GLUTARALDEHYDE

GLUTARALDEHYDE

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.

CAS: 111-30-8
European Community (EC) Number: 203-856-5

IUPAC Name: pentanedial
Molecular Formula: C5H8O2
Molecular Weight: 100.12

Color/Form: Colorless liquid
Boiling Point: 369 to 372 °F at 760 mmHg (decomposes)
Melting Point: less than 20 °F 
Solubility: greater than or equal to 100 mg/mL at 72 °F 
Density: 1.062 to 1.124 at 68 °F 
Vapor Pressure: 17 mmHg at 68 °F 

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, 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.

SYNONYMS:

glutaraldehyde
Pentanedial
Glutaral
111-30-8
Glutaric dialdehyde
Cidex
1,5-Pentanedial
Sonacide
Glutardialdehyde
Pentane-1,5-dial
Glutaric acid dialdehyde
Glutaric aldehyde
Glutaraldehyd
Glutaralum
Glutarol
Ucarcide
Aldesan
Alhydex
Hospex
1,3-Diformylpropane
Gluteraldehyde
1,5-Pentanedione
Aldesen
Novaruca
Sporicidin
Sterihyde L
Aldehyd gutarowy
NCI-C55425
Glutaclean
Sterihyde
Aqucar
Veruca-sep
Relugan GT
Relugan GTW
component of Cidex
Glutarex 28
NSC 13392
Sonacide (TN)
Cidex 7
Ucarcide 250
Relugan GT 50
Sterihyde L (TN)
Coldcide-25 microbiocide
NSC-13392
Glutaral (JAN/USP/INN)
Potentiated acid glutaraldehyde
CHEBI:64276
T3C89M417N
1, 5-Pentanedial
MFCD00007025
NCGC00091110-01
Caswell No. 468
Glutaraldehyd [Czech]
1,3-Diformyl propane
Diswart
Gludesin
Glutaralum [INN-Latin]
Glutarol-1,5-pentanedial
Aldehyd glutarowy [Polish]
Glutaral [USAN:INN:JAN]
CAS-111-30-8
CCRIS 3800
HSDB 949
EINECS 203-856-5
EPA Pesticide Chemical Code 043901
BRN 0605390
pentandial
Dioxopentane
Glutural
Ucarset
Verucasep
Virsal
UNII-T3C89M417N
Glutaral(usan)
glutaric dihydride
Glutaral [USAN:USP:INN:JAN]
GLUTARALDEHYDE, 25% SOLN
Bactron K31
Ucarcide 225
GLUTARAL [HSDB]
GLUTARAL [INCI]
GLUTARAL [USAN]
pentane-1,5-dialdehyde
GLUTARAL [INN]
GLUTARAL [JAN]
Glutaral, INN, USAN
GLUTARAL [MART.]
Protectol GDA, GT 50
SCHEMBL836
WLN: VH3VH
GLUTARAL [WHO-DD]
EC 203-856-5
GLUTARALDEHYDE [MI]
Pentane-1,5-dial solution
GLUTARALDEHYDE [FCC]
4-01-00-03659 (Beilstein Handbook Reference)
BIDD:ER0299
GLUTARALDEHYDE [VANDF]
GLUTARAL [USP IMPURITY]
CHEMBL1235482
DTXSID6025355
AMY3308
Bio1_000462
Bio1_000951
Bio1_001440
Glutaraldehyde solution, 25% w/w
Glutaraldehyde solution, 50% w/w
Glutaraldehyde solution, 70% w/w
NSC13392
STR01121
ZINC1729593
Tox21_111083
Tox21_201742
Tox21_303295
STL281872
AKOS008967285
Glutaraldehyde (50per cent in water)
DB03266
Glutaric dialdehyde, 25%sol. In water
Glutaric dialdehyde, 25% sol. in water
NCGC00091110-02
NCGC00091110-03
NCGC00257231-01
NCGC00259291-01
FT-0626730
G0067
G0068EN300-18037
D01120
A802339
Q416475
Q-201162
Z57127529
F2191-0161