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Disaccharide
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Sucrose, a disaccharide formed from condensation of a molecule of glucose and a molecule of fructose
A disaccharide (also called a double sugar or bivose[1]) is the sugar formed when two monosaccharides (simple sugars) are joined by glycosidic linkage. Like monosaccharides, disaccharides are soluble in water. Three common examples are sucrose, lactose,[2] and maltose.
Disaccharides are one of the four chemical groupings of carbohydrates (monosaccharides, disaccharides, oligosaccharides, and polysaccharides). The most common types of disaccharides—sucrose, lactose, and maltose—have twelve carbon atoms, with the general formula C12H22O11. The differences in these disaccharides are due to atomic arrangements within the molecule.[3]
The joining of simple sugars into a double sugar happens by a condensation reaction, which involves the elimination of a water molecule from the functional groups only. Breaking apart a double sugar into its two simple sugars is accomplished by hydrolysis with the help of a type of enzyme called a disaccharidase. As building the larger sugar ejects a water molecule, breaking it down consumes a water molecule. These reactions are vital in metabolism. Each disaccharide is broken down with the help of a corresponding disaccharidase (sucrase, lactase, and maltase).
Contents
1 Classification
2 Formation
3 Properties
4 Assimilation
5 Common disaccharides
6 References
7 External links
Classification[edit]
There are two functionally different classes of disaccharides:
Reducing disaccharides, in which one monosaccharide, the reducing sugar of the pair, still has a free hemiacetal unit that can perform as a reducing aldehyde group; cellobiose and maltose are examples of reducing disaccharides, each with one hemiacetal unit, the other occupied by the glycosidic bond, which prevents it from acting as a reducing agent.
Non-reducing disaccharides, in which the component monosaccharides bond through an acetal linkage between their anomeric centers. This results in neither monosaccharide being left with a hemiacetal unit that is free to act as a reducing agent. Sucrose and trehalose are examples of non-reducing disaccharides because their glycosidic bond is between their respective hemiacetal carbon atoms. The reduced chemical reactivity of the non-reducing sugars in comparison to reducing sugars, may be an advantage where stability in storage is important.
[4] [5]
Formation[edit]
The formation of a disaccharide molecule from two monosaccharide molecules proceeds by displacing a hydroxyl radical from one molecule and a hydrogen nucleus (a proton) from the other, so that the now vacant bonds on the monosaccharides join the two monomers together. The vacant bonds on the hydroxyl radical and the proton unite in their turn, forming a molecule of water, that then goes free. Because of the removal of the water molecule from the product, the term of convenience for such a process is "dehydration reaction" (also "condensation reaction" or "dehydration synthesis"). For example, milk sugar (lactose) is a disaccharide made by condensation of one molecule of each of the monosaccharides glucose and galactose, whereas the disaccharide sucrose in sugar cane and sugar beet, is a condensation product of glucose and fructose. Maltose, another common disaccharide, is condensed from two glucose molecules.[6]
The dehydration reaction that bonds monosaccharides into disaccharides (and also bonds monosaccharides into more complex polysaccharides) forms what are called glycosidic bonds.[7]
Properties[edit]
The glycosidic bond can be formed between any hydroxyl group on the component monosaccharide. So, even if both component sugars are the same (e.g., glucose), different bond combinations (regiochemistry) and stereochemistry (alpha- or beta-) result in disaccharides that are diastereoisomers with different chemical and physical properties.
Depending on the monosaccharide constituents, disaccharides are sometimes crystalline, sometimes water-soluble, and sometimes sweet-tasting and sticky-feeling.
Assimilation[edit]
See also: carbohydrate digestion
Digestion involves breakdown to the monosaccharides.
Common disaccharides[edit]
Disaccharide
Unit 1
Unit 2
Bond
Sucrose (table sugar, cane sugar, beet sugar, or saccharose) Glucose Fructose α(1→2)β
Lactulose Galactose Fructose β(1→4)
Lactose (milk sugar) Galactose Glucose β(1→4)
Maltose (malt sugar) Glucose Glucose α(1→4)
Trehalose Glucose Glucose α(1→1)α
Cellobiose Glucose Glucose β(1→4)
Chitobiose Glucosamine Glucosamine β(1→4)
Maltose, cellobiose, and chitobiose are hydrolysis products of the polysaccharides starch, cellulose, and chitin, respectively.
Less common disaccharides include:[8]
Disaccharide
Units
Bond
Kojibiose two glucose monomers α(1→2) [9]
Nigerose two glucose monomers α(1→3)
Isomaltose two glucose monomers α(1→6)
β,β-Trehalose two glucose monomers β(1→1)β
α,β-Trehalose two glucose monomers α(1→1)β[10]
Sophorose two glucose monomers β(1→2)
Laminaribiose two glucose monomers β(1→3)
Gentiobiose two glucose monomers β(1→6)
Turanose a glucose monomer and a fructose monomer α(1→3)
Maltulose a glucose monomer and a fructose monomer α(1→4)
Palatinose a glucose monomer and a fructose monomer α(1→6)
Gentiobiulose a glucose monomer and a fructose monomer β(1→6)
Mannobiose two mannose monomers either α(1→2), α(1→3), α(1→4), or α(1→6)
Melibiose a galactose monomer and a glucose monomer α(1→6)
Melibiulose a galactose monomer and a fructose monomer α(1→6)
Rutinose a rhamnose monomer and a glucose monomer α(1→6)
Rutinulose a rhamnose monomer and a fructose monomer β(1→6)
Xylobiose two xylopyranose monomers β(1→4)
References[edit]
Jump up ^ Biose on www.merriam-webster.org
Jump up ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "disaccharides".
Jump up ^ Biology- A course for O Level. p. 59. ISBN 9810190964.
Jump up ^ "Nomenclature of Carbohydrates (Recommendations 1996)2-Carb-36 Disaccharides".
Jump up ^ "Disaccharides and Oligosaccharides". Retrieved 2008-01-29.
Jump up ^ Whitney, Ellie; Sharon Rady Rolfes (2011). Peggy Williams, ed. Understanding Nutrition (Twelfth ed.). California: Wadsworth, Cengage Learning. p. 100. ISBN 0-538-73465-5.
Jump up ^ "Glycosidic Link". OChemPal. Utah Valley University. Retrieved 11 December 2013.
Jump up ^ F.W.Parrish; W.B.Hahn, G.R.Mandels (July 1968). "Crypticity of Myrothecium verrucaria Spores to Maltose and Induction of Transport by Maltulose, a Common Maltose Contaminant" (PDF). J. Bacteriol. American Society for Microbiology. 96 (1): 227–233. PMC 252277. PMID 5690932. Retrieved 2008-11-21.
Jump up ^ Matsuda, K.; Abe, Y; Fujioka, K (November 1957). "Kojibiose (2-O-alpha-D-Glucopyranosyl-D-Glucose): Isolation and Structure: Chemical Synthesis". Nature. 180 (4593): 985–6. doi:10.1038/180985a0. PMID 13483573.
Jump up ^ T. Taga; Y. Miwa; Z. Min (1997). "α,β-Trehalose Monohydrate". Acta Crystallogr. C. 53 (2): 234–236. doi:10.1107/S0108270196012693.
External links[edit]
Disaccharides at the US National Library of Medicine Medical Subject Headings (MeSH)
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text:
Benzalkonium chloride
From Wikipedia, the free encyclopedia
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Benzalkonium chloride
Names
Other names
N-Alkyl-N-benzyl-N,N-dimethylammonium chloride; Alkyldimethylbenzylammonium chloride; ADBAC; BC50 BC80; Quaternary ammonium compounds; quats
Identifiers
CAS Number
8001-54-5 Y
ChEBI
CHEBI:3020
ChEMBL
ChEMBL502109
ECHA InfoCard 100.058.301
EC Number 264-151-6
KEGG
D00857 Y
RTECS number BO3150000
UNII
F5UM2KM3W7 Y
Properties
Chemical formula
variable
Molar mass variable
Appearance 100% is white or yellow powder; gelatinous lumps; Solutions BC50 (50%) & BC80 (80%) are colorless to pale yellow solutions
Density 0.98 g/cm3
Solubility in water
very soluble
Pharmacology
ATC code
D08AJ01 (WHO)
Hazards
EU classification (DSD) (outdated)
C, N [1]
R-phrases (outdated) R21/22, R34, R50 [1]
S-phrases (outdated) (S2), S36/37/39, S45, S61 [1]
NFPA 704
0
3
0
Flash point 250 °C (482 °F; 523 K) (if solvent based)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
verify (what is Y ?)
Infobox references
Benzalkonium chloride, also known as BZK, BKC, BAC, alkyldimethylbenzylammonium chloride and ADBAC, is a type of cationic surfactant. It is an organic salt classified as a quaternary ammonium compound. It has three main categories of use: as a biocide, a cationic surfactant, and as a phase transfer agent.[2] ADBACs are a mixture of alkylbenzyldimethylammonium chlorides, in which the alkyl group has various even-numbered alkyl chain lengths.
Contents
[hide]
1 Solubility and physical properties
2 Cationic surfactant
3 Phase transfer agent
4 Bioactive agents
4.1 Medicine
4.2 Adverse effects
5 Toxicology
6 Biological activity
7 Degradation
8 Regulation
9 See also
10 References
11 Further reading
12 External links
Solubility and physical properties[edit]
Depending on purity, benzalkonium chloride ranges from colourless to a pale yellow (impure). Benzalkonium chloride is readily soluble in ethanol and acetone. Although dissolution in water is slow, aqueous solutions are easier to handle and are preferred. Aqueous solutions should be neutral to slightly alkaline. Solutions foam when shaken. Concentrated solutions have a bitter taste and a faint almond-like odour.
Standard concentrates are manufactured as 50% and 80% w/w solutions, and sold under trade names such as BC50, BC80, BAC50, BAC80, etc. The 50% solution is purely aqueous, while more concentrated solutions require incorporation of rheology modifiers (alcohols, polyethylene glycols, etc.) to prevent increases in viscosity or gel formation under low temperature conditions.
Cationic surfactant[edit]
Benzalkonium chloride also possesses surfactant properties, dissolving the lipid phase of the tear film and increasing drug penetration, making it a useful excipient.[3]
Laundry detergents and treatments
Softeners for textiles
Phase transfer agent[edit]
Main article: Phase transfer catalysis
Benzalkonium chloride is a mainstay of phase-transfer catalysis, an important technology in the synthesis of organic compounds, including drugs.
Bioactive agents[edit]
Especially for their antimicrobial activity, benzalkonium chloride is an active ingredient in many consumer products:
Pharmaceutical products such as eye, ear and nasal drops or sprays, as a preservative
Personal care products such as hand sanitizers, wet wipes, shampoos, deodorants and cosmetics
Skin antiseptics, such as Bactine and Dettol.
Throat lozenges[4] and mouthwashes, as a biocide
Spermicidal creams
Over-the-counter single-application treatments for herpes, cold-sores, and fever blisters, such as RELEEV and Viroxyn
Burn and ulcer treatment
Spray disinfectants for hard surface sanitization
Cleaners for floor and hard surfaces as a disinfectant, such as Lysol
Algaecides for clearing of algae, moss, lichens from paths, roof tiles, swimming pools, masonry, etc.
Benzalkonium chloride is also used in many non-consumer processes and products, including as an active ingredient in surgical disinfection. A comprehensive list of uses includes industrial applications.[5] An advantage of benzalkonium chloride, not shared by ethanol-based antiseptics or hydrogen peroxide antiseptic, is that it does not cause a burning sensation when applied to broken skin.[citation needed],
Medicine[edit]
Benzalkonium chloride is a frequently used preservative in eye drops; typical concentrations range from 0.004% to 0.01%. Stronger concentrations can be caustic[6] and cause irreversible damage to the corneal endothelium.[7]
Avoiding the use of benzalkonium chloride solutions while contact lenses are in place is discussed in the literature.[8][9]
Adverse effects[edit]
Although historically benzalkonium chloride has been ubiquitous as a preservative in ophthalmic preparations, its ocular toxicity and irritant properties,[10] in conjunction with consumer demand, have led pharmaceutical companies to increase production of preservative-free preparations, or to replace benzalkonium chloride with preservatives which are less harmful.
Many mass-marketed inhaler and nasal spray formulations contain benzalkonium chloride as a preservative, despite substantial evidence that it can adversely affect ciliary motion, mucociliary transport, nasal mucosal histology, human neutrophil function, and leukocyte response to local inflammation.[11] Although some studies have found no correlation between use of benzalkonium chloride in concentrations at or below 0.1% in nasal sprays and drug-induced rhinitis,[12] others have recommended that benzalkonium chloride in nasal sprays be avoided.[13][14] In the United States, nasal steroid preparations that are free of benzalkonium chloride include budesonide, triamcinolone acetonide, dexamethasone, and Beconase and Vancenase aerosol inhalers.[11]
Benzalkonium chloride is irritant to middle ear tissues at typically used concentrations. Inner ear toxicity has been demonstrated.[15]
Occupational exposure to benzalkonium chloride has been linked to the development of asthma.[16] In 2011, a large clinical trial designed to evaluate the efficacy of hand sanitizers based on different active ingredients in preventing virus transmission amongst schoolchildren was re-designed to exclude sanitizers based on benzalkonium chloride due to safety concerns.[17]
Benzalkonium chloride has been in common use as a pharmaceutical preservative and antimicrobial since the 1940s. While early studies confirmed the corrosive and irritant properties of benzalkonium chloride, investigations into the adverse effects of, and disease states linked to, benzalkonium chloride have only surfaced during the past 30 years.
Benzalkonium chloride is classed as a Category III antiseptic active ingredient by the United States Food and Drug Administration. Ingredients are categorised as Category III when "available data are insufficient to classify as safe and effective, and further testing is required”. Benzalkonium chloride is excluded from the current United States Food and Drug Administration review of the safety and effectiveness of consumer antiseptics and topical antimicrobial over-the-counter drug products, meaning it will remain a Category III ingredient.[18] There is acknowledgement that more data are required on its safety, efficacy and effectiveness, especially with relation to:
Human pharmacokinetic studies, including information on its metabolites
Studies on animal absorption, distribution, metabolism, and excretion
Data to help define the effect of formulation on dermal absorption
Carcinogenicity
Studies on developmental and reproductive toxicology
Potential hormonal effects
Assessment of the potential for development of bacterial resistance
Toxicology[edit]
RTECS lists the following acute toxicity data:[19]
Organism
Route of exposure
Dose (LD50)
Rat Intravenous 13.9 mg/kg
Rat Oral 240 mg/kg
Rat Intraperitoneal 14.5 mg/kg
Rat Subcutaneous 400 mg/kg
Mouse Subcutaneous 64 mg/kg
Benzalkonium chloride is a human skin and severe eye irritant.[20] It is a suspected respiratory toxicant, immunotoxicant, gastrointestinal toxicant and neurotoxicant.[21][22][23]
Benzalkonium chloride formulations for consumer use are dilute solutions. Concentrated solutions are toxic to humans, causing corrosion/irritation to the skin and mucosa, and death if taken internally in sufficient volumes. 0.1% is the maximum concentration of benzalkonium chloride that does not produce primary irritation on intact skin or act as a sensitizer.[24]
Poisoning by benzalkonium chloride is recognised in the literature.[25] A 2014 case study detailing the fatal ingestion of up to 8.1 oz (240ml) of 10% benzalkonium chloride in a 78-year-old male also includes a summary of the currently published case reports of benzalkonium chloride ingestion. While the majority of cases were caused by confusion about the contents of containers, one case cites incorrect pharmacy dilution of benzalkonium chloride as the cause of poisoning of two infants.[26]
Benzalkonium chloride poisoning of domestic pets has been recognised as a result of direct contact with surfaces cleaned with disinfectants utilising benzalkonium chloride as an active ingredient.[27]
Biological activity[edit]
The greatest biocidal activity is associated with the C12 dodecyl & C14 myristyl alkyl derivatives. The mechanism of bactericidal/microbicidal action is thought to be due to disruption of intermolecular interactions. This can cause dissociation of cellular membrane lipid bilayers, which compromises cellular permeability controls and induces leakage of cellular contents. Other biomolecular complexes within the bacterial cell can also undergo dissociation. Enzymes, which finely control a wide range of respiratory and metabolic cellular activities, are particularly susceptible to deactivation. Critical intermolecular interactions and tertiary structures in such highly specific biochemical systems can be readily disrupted by cationic surfactants.
Benzalkonium chloride solutions are fast-acting biocidal agents with a moderately long duration of action. They are active against bacteria and some viruses, fungi, and protozoa. Bacterial spores are considered to be resistant. Solutions are bacteriostatic or bactericidal according to their concentration. Gram-positive bacteria are generally more susceptible than gram-negative bacteria. Activity is not greatly affected by pH, but increases substantially at higher temperatures and prolonged exposure times.
In a 1998 study utilizing the FDA protocol, a non-alcohol sanitizer with benzalkonium chloride as the active ingredient met the FDA performance standards, while Purell, a popular alcohol-based sanitizer, did not. The study, which was undertaken and reported by a leading US developer, manufacturer and marketer of topical antimicrobial pharmaceuticals based on quaternary ammonium compounds, found that their own benzalkonium chloride-based sanitizer performed better than alcohol-based hand sanitizer after repeated use.[28]
Advancements in the quality and efficacy of benzalkonium chloride in current non-alcohol hand sanitizers has addressed the CDC concerns regarding gram negative bacteria, with the leading products being equal if not more effective against gram negative, particularly New Delhi metallo-beta-lactamase 1 and other antibiotic resistant bacteria.[citation needed]
Newer formulations using benzalkonium blended with various quaternary ammonium derivatives can be used to extend the biocidal spectrum and enhance the efficacy of benzalkonium based disinfection products.[citation needed] Formulation techniques have been used to great effect in enhancing the virucidal activity of quaternary ammonium-based disinfectants such as Virucide 100 to typical healthcare infection hazards such as hepatitis and HIV.[citation needed] The use of appropriate excipients can also greatly enhance the spectrum, performance and detergency, and prevent deactivation under use conditions.[citation needed] Formulation can also help minimise deactivation of benzalkonium solutions in the presence of organic and inorganic contamination.[citation needed]
Degradation[edit]
Biodegradation Pathways of BAC with Fenton Process (H2O2/Fe2+)[29]
Benzalkonium chloride degradation follows consecutive debenzylation, dealkylation, and demethylation steps producing benzyl chloride, alkyl dimethyl amine, dimethyl amine, long chain alkane, and ammonia.[29] The intermediates, major, and minor products can then be broken down into CO2, H2O, NH3, and Cl–. The first step to the biodegradation of BAC is the fission or splitting of the alkyl chain from the quaternary nitrogen as shown in the diagram. This is done by abstracting the hydrogen from the alkyl chain by using a hydroxyl radical leading to a carbon centered radical. This results in benzyl dimethyl amine as the first intermediate and dodecanal as the major product.[29] From here, benzyl dimethyl amine can be oxidized to benzoic acid using the Fenton process. The trimethyl amine group in dimethylbenzylamine can be cleaved to form a benzyl that can be further oxidized to benzoic acid. Benzoic acid uses hydroxylation (adding a hydroxyl group) to form p-hydroxybenzoic acid. Benzyldimethylamine can then be converted into ammonia by performing demethylation twice, which removes both methyl groups, followed by debenzylation, removing the benzyl group using hydrogenation.[29] The diagram represents suggested pathways of the biodegradation of BAC for both the hydrophobic and the hydrophilic regions of the surfactant. Since Stearalkonium chloride is a type of BAC, the biodegradation process should happen in the same manner.
Regulation[edit]
In September 2016, the FDA announced a ban on nineteen ingredients in consumer antibacterial soaps citing a lack of evidence for safety and effectiveness. A ban on three additional ingredients, including benzalkonium chloride, was deferred to allow ongoing studies to be completed.[30]
See also[edit]
Stearalkonium chloride
Polyaminopropyl biguanide, an alternative preservative for contact lens solutions
Ethylenediaminetetraacetic acid
Triclosan
Thiomersal
References[edit]
^ Jump up to: a b c "C&L Inventory - ECHA". echa.europa.eu.
Jump up ^ Maximilian Lackner, Josef Peter Guggenbichler "Antimicrobial Surfaces" Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2013. doi:10.1002/14356007.q03_q01
Jump up ^ Bartlett, J (2013). Clinical Ocular Pharmacology (2 ed.). Elsevier. p. 20. ISBN 1-483-19391-8.
Jump up ^ "Bradosol".
Jump up ^ Ash, M; Ash, I (2004). Handbook of Preservatives. Synapse Info Resources. p. 286. ISBN 1-890-59566-7.
Jump up ^ Nelson, L; Goldfrank, L (2011). Goldfrank's Toxicologic Emergencies (9 ed.). McGraw-Hill Medical. p. 803. ISBN 0-071-60593-2.
Jump up ^ Baudouin, C; Creuzot-Garcher, C; Hoang-Xuan, T (2001). Inflammatory Diseases of the Conjunctiva (1, illustrated ed.). Thieme. p. 141. ISBN 978-3-131-25871-7.
Jump up ^ Otten, Mary; Szabocsik, John M. (1976). "Measurement of Preservative Binding with SOFLENS (polymacon) Contact Lens". Clinical and Experimental Optometry. 59 (8): 277. doi:10.1111/j.1444-0938.1976.tb01445.x.
Jump up ^ M Akers, "Consideration in selecting antimicrobial preservative agents for parenteral product development", Pharmaceutical Technology, May, p. 36 (1984).
Jump up ^ Baudouin, C; Labbé, A; Liang, H; Pauly, A; Brignole-Baudouin, F (2010). "Preservatives in eyedrops: the good, the bad and the ugly". Prog Retin Eye Res. 29 (4): 312–34. doi:10.1016/j.preteyeres.2010.03.001. PMID 20302969.
^ Jump up to: a b Kennedy, D W; Bolger, W E; Zinreich, S J (2001). Diseases of the Sinuses Diagnosis and Management. B.C. Decker Inc. p. 162. ISBN 1-550-09045-3.
Jump up ^ Marple, B; Roland, P; Benninger, M (2004). "Safety review of benzalkonium chloride used as a preservative in intranasal solutions: an overview of conflicting data and opinions". Otolaryngology--head and neck surgery : official journal of American Academy of Otolaryngology-Head and Neck Surgery. 130 (1): 131–41. doi:10.1016/j.otohns.2003.07.005. PMID 14726922.
Jump up ^ Beule, A. G. (2010). "Physiology and pathophysiology of respiratory mucosa of the nose and the paranasal sinuses". GMS Curr Top Otorhinolaryngol Head Neck Surg. 9: Doc07. doi:10.3205/cto000071. PMC 3199822  . PMID 22073111.
Jump up ^ Graf, P (2005). "Rhinitis medicamentosa: a review of causes and treatment". Treatments in respiratory medicine. 4 (1): 21–9. doi:10.2165/00151829-200504010-00003. PMID 15725047.
Jump up ^ Snow, J. B.; Wackym, P. A. (2009). Ballenger's Otorhinolaryngology: Head and Neck Surgery (revised ed.). PMPH-USA. p. 277. ISBN 1-550-09337-1.
Jump up ^ Malo, J; Chan-Yeung, M; Bernstein, D I (2013). Asthma in the Workplace (4, illustrated, revised ed.). CRC Press. p. 198. ISBN 1-842-14591-6.
Jump up ^ Gerald, L B; Gerald, J K; McClure, L A; Harrington, K; Erwin, S; Bailey, W C (June 2011). "Redesigning a large school-based clinical trial in response to changes in community practice". Clin Trials. 8 (3): 311–319. doi:10.1177/1740774511403513. PMC 3145214  . PMID 21730079.
Jump up ^ "Safety and Effectiveness of Consumer Antiseptics; Topical Antimicrobial Drug Products for Over-the-Counter Human Use; Proposed Amendment of the Tentative Final Monograph; Reopening of Administrative Record".
Jump up ^ "RTECS BO3150000 Ammonium, alkyldimethylbenzyl - , chloride".
Jump up ^ Lewis R J Sr (2004). Sax's Dangerous Properties of Industrial Materials (11 ed.). Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. p. 104. doi:10.1002/0471701343.
Jump up ^ "TOXNET Benzalkonium Chloride Compounds".
Jump up ^ "Haz-Map Benzalkonium Chloride".
Jump up ^ "NIOSH ICSC Benzalkonium Chloride".
Jump up ^ Seymour Stanton Block (2001). Disinfection, sterilization, and preservation (5, illustrated ed.). Lippincott Williams & Wilkins. p. 311. ISBN 0-683-30740-1.
Jump up ^ Dart, R C (2004). Medical Toxicology (illustrated, revised ed.). Lippincott Williams & Wilkins. p. 125. ISBN 0-781-72845-2.
Jump up ^ Gossel, T A (1994). Principles Of Clinical Toxicology, Third Edition (3, illustrated, revised ed.). CRC Press. ISBN 9780781701259.
Jump up ^ Campbell, A; Chapman, M (2008). Handbook of Poisoning in Dogs and Cats. John Wiley & Sons. p. 17. ISBN 0-470-69844-6.
Jump up ^ Dyer, David; Gerenraich, Kenneth; Whams, Peter (1998). "Testing a New Alcohol-Free Hand Sanitizer to Combat Infection". AORN Journal Vol 68 Issue 2: 239–251.
^ Jump up to: a b c d Rowe, Raymond (2009). Handbook of Pharmaceutical Excipients 6th Edition. London, UK: Pharmaceutical Press. pp. 56–58. ISBN 978 1 58212 135 2.
Jump up ^ "Safety and Effectiveness of Consumer Antiseptics; Topical Antimicrobial Drug Products for Over-the-Counter Human Use". 2016-09-06. Retrieved 2016-10-05.
Further reading[edit]
Rieger, M M (1997). "The Skin Irritation Potential of Quaternaries" (PDF). Soc. Cosmet. Chem. 48: 307–317. Archived from the original (PDF) on 2014-12-07.
Thorup I: Evaluation of health hazards by exposure to Quaternary ammonium compounds, The Institute of Food Safety and Toxicology, Danish Veterinary and Food Administration, http://www2.mst.dk/common/Udgivramme/Frame.asp?http://www2.mst.dk/udgiv/publications/2000/87-7944-210-2/html/kap04_eng.htm[permanent dead link]
Verret, DJ; Marple, BF. (Feb 2005). "Effect of topical nasal steroid sprays on nasal mucosa and ciliary function". Curr Opin Otolaryngol Head Neck Surg. 13 (1): 14–8. doi:10.1097/00020840-200502000-00005. PMID 15654209.
External links[edit]
International Programme on Chemical Safety, International Chemical Safety Card (ICSC) - Benzalkonium Chloride
National Institute for Occupational Safety and Health (NIOSH), International Chemical Safety Card (ICSC) - Benzalkonium Chloride
International Programme on Chemical Safety, Poisons Information Monograph (PIMs) - Benzalkonium Chloride
Haz-Map Category Details - Benzalkonium Chloride
ToxNet Human Safety Database - Benzalkonium Chloride Compounds
Recognition and Management of Pesticide Poisonings, United States Environmental Protection Agency, Office of Pesticide Programs, Sixth Edition, 2013
CDC Healthcare Infection Control Practices Advisory Committee (HICPAC), Guideline for Disinfection and Sterilization in Healthcare Facilities, 2008
Santa Cruz Biotechnology, Inc. MSDS
Spectrum Labs "Clear Bath" Algae Inhibitor MSDS
Nile Chemicals MSDS
TCI America MSDS
Sciencelab.com, Inc. MSDS
Nasal Saline Sprays - The Additives May Be the Problem
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values: بنزالکونیم کلرید – Persian

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values: 염화 벤잘코늄 – Korean

values:
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values: बेन्जालकोनियम क्लोराइड – Hindi

values:
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values: בנזלקוניום כלוריד – Hebrew

values:
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values:
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values: Бензалкониум хлорид – Macedonian

values:
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values:
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values: 塩化ベンザルコニウム – Japanese

values:
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values: Бензалкония хлорид – Russian

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