Glutaraldehyde

Last updated

Contents

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 carbonyl group that are reactive to primary amine groups (even as its hydrates), it can function as a crosslinking agent for any substance with primary amine groups and develop imine connected links. Crosslinking rigidifies and deactivates many biological functions, so in this way, glutaraldehyde solutions are used as biocides and as fixative. 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">Ketone</span> Organic compounds of the form >C=O

In organic chemistry, a ketone is an organic compound with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<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.

In chemistry, a hydration reaction is a chemical reaction in which a substance combines with water. In organic chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed industrially to produce ethanol, isopropanol, and butan-2-ol.

<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">Imine</span> Organic compound or functional group containing a C=N bond

In organic chemistry, an imine is a functional group or organic compound containing a carbon–nitrogen double bond. The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions.

<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 Mannich base is a beta-amino-ketone, which is formed in the reaction of an amine, formaldehyde and a carbon acid. The Mannich base is an endproduct in the Mannich reaction, which is nucleophilic addition reaction of a non-enolizable aldehyde and any primary or secondary amine to produce resonance stabilized imine. The addition of a carbanion from a CH acidic compound to the imine gives the Mannich base.

<span class="mw-page-title-main">Hemiaminal</span> Organic compound or group with a hydroxyl and amine attached to the same carbon

In organic chemistry, a hemiaminal is a functional group or type of chemical compound that has a hydroxyl group and an amine attached to the same carbon atom: −C(OH)(NR2)−. R can be hydrogen or an alkyl group. Hemiaminals are intermediates in imine formation from an amine and a carbonyl by alkylimino-de-oxo-bisubstitution. Hemiaminals can be viewed as a blend of aminals and geminal diol. They are a special case of amino alcohols.

<span class="mw-page-title-main">Eschweiler–Clarke reaction</span> Chemical reaction

The Eschweiler–Clarke reaction is a chemical reaction whereby a primary amine is methylated using excess formic acid and formaldehyde. Reductive amination reactions such as this one will not produce quaternary ammonium salts, but instead will stop at the tertiary amine stage. It is named for the German chemist Wilhelm Eschweiler (1860–1936) and the British chemist Hans Thacher Clarke (1887–1972).

Reductive amination is a form of amination that involves the conversion of a carbonyl group to an amine via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde. It is a common method to make amines and is widely used in green chemistry since it can be done catalytically in one-pot under mild conditions. In biochemistry, dehydrogenase enzymes use reductive amination to produce the amino acid, glutamate. Additionally, there is ongoing research on alternative synthesis mechanisms with various metal catalysts which allow the reaction to be less energy taxing, and require milder reaction conditions. Investigation into biocatalysts, such as imine reductases, have allowed for higher selectivity in the reduction of chiral amines which is an important factor in pharmaceutical synthesis.

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.

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">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.

<span class="mw-page-title-main">Keggin structure</span> Best known structural form for heteropoly acids

The Keggin structure is the best known structural form for heteropoly acids. It is the structural form of α-Keggin anions, which have a general formula of [XM12O40]n−, where X is the heteroatom, M is the addendum atom, and O represents oxygen. The structure self-assembles in acidic aqueous solution and is a commonly used type of polyoxometalate catalysts.

<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.

The Crabbé reaction is an organic reaction that converts a terminal alkyne and aldehyde into an allene in the presence of a soft Lewis acid catalyst and secondary amine. Given continued developments in scope and generality, it is a convenient and increasingly important method for the preparation of allenes, a class of compounds often viewed as exotic and synthetically challenging to access.

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

Terephthalaldehyde (TA) is an organic compound with the formula C6H4(CHO)2. It is one of three isomers of benzene dicarboxaldehyde, in which the aldehyde moieties are positioned in the para conformation on the benzene ring. Terephthalaldehyde appears as a white to beige solid, typically in the form of a powder. It is soluble in many organic solvents, such as alcohols (e.g., methanol or ethanol) and ethers (e.g., tetrahydrofuran or diethylether).

Polyimines are classified as polymer materials that contain imine groups, which are characterised by a double bond between a carbon and nitrogen atom. The term polyimine can also be found occasionally in covalent organic frameworks (COFs). In (older) literature, polyimines are sometimes also referred to as poly(azomethine) or polyschiff.

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, Springer-Nature, 33 (10): 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, American Medical Association, 97 (3): 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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.