|Preferred IUPAC name
Glutaric acid dialdehyde
3D model (JSmol)
CompTox Dashboard (EPA)
|Melting point||−14 °C (7 °F; 259 K)|
|Boiling point||187 °C (369 °F; 460 K)|
|Vapor pressure||17 mmHg (20°C)|
|Safety data sheet||CAS 111-30-8|
|GHS Signal word||Danger|
|H302, H314, H317, H331, H334, H400|
|P260, P264, P270, P271, P272, P273, P280, P284, P301+312, P330, P302+352, P332+313, P304+340, P305+351+338, P311, P403+233, P405, P501|
|NFPA 704 (fire diamond)|
Threshold limit value (TLV)
|0.2 ppm (0.82 mg/m3) (TWA), 0.05 ppm (STEL)|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|134 mg/kg (rat, oral); 2,560 mg/kg (rabbit, dermal)|
|NIOSH (US health exposure limits):|
|0.2 ppm (0.8 mg/m3)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Glutaraldehyde, sold under the brandname Cidex and Glutaral among others, is a disinfectant, medication, preservative, and fixative. As a disinfectant, it is used to sterilize surgical instruments and other areas of hospitals. As a medication, it is used to treat warts on the bottom of the feet. Glutaraldehyde is applied as a liquid.
Side effects include skin irritation. If exposed to large amounts, nausea, headache, and shortness of breath may occur. Protective equipment is recommended when used, especially in high concentrations. Glutaraldehyde is effective against a range of microorganisms including spores. Glutaraldehyde is a dialdehyde. It works by a number of mechanisms.
Glutaraldehyde came into medical use in the 1960s. It is on the World Health Organization's List of Essential Medicines. There are a number of other commercial uses such as leather tanning.
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 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.
As a medication it is used to treat plantar warts. For this purpose, a 10% w/v solution is used. It dries the skin, facilitating physical removal of the wart. Trade names include Diswart Solution and Glutarol.
Side effects include skin irritation. If exposed to large amounts, nausea, headache, and shortness of breath may occur. Protective equipment is recommended when used, especially in high concentrations. Glutaraldehyde is effective against a range of microorganisms including spores.
As a strong sterilant, glutaraldehyde is toxic and a strong irritant. There is no strong evidence of carcinogenic activity. Some occupations that work with this chemical have an increased risk of some cancers.
Mechanism of action
A number of mechanisms have been invoked to explain the biocidal properties of glutaraldehyde. 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.
Production and reactions
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]
History and culture
Glutaraldehyde came into medical use in the 1960s. It is on the World Health Organization's List of Essential Medicines, the safest and most effective medicines needed in a health system. There are a number of other commercial uses such as leather tanning.
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.
As a biocide, glutaraldehyde is a component of hydraulic fracturing ("fracking") fluid. It is included in the additive called Alpha 1427. 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.[medical citation needed]
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- 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.
- Whipple Earl B.; Ruta Michael (1974). "Structure of Aqueous Glutaraldehyde". J. Org. Chem. 39: 1666–1668. doi:10.1021/jo00925a015.
- HCC lecture notes, 15 Archived 2015-05-02 at the Wayback Machine: Control of microorganisms Archived 2015-09-24 at the Wayback Machine
- Morgantown Utility Board. "Fracking Fluid Additives - Fracking Fluid MSDS's". Archived from the original on 5 February 2015. Retrieved 5 February 2015.. Links to documents, including Alpha 1427 Material Safety Data Sheet
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- NIST WebBook
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