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Glutaraldehyde

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Glutaraldehyde is an organic compound with the formula (CH2)3(CHO)2. The molecule consists of a five carbon chain doubly terminated with formyl (CHO) groups. It is usually used as a solution in water, and such solutions exists as a collection of hydrates, cyclic derivatives, and condensation products, several of which interconvert. Because the molecule has two aldehyde functional groups, glutaraldehyde (and its hydrates) can crosslink substances with primary amine groups, through condensation. Crosslinking can rigidify and deactivate proteins and other molecules that are critical for normal biological function, such as DNA, and so glutaraldehyde solutions are effective biocides and fixatives. It is sold under the brandnames Cidex and Glutaral.[3][4][5][6] As a disinfectant, it is used to sterilize surgical instruments.[3]

Glutaraldehyde
Skeletal formula of glutaraldehyde
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
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H302, H314, H317, H331, H334, H400
P260, P264, P270, P271, P272, P273, P280, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P311, P330, P332+P313, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point noncombustible[2]
0.2 ppm (0.82 mg/m3) (TWA), 0.05 ppm (STEL)
Lethal dose or concentration (LD, LC):
134 mg/kg (rat, oral); 2,560 mg/kg (rabbit, dermal)
NIOSH (US health exposure limits):
REL (Recommended)
 0.2 ppm (0.8 mg/m3)[2]
Safety data sheet (SDS) CAS 111-30-8
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 ?)

Uses

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Biochemistry

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Glutaraldehyde is used in biochemistry applications as an amine-reactive homobifunctional crosslinker and fixative.[7][8] It kills cells quickly by crosslinking their proteins. It is usually employed alone or mixed with formaldehyde[9] 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.

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.[10]

Material Science

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In material science glutaraldehyde application areas range from polymers to metals and biomaterials. Glutaraldehyde is commonly used as fixing agent before characterization of biomaterials for microscopy. Glutaraldehyde is a powerful crosslinking agent for many polymers containing primary amine groups.[11][12] Glutaraldehdye also can be used for an interlinking agent to improve the adhesion force between two polymeric coatings.[13] Glutaraldehyde is also used to protect against corrosion of undersea pipes.[14]

Medical

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Clinical uses

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Glutaraldehyde is used as a disinfectant and medication.[3][4][15] Usually applied as a solution, it is used to sterilize surgical instruments and other areas.[3]

Dermatological uses

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As a medication it is used to treat plantar warts.[4] For this purpose, a 10% w/v solution is used. It dries the skin, facilitating physical removal of the wart.[16]

Glutaraldehyde is also used in the treatment of hyperhidrosis under the control of dermatologists in people who have frequent sweating but do not respond to aluminum chloride. Glutaraldehyde solution is an effective agent to treat palmar and plantar hyperhidrosis as an alternative to tannic acid and formaldehyde.[17]

Other Uses

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Aquaria

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Glutaraldehyde diluted with water is often marketed as alternative to carbon dioxide gas injection for aquarium plants, but it lacks any characteristics that promote the growth of aquatic plants, and does not raise the CO2 concentration of water it is added to [citation needed]. Aquarists also commonly use it in low concentrations as an algicide.[18]

Safety

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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, especially in high concentrations.[3] Glutaraldehyde is effective against a range of microorganisms including spores.[3][19] Glutaraldehyde is a dialdehyde.[20] It works by a number of mechanisms.[19]

As a strong sterilant, glutaraldehyde is toxic and a strong irritant.[21] There is no strong evidence of carcinogenic activity,[22] However, some occupations that work with this chemical have an increased risk of some cancers.[22]

Production and reactions

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Production

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Glutaraldehyde is produced industrially by the catalytic oxidation of cyclopentene by hydrogen peroxide, which can be achieved in the presence of various tungstic acid-based heteropoly acid catalysts.[23][24] This reaction essentially mimics ozonolysis. Alternatively it can be made by the Diels-Alder reaction of acrolein and vinyl ethers followed by hydrolysis.[25]

 

Reactions

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Like other dialdehydes, (e.g., glyoxal) and simple aldehydes (e.g., formaldehyde), glutaraldehyde hydrates in aqueous solution, forming gem-diols. These diols in turn equilibrate with cyclic hemiacetal.[26][25][7] Monomeric glutaraldehyde polymerizes by aldol condensation and Michael reactions yielding alpha, beta-unsaturated poly-glutaraldehyde and related oligomers. This reaction occurs at alkaline pH values.[27]

 

A number of mechanisms have been invoked to explain the biocidal and fixative properties of glutaraldehyde.[19] Like many other aldehydes, it reacts with primary amines and thiol groups, which are common functional groups in proteins, nucleic acids and polymeric materials. Being bi-functional, glutaraldehyde is a crosslinker, which rigidifies macromolecular structures and shuts down their reactivity.[28]

 
Imine formation from a primary amines and the carbonyls of glutaraldehyde is the basis of its fixative and biocidal properties.

The aldehyde groups in glutaraldehyde are susceptible to formation of imines by reaction with the amines of lysine and nucleic acids. The derivatives from aldol condensation of pairs of glutaraldehyde also undergo imine formation.[27]

References

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  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 "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 World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 323, 325. hdl:10665/44053. ISBN 9789241547659.
  4. ^ a b c d 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 6 October 2022. Retrieved 9 September 2017.
  6. ^ Sullivan, John Burke; Krieger, Gary R. (2001). Clinical Environmental Health and Toxic Exposures. Lippincott Williams & Wilkins. p. 601. ISBN 9780683080278. Archived from the original on 10 October 2022. Retrieved 19 September 2020.
  7. ^ a b Srinivasan, Mythily; Sedmak, Daniel; Jewell, Scott (2002). "Effect of Fixatives and Tissue Processing on the Content and Integrity of Nucleic Acids". The American Journal of Pathology. 161 (6): 1961–1971. doi:10.1016/S0002-9440(10)64472-0. PMC 1850907. PMID 12466110.
  8. ^ Vakili, Mohammadtaghi; Rafatullah, Mohd; Salamatinia, Babak; Abdullah, Ahmad Zuhairi; Ibrahim, Mahamad Hakimi; Tan, Kok Bing; Gholami, Zahra; Amouzgar, Parisa (2014). "Application of chitosan and its derivatives as adsorbents for dye removal from water and wastewater: A review". Carbohydrate Polymers. 113: 115–130. doi:10.1016/j.carbpol.2014.07.007. PMID 25256466.
  9. ^ Karnovsky, M.J. (1965). A formaldehyde-glutaraldehyde fixative of high osmolality for use in electron microscopy. Journal of Cell Biology 27: 137A–138A
  10. ^ Boostrix prescribing information Archived 1 February 2011 at the Wayback Machine, ©2009, GlaxoSmithKline
  11. ^ Al-Muhanna, Muhanna K.; Anwar, Naushad; Hasnain, Md Saquib; Nayak, Amit Kumar (1 January 2023), Nayak, Amit Kumar; Hasnain, Md Saquib (eds.), "Chapter 1 - Synthesis of tailor-made polysaccharides: An overview", Tailor-Made Polysaccharides in Drug Delivery, Academic Press, pp. 1–27, doi:10.1016/b978-0-12-821286-8.00013-6, ISBN 978-0-12-821286-8, retrieved 3 June 2024
  12. ^ Kozlovskaya, V.; Kharlampieva, E.; Sukhishvili, S.A. (2017), "1.25 Polymer Films Using LbL Self-Assembly", Comprehensive Biomaterials II, Elsevier, pp. 554–569, doi:10.1016/b978-0-08-100691-7.00177-4, ISBN 978-0-08-100692-4, retrieved 3 June 2024
  13. ^ Erisen, Deniz. E (23 September 2022), "A novel chitosan and polydopamine interlinked bioactive coating for metallic biomaterials", Journal of Materials Science: Materials in Medicine, 33 (10), Springer-Nature: 65, doi:10.1007/s10856-022-06688-x, ISSN 1573-4838, PMC 9499904, PMID 36138240
  14. ^ Falck, Christian; Kleppe, Terje; Maribu, Jarleiv (23 December 1993). Commissioning of long subsea pipelines - environmental aspects (PDF). Norway (published 31 December 1997). OSTI 593571.
  15. ^ Bonewit-West, Kathy (2015). Clinical Procedures for Medical Assistants. Elsevier Health Sciences. p. 96. ISBN 9781455776610. Archived from the original on 23 September 2017.
  16. ^ NHS Choices: Glutarol Archived 5 February 2015 at the Wayback Machine
  17. ^ Juhlin, L; Hansson, H (1968), "Topical glutaraldehyde for plantar hyperhidrosis", Archives of Dermatology, 97 (3), American Medical Association: 327–330, doi:10.1001/archderm.1968.01610090099017, ISSN 0003-987X, PMID 5641337
  18. ^ Antiquis, Avus (20 September 2017). "Glutaraldehyde Revisited". praquatics.com - Aquarium Forums By Hobbyists For Hobbyists. Archived from the original on 14 February 2022. Retrieved 10 October 2022.
  19. ^ a b c 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 23 September 2017.
  20. ^ Pfafflin, James R.; Ziegler, Edward N. (2006). Encyclopedia of Environmental Science and Engineering: A-L. CRC Press. p. 235. ISBN 9780849398438. Archived from the original on 10 October 2022. Retrieved 19 September 2020.
  21. ^ Canadian Centre for Occupational Health and Safety (CCOHS) (a federal government site) > OSH Answers > Diseases, Disorders & Injuries > Asthma Archived 27 April 2009 at the Wayback Machine Document last updated on 8 February 2005
  22. ^ a b Toxicology and Carcinogenesis Studies of Glutaraldehyde Archived 10 October 2012 at the Wayback Machine
  23. ^ Chandler, Malcolm (15 April 2001). "Hydrogen Peroxide-Tungstic Acid". Encyclopedia of Reagents for Organic Synthesis: rh046. doi:10.1002/047084289X.rh046. ISBN 0471936235.
  24. ^ Furukawa, Hiroshi; Nakamura, Teiji; Inagaki, Hiroyuki; Nishikawa, Eiichiro; Imai, Chihiro; Misono, Makoto (5 May 1988). "Oxidation of Cyclopentene with Hydrogen Peroxide Catalyzed by 12-Heteropoly Acids". Chemistry Letters. 17 (5): 877–880. doi:10.1246/cl.1988.877.
  25. ^ 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. ISBN 978-3527306732.
  26. ^ Whipple Earl B.; Ruta Michael (1974). "Structure of Aqueous Glutaraldehyde". J. Org. Chem. 39 (12): 1666–1668. doi:10.1021/jo00925a015.
  27. ^ a b Migneault, Isabelle; Dartiguenave, Catherine; Bertrand, Michel J.; Waldron, Karen C. (2004). "Glutaraldehyde: Behavior in aqueous solution, reaction with proteins, and application to enzyme crosslinking". BioTechniques. 37 (5): 790–802. doi:10.2144/04375RV01. PMID 15560135.
  28. ^ 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.
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