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Glutaraldehyde, sold under the brandname Cidex and Glutaral among others, is a disinfectant and medication.[3][4][5] As a disinfectant it is used to sterilize surgical instruments and other areas.[3] As a medication it is used to treat warts on the bottom of the feet.[4] It is applied as a liquid.[3]

Glutaraldehyde
Skeletal formula of glutaraldehyde
Ball-and-stick model of the glutaraldehyde molecule
Names
Preferred IUPAC name
Pentanedial[1]
Other names
Glutaraldehyde
Glutardialdehyde
Glutaric acid dialdehyde
Glutaric aldehyde
Glutaric dialdehyde
1,5-Pentanedial
Identifiers
3D model (JSmol)
ChemSpider
DrugBank
ECHA InfoCard 100.003.506
KEGG
UNII
Properties
C5H8O2
Molar mass 100.117
Appearance Clear liquid
Odor pungent[2]
Density 1.06 g/mL
Melting point −14 °C (7 °F; 259 K)
Boiling point 187 °C (369 °F; 460 K)
Miscible, reacts
Vapor pressure 17 mmHg (20°C)[2]
Hazards
Flash point noncombustible[2]
US health exposure limits (NIOSH):
PEL (Permissible)
none[2]
REL (Recommended)
C 0.2 ppm (0.8 mg/m3)[2]
IDLH (Immediate danger)
N.D.[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Side effects include skin irritation.[4] If exposed to large amounts, nausea, headache, and shortness of breath may occur.[3] Protective equipment is recommended when used.[3] Glutaraldehyde is effective against a range of microorganisms including spores.[3][6] It works by a number of mechanisms.[6]

Glutaraldehyde came into medical use in the 1960s.[7] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[8] The wholesale cost in the developing world is about US$1.50–7.40 per liter of 2% solution.[9] There are a number of other commercial uses such as leather tanning.[10]

Contents

UsesEdit

DisinfectionEdit

Glutaraldehyde is a disinfectant and medication.[3][4][11]

Usually applied as a solution, it is used to sterilize surgical instruments and other areas.[3]

FixativeEdit

Glutaraldehyde is used in biochemistry applications as an amine-reactive homobifunctional crosslinker and fixative prior to SDS-PAGE, staining, or electron microscopy. It kills cells quickly by crosslinking their proteins. It is usually employed alone or mixed with formaldehyde[12] as the first of two fixative processes to stabilize specimens such as bacteria, plant material, and human cells. A second fixative procedure uses osmium tetroxide to crosslink and stabilize cell and organelle membrane lipids. Fixation is usually followed by dehydration of the tissue in ethanol or acetone, followed by embedding in an epoxy resin or acrylic resin.

Another application for treatment of proteins with glutaraldehyde is the inactivation of bacterial toxins to generate toxoid vaccines, e.g., the pertussis (whooping cough) toxoid component in the Boostrix Tdap vaccine produced by GlaxoSmithKline.[13]

In a related application, glutaraldehyde is sometimes employed in the tanning of leather and in embalming.

Wart treatmentEdit

As a medication it is used to treat warts on the bottom of the feet.[4] For this purpose, a 10% w/w solution is used. It dries the skin, facilitating physical removal of the wart.[14] Trade names include Diswart Solution and Glutarol.

SafetyEdit

Side effects include skin irritation.[4] If exposed to large amounts, nausea, headache, and shortness of breath may occur.[3] Protective equipment is recommended when used.[3] Glutaraldehyde is effective against a range of microorganisms including spores.[3][6]

As a strong sterilant, glutaraldehyde is toxic and a strong irritant.[15] There is no strong evidence of carcinogenic activity.[16] Some occupations that work with this chemical have an increased risk of some cancers.[16]

Mechanism of actionEdit

A number of mechanisms have been invoked to explain the biocidal properties of glutaraldehyde.[6] Like many other aldehydes, it reacts with amines and thiol groups, which are common functional groups in proteins. Being bi-function, it is also a potential crosslinker.[17]

Production and reactionsEdit

 
Synthesis of glutaraldehyde via the Diels-Alder reaction.

Glutaraldehyde is produced industrially by the oxidation of cyclopentene. Alternatively it arises by the Diels-Alder reaction of acrolein and vinyl ethers followed by hydrolysis.[18]

Like other simple aldehydes (e.g., formaldehyde), glutaraldehyde converts in aqueous solution to various hydrate. Like many dialdehydes, (e.g., glyoxal), these hydrates convert to other equilibrating species.[19][18]

 

Monomeric glutaraldehyde polymerize by aldol condensation reaction yielding alpha, beta-unsaturated poly-glutaraldehyde. This reaction usually occurs at alkaline pH values.

History and cultureEdit

Glutaraldehyde came into medical use in the 1960s.[20] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[8] The wholesale cost in the developing world is about US$1.50–7.40 per liter of 2% solution.[9] There are a number of other commercial uses such as leather tanning.[21]

A glutaraldehyde solution of 0.1% to 1.0% concentration may be used as a biocide for system disinfection and as a preservative for long-term storage. It is a sterilant, killing endospores in addition to many microorganisms and viruses.[22]

As a biocide, glutaraldehyde is a component of hydraulic fracturing ("fracking") fluid. It is included in the additive called Alpha 1427.[23] Bacterial growth impairs extraction of oil and gas from these wells. Glutaraldehyde is pumped as a component of the fracturing fluid to inhibit microbial growth.

ReferencesEdit

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 907. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ a b c d e f "CDC - NIOSH Pocket Guide to Chemical Hazards -Glutaraldehyde". www.cdc.gov. Archived from the original on 13 January 2017. Retrieved 11 January 2017.
  3. ^ a b c d e f g h i j k WHO Model Formulary 2008 (PDF). World Health Organization. 2009. pp. 323, 325. ISBN 9789241547659. Archived (PDF) from the original on 13 December 2016. Retrieved 8 January 2017.
  4. ^ a b c d e f British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 825. ISBN 9780857111562.
  5. ^ Bonewit-West, Kathy (2015). Clinical Procedures for Medical Assistants. Elsevier Health Sciences. p. 96. ISBN 9781455776610. Archived from the original on 2017-09-23.
  6. ^ a b c d Fraise, Adam P.; Maillard, Jean-Yves; Sattar, Syed (2012). Russell, Hugo and Ayliffe's Principles and Practice of Disinfection, Preservation and Sterilization. John Wiley & Sons. p. Chapter 2. ISBN 9781118425862. Archived from the original on 2017-09-23.
  7. ^ Booth, Anne (1998). Sterilization of Medical Devices. CRC Press. p. 8. ISBN 9781574910872. Archived from the original on 2017-09-23.
  8. ^ a b "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016.
  9. ^ a b "Glutaraldehyde". International Drug Price Indicator Guide. Retrieved 8 December 2016.
  10. ^ Rietschel, Robert L.; Fowler, Joseph F.; Fisher, Alexander A. (2008). Fisher's Contact Dermatitis. PMPH-USA. p. 359. ISBN 9781550093780. Archived from the original on 2017-09-23.
  11. ^ Bonewit-West, Kathy (2015). Clinical Procedures for Medical Assistants. Elsevier Health Sciences. p. 96. ISBN 9781455776610. Archived from the original on 2017-09-23.
  12. ^ Karnovsky, M.J. (1965). A formaldehyde-glutaraldehyde fixative of high osmolality for use in electron microscopy. Journal of Cell Biology 27: 137A–138A
  13. ^ Boostrix prescribing information Archived 2011-02-01 at the Wayback Machine., ©2009, GlaxoSmithKline
  14. ^ NHS Choices: Glutarol Archived 2015-02-05 at the Wayback Machine.
  15. ^ Canadian Centre for Occupational Health and Safety (CCOHS) (a federal government site) > OSH Answers > Diseases, Disorders & Injuries > Asthma Archived 2009-04-27 at the Wayback Machine. Document last updated on February 8, 2005
  16. ^ a b Toxicology and Carcinogenesis Studies of Glutaraldehyde Archived 2012-10-10 at the Wayback Machine.
  17. ^ H. Uhr, B. Mielke, O. Exner, K. R. Payne, E. Hill (2013), "Biocides", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a16_563.pub2
  18. ^ a b Christian Kohlpaintner, Markus Schulte, Jürgen Falbe, Peter Lappe, Jürgen Weber (2008), "Aldehydes, Aliphatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a01_321.pub2
  19. ^ Whipple Earl B.; Ruta Michael (1974). "Structure of Aqueous Glutaraldehyde". J. Org. Chem. 39: 1666–1668. doi:10.1021/jo00925a015.
  20. ^ Booth, Anne (1998). Sterilization of Medical Devices. CRC Press. p. 8. ISBN 9781574910872. Archived from the original on 2017-09-23.
  21. ^ Rietschel, Robert L.; Fowler, Joseph F.; Fisher, Alexander A. (2008). Fisher's Contact Dermatitis. PMPH-USA. p. 359. ISBN 9781550093780. Archived from the original on 2017-09-23.
  22. ^ HCC lecture notes, 15 Archived 2015-05-02 at the Wayback Machine.: Control of microorganisms Archived 2015-09-24 at the Wayback Machine.
  23. ^ Morgantown Utility Board. "Fracking Fluid Additives - Fracking Fluid MSDS's". Archived from the original on 2015-02-05.. Links to documents, including Alpha 1427 Material Safety Data Sheet

External linksEdit