Grapefruit mercaptan

Grapefruit mercaptan
Grapefruit mercaptan	Grapefruit mercaptan
Names
	Preferred IUPAC name 2-[(1R)-4-Methylcyclohex-3-en-1-yl]propane-2-thiol
	Other names grapefruit mercaptan; 1-p-menthene-8-thiol; α,α,4-trimethylcyclohex-3-ene-1-methane thiol; thioterpineol
Identifiers
CAS Number	71159-90-5 (racemate) ; 83150-78-1 (R enantiomer) ;
3D model ( JSmol)	Interactive image;
ChemSpider	21163535 ;
ECHA InfoCard	100.072.886
EC Number	275-223-1;
PubChem CID	6427135;
UNII	7AT54D0N8R ;
CompTox Dashboard (EPA)	DTXSID00894921 ;
	InChI InChI=1S/C10H18S/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3/t9-/m0/s1 Key: ZQPCOAKGRYBBMR-VIFPVBQESA-N ; InChI=1/C10H18S/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3/t9-/m0/s1 Key: ZQPCOAKGRYBBMR-VIFPVBQEBF;
	SMILES SC(C)(C)[C@@H]1CCC(C)=CC1;
Properties
Chemical formula	C10H18S
Molar mass	170.31 g/mol
Density	1.03 g/cm3
Melting point	< 25 °C (77 °F; 298 K)
Boiling point	58 °C (136 °F; 331 K) at .33 mmHg
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319
Precautionary statements	P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Grapefruit mercaptan is a natural

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.^[1] This characteristic aroma is a property of only the R enantiomer.^[2]

Pure grapefruit mercaptan, or citrus-derived oils rich in grapefruit mercaptan, are sometimes used in

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.[3]