Grapefruit mercaptan

Chembox new
Name = Grapefruit mercaptan
ImageFileL1 = Grapefruit-mercaptan-2D-skeletal-vertical.png ImageSizeL1 = 100px
ImageNameL1 = Grapefruit mercaptan
ImageFileR1 = Grapefruit-mercaptan-3D-balls.png ImageSizeR1 = 150px
ImageNameR1 = Grapefruit mercaptan
IUPACName = (R)-2-(4-methylcyclohex-3-enyl)propane-2-thiol
OtherNames = grapefruit mercaptan
1-"p"-methene-8-thiol
α,α,4-trimethylcyclohex-3-ene-1-methane thiol
thioterpineol
Section1 = Chembox Identifiers
CASOther = racemate: 71159-90-5
R isomer: 83150-78-1
SMILES = CC1=CC [C@H] ( [C@] (C)(S)C)CC1
Section2 = Chembox Properties
Formula = C₁₀H₁₈S
MolarMass = 170.31 g/mol
Density = 1.03 g/cm³
MeltingPt =<25 °C
BoilingPt = 58 °C at .33 mmHg

Grapefruit mercaptan is the common name for a natural organic compound found in grapefruit. It is a monoterpenoid that contains a thiol (or 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 which 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. [cite journal|author=Buettner A., Schieberle P.|title=Characterization of the Most Odor-Active Volatiles in Fresh, Hand-Squeezed Juice of Grapefruit (Citrus paradisi Macfayden)|journal= J. Agric. Food Chem.|volume= 47|issue= 12|pages= 5189–5193|year= 1999|doi=10.1021/jf990071l] This characteristic aroma is a property of only the R-stereoisomer. [cite journal|author=Lehmann D., Dietrich A., Hener U., Mosandl A. |title=Stereoisomeric flavor compounds. LXX: 1-p-menthene-8-thiol: separation and sensory evaluation of the enantiomers by enantioselective gas chromatography-olfactometry|journal=Phytochemical Analysis|volume=6|issue= 5|pages=255–257|year= 1994 | doi = 10.1002/pca.2800060506]

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.

ee also

*Nootkatone

References