Glutaraldehyde is an organic compound with the formulat CH2(CH2CHO)2. This pungent colorless oily liquid is used to disinfect medical and dental equipment. It is also used for
industrial water treatmentIndustrial Water Treatment can be classified into the following categories:* Boiler water treatment* Cooling water treatment* Wastewater treatment...
and as a chemical preservative.
Glutaraldehyde is produced industrially by the oxidation of cyclopentene and by the
Diels-Alder reactionThe Diels-Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system. The reaction can proceed even if some of the atoms in the newly-formed ring are not carbon...
of
acroleinAcrolein is the simplest unsaturated aldehyde. It is produced widely but is most often immediately reacted with other products due to its instability and toxicity. It has a piercing, disagreeable, acrid smell similar to that of burning fat.-Synthesis:Acrolein is prepared industrially by oxidation...
and methyl vinyl ether followed by hydrolysis. Like other dialdehydes (e.g.
Glutaraldehyde is an organic compound with the formulat CH2(CH2CHO)2. This pungent colorless oily liquid is used to disinfect medical and dental equipment. It is also used for
industrial water treatmentIndustrial Water Treatment can be classified into the following categories:* Boiler water treatment* Cooling water treatment* Wastewater treatment...
and as a chemical preservative.
Production and structure
Glutaraldehyde is produced industrially by the oxidation of cyclopentene and by the
Diels-Alder reactionThe Diels-Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system. The reaction can proceed even if some of the atoms in the newly-formed ring are not carbon...
of
acroleinAcrolein is the simplest unsaturated aldehyde. It is produced widely but is most often immediately reacted with other products due to its instability and toxicity. It has a piercing, disagreeable, acrid smell similar to that of burning fat.-Synthesis:Acrolein is prepared industrially by oxidation...
and methyl vinyl ether followed by hydrolysis. Like other dialdehydes (e.g.
glyoxalGlyoxal is an organic compound with the formula OCHCHO. This yellow colored liquid is the smallest dialdehyde .-Production:...
, it does not exist typically as the drialdehyde but as the hydrate.
Monomeric glutaraldehyde can polymerize by
aldol condensationAn Aldol condensation is an organic reaction in which an enolate ion reacts with a carbonyl compound to form a β-hydroxyaldehyde or β-hydroxyketone, followed by dehydration to give a conjugated enone....
reaction yielding alpha, beta-unsaturated poly-glutaraldehyde. This reaction usually occurs at alkaline pH values.
Fixative
A glutaraldehyde solution of 0.1% to 1.0% concentration may be used for system disinfection and as a preservative for long term storage. Glutaraldehyde is used in biological
electron microscopyAn electron microscope is a type of microscope, a scientific instrument which is used to magnify things on a fine scale. That uses a particle beam of electrons to illuminate a specimen and create a highly-magnified image...
as a fixative. It kills cells quickly by crosslinking their proteins and is usually employed alone or mixed with
formaldehydeFormaldehyde is a chemical compound with the formula CH2O. It is the simplest aldehyde. Formaldehyde also exists as the cyclic trimer trioxane and the polymer paraformaldehyde. It exists in water as the hydrate H2C2. Aqueous solutions of formaldehyde are referred...
as the first of two
fixativeA fixative is a stabilizing or preservative agent:*Fixative *Fixation , a solution used to preserve or harden fresh tissue of cell specimens for microscopic examination.*Fixative *embalming chemicals...
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
organelleIn cell biology, an organelle is a specialized subunit within a cell that has a specific function, and is usually separately enclosed within its own lipid membrane....
membrane lipidsThe three major classes of membrane lipids are phospholipids, glycolipids, and cholesterol.-Phospholipids :Phospholipids and glycolipids consist of two long, nonpolar hydrocarbon chains linked to a hydrophilic head group....
.
FixationIn the fields of histology, pathology, and cell biology, fixation is a chemical process by which biological tissues are preserved from decay, either through autolysis or putrefaction...
is usually followed by dehydration of the tissue in
ethanolEthanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug, best known as the type of alcohol found in alcoholic beverages and in modern thermometers. Ethanol is one of the oldest recreational drugs...
or
acetoneAcetone is the organic compound with the formula OC2. This colorless, mobile, flammable liquid is the simplest example of the ketones. Owing to the fact that acetone is miscible with water it serves as an important solvent in its own right, typically as the solvent of choice for...
, followed by embedding in an epoxy resin or acrylic resin.
In a related application, glutaraldehyde is employed in the tanning of leather.
Biochemical reagent
Glutaraldehyde is frequently used in biochemistry applications as an amine-reactive homobifunctional
crosslinkerCross-links are bonds that link one polymer chain to another. They can be covalent bonds or ionic bonds. "Polymer chains" can refer to synthetic polymers or natural polymers . When the term "cross-linking" is used in the synthetic polymer science field, it usually refers to the use of...
. The oligomeric state of proteins can be examined through this application. Glutaraldehyde is also used in
SDS-PAGESDS-PAGE, sodium dodecyl sulfate polyacrylamide gel electrophoresis, is a technique widely used in biochemistry, forensics, genetics and molecular biology to separate proteins according to their electrophoretic mobility...
to fix proteins and peptides prior to staining. Typically, a gel is treated with a 5% solution for approximately one half hour, after which it must be thoroughly washed to remove the yellow stain brought about by reacting with free
trisTris is an abbreviation of the organic compound known as trisaminomethane, with the formula
3CNH
2. Tris is extensively used in biochemistry and molecular biology...
.
Algaecidal activity
A
polymerizedIn polymer chemistry, polymerization is a process of reacting monomer molecules together in a chemical reaction to form three-dimensional networks or polymer chains...
isomerIn chemistry, isomers are compounds with the same molecular formula but different structural formulas. The word is derived from the Greek ισομερης, isomerès; isos = "equal", méros = "part"....
of glutaraldehyde known as polycycloglutaracetal is a fertilizer for aquatic plants. It is claimed that it provides a bioavailable source of carbon for higher plants that is not available to algae. Though not marketed as such due to federal regulations, the biocidal effect of glutaraldehyde kills most algae at concentrations of 0.5 - 5.0 ppm. These levels are not harmful to most aquatic fauna and flora. Adverse reactions have been observed by some aquarists at these concentrations in some aquatic
mossesFissidens is the only genus of moss in family Fissidentaceae.Selected species:* Fissidens adianthoides, Hedw.* Fissidens allenianus* Fissidens appalachensis* Fissidens arcticus* Fissidens bryoides* Fissidens clebschii...
,
liverwortsRiccia is a genus of liverworts in the order Marchantiales. One of the more than 100 species in this genus is the "slender riccia" , which can be found floating in ponds, and is sometimes used in aquariums....
, and
vascular plantsElodea is a genus of aquatic plants often called the waterweeds. Elodea is native to North America and is also widely used as aquarium vegetation. The introduction of some species of Elodea into waterways in parts of Europe, Australia, Africa, Asia, and New Zealand has created a significant problem...
.
Safety
As a strong disinfectant, glutaraldehyde is toxic and can cause severe eyeEyes are organs that detect light, and send electrical impulses along the optic nerve to the visual and other areas of the brain. Complex optical systems with resolving power have come in ten fundamentally different forms, and 96% of animal species possess a complex optical system...
, noseAnatomically, a nose is a protuberance in vertebrates that houses the nostrils, or nares, which admit and expel air for respiration in conjunction with the mouth....
, throatIn anatomy, the throat is the anterior part of the neck, in front of the vertebral column. It consists of the pharynx and larynx. An important feature of the throat is the epiglottis, a flap which separates the esophagus from the trachea and prevents inhalation of food or drink.The throat...
and lungThe lung or pulmonary system is the essential respiration organ in air-breathing animals, including most tetrapods, a few fish and a few snails. In mammals and the more complex life forms, the two lungs are located in the chest on either side of the heart...
irritation, along with headacheIn medicine a headache or cephalalgia is a symptom of a number of different conditions of the head. Some of the causes are benign while others are medical emergencies.There are a number of different classification systems for headaches...
s, drowsiness and dizziness. It is a main source of occupational asthmaOccupational asthma is an occupational condition defined as: "a disease characterized by variable airflow limitation and/or airway hyper-responsiveness due to causes and conditions attributable to a particular occupational environment and not stimuli encountered outside the...
among health care providers.
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