glutaraldehyde

Glutaraldehyde
IUPAC name	Pentane-1,5-dial
Other names	Pentanedial, Glutardialdehyde, Glutaric acid dialdehyde, Glutaric aldehyde, Glutaric dialdehyde, 1,5-Pentanedial
Identifiers
CAS number	111-30-8 Y
PubChem	3485
SMILES	O=CCCCC=O
ChemSpider ID	3365
Properties
Molecular formula	C5H8O2
Molar mass	100.12 g mol−1
Appearance	Clear liquid
Density	1.06 g/mL
Melting point	-14 °C, 259 K, 7 °F
Boiling point	187 °C, 460 K, 369 °F
Solubility in water	Miscible
Y (what is this?)  (verify) 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. This pungent colorless oily liquid is used to disinfect medical and dental equipment. It is also used for industrial water treatment and as a chemical preservative.^[1]

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 typically as the drialdehyde but as the hydrate.^[2]

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^[3] 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.

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 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 one half hour, after which it must be thoroughly washed to remove the yellow stain brought about by reacting with free tris.

Algaecidal activity

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. ^[4]

Safety

As a strong disinfectant, glutaraldehyde is toxic and can cause 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.^[5]

References

External links

• National Pollutant Inventory - Glutaraldehyde Fact Sheet
• National Institute for Occupational Safety and Health - Glutaraldehyde
• NIST WebBook
• Hazardous Chemical Information