Chemical Description

Glutaraldehyde is a C5 dialdehyde and a biomimetic equivalent of l-lysine.

Synthesis Reference(s)

Tetrahedron, 48, p. 3503, 1992 DOI: 10.1016/S0040-4020(01)88489-1

Air & Water Reactions

Polymerizes in the presence of water.

Reactivity Profile

GLUTARALDEHYDE may discolor on exposure to air. Pentanedial polymerizes on heating. Pentanedial is incompatible with strong oxidizing agents. Pentanedial polymerizes in the presence of water.

Health Hazard

Glutaraldehyde is a strong irritant to the nose,eyes, and skin. In rabbits, 250 μg and 500 mg in 24 hours produced severe irritation in theeyes and skin, respectively. The corrosiveeffect on human skin of 6 mg over 3 dayswas severe. However, the acute toxicity ofglutaraldehyde by the oral and dermal routesis low to mild. Ohsumi and Kuroki (1988)determined that the symptoms of acute toxicityof this compound were less severethan those of formaldehyde. But the restraintof growth was more pronounced in micetreated with glutaraldehyde. An oral LD50value of 1300 mg/kg was reported for mice.Inhalation of this compound can cause upperrespiratory tract irritation, headache, and nervousness.Mice exposed at 33 ppm showedsymptoms of hepatitis.

Fire Hazard

Literature sources indicate that Pentanedial is nonflammable.

Flammability and Explosibility

Nonflammable

Biochem/physiol Actions

Glutaraldehyde is an effective protein crosslinker and finds application in techniques like enzyme immobilisation microscopy, histochemistry and cytochemistry. It exists in different forms under acidic or neutral conditions. It is a biocide widely used as a disinfectant in hospitals and industries and is toxic to aquatic organisms. Its allergic nature leads to hypersensitivity reactions. Contact of glutaraldehyde vapors in endoscopy contributes to Colitis.

Contact allergens

Glutaraldehyde is a well-know sensitizer in cleaners and health workers. It can also be found in X-ray developers or in cosmetics.

Safety Profile

Poison by ingestion, intravenous, and intraperitoneal routes. Moderately toxic by inhalation, skin contact, and subcutaneous routes. Experimental teratogenic and reproductive effects. A severe eye and human skin irritant. Mutation data reported. When heated to decomp osition it emits acrid smoke and irritating fumes. See also ALDEHYDES.

Potential Exposure

Glutaraldehyde is used in leather tanning; in embalming fluids; as a germicide; as a cross-linking agent for protein and polyhydroxy materi als; as a fixative for tissues; and as an intermediate. Buffered solutions are used as antimicrobial agents in hospitals.

Shipping

UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Likely impurities are oxidation products-acids, semialdehydes and polymers. It can be purified by repeated washing with activated charcoal (Norit) followed by vacuum filtration, using 15-20g charcoal/100mL of glutaraldehyde solution. Distil it at 60-65o/15mm, discarding the first 5-10%, then dilute with an equal volume of freshly distilled water at 70-75o, using magnetic stirring under nitrogen. The solution is stored at low temperature (3-4o), in a tightly stoppered container, and protected from light. Standardise by titration with hydroxylamine. [Anderson J Histochem Cytochem 15 652 1967, Beilstein 1 IV 3659.]

Incompatibilities

Water contact forms a polymer solution. A strong reducing agent. Incompatible with strong acids; caustics, ammonia, amines, and strong oxidizers. Note: Alkaline solutions of glutaraldehyde (i.e., activated glutar aldehyde) react with alcohol, ketones, amines, hydrazines, and proteins.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinera tor equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

Definition

ChEBI: A dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.

General Description

Light yellow liquid. Mixes with water.