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Grapefruit mercaptan is the common name for 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 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.

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  • Grapefruit mercaptan
  • Mercaptano da toronja
  • チオテルピネオール
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  • チオテルピネオール (thioterpineol)、別名グレープフルーツメルカプタン (grapefruit mercaptan) はグレープフルーツに含まれる有機化合物の一種である。チオール基（メルカプト基）を持つモノテルペンで、テルピネオールのヒドロキシ基がチオールで置き換えられた構造を持つ。揮発性のあるチオールは一般的に非常に強い悪臭を持つが、チオテルピネオールのにおいは不快ではない。グレープフルーツの香りの主成分であり、これは2つのエナンチオマー（鏡像異性体）のうち (R) 体に由来する。最もにおい閾値の低い化合物のひとつとされ、ヒトの鼻は10−4 ppb の濃度でも感じることができる。 純粋なチオテルピネオール、またはこれを多く含む柑橘類由来の精油は香料や食品添加剤として利用される。チオテルピネオールは分解すると不快臭を持つ化合物を生じるため、代替品が探索されている。
  • Grapefruit mercaptan is the common name for 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 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.
  • Mercaptano da toronja é o nome vulgar para um composto orgânico natural encontrado na toronja. É um monoterpenóide que contém um grupo funcional tiol (aka mercaptano). Estruturalmente um grupo hidróxi de terpineol é substituído pelo tiol no mercaptano de toronja, por isso também chamado tioterpineol. Tióis voláteis têm odores tipicamente muito fortes, muitas vezes que podem ser detectados por seres humanos em concentrações muito baixas. O mercaptano de toronja tem um odor muito potente, mas não desagradável, e é o constituinte químico principal responsável pela aroma da toronja.
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