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Glutaraldehyde

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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 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C5H8O2/c6-4-2-1-3-5-7/h4-5H,1-3H2 checkY
    Key: SXRSQZLOMIGNAQ-UHFFFAOYSA-N checkY
  • InChI=1/C5H8O2/c6-4-2-1-3-5-7/h4-5H,1-3H2
    Key: SXRSQZLOMIGNAQ-UHFFFAOYAO
  • O=CCCCC=O
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]
NIOSH (US health exposure limits):
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).
checkY verify (what is checkY☒N ?)

Formaldehyde, sold under the brandname Cidex and Glutaral among others, is a disinfectant, medication, preservative, and fixative.[3][4][5][6] As a disinfectant it is used to sterilize surgical instruments and other areas of hospitals.[3] As a medication it is used to warts on the bottom of the feet.[4] As a preservative, it is used in some cosmetics.[7][8] Glutaraldehyde is applied as a liquid.[3]

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][9] It works by a number of mechanisms.[9]

Glutaraldehyde came into medical use in the 1960s.[10] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[11] The wholesale cost in the developing world is about US$1.50–7.40 per liter of 2% solution.[12] There are a number of other commercial uses such as leather tanning.[13]

Uses

Disinfection

Glutaraldehyde is used as a disinfectant and medication.[3][4][14]

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

Fixative

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[15] 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.[16]

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

Wart treatment

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.[17] Trade names include Diswart Solution and Glutarol.

Safety

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][9]

As a strong sterilant, glutaraldehyde is toxic and a strong irritant.[18] There is no strong evidence of carcinogenic activity.[19] Some occupations that work with this chemical have an increased risk of some cancers.[19]

Mechanism of action

A number of mechanisms have been invoked to explain the biocidal properties of glutaraldehyde.[9] 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.[20]

Production and reactions

Synthesis of glutaraldehyde via the Diels-Alder reaction.

Glutaraldehyde is produced industrially by the oxidation of cyclopentene. Alternatively it can be made by the Diels-Alder reaction of acrolein and vinyl ethers followed by hydrolysis.[21]

Like many other dialdehydes, (e.g., glyoxal) and simple aldehydes (e.g., formaldehyde), glutaraldehyde converts in aqueous solution to various hydrates that in turn convert to other equilibrating species.[clarification needed][22][21]

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

History and culture

Glutaraldehyde came into medical use in the 1960s.[23] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[11] The wholesale cost in the developing world is about US$1.50–7.40 per liter of 2% solution.[12] There are a number of other commercial uses such as leather tanning.[24]

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.[25]

As a biocide, glutaraldehyde is a component of hydraulic fracturing ("fracking") fluid. It is included in the additive called Alpha 1427.[26] 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.

References

  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. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  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 from the original (PDF) on 13 December 2016. Retrieved 8 January 2017. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  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.
  6. ^ Sullivan, John Burke; Krieger, Gary R. (2001). Clinical Environmental Health and Toxic Exposures. Lippincott Williams & Wilkins. p. 601. ISBN 9780683080278.
  7. ^ "GLUTARAL || Skin Deep® Cosmetics Database | EWG". www.ewg.org. Retrieved 2019-02-25.
  8. ^ OECD Screening Information Database (2019). "GLUTARADEHYDE CAS N°: 111-30-8" (PDF). {{cite web}}: Cite has empty unknown parameter: |dead-url= (help)
  9. ^ 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. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  10. ^ Booth, Anne (1998). Sterilization of Medical Devices. CRC Press. p. 8. ISBN 9781574910872. Archived from the original on 2017-09-23. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  11. ^ a b "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived from the original (PDF) on 13 December 2016. Retrieved 8 December 2016. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  12. ^ a b "Glutaraldehyde". International Drug Price Indicator Guide. Retrieved 8 December 2016.
  13. ^ 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. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  14. ^ Bonewit-West, Kathy (2015). Clinical Procedures for Medical Assistants. Elsevier Health Sciences. p. 96. ISBN 9781455776610. Archived from the original on 2017-09-23. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  15. ^ Karnovsky, M.J. (1965). A formaldehyde-glutaraldehyde fixative of high osmolality for use in electron microscopy. Journal of Cell Biology 27: 137A–138A
  16. ^ Boostrix prescribing information Archived 2011-02-01 at the Wayback Machine, ©2009, GlaxoSmithKline
  17. ^ NHS Choices: Glutarol Archived 2015-02-05 at the Wayback Machine
  18. ^ 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
  19. ^ a b Toxicology and Carcinogenesis Studies of Glutaraldehyde Archived 2012-10-10 at the Wayback Machine
  20. ^ 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. ISBN 978-3527306732.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)
  21. ^ a b "Aldehydes, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2008. doi:10.1002/14356007.a01_321.pub2. ISBN 978-3527306732. {{cite encyclopedia}}: Unknown parameter |authors= ignored (help)
  22. ^ Whipple Earl B.; Ruta Michael (1974). "Structure of Aqueous Glutaraldehyde". J. Org. Chem. 39: 1666–1668. doi:10.1021/jo00925a015.
  23. ^ Booth, Anne (1998). Sterilization of Medical Devices. CRC Press. p. 8. ISBN 9781574910872. Archived from the original on 2017-09-23. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  24. ^ 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. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  25. ^ HCC lecture notes, 15 Archived 2015-05-02 at the Wayback Machine: Control of microorganisms Archived 2015-09-24 at the Wayback Machine
  26. ^ Morgantown Utility Board. "Fracking Fluid Additives - Fracking Fluid MSDS's". Archived from the original on 2015-02-05. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help). Links to documents, including Alpha 1427 Material Safety Data Sheet
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