Glutaraldehyde
Encyclopedia
Glutaraldehyde is an organic compound
with the formula CH2(CH2CHO)2. A pungent colorless oily liquid, glutaraldehyde is used to disinfect medical and dental equipment. It is also used for industrial water treatment
and as a chemical preservative.
and by the Diels-Alder reaction
of acrolein
and methyl vinyl ether
followed by hydrolysis. Like other dialdehydes (e.g., glyoxal
), it does not exist typically as the dialdehyde but as the hydrate.
Monomeric glutaraldehyde can polymerize by aldol condensation
reaction yielding alpha, beta-unsaturated poly-glutaraldehyde. This reaction usually occurs at alkaline pH values.
as a fixative. It kills cells quickly by crosslinking their proteins and 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 example of an application for treatment of proteins with glutaraldehyde is the inactivation of bacterial toxins to create 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.
. The oligomeric state of proteins can be examined through this application. Glutaraldehyde is also used in SDS-PAGE
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 tris
.
isomer
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 mosses
, liverworts
, and vascular plants
.
, nose
, throat
, and lung
irritation, along with headache
s, drowsiness and dizziness. It is a main source of occupational asthma
among health care providers.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
with the formula CH2(CH2CHO)2. A pungent colorless oily liquid, glutaraldehyde is used to disinfect medical and dental equipment. It is also used for industrial water treatment
Industrial water treatment
Industrial 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 cyclopenteneCyclopentene
Cyclopentene is a chemical compound with the formula 58. It is a colorless liquid with a petrol-like odor. It is one of the cycloalkenes.Cyclopentene is produced industrially in large amounts...
and by the Diels-Alder reaction
Diels-Alder reaction
The 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 acrolein
Acrolein
Acrolein is the simplest unsaturated aldehyde. It is produced widely but is most often immediately reacted with other products due to its instability and toxicity...
and methyl vinyl ether
Methyl vinyl ether
Methyl vinyl ether is an organic compound with the chemical formula C3H6O. It is the simplest chemical that contains both an alkene group and an alkyl group with an ether linkage. The compound can be made by reaction of acetylene and methanol in presence of a base. The alkene portion of the...
followed by hydrolysis. Like other dialdehydes (e.g., glyoxal
Glyoxal
Glyoxal is an organic compound with the formula OCHCHO. This yellow colored liquid is the smallest dialdehyde . Its tautomer acetylenediol is unstable.-Production:...
), it does not exist typically as the dialdehyde but as the hydrate.
Monomeric glutaraldehyde can polymerize by aldol condensation
Aldol condensation
An aldol condensation is an organic reaction in which an enol or an enolate ion reacts with a carbonyl compound to form a β-hydroxyaldehyde or β-hydroxyketone, followed by a 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 microscopyElectron microscope
An electron microscope is a type of microscope that uses a beam of electrons to illuminate the specimen and produce a magnified image. Electron microscopes have a greater resolving power than a light-powered optical microscope, because electrons have wavelengths about 100,000 times shorter than...
as a fixative. It kills cells quickly by crosslinking their proteins and is usually employed alone or mixed with formaldehyde
Formaldehyde
Formaldehyde is an organic compound with the formula CH2O. It is the simplest aldehyde, hence its systematic name methanal.Formaldehyde is a colorless gas with a characteristic pungent odor. It is an important precursor to many other chemical compounds, especially for polymers...
as the first of two fixative
Fixative
A fixative is a stabilizing or preservative agent:*Fixative , a liquid usually sprayed over a finished piece of artwork to better preserve it and prevent smudging...
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
Organelle
In 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 bilayer....
membrane lipids
Membrane lipids
The 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....
. Fixation
Fixation (histology)
In the fields of histology, pathology, and cell biology, fixation is a chemical process by which biological tissues are preserved from decay, thereby preventing autolysis or putrefaction...
is usually followed by dehydration of the tissue in ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
or acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...
, followed by embedding in an epoxy resin or acrylic resin.
Another example of an application for treatment of proteins with glutaraldehyde is the inactivation of bacterial toxins to create toxoid
Toxoid
A toxoid is a bacterial toxin whose toxicity has been weakened or suppressed either by chemical or heat treatment, while other properties, typically immunogenicity, are maintained. In international medical literature the preparation also is known as Anatoxin or Anatoxine...
vaccines, e.g., the pertussis
Pertussis
Pertussis, also known as whooping cough , is a highly contagious bacterial disease caused by Bordetella pertussis. Symptoms are initially mild, and then develop into severe coughing fits, which produce the namesake high-pitched "whoop" sound in infected babies and children when they inhale air...
(whooping cough) toxoid component in the Boostrix Tdap vaccine produced by GlaxoSmithKline
GlaxoSmithKline
GlaxoSmithKline plc is a global pharmaceutical, biologics, vaccines and consumer healthcare company headquartered in London, United Kingdom...
.
In a related application, glutaraldehyde is sometimes employed in the tanning of leather.
Biochemical reagent
Glutaraldehyde is frequently used in biochemistry applications as an amine-reactive homobifunctional crosslinkerCross-link
Cross-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-PAGE
SDS-PAGE
SDS-PAGE, sodium dodecyl sulfate polyacrylamide gel electrophoresis, describes a collection of related techniques 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 tris
Tris
Tris is an abbreviation of the organic compound known as trisaminomethane, with the formula 3CNH2. Tris is extensively used in biochemistry and molecular biology. In biochemistry, tris is widely used as a component of buffer solutions, such as in TAE and TBE buffer, especially for solutions of...
.
Wart treatment
A solution of 10 % w/w glutaraldehyde is sold under the name "Diswart Solution" to remove common and plantar warts. Product claims include: "Inactivates viruses and bacteria. Dries the wart surface. Stains the area treated brown, but will not harm the surrounding skin."Algaecidal activity
A polymerizedPolymerization
In polymer chemistry, polymerization is a process of reacting monomer molecules together in a chemical reaction to form three-dimensional networks or polymer chains...
isomer
Isomer
In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
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 mosses
Fissidens
Fissidens is a genus of moss in family Fissidentaceae.Selected species:* Fissidens adianthoides, Hedw.* Fissidens allenianus* Fissidens appalachensis* Fissidens arcticus* Fissidens bryoides* Fissidens clebschii...
, liverworts
Riccia
Riccia 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 plants
Elodea
Elodea 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 eyeHuman eye
The human eye is an organ which reacts to light for several purposes. As a conscious sense organ, the eye allows vision. Rod and cone cells in the retina allow conscious light perception and vision including color differentiation and the perception of depth...
, nose
Human nose
The visible part of the human nose is the protruding part of the face that bears the nostrils. The shape of the nose is determined by the ethmoid bone and the nasal septum, which consists mostly of cartilage and which separates the nostrils...
, throat
Throat
In vertebrate anatomy, the throat is the anterior part of the neck, in front of the vertebral column. It consists of the pharynx and larynx...
, and lung
Lung
The lung is the essential respiration organ in many 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 near the backbone on either side of the heart...
irritation, along with headache
Headache
A headache or cephalalgia is pain anywhere in the region of the head or neck. It can be a symptom of a number of different conditions of the head and neck. The brain tissue itself is not sensitive to pain because it lacks pain receptors. Rather, the pain is caused by disturbance of the...
s, drowsiness and dizziness. It is a main source of occupational asthma
Occupational asthma
Occupational 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 workplace".Asthma is...
among health care providers.