Ball-and-stick model of the glutaraldehyde molecule
Glutaric acid dialdehyde
|Main uses||Disinfectant, warts|
|Defined daily dose||Not established|
|Chemical and physical data|
|Molar mass||100.117 g·mol−1|
|3D model (JSmol)|
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. The wholesale cost in the developing world is about US$1.50–7.40 per liter of 2% solution. 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. 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.In a related application, glutaraldehyde is sometimes employed in the tanning of leather and in embalming.
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
Glutaraldehyde is produced industrially by the oxidation of cyclopentene. Alternatively it can be made by the Diels-Alder reaction of acrolein and vinyl ethers followed by hydrolysis.Glutaraldehyde converts in aqueous solution to various hydrates that in turn convert to other equilibrating species
History and culture
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.A glutaraldehyde solution of 2.0% concentration may be used as a biocide for sterilization of surgical equipment 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. Bacterial growth impairs extraction from these wells, glutaraldehyde is pumped as a component of the fracturing fluid to inhibit microbial growth.
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