PRODUCTS

GLUTARALDEHYDE

Glutaraldehyde is an organic compound with the formula (CH2)3(CHO)2.
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.

CAS Number: 111-30-8
EC Number: 203-856-5
IUPAC Name: pentanedial
Chemical Formula: C5H8O2

Other names: glutaraldehyde, Pentanedial, 111-30-8, Glutaral, Glutaric dialdehyde, 1,5-Pentanedial, Cidex, Glutardialdehyde, Sonacide, Glutaric acid dialdehyde, Glutaric aldehyde, Glutaraldehyd, Glutaralum, Aldesan, Alhydex, Glutarol, Hospex, Pentane-1,5-dial, Ucarcide, 1,3-Diformylpropane, 1,5-Pentanedione, Gluteraldehyde, Aldesen, Sterihyde L, Aldehyd glutarowy, Novaruca, Sporicidin, Caswell No. 468, NCI-C55425, NSC 13392, pentandial, Dioxopentane, Glutaclean, CCRIS 3800, HSDB 949, Sterihyde, Aqucar, Glutaralum [INN-Latin], Veruca-sep, Coldcide-25 microbiocide, Relugan GT, Relugan GTW, component of Cidex, EINECS 203-856-5, Glutarex 28, NSC-13392, Sonacide (TN), Cidex 7, EPA Pesticide Chemical Code 043901, Potentiated acid glutaraldehyde, Ucarcide 250, UNII-T3C89M417N, BRN 0605390, Relugan GT 50, Sterihyde L (TN), DTXSID6025355, CHEBI:64276, T3C89M417N, Glutaral (JAN/USP/INN), DTXCID605355, Glutaral [USAN:USP:INN], EC 203-856-5, 4-01-00-03659 (Beilstein Handbook Reference), MFCD00007025, NCGC00091110-01, Glutaralum (INN-Latin), GLUTARAL (MART.), GLUTARAL [MART.], GLUTARAL (USP IMPURITY), GLUTARAL [USP IMPURITY], Glutaraldehyde (50% in water), Glutaraldehyd [Czech], Glutaral (USAN:USP:INN), 1,3-Diformyl propane, Diswart, Gludesin, Glutarol-1,5-pentanedial, Aldehyd glutarowy [Polish], Glutaral [USAN:INN], CAS-111-30-8, Glutural, Ucarset, Verucasep, Virsal, Cudex, Glutaral(usan), glutaric dihydride, GLUTARALDEHYDE, 25% SOLN, Glutamic dialdehyde, Pond Health Guard, Bactron K31, Ucarcide 225, MINOXIDIL_met005, GLUTARAL [HSDB], GLUTARAL [USAN], pentane-1,5-dialdehyde, GLUTARAL [INN], GLUTARAL [JAN], Glutaral, INN, USAN, Protectol GDA, GT 50, SCHEMBL836, WLN: VH3VH, DIPYRIDAMOLE_met034, GLUTARAL [WHO-DD], GLUTARALDEHYDE [MI], Pentane-1,5-dial solution, GLUTARALDEHYDE [FCC], Pesticide Code: 043901, BIDD, GLUTARALDEHYDE [VANDF], CHEMBL1235482, AMY3308, Bio1_000462, Bio1_000951, Bio1_001440, Glutaraldehyde solution, 25% w/w, Glutaraldehyde solution, 50% w/w, Glutaraldehyde solution, 70% w/w, NSC13392, STR01121, Tox21_111083, Tox21_201742, Tox21_303295, STL281872, AKOS008967285, Glutaraldehyde (50per cent in water), 1ST2528, DB03266, Glutaric dialdehyde, 25%sol. In water, Glutaric dialdehyde, 25% sol. in water, NCGC00091110-02, NCGC00091110-03, NCGC00257231-01, NCGC00259291-01, DA-53608, G0067, G0068, NS00004136, EN300-18037, D01120, A802339, Q416475, Q-201162, Z57127529, F2191-0161

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 proteins.
It is usually employed alone or mixed with formaldehyde[9] 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.

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.

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 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.[4] 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 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 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 CO2 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 including spores.
Glutaraldehyde is a dialdehyde.
It works by a number of mechanisms.

As a strong sterilant, glutaraldehyde is toxic and a strong irritant.
There is no strong evidence of carcinogenic activity, However, some occupations that work with this chemical have an increased risk of some cancers.

Molar mass: 100.117
Appearance: Clear liquid
Odor: pungent
Density: 1.06 g/mL

Melting point: −14 °C
Boiling point: 187 °C
Solubility in water: Miscible
XLogP3-AA: -0.5

Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 4
Exact Mass: 100.052429494 g/mol
Monoisotopic Mass: 100.052429494 g/mol

Topological Polar Surface Area: 34.1Å²
Heavy Atom Count: 7
Complexity: 51.1
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Glutaral is used as an antimicrobial agent in sugar mills and as a fixing agent in the immobilisation of glucose isomerase enzyme preparations for use in the manufacture of high fructose corn syrup A polymerized 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.

Glutaraldehyde is a colorless liquid with a pungent odor used to disinfect medical and dental equipment. It is also used for industrial water treatment and as a chemical preservative. Glutaraldehyde is an oily liquid at room temperature (density 1.06 g/mL), and miscible with water, alcohol, and benzene.

It is used as a tissue fixative in electron microscopy. It is employed as an embalming fluid, is a component of leather tanning solutions, and occurs as an intermediate in the production of certain industrial chemicals. Glutaraldehyde is frequently used in biochemistry applications as an amine-reactive homobifunctional crosslinker.

The oligomeric state of proteins can be examined through this application. However, it is toxic, causing severe eye, nose, throat and lung irritation, along with headaches, drowsiness and dizziness. It is a main source of occupational asthma among health care providers. Glutaral has been shown to exhibit antibiotic function (A7907). Glutaral belongs to the family of Aldehydes. These are organic compounds containing the aldehyde functional group.

Glutaraldehyde is a colorless, oily liquid with a sharp, pungent odor.
Glutaraldehyde is used for industrial, laboratory, agricultural, medical, and some household purposes, primarily for disinfecting and sterilization of surfaces and equipment.

For example, it is used in oil and gas recovery operations and pipelines, waste water treatment, x-ray processing, embalming fluid, leather tanning, paper industry, in fogging and cleaning of poultry houses, and as a chemical intermediate in the production of various materials.
It may be used in select goods, such as paint and laundry detergent.

Glutaraldehyde, C5H8O2 or OCH(CH₂)₃CHO, is a transparent oily, liquid with a pungent odor.
The molecule consists of a five carbon chain doubly terminated with formyl (CHO) groups.
Glutaraldehyde 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.

For example, Glutaraldehyde is used in oil and gas recovery operations and pipelines, waste water treatment, x-ray processing, embalming fluid, leather tanning, paper industry, in fogging and cleaning of poultry houses, and as a chemical intermediate in the production of various materials.
Glutaraldehyde may be used in select goods, such as paint and laundry detergent.

Glutaraldehyde is a dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.
Glutaraldehyde has a role as a cross-linking reagent, a disinfectant and a fixative.

Glutaraldehyde solution is a light yellow liquid.
Glutaraldehyde mixes with water.

Glutaraldehyde is an organic compound with the formula (CH2)3(CHO)2.
The molecule consists of a five carbon chain doubly terminated with formyl (CHO) groups.
Glutaraldehyde 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 is reactive to primary amine groups (even as its hydrates), Glutaraldehyde can function as a crosslinking 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.
As a disinfectant, Glutaraldehyde is used to sterilize surgical instruments.

Glutaraldehyde is used for a number of applications:
Disinfectant for surgical instruments that cannot be heat sterilized
A cross-linking and tanning agent
A biocide in metalworking fluids and in oil and gas pipelines
An antimicrobial in water-treatment systems

A slimicide in paper manufacturing
A preservative in cosmetics
A disinfectant in animal housing
A tissue fixative in histology and pathology labs

A hardening agent in the development of X-rays
In embalming solutions
In the preparation of grafts and bioprostheses
In various clinical applications

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

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.

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

Dermatological uses
As a medication Glutaraldehyde is used to treat plantar warts.
For this purpose, a 10% w/v solution is used.
Glutaraldehyde dries the skin, facilitating physical removal of the wart.

Glutaraldehyde is also used in the treatment of hyperhidrosis 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 and formaldehyde.

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.

Production
Glutaraldehyde is produced industrially by the catalytic oxidation of cyclopentene by hydrogen peroxide, 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.

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.

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.

Glutaraldehyde has been a suggested alternative to formocresol as a tissue fixative for vital pulpotomy.
Histologic studies showed that it produced rapid surface fixation of pulp tissue but with limited depth of penetration, so a larger amount of radicular pulp tissue remained vital.
Fixed pulp tissue may be replaced with dense collagenous tissue over time.
Studies have also demonstrated less systemic distribution than was thought to occur with formocresol.

Glutaraldehyde possesses unique characteristics that render it one of the most effective protein crosslinking reagents.
Glutaraldehyde can be present in at least 13 different forms depending on solution conditions such as pH, concentration, temperature, etc.
Substantial literature is found concerning the use of glutaraldehyde for protein immobilization, yet there is no agreement about the main reactive species that participates in the crosslinking process because monomeric and polymeric forms are in equilibrium.

Glutaraldehyde may react with proteins by several means such as aldol condensation or Michael-type addition, and we show here 8 different reactions for various aqueous forms of this reagent.
As a result of these discrepancies and the unique characteristics of each enzyme, crosslinking procedures using glutaraldehyde are largely developed through empirical observation.

The choice of the enzyme-glutaraldehyde ratio, as well as their final concentration, is critical because insolubilization of the enzyme must result in minimal distortion of its structure in order to retain catalytic activity.
The purpose of this paper is to give an overview of glutaraldehyde as a crosslinking reagent by describing its structure and chemical properties in aqueous solution in an attempt to explain its high reactivity toward proteins, particularly as applied to the production of insoluble enzymes.