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
ChemSpider	3365^Y
UNII	T3C89M417N^Y
DrugBank	DB03266
KEGG	D01120^Y
Jmol-3D images	Image 1
SMILES O=CCCCC=O
InChI InChI=1S/C5H8O2/c6-4-2-1-3-5-7/h4-5H,1-3H2^Y Key: SXRSQZLOMIGNAQ-UHFFFAOYSA-N^Y InChI=1/C5H8O2/c6-4-2-1-3-5-7/h4-5H,1-3H2 Key: SXRSQZLOMIGNAQ-UHFFFAOYAO
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, reacts
Y (verify) (what is: Y/N?) 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.^[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.^[1]

Like other dialdehydes (e.g., glyoxal), it does not exist as the dialdehyde but as the hydrate. These hydrates adopt several structures.^[2]

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

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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.

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.^[4]

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."

Hydraulic Fracturing (Fracking) Fluid

Glutaraldehyde has been listed as a component of hydraulic fracturing "fracking" fluid. It is included in the additive called Alpha 1427, as a biocide, according to Material Safety Data Sheets released to the Morgantown Utility Board by Northeast Natural Energy.^[5]^[6]

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