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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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rdf:type
rdfs:label
  • Grapefruit mercaptan (en)
  • チオテルピネオール (ja)
  • Mercaptano da toronja (pt)
rdfs:comment
  • 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。 (ja)
  • 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. (pt)
  • 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. (en)
foaf:name
  • Grapefruit mercaptan (en)
name
  • Grapefruit mercaptan (en)
foaf:depiction
  • http://commons.wikimedia.org/wiki/Special:FilePath/Grapefruit_mercaptan.svg
  • http://commons.wikimedia.org/wiki/Special:FilePath/Grapefruit-mercaptan-3D-balls.png
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  • Grapefruit mercaptan.svg (en)
ImageFileR
  • Grapefruit-mercaptan-3D-balls.png (en)
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  • Grapefruit mercaptan (en)
ImageNameR
  • Grapefruit mercaptan (en)
OtherNames
  • 1 (xsd:integer)
  • grapefruit mercaptan (en)
  • thioterpineol (en)
  • α,α,4-trimethylcyclohex-3-ene-1-methane thiol (en)
PIN
Verifiedfields
  • changed (en)
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  • changed (en)
has abstract
  • 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. 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 2×10−5 ppb, or equivalently a concentration of 2×10−14. This corresponds to being able to detect 2×10−5 mg in one metric ton of water - one of the lowest detection thresholds ever recorded for a naturally occurring compound. (en)
  • 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。 (ja)
  • 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. (pt)
gold:hypernym
prov:wasDerivedFrom
page length (characters) of wiki page
alternative name
  • 1-p-menthene-8-thiol (en)
  • grapefruit mercaptan (en)
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