Putrescine
A diamine responsible for the odor of putrefying flesh.
Putrescine is an organic compound with the formula (CH2)4(NH2)2. It is a colorless solid that melts near room temperature and is classified as a diamine. Together with cadaverine, it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors.
- chemical_formula
- (CH2)4(NH2)2
- classification
- diamine
- first_described_by
- Ludwig Brieger
- industrial_production_method
- hydrogenation of succinonitrile
Lore & Background
It is produced on an industrial scale by the hydrogenation of succinonitrile, and biotechnological production from renewable feedstock using a metabolically engineered strain of Escherichia coli has been investigated. Putrescine is synthesized in small quantities by healthy living cells via ornithine decarboxylase, and biologically via two pathways starting from arginine. In plants, putrescine is widely found and is often the most common polyamine. It plays roles in development and stress responses, and its absence is associated with increased parasite and fungal populations. The fungus Piriformospora indica promotes putrescine production in plants, leading to enhanced root growth. Putrescine is also found in all organisms, including as a component of bad breath, bacterial vaginosis, semen, and some microalgae. Putrescine reacts with adipic acid to yield the polyamide nylon 46, marketed as Stanyl. It has been proposed as a biochemical marker for determining how long a corpse has been decomposing. In agriculture, applying putrescine to plants lowers ethylene production, increases resistance to high temperatures and drought, and when applied post-harvest, delays ripening and extends shelf life of various fruits.
Reader's Guide
Putrescine is significant as a key contributor to the odor of decaying organic matter, alongside cadaverine, and as a biochemical marker in forensic taphonomy. Its industrial use in producing nylon 46 demonstrates its commercial value. Biologically, putrescine is a precursor to the polyamines spermidine and spermine, and it can act as a minor precursor to the neurotransmitter GABA in the brain, with recent research indicating that monoamine oxidase B mediates GABA synthesis via the putrescine pathway in astrocytes. In plants, putrescine is involved in development and stress responses, and its production can be enhanced by soil fungi, promoting root growth. Its role in extending the shelf life of fruits and improving plant resistance to environmental stress highlights its agricultural applications. The compound's low acute oral toxicity in rats suggests a relatively safe profile at moderate doses. The discovery of its role in GABA synthesis in the brain, particularly in the striatum, has implications for understanding dopamine regulation and neurological function.
Did You Know?
- Putrescine is a colorless solid that melts near room temperature.
- It is produced industrially by the hydrogenation of succinonitrile.
- Putrescine is a precursor to the polyamines spermidine and spermine.
- Applying putrescine post-harvest delays fruit ripening and extends shelf life.
Frequently Asked Questions
What is Putrescine?
Putrescine is a colorless diamine with the molecular formula (CH₂)₄(NH₂)₂ that melts at roughly room temperature. It is best known as one of the two primary compounds behind the stench of decaying tissue.
Why is Putrescine so strongly associated with bad smells?
Working alongside cadaverine, Putrescine is the main driver of the putrid odor released when flesh breaks down. It also contributes to various other unpleasant smells beyond just decomposition.
How is Putrescine produced on an industrial scale?
Commercially, Putrescine is manufactured through the hydrogenation of succinonitrile, a process that adds hydrogen across the nitrile groups to yield the diamine.
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