18472-51-0

Basic information

• Product Name: Chlorhexidine digluconate
• Synonyms: .alpha.-Cymen-5-ol;1,1’-hexamethylenebis(5-(p-chlorophenyl)-biguaniddigluconate;1,6-bis(5-(p-chlorophenyl)biguandino)hexanedigluconate;3-Methyl-4-(1-methylethyl)phenol;abacil;arlacideg;bacticlens;caswellno.481g
• CAS NO: 18472-51-0
• Molecular Formula: 2C₆H₁₂O₇*C₂₂H₃₀Cl₂N₁₀
• Molecular Weight: 897.76
• EINECS: 242-354-0
• Product Categories: API;Broad-spectrum antimicrobial, bactericidal effect;Disinfectant
• Mol File: 18472-51-0.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 699.3 °C at 760 mmHg
• Flash Point: 376.7 °C
• Appearance: Colorless/Liquid
• Density: 1.06 g/mL at 25 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: water: soluble50% (w/v)
• Water Solubility: 750g/L at 20℃
• Sensitive: Light Sensitive
• Merck: 14,2091
• CAS DataBase Reference: Chlorhexidine digluconate(CAS DataBase Reference)
• NIST Chemistry Reference: Chlorhexidine digluconate(18472-51-0)
• EPA Substance Registry System: Chlorhexidine digluconate(18472-51-0)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 61
• RIDADR: UN 3082 9 / PGIII
• RTECS: DU1950000
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 18472-51-0(Hazardous Substances Data)

Usage

Description

Chlorhexidine digluconate solution is a bis(biguanide) family cationic broad spectrum antibiotic that is available in a range of concentrations and has been safely used for over 40 years for a variety of health-related applications; but its specific use for umbilical cord care was uniquely tested in three clinical trials in Nepal, Bangladesh, and Pakistan, in the form of 7.1% chlorhexidine digluconate (CHX). Given the promising results of the trials, in 2013 the World Health Organization (WHO) added CHX to its Model List of Essential Medicines for Children; and in 2014 the WHO issued a new guideline on umbilical cord care, which included a formal recommendation on the use of chlorhexidine. Chlorhexidine digluconate is a broad spectrum antiseptic. Its mechanism of action involves destabilization of the outer bacterial membrane. It is effective on both Gram-positive and Gram-negative bacteria, although it is less effective with some Gram-negative bacteria.It has both bactericidal and bacteriostatic mechanisms of action, the mechanism of action being membrane disruption, not ATPase inactivation as previously thought.It is also useful against fungi and enveloped viruses, though this has not been extensively investigated. Chlorhexidine is harmful in high concentrations, but is used safely in low concentrations in many products, such as mouthwash and contact lens solutions.

Chemical Properties

Almost colourless or pale-yellowish liquid.

Originator

Abacil,Polfa-Lodz SA,Poland

Uses

Different sources of media describe the Uses of 18472-51-0 differently. You can refer to the following data:
1. chlorhexidine digluconate is a preservative generally used in concentrations of 0.01 to 0.1 percent to protect against bacteria. It is unstable at high temperatures. Chlorhexidine digluconate is more widely used in europe than in the united States.
2. Hydrogenolysis of benzyl-nitrogen bonds. Chlorhexidine gluconate is an antimicrobial irrigant that is used as an antiseptic for the skin in the healthcare industry. It is used in hospitals to prevent infection of patients during surgeries and can also be found in mouthrinses.
3. Chlorhexidine is used primarily as a topical antiseptic/disinfectant in wound healing, at catheterization sites, in various dental applications and in surgical scrubs. The gluconate salt form of chlorhexidine, a biguanide compound used as an antiseptic agent with topical antibacterial activity. Chlorhexidine gluconate is positively charged and reacts with the negatively charged microbial cell surface, thereby destroying the integrity of the cell membrane. Subsequently, chlorhexidine gluconate penetrates into the cell and causes leakage of intracellular components leading to cell death. Since gram positive bacteria are more negatively charged, they are more sensitive to this agent. Chlorhexidine digluconate 20% solution is a broad spectrum bacteriostatis antiseptic agent, oral care agent, disinfectant, cosmetic biocide, and preservative. It is very effective against plaque, oral flora including Candida and is active against gram-positive and gram-negative organisms, facultative anaerobes, aerobes, and yeast. It can be used in antiseptic soap, mouthwash that fights plaque, disinfecting wounds and burns, vaginal flushing, hair dyes and bleaches, makeup, and other skin and hair care products.

Manufacturing Process

35 parts of hexamethylene bis-dicyandiamide, 35 parts of p-chloroaniline hydrochloride and 250 parts of β-etoxyethanol are stirred together at 130- 140°C for 2 hours under reflux. The mixture is then cooled and filtered. The solid is washed with water and crystallised from 50% aqueous acetic acid. 1,1'-Hexamethylene bis(5-(p-chlorophenyl)biguanide) is obtained as colorless plates, melting point 258-260°C. By addition of D-gluconic acid to aqueous solution of chlorhexidine base is prepared 1,1'-hexamethylenebis(5-(pchlorophenyl)biguanide)digluconate (1:2).

Brand name

Dyna-Hex (Xttrium); Hibiclens (Regent); Peridex (Zila); Periochip (Dexcel); Periogard (Colgate); Prevacare (Johnson & Johnson).

Therapeutic Function

Antiseptic

General Description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Flammability and Explosibility

Notclassified

Biochem/physiol Actions

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

Clinical Use

1,6-Di(4 -chlorophenyldiguanido)hexane gluconate (Hibiclens)is the most effective of a series of antibacterial biguanides originallydeveloped in Great Britain.The antimicrobial properties of the biguanides were discoveredas a result of earlier testing of these compounds aspossible antimalarial agents. Although thebiguanides are technically not bisquaternary ammoniumcompounds and, therefore, should probably be classifiedseparately, they share many physical, chemical, and antimicrobialproperties with the cationic surfactants. Thebiguanides are strongly basic, and they exist as dications atphysiological pH. In chlorhexidine, the positive charges arecounterbalanced by gluconate anions (not shown). Likecationic surfactants, these undergo inactivation when mixedwith anionic detergents and complex anions such as phosphate,carbonate, and silicate.Chlorhexidine has broad-spectrum antibacterial activitybut is not active against acid-fast bacteria, spores, orviruses. It has been used for such topical uses as preoperativeskin disinfection, wound irrigation, mouthwashes, andgeneral sanitization. Chlorhexidine is not absorbedthrough skin or mucous membranes and does not causesystemic toxicity.

InChI:InChI=1/C22H30Cl2N10.2C6H12O7/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*7-1-2(8)3(9)4(10)5(11)6(12)13/h5-12H,1-4,13-14H2,(H5,25,27,29,31,33)(H5,26,28,30,32,34);2*2-5,7-11H,1H2,(H,12,13)

Synthetic route

triclosan (3380-34-5) + chlorhexidine digluconate (18472-51-0) → chlorohexidine triclosan complex

Conditions	Yield
Stage #1: triclosan With sodium hydroxide In water Heating; Stage #2: chlorhexidine digluconate In water Product distribution / selectivity;

chlorhexidine digluconate (18472-51-0) → chlorhexidine triphosphate

Conditions	Yield
With Sodium tripolyphosphate In water at 20℃;

chlorhexidine digluconate (18472-51-0) → chlorhexidine pyrophosphate

Conditions	Yield
With sodium pyrophosphate In water at 20℃;

chlorhexidine digluconate (18472-51-0) → chlorhexidine nitrate

Conditions	Yield
With calcium(II) nitrate tetrahydrate In water at 20℃;

chlorhexidine digluconate (18472-51-0) → chlorhexidine carbonate

Conditions	Yield
With calcium carbonate In water at 20℃;

chlorhexidine digluconate (18472-51-0) → chlorhexidine orthophosphate

Conditions	Yield
With disodium hydrogenphosphate In water at 20℃;

chlorhexidine digluconate (18472-51-0) → chlorhexidine hexametaphosphate

Conditions	Yield
With sodium hexametaphosphate In water at 20℃;

sodium cyclamate (139-05-9) + chlorhexidine digluconate (18472-51-0) → chlorhexidine dicyclamate

Conditions	Yield
In water

Downstream Products

• 89697-78-9 chlorhexidine orthophosphate 

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