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Glutaraldehyde

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Glutaraldehyde
Names
IUPAC name
Pentane-1,5-dial
Other names
Pentanedial, Glutardialdehyde, Glutaric acid dialdehyde, Glutaric aldehyde, Glutaric dialdehyde, 1,5-Pentanedial
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.506 Edit this at Wikidata
  • O=CCCCC=O
Properties
C5H8O2
Molar mass 100.117
Appearance Clear liquid
Density 1.06 g/mL
Melting point −14 °C (7 °F; 259 K)
Boiling point 187 °C (369 °F; 460 K)
Miscible
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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. However, it is toxic, causing severe eye, nose, throat and lung irritation, along with headaches, drowsiness and dizziness.

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.

Monomeric glutaraldehyde can polymerize by aldol condensation reaction yielding alpha,beta-unsaturated poly-glutaraldehyde. This reaction usually occurs at alkaline pH values.

Uses

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[1] 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.

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.

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. [2]

References

  1. ^ Karnovsky, M.J. (1965). A formaldehyde-glutaraldehyde fixative of high osmolality for use in electron microscopy. Journal of Cell Biology 27: 137A–138A
  2. ^ http://www.americanaquariumproducts.com/AquariumPlants.html

1.^Aquarium Plants: Lighting, CO2, Ferts, Substrate http://www.americanaquariumproducts.com/AquariumPlants.html

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