Glutaraldehyde

Source: Wikipedia, the free encyclopedia.

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 ?)

Glutaraldehyde is an

surgical instruments.[3]

Uses

Biochemistry

Glutaraldehyde is used in biochemistry applications as an amine-reactive homobifunctional

membrane lipids
.

Another application for treatment of proteins with glutaraldehyde is the inactivation of bacterial toxins to generate

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

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

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.

algicide.[16]

Safety

Side effects include skin irritation.

dialdehyde.[18] It works by a number of mechanisms.[17]

As a strong sterilant, glutaraldehyde is

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

Diels-Alder reaction of acrolein and vinyl ethers followed by hydrolysis.[23]

Reactions

Like other dialdehydes, (e.g.,

Michael reactions yielding alpha, beta-unsaturated poly-glutaraldehyde and related oligomers. This reaction occurs at alkaline pH values.[25]

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

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.

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]

References

  1. 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. ^
    ISBN 9789241547659
    .
  4. ^
    ISBN 9780857111562
    .
  5. ISBN 9781455776610. Archived
    from the original on 6 October 2022. Retrieved 9 September 2017.
  6. ISBN 9780683080278. Archived
    from the original on 10 October 2022. Retrieved 19 September 2020.
  7. ^
    PMID 12466110
    .
  8. 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. PMID 36138240
  12. OSTI 593571. {{cite journal}}: Cite journal requires |journal= (help
    )
  13. ISBN 9781455776610. Archived
    from the original on 23 September 2017.
  14. ^ NHS Choices: Glutarol Archived 5 February 2015 at the Wayback Machine
  15. 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. ^
    ISBN 9781118425862. Archived
    from the original on 23 September 2017.
  18. 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. ^ a b Toxicology and Carcinogenesis Studies of Glutaraldehyde Archived 10 October 2012 at the Wayback Machine
  21. ISBN 0471936235
    .
  22. doi:10.1246/cl.1988.877
    .
  23. ^
    ISBN 978-3527306732
    .
  24. doi:10.1021/jo00925a015
    .
  25. ^
    PMID 15560135
    .
  26. ISBN 978-3527306732
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Glutaraldehyde&oldid=1213537612"