2-Oxetanone

Toxicity

Based on experimental trials, it has been determined that propiolactone is a human carcinogen. The results have shown the generation of tumors in several tissues and from different administration routes.

Description

Beta-propiolactone is a colorless liquid with a strong, slightly sweet odor. It may occur naturally, but no clear documentation of its occurrence in nature was found, and it must be synthesized for commercial purposes. Beta-propiolactone is unstable at room temperature but stable when stored at 5
C in glass containers.
Its tendency to be unstable and react with other molecules in the vicinity is responsible for both its toxicity and its usefulness. Significant commercial production of beta-propiolactone took place during the late 1950s through the mid-1970s, when it was widely used in chemical synthesis in reactions with other molecules to produce new chemicals. All lactones are characterized by a ring structure consisting of two or more carbon atoms – as can be seen from its structure, beta-propiolactone has three in its ring – and a single oxygen, coupled with an adjacent ketone. The fewer the carbons in the ring, the more ‘strained’ is the ring structure and the more unstable and reactive its characteristics. When the ring bonds break, the betapropiolactone molecules attach to other nearby molecules.

The Uses of 2-Oxetanone

Reacts with bacteriphage DNA causing inactivation, repair and recombination

Indications

Propiolactone was used for vaccines, tissue grafts, surgical instruments, and enzymes, as a sterilant of blood plasma, water, milk and nutrient broth as a vapor-phase disinfectant in enclosed spaces. Its sporicidal action is used against vegetative bacteria, pathologic fungi, and viruses. It is no longer used in medical procedures or in food.

Background

Propiolactone is a lactone compound with a four-membered ring. It is a colorless liquid with a pungent slightly sweet odor. Propiolactone is a disinfectant used for the sterilization of blood plasma, vaccines, tissue grafts, surgical instruments, and enzymes. It has been used against bacteria, fungi, and virus. It is currently FDA approved for its use as an indirect additive used in food contact substances. Propiolactone was first commercially available in the United States in 1958.

Pharmacokinetics

When employed under conditions of maximum effectiveness, propiolactone is approximately 25 more active as a vapor phase disinfectant than formaldehyde, 4000 times more active than ethylene oxide and 50000 times more active than methyl bromide. It has been shown to be mutagenic by inducing cell transformation, chromosomal aberrations and chromatoid exchange. Propiolactone has been shown to be mutagenic in both somatic and germ cells.

Metabolism

Propiolactone is completely hydrolyzed after 3 hours of being in an aqueous solution and this time can be even faster in the presence of cellular debris and cell culture media. When in water, the lactone ring opens at the alkyl and acyl bonds. The degradation products of propiolactone are not toxic.