Glutaraldehyde is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula . 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. As a disinfectant, it is used to sterilize surgical instruments.

Uses

Biochemistry

Glutaraldehyde is used in biochemistry applications as an amine-reactive homobifunctional crosslinker and fixative. It kills cells quickly by crosslinking their

protein Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residue (biochemistry), residues. Proteins perform a vast array of functions within organisms, including Enzyme catalysis, catalysing metab ...

s. It is usually employed alone or mixed with formaldehydeKarnovsky, M.J. (1965). A formaldehyde-glutaraldehyde fixative of high osmolality for use in electron microscopy. Journal of Cell Biology 27: 137A–138A 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 In cell biology, an organelle is a specialized subunit, usually within a cell (biology), cell, that has a specific function. The name ''organelle'' comes from the idea that these structures are parts of cells, as Organ (anatomy), organs are to th ...

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

toxoid A toxoid is an inactivated toxin (usually an exotoxin) whose toxicity has been suppressed either by chemical (formalin) or heat treatment, while other properties, typically immunogenicity, are maintained. Toxins are secreted by bacteria, wherea ...

vaccines, e.g., the pertussis (whooping cough) toxoid component in Tdap vaccines.

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

Medical

Clinical uses

Glutaraldehyde is used as a

disinfectant A disinfectant is a chemical substance or compound used to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than ...

and medication. Usually applied as a solution, it is used to sterilize surgical instruments and other areas.

Dermatological uses

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. Glutaraldehyde is also used in the treatment of

hyperhidrosis Hyperhidrosis is a medical condition in which a person exhibits excessive perspiration, sweating, more than is required for the Thermoregulation, regulation of body temperature. Although it is primarily a physical burden, hyperhidrosis can deterio ...

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 Tannic acid is a specific form of tannin, a type of polyphenol. Its weak acidity (Acid dissociation constant, pKa around 6) is due to the numerous phenol groups in the structure. The chemical formula for commercial tannic acid is often given as ...

and formaldehyde.

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 concentration of water it is added to . Aquarists also commonly use it in low concentrations as an algicide.

Safety

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 A microorganism, or microbe, is an organism of microscopic size, which may exist in its single-celled form or as a colony of cells. The possible existence of unseen microbial life was suspected from antiquity, with an early attestation in ...

including spores. Glutaraldehyde is a dialdehyde. It works by a number of mechanisms. As a strong sterilant, glutaraldehyde is toxic and a strong irritant.Canadian Centre for Occupational Health and Safety (CCOHS) (a federal government site) > OSH Answers > Diseases, Disorders & Injuries > Asthma
Document last updated on 8 February 2005 There is no strong evidence of

carcinogenic A carcinogen () is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and Biological agent, biologic agent ...

activity,Toxicology and Carcinogenesis Studies of Glutaraldehyde
However, some occupations that work with this chemical have an increased risk of some cancers.

Production and reactions

Production

Glutaraldehyde is produced industrially by the catalytic oxidation of

cyclopentene Cyclopentene is a chemical compound with the formula . It is a colorless liquid with a petrol-like odor. It has few applications, and thus is mainly used as a minor component of gasoline, present in concentrations of less than 1%. It is one of t ...

hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscosity, viscous than Properties of water, water. It is used as an oxidizer, bleaching agent, and antiseptic, usua ...

, which can be achieved in the presence of various tungstic acid-based heteropoly acid catalysts. This reaction essentially mimics ozonolysis. Alternatively it can be made by the Diels-Alder reaction of acrolein and vinyl ethers followed by hydrolysis. :

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. 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. : GlutaldehydeHydrateEquilibria

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

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.

References

External links

Glutaraldehyde: Sources of emissions
AU National Pollutant Inventory
Glutaraldehyde
US National Institute for Occupational Safety and Health
Glutaraldehyde
NIST Standard Reference Data {{Portal bar, Medicine Aldehydes Anatomical preservation Disinfectants World Health Organization essential medicines Wikipedia medicine articles ready to translate