Glutaraldehyde is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

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

carbonyl group In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containing a ...

is reactive to primary

amine group In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent ...

s (even as its hydrates), it can function as a

crosslink 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 ...

ing 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 brandname Cidex and Glutaral. As a disinfectant, it is used to sterilize

surgical instruments A surgical instrument is a tool or device for performing specific actions or carrying out desired effects during a surgery or operation, such as modifying biological tissue, or to provide access for viewing it. Over time, many different kinds of ...

Uses

Biochemistry

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

crosslinker 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 ...

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 residues. Proteins perform a vast array of functions within organisms, including catalysing metabolic reactions, DNA replication, respo ...

s. It is usually employed alone or mixed with

formaldehyde Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section F ...

Karnovsky, 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 Osmium tetroxide (also osmium(VIII) oxide) is the chemical compound with the formula OsO4. The compound is noteworthy for its many uses, despite its toxicity and the rarity of osmium. It also has a number of unusual properties, one being that the ...

to crosslink and stabilize cell and

organelle In cell biology, an organelle is a specialized subunit, usually within a cell, that has a specific function. The name ''organelle'' comes from the idea that these structures are parts of cells, as organs are to the body, hence ''organelle,'' the ...

membrane lipids Membrane lipids are a group of compounds (structurally similar to fats and oils) which form the double-layered surface of all cells (lipid bilayer). The three major classes of membrane lipids are phospholipids, glycolipids, and cholesterol. Lipid ...

. 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, also known as pertussis or the 100-day cough, is a highly contagious bacterial disease. Initial symptoms are usually similar to those of the common cold with a runny nose, fever, and mild cough, but these are followed by two or ...

(whooping cough) toxoid component in the Boostrix

Tdap The DPT vaccine or DTP vaccine is a class of combination vaccines against three infectious diseases in humans: diphtheria, pertussis (whooping cough), and tetanus. The vaccine components include diphtheria and tetanus toxoids and either kille ...

vaccine produced by

GlaxoSmithKline GSK plc, formerly GlaxoSmithKline plc, is a British multinational pharmaceutical and biotechnology company with global headquarters in London, England. Established in 2000 by a merger of Glaxo Wellcome and SmithKline Beecham. GSK is the ten ...

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 contain primer 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 st ...

and medication. Usually applied as a solution, it is used to sterilize

and other areas.

Dermatological uses

As a medication it is used to treat

plantar wart A plantar wart, or verruca vulgaris, is a wart occurring on the sole (foot), bottom of the foot or toes. Its color is typically similar to that of the skin. Small black dots often occur on the surface. One or more may occur in an area. They may r ...

s. 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 condition characterized by abnormally increased sweating, in excess of that required for regulation of body temperature. Although primarily a benign physical burden, hyperhidrosis can deteriorate quality of life from a psychologi ...

under the control of dermatologists. In people who have frequent sweating but do not respond to

aluminum chloride Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula . It forms hexahydrate with the formula , containing six water molecules of hydration. Both are colourless crystals, but samples are often contam ...

. 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 ( pKa around 6) is due to the numerous phenol groups in the structure. The chemical formula for commercial tannic acid is often given as C76H52O46, which correspon ...

and

Safety

Side effects include skin irritation. If exposed to large amounts, nausea, headache, and shortness of breath may occur.

Protective equipment Personal protective equipment (PPE) is protective clothing, helmets, goggles, or other garments or equipment designed to protect the wearer's body from injury or infection. The hazards addressed by protective equipment include physical, ele ...

is recommended when used, especially in high concentrations. Glutaraldehyde is effective against a range of

microorganisms A microorganism, or microbe,, ''mikros'', "small") and ''organism'' from the el, ὀργανισμός, ''organismós'', "organism"). It is usually written as a single word but is sometimes hyphenated (''micro-organism''), especially in olde ...

including

spores In biology, a spore is a unit of sexual or asexual reproduction that may be adapted for dispersal and for survival, often for extended periods of time, in unfavourable conditions. Spores form part of the life cycles of many plants, algae, f ...

. Glutaraldehyde is a

dialdehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group ...

. It works by a number of mechanisms. As a strong sterilant, glutaraldehyde is

toxic Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subst ...

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 substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive substan ...

activity.Toxicology and Carcinogenesis Studies of Glutaraldehyde
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 viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3%� ...

, which can be achieved in the presence of various

tungstic acid Tungstic acid refers to hydrated forms of tungsten trioxide, WO3. Both a monohydrate (WO3·H2O) and hemihydrate (WO3·1/2 H2O) are known. Molecular species akin to sulfuric acid, i.e. (HO)2WO2 are not observed. The solid-state structure of ...

-based

heteropoly acid In chemistry, the heteropolymetalates are a subset of the polyoxometalates, which consist of three or more transition metal oxyanions linked together by shared oxygen atoms to form a closed 3-dimensional molecular framework. In contrast to isopo ...

catalysts. This reaction essentially mimics

ozonolysis In organic chemistry, ozonolysis is an organic reaction where the unsaturated bonds of alkenes (), alkynes (), or azo compounds () are cleaved with ozone (). Alkenes and alkynes form organic compounds in which the multiple carbon–carbon b ...

. Alternatively it can be made by the Diels-Alder reaction of

acrolein Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a piercing, acrid smell. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fa ...

and vinyl ethers followed by hydrolysis. :

Reactions

Like other dialdehydes, (e.g.,

glyoxal Glyoxal is an organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of ...

) and simple aldehydes (e.g.,

), glutaraldehyde hydrates in aqueous solution, forming gem-diols. These diols in turn equilibrate with cyclic

hemiacetal A hemiacetal or a hemiketal has the general formula R1R2C(OH)OR, where R1 or R2 is hydrogen or an organic substituent. They generally result from the addition of an alcohol to an aldehyde or a ketone, although the latter are sometimes called hemike ...

. Monomeric glutaraldehyde polymerizes by

aldol condensation An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration to ...

and

Michael reaction In organic chemistry, the Michael reaction or Michael addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a carbon ...

s yielding alpha, beta-unsaturated poly-glutaraldehyde and related

oligomer In chemistry and biochemistry, an oligomer () is a molecule that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules, monomers.Quote: ''Oligomer molecule: A molecule of intermediate relativ ...

s. This reaction occurs at alkaline pH values. : 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

, which rigidifies macromolecular structures and shuts down their reactivity. The aldehyde groups in glutaraldehyde are susceptible to formation of imines by reaction with the amines of lysine and nucleic acids. The derivatives from

of pairs of glutaraldehyde also undergo imine formation.

Use in the Aquarium Hobby

Glutaraldehyde diluted with water is often sold as alternative to carbon dioxide gas injection for aquarium plants. It is commonly also used by aquarists in low doses as an algaecide.

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