Furan-2-ylmethanethiol

Furan-2-ylmethanethiol is a chemical compound that belongs to the class of organic compounds known as thiols. It is characterized by the presence of a furan ring and a sulfhydryl (-SH) group. This compound is notable for its role in the flavor profile of various foods, particularly coffee and roasted meat.

Structure and Properties

Furan-2-ylmethanethiol consists of a five-membered furan ring attached to a methanethiol group. The furan ring is an aromatic compound containing four carbon atoms and one oxygen atom. The methanethiol group consists of a carbon atom bonded to a sulfur atom, which is in turn bonded to a hydrogen atom.

The presence of the sulfur atom in the methanethiol group is responsible for the compound's strong, distinctive odor. This is a common characteristic of thiols, which are often associated with pungent smells.

Occurrence and Use

Furan-2-ylmethanethiol is found naturally in a variety of foods. It is one of the key compounds responsible for the aroma of roasted coffee. During the roasting process, furan-2-ylmethanethiol is formed from the Maillard reaction, a type of non-enzymatic browning reaction that occurs between amino acids and reducing sugars.

In addition to coffee, furan-2-ylmethanethiol is also found in roasted meat and other cooked foods. It contributes to the savory, meaty flavor known as umami, which is considered one of the five basic tastes.

Safety and Toxicity

Like many thiols, furan-2-ylmethanethiol has a strong odor that can be unpleasant in high concentrations. However, it is generally considered safe for consumption in the small amounts found in food.

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  Furan-2-ylmethanethiol structure

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  Synthesis of Furfuryl mercaptan