N1-biguanido)hexane; 1,1′-Hexamethylenebis(5-[p-chlorophenyl]biguanide)
Empirical Formula (Hill Notation):
C22H30Cl2N10 · 2C2H4O2 · xH2O
CAS Number:
206986-79-0
Molecular Weight:
625.55 (anhydrous basis)
EC Number:
200-302-4
MDL number:
MFCD00012532
PubChem Substance ID:
24892838
NACRES:
NA.85

Quality Level

200

form

powder

CMC

0.01% (25°C)(w/v)

solubility

ethanol: 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

cell membrane | interferes

storage temp.

room temp

SMILES string

ClC1=CC=C(NC(NC(NCCCCCCNC(NC(NC2=CC=C(Cl)C=C2)=N)=N)=N)=N)C=C1.OC(C)=O.OC(C)=O

InChI

1S/C22H30Cl2N10.2C2H4O2/c23-15-5-9-17(10-6-15)31-21(27)33-19(25)29-13-3-1-2-4-14-30-20(26)34-22(28)32-18-11-7-16(24)8-12-18;2*1-2(3)4/h5-12H,1-4,13-14H2,(H5,25,27,29,31,33)(H5,26,28,30,32,34);2*1H3,(H,3,4)

InChI key

WDRFFJWBUDTUCA-UHFFFAOYSA-N

Related Categories

Application

Used to study mechanism of membrane dysruption by bis(biguanide) molecules.

Biochem/physiol Actions

Chlorhexidine is a cationic broad-spectrum antimicrobial agent belonging to the bis(biguanide) family. Its mechanism of action involves destabilization of the outer bacterial membrane. It is effective against both Gram-positive and Gram-negative bacteria. Chlorhexidine is used primarily as a topical antiseptic/disinfectant in wound healing, at catheterization sites, in various dental applications and in surgical scrubs.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Disclaimer

The product is not intended for use as a biocide under global biocide regulations, including but not limited to US EPA′s Federal Insecticide Fungicide and Rodenticide Act, European Biocidal Products Regulation, Canada’s Pest Management Regulatory Agency, Turkey’s Biocidal Products Regulation, Korea’s Consumer Chemical Products and Biocide Safety Management Act (K-BPR) and others.

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Angela R Schug et al.
Veterinary microbiology, 248, 108791-108791 (2020-08-23)
Biocide susceptibility testing (BST) of bacteria lacks standardised methods. Based on a recently established broth macrodilution BST method, a broth microdilution method for BST was developed. To establish the respective protocol, four reference strains Staphylococcus aureus ATCC® 6538, Enterococcus hirae
E Zaura-Arite et al.
Journal of dental research, 80(5), 1436-1440 (2001-07-05)
Culturing of dispersed plaque samples and vitality staining of plaque smears are the most commonly used methods for evaluating the effects of antimicrobials on dental plaque. The visualization of the antimicrobial action on oral biofilm present on the substrate surface
C Harrison et al.
International journal of STD & AIDS, 9(2), 92-97 (1998-03-20)
The effect of chlorhexidine and nonoxynol-9, either singly or in combination, on the replication and infectivity of HIV and the survival of both lymphocytes (MT2 cells) and human spermatozoa, was studied in vitro. Exposure of MT2 cells to 200 microg/ml
T J Karpanen et al.
The Journal of antimicrobial chemotherapy, 62(5), 1031-1036 (2008-08-16)
Effective skin antisepsis and disinfection of medical devices are key factors in preventing many healthcare-acquired infections associated with skin microorganisms, particularly Staphylococcus epidermidis. The aim of this study was to investigate the antimicrobial efficacy of chlorhexidine digluconate (CHG), a widely
Synthesis, characterization and antibacterial properties of dihydroxy quaternary ammonium salts with long chain alkyl bromides.
Liu WS, Wang CH, Sun JF, et al.
Chemical Biology & Drug Design, 85(1), 91-97 (2014)
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