Grapefruit mercaptan is a natural organic compound found in grapefruit. It is a monoterpenoid that contains a thiol (also known as a mercaptan) functional group. Structurally, a hydroxy group of terpineol is replaced by the thiol in grapefruit mercaptan, so it is also called thioterpineol. Volatile thiols typically have very strong, often unpleasant odors that can be detected by humans in very low concentrations. Grapefruit mercaptan has a very potent, but not unpleasant, odor, and it is the chemical constituent primarily responsible for the aroma of grapefruit. This characteristic aroma is a property of only the R enantiomer. The aroma of the racemate is described as "sulfurous, aromatic, grapefruit". Pure grapefruit mercaptan, or citrus-derived oils rich in grapefruit mercaptan, are sometimes used in perfumery and the flavor industry to impart citrus aromas and flavors. However, both industries actively seek substitutes for grapefruit mercaptans for use as a grapefruit flavorant, since its decomposition products are often highly disagreeable to the human sense of smell. The detection threshold for the (+)-(R) enantiomer of grapefruit mercaptan is 3.4×10−5 ppb, or equivalently a concentration of 0.000034 nanograms per litre of air. This is the lowest detection thresholds recorded.
See also Nootkatone, another aroma compound in grapefruit Terpineol, where a hydroxyl is in place of the thiol
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