bis((2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid); N-(4-chlorophenyl)-1-3-(6-{N-[3-(4-chlorophenyl)carbamimidamidomethanimidoyl]amino}hexyl)carbamimidamidomethanimidamide

• ChemBase ID: 132286
• Molecular Formular: C34H54Cl2N10O14
• Molecular Mass: 897.75716
• Monoisotopic Mass: 896.31980182
• SMILES: c1cc(ccc1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)Nc1ccc(cc1)Cl)Cl.C([C@H]([C@H]([C@@H]([C@H](C(=O)O)O)O)O)O)O.C([C@H]([C@H]([C@@H]([C@H](C(=O)O)O)O)O)O)O
• Canonical SMILES: N=C(NC(=N)Nc1ccc(cc1)Cl)NCCCCCCNC(=N)NC(=N)Nc1ccc(cc1)Cl.OC[C@H]([C@H]([C@@H]([C@H](C(=O)O)O)O)O)O.OC[C@H]([C@H]([C@@H]([C@H](C(=O)O)O)O)O)O
• InChI: InChI=1S/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)/t;2*2-,3-,4+,5-/m.11/s1
• InChIKey: YZIYKJHYYHPJIB-UUPCJSQJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis((2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid); N-(4-chlorophenyl)-1-3-(6-{N-[3-(4-chlorophenyl)carbamimidamidomethanimidoyl]amino}hexyl)carbamimidamidomethanimidamide
• IUPAC Traditional name: chlorhexidine digluconate
• Synonyms: 1,6-Bis(N5-[p-chlorophenyl]-N1-biguanido)hexane; 1,1′-Hexamethylenebis(5-[p-chlorophenyl]biguanide); Chlorhexidine digluconate solution; Chlorhexidine digluconate; 氯己定 二葡糖酸盐 溶液; 葡萄糖酸氯己定

Database IDs

• CAS Number: 18472-51-0
• EC Number: 242-354-0
• MDL Number: MFCD00083599
• PubChem SID: 162226563
• PubChem CID: 9552081

CALCULATED PROPERTIES

• H Acceptors: 10
• H Donor: 10
• LogD (pH = 5.5): -4.561288
• LogD (pH = 7.4): -1.3018613
• Log P: 4.5103693
• Molar Refractivity: 181.7146 cm^3
• Polarizability: 51.81197 Å^3
• Polar Surface Area: 167.58 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Liquid
• Density: 1.06; 1.06 g/mL at 25 °C(lit.)

Safety Information

• Storage Warning: Light Sensitive
• European Hazard Symbols: Nature polluting (N)
• German water hazard class: 3
• Risk Statements: 50/53
• Safety Statements: 61
• TSCA Listed: 是
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H400-H411
• GHS Precautionary statements: P273
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: 2-8°C

Product Information

• Purity: 20% w/v aq. soln., non-sterile
• Concentration: 20% in H2O

DETAILS

Sigma Aldrich - C9394

Application
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Chlorhexidine is used primarily as a topical antiseptic/disinfectant in wound healing, at catheterization sites, in various dental applications and in surgical scrubs. It has been used to study how essential oils improve skin antisepsis when combined with chlorhexidine digluconate1 and is used for skin permeation studies2 . Chronic rinsing with chlorhexidine has been shown to decrease the saltiness of NaCl and the bitterness of quinine3.
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.