Glutaraldehyde

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Glutaraldehyde
Glutaraldehyde structure.png
Glutaraldehyde 3D ball.png
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C5H8O2/c6-4-2-1-3-5-7/h4-5H,1-3H2 Yes check.svgY
    Key: SXRSQZLOMIGNAQ-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceClear 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:
GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
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.svgHealth 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Uses

Biochemistry

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

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.[ citation needed ]. Glutaraldehdye also can be used for an interlinking agent to improve the adhesion force between two polymeric coatings. [11] Glutaraldehyde is also used to protect against corrosion of undersea pipes. [12]

Medical

Clinical uses

Glutaraldehyde is used as a disinfectant and medication. [3] [4] [13] Usually applied as a solution, it is used to sterilize surgical instruments and other areas. [3]

Dermatological uses

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. [14]

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. [15]

Other Uses

Aquaria

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. Aquarists also commonly use it in low concentrations as an algicide. [16]

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, especially in high concentrations. [3] Glutaraldehyde is effective against a range of microorganisms including spores. [3] [17] Glutaraldehyde is a dialdehyde. [18] It works by a number of mechanisms. [17]

As a strong sterilant, glutaraldehyde is toxic and a strong irritant. [19] There is no strong evidence of carcinogenic activity, [20] However, some occupations that work with this chemical have an increased risk of some cancers. [20]

Production and reactions

Production

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. [21] [22] This reaction essentially mimics ozonolysis. Alternatively it can be made by the Diels-Alder reaction of acrolein and vinyl ethers followed by hydrolysis. [23]

Glutaraldehyde synthesis (2).svg

Reactions

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. [24] [23] [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. [25]

GlutaldehydeHydrateEquilibria.png

A number of mechanisms have been invoked to explain the biocidal and fixative properties of glutaraldehyde. [17] 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. [26]

Imine formation from a primary amines and the carbonyls of glutaraldehyde is the basis of its fixative and biocidal properties. Imine-synthesis.svg
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. [25]

Related Research Articles

<span class="mw-page-title-main">Aldehyde</span> Organic compound containing the functional group R−CH=O

In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology.

<span class="mw-page-title-main">Formaldehyde</span> Organic compound (H–CHO); simplest aldehyde

Formaldehyde ( for-MAL-di-hide, fər-) (systematic name methanal) is an organic compound with the chemical formula CH2O and structure H−CHO, more precisely H2C=O. The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as aqueous solutions (formalin), which consists mainly of the hydrate CH2(OH)2. It is the simplest of the aldehydes (R−CHO). As a precursor to many other materials and chemical compounds, in 2006 the global production of formaldehyde was estimated at 12 million tons per year. It is mainly used in the production of industrial resins, e.g., for particle board and coatings. Small amounts also occur naturally.

A polyamide is a polymer with repeating units linked by amide bonds.

<span class="mw-page-title-main">Sterilization (microbiology)</span> Process that eliminates all biological agents on an object or in a volume

Sterilization refers to any process that removes, kills, or deactivates all forms of life and other biological agents present in or on a specific surface, object, or fluid. Sterilization can be achieved through various means, including heat, chemicals, irradiation, high pressure, and filtration. Sterilization is distinct from disinfection, sanitization, and pasteurization, in that those methods reduce rather than eliminate all forms of life and biological agents present. After sterilization, an object is referred to as being sterile or aseptic.

<span class="mw-page-title-main">Dicarbonyl</span> Molecule containing two adjacent C=O groups

In organic chemistry, a dicarbonyl is a molecule containing two carbonyl groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls are in close enough proximity that their reactivity is changed, such as 1,2-, 1,3-, and 1,4-dicarbonyls. Their properties often differ from those of monocarbonyls, and so they are usually considered functional groups of their own. These compounds can have symmetrical or unsymmetrical substituents on each carbonyl, and may also be functionally symmetrical or unsymmetrical.

<span class="mw-page-title-main">Aldol condensation</span> Type of chemical reaction

An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties react to form a β-hydroxyaldehyde or β-hydroxyketone, and this is then followed by dehydration to give a conjugated enone.

<span class="mw-page-title-main">Cross-link</span> Bonds linking one polymer chain to another

In chemistry and biology a cross-link is a bond or a short sequence of bonds that links one polymer chain to another. These links may take the form of covalent bonds or ionic bonds and the polymers can be either synthetic polymers or natural polymers.

In organic chemistry, the Mannich reaction is a three-component organic reaction that involves the amino alkylation of an acidic proton next to a carbonyl functional group by formaldehyde and a primary or secondary amine or ammonia. The final product is a β-amino-carbonyl compound also known as a Mannich base. Reactions between aldimines and α-methylene carbonyls are also considered Mannich reactions because these imines form between amines and aldehydes. The reaction is named after Carl Mannich.

A calixarene is a macrocycle or cyclic oligomer based on a methylene-linked phenols. With hydrophobic cavities that can hold smaller molecules or ions, calixarenes belong to the class of cavitands known in host–guest chemistry.

Thiazolidine is a heterocyclic organic compound with the formula (CH2)3(NH)S. It is a 5-membered saturated ring with a thioether group and an amine group in the 1 and 3 positions. It is a sulfur analog of oxazolidine. Thiazolidine is a colorless liquid. Although the parent thiazolidine is only of academic interest, some derivatives, i.e., the thiazolidines, are important, such as the antibiotic penicillin.

Dynamic covalent chemistry (DCvC) is a synthetic strategy employed by chemists to make complex molecular and supramolecular assemblies from discrete molecular building blocks. DCvC has allowed access to complex assemblies such as covalent organic frameworks, molecular knots, polymers, and novel macrocycles. Not to be confused with dynamic combinatorial chemistry, DCvC concerns only covalent bonding interactions. As such, it only encompasses a subset of supramolecular chemistries.

<span class="mw-page-title-main">Ethylenediamine</span> Chemical compound

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.

<span class="mw-page-title-main">Paraformaldehyde</span> Chemical compound

Paraformaldehyde (PFA) is the smallest polyoxymethylene, the polymerization product of formaldehyde with a typical degree of polymerization of 8–100 units. Paraformaldehyde commonly has a slight odor of formaldehyde due to decomposition. Paraformaldehyde is a poly-acetal.

Salicylic aldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula C6H4OH(CHO). Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. This colorless oily liquid has a bitter almond odor at higher concentration. Salicylaldehyde is a precursor to coumarin and a variety of chelating agents.

<span class="mw-page-title-main">Prins reaction</span> Chemical reaction involving organic compounds

The Prins reaction is an organic reaction consisting of an electrophilic addition of an aldehyde or ketone to an alkene or alkyne followed by capture of a nucleophile or elimination of an H+ ion. The outcome of the reaction depends on reaction conditions. With water and a protic acid such as sulfuric acid as the reaction medium and formaldehyde the reaction product is a 1,3-diol (3). When water is absent, the cationic intermediate loses a proton to give an allylic alcohol (4). With an excess of formaldehyde and a low reaction temperature the reaction product is a dioxane (5). When water is replaced by acetic acid the corresponding esters are formed.

<span class="mw-page-title-main">Fixation (histology)</span> Preservation of biological tissue

In the fields of histology, pathology, and cell biology, fixation is the preservation of biological tissues from decay due to autolysis or putrefaction. It terminates any ongoing biochemical reactions and may also increase the treated tissues' mechanical strength or stability. Tissue fixation is a critical step in the preparation of histological sections, its broad objective being to preserve cells and tissue components and to do this in such a way as to allow for the preparation of thin, stained sections. This allows the investigation of the tissues' structure, which is determined by the shapes and sizes of such macromolecules as proteins and nucleic acids.

<i>N</i>,<i>N</i>-Methylenebisacrylamide Chemical compound, polyacrylamide crosslinker

N,N′-Methylenebisacrylamide (MBAm or MBAA, colloquially "bis") is the organic compound with the formula CH2[NHC(O)CH=CH2]2. A colorless solid, this compound is a crosslinking agent in polyacrylamides, e.g., as used for SDS-PAGE.

A thermoset polymer matrix is a synthetic polymer reinforcement where polymers act as binder or matrix to secure in place incorporated particulates, fibres or other reinforcements. They were first developed for structural applications, such as glass-reinforced plastic radar domes on aircraft and graphite-epoxy payload bay doors on the Space Shuttle.

<span class="mw-page-title-main">Hexahydro-1,3,5-triazine</span> Class of chemical compounds

In chemistry, hexahydro-1,3,5-triazine is a class of heterocyclic compounds with the formula (CH2NR)3. Known as aldehyde ammonias, these compounds characteristically crystallize with water. They are reduced derivatives of 1,3,5-triazine, which have the formula (CHN)3, a family of aromatic heterocycles.

Hydroxymethylation is a chemical reaction that installs the CH2OH group. The transformation can be implemented in many ways and applies to both industrial and biochemical processes.

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. 1 2 3 4 "CDC - NIOSH Pocket Guide to Chemical Hazards -Glutaraldehyde". www.cdc.gov. Archived from the original on 13 January 2017. Retrieved 11 January 2017.
  3. 1 2 3 4 5 6 7 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. 1 2 3 4 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. 1 2 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. ↑ 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
  12. ↑ Falck, Christian; Kleppe, Terje; Maribu, Jarleiv (23 December 1993). "Commissioning of long subsea pipelines - environmental aspects" (PDF). Norway (published 31 December 1997). OSTI   593571.{{cite journal}}: Cite journal requires |journal= (help)
  13. ↑ Bonewit-West, Kathy (2015). Clinical Procedures for Medical Assistants. Elsevier Health Sciences. p. 96. ISBN   9781455776610. Archived from the original on 23 September 2017.
  14. ↑ NHS Choices: Glutarol Archived 5 February 2015 at the Wayback Machine
  15. ↑ 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
  16. ↑ 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.
  17. 1 2 3 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.
  18. ↑ 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.
  19. ↑ 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
  20. 1 2 Toxicology and Carcinogenesis Studies of Glutaraldehyde Archived 10 October 2012 at the Wayback Machine
  21. ↑ Chandler, Malcolm (15 April 2001). "Hydrogen Peroxide-Tungstic Acid". Encyclopedia of Reagents for Organic Synthesis: rh046. doi:10.1002/047084289X.rh046. ISBN   0471936235.
  22. ↑ 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.
  23. 1 2 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.
  24. ↑ Whipple Earl B.; Ruta Michael (1974). "Structure of Aqueous Glutaraldehyde". J. Org. Chem. 39 (12): 1666–1668. doi:10.1021/jo00925a015.
  25. 1 2 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.
  26. ↑ 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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