Thiols are organic compounds with a sulfur atom and a hydrogen atom attached to a carbon atom, giving them a distinct odor. They are found in skunk spray, flatulence, and garlic, among other things. Thiols are used in various industries and are sometimes referred to as mercaptans.
Thiols are a class of organic compounds that contain a sulfhydryl group (SH), also known as a thiol group, composed of a sulfur atom and a hydrogen atom attached to a carbon atom. This molecular structure is what distinguishes thiols from other organic chemical compounds with an oxygen-carbon bond configuration, such as phenols and alcohols. It is also what gives many highly volatile thiols a persistent and very unpleasant odor reminiscent of rotten eggs.
There are many examples of the odorous properties of naturally occurring thiol groups. In fact, thiols are responsible for the telltale odor that lingers after a skunk sprays in self-defense. The animal’s secretion, which is a yellowish oil generated by special glands under the tail, contains (E)-2-butene-1-thiol and 3-methyl-1-butanethiol, as well as thiol acetate derivatives. The formula is so pungent that a concentration of one in 10 parts per billion is enough to make a human nose wrinkle in disgust. However, while the impact may be insignificant in comparison, it is interesting to note that the same compounds are responsible for the bouquet associated with flatulence and bad breath in humans.
Thiols also give many botanicals their aromatic properties, not all of which are offensive. Grapefruit, for example, contains thioterpineol, which gives the fruit its distinctive but not unpleasant scent. Thiols are also involved in producing the intoxicating aroma familiar to those who brew or wine at home. These organic compounds are also components of alliums, such as onions and garlic. The fact that thiols bind easily to proteins found in human skin explains why the odor from handling these foods often remains faintly, even after washing.
The olfactory properties of these chemical groups have been used in practice in many industries. For example, thiols are added to natural gas used for heating and cooking in homes as a safety feature since the escaping fumes would otherwise not be detected in the event of a leak. They are also added to jet fuel, used in the production of pulp and petroleum products, and can be found in some medicines and pesticides.
Thiol compounds are commonly referred to as mercaptans, although the International Union of Pure and Applied Chemistry (IUPAC) deems the term antiquated in modern nomenclature. However, its use persists. In fact, as an additive used in the examples illustrated above, the main ingredient is commonly known as t-butyl mercaptan. Supposedly, thiols earned this synonym from the Latin mercurium captans, which translates to “grab mercury.” This is in reference to the fact that the SH group in these compounds reacts readily with mercury. In fact, mercury salts, still known as mercaptides, are sometimes used to detect the presence of thiol compounds.
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