Glutaraldehyde
| Glutaraldehyde | |
|---|---|
| Skeletal formula | |
| Ball-and-stick model | |
| Pentane-1,5-dial | |
| Other names Pentanedial, Glutardialdehyde, Glutaric acid dialdehyde, Glutaric aldehyde, Glutaric dialdehyde, 1,5-Pentanedial | |
| Identifiers | |
| CAS number | 111-30-8 7px |
| PubChem | 3485 |
| ChemSpider | 3365 7px |
| UNII | T3C89M417N 7px |
| DrugBank | DB03266 |
| KEGG | D01120 7px |
| Jmol-3D images | Image 1 |
| |
| Molecular formula | C5H8O2 |
| Molar mass | 100.12 g mol−1 |
| 14px (verify) (what is: 10px/10px?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
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 preservative. It is mainly available as an aqueous solution, and in these solutions the aldehyde groups are hydrated.
It is by far the most commonly used oilfield non-oxidizing biocide. The kill mechanism is by cross-linking outer proteins of cells and preventing cell permeability. Glutaraldehyde's effectiveness as biocide is pH sensitive. It works well in neutral to alkaline water.
Contents
Production and structure
Glutaraldehyde is produced industrially by the oxidation of cyclopentene 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 as the dialdehyde but as the hydrate. These hydrates adopt several structures.[1]
Monomeric glutaraldehyde can polymerize by aldol condensation reaction yielding alpha, beta-unsaturated poly-glutaraldehyde. This reaction usually occurs at alkaline pH values.
Uses
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 microscopy as a fixative. It kills cells quickly by crosslinking their proteins and is usually employed alone or mixed with formaldehyde[2] 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.[3]
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 crosslinker. 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 half an hour, after which it must be thoroughly washed to remove the yellow stain brought about by reacting with free tris.
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."
Safety
As a strong disinfectant, glutaraldehyde is toxic and a strong irritant.[4] There is no evidence of carcinogenic activity.[5]
References
- ↑ Earl B. Whipple, Michael Ruta "Structure of Aqueous Glutaraldehyde" J. Org. Chem., 1974, vol. 39, 1666-1668. doi:10.1021/jo00925a015
- ↑ Karnovsky, M.J. (1965). A formaldehyde-glutaraldehyde fixative of high osmolality for use in electron microscopy. Journal of Cell Biology 27: 137A–138A
- ↑ Boostrix prescribing information, ©2009, GlaxoSmithKline
- ↑ Canadian Centre for Occupational Health and Safety (CCOHS) (a federal government site) > OSH Answers > Diseases, Disorders & Injuries > Asthma Document last updated on February 8, 2005
- ↑ Toxicology and Carcinogenesis Studies of Glutaraldehyde
External links
