trans-3-Methyl-4-octanolide
| trans-3-Methyl-4-octanolide |
|
(4S,5R)-5-butyl-4-methyldihydrofuran-2(3H)-one
|
| Identifiers |
| PubChem |
11105597 (4R,5S), 11084123 (4S,5R) |
| ChemSpider |
9280733 (4R,5S) Y, 9259269 (4S,5R) |
| Jmol-3D images |
Image 1
Image 2 |
-
O=C1O[C@@H](CCCC)[C@@H](C1)C (4R,5S)
CCCC[C@H]1OC(=O)C[C@@H]1C (4R,5S)
|
-
InChI=1S/C9H16O2/c1-3-4-5-8-7(2)6-9(10)11-8/h7-8H,3-6H2,1-2H3/t7-,8+/m1/s1 (4R,5S) Y
InChI=1S/C9H16O2/c1-3-4-5-8-7(2)6-9(10)11-8/h7-8H,3-6H2,1-2H3/t7-,8+/m0/s1 (4S,5R)
|
| Properties |
| Molecular formula |
C9H16O2 |
| Molar mass |
156.222 |
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| Infobox references |
trans-3-Methyl-4-octanolide, also called trans-β-methyl-γ-octalactone is a chemical compound of the lactone family with formula C9H16O2. It exists in two stereoisomers: (3R,4S) and (3S,4R).
The (3S,4R) form is found in whiskey and other alcoholic beverages that have been aged in oak barrels, together with the more important cis isomer.[1][2] It has a coconut, celery or fresh wood aroma, that can be detected by humans at the concentration of 20 μg/L in air.[3] A mixture of the cis and trans isomers is repellent for mosquitos and flies.[4]
The (3S,4R) isomer is extracted by the alchoolic beverage from some precursor substances in the oak wood.[5] It can be synthesized in various ways.[3][6][7]
See also
-
References
- ^ "Aromas and Flavours". Wine-Pages.com. http://www.wine-pages.com/guests/tom/taste5.htm. Retrieved 2007-12-18.
- ^ Hans-Dieter Belitz, Peter Schieberle, and Werner Grosch (2004) Food Chemistry, page 383. Springer, ISBN 3540408185
- ^ a b Eric Masson, Raymond Baumes, Christine Le Guernevé, and Jean-Louis Puech (2000) Identification of a Precursor of β-Methyl-γ-octalactone in the Wood of Sessile Oak (Quercus petraea (Matt.) Liebl.). J. Agric. Food Chem. volume 48, pages 4306-4309
- ^ Yukio Suzuki, Wakako Mori, Hiroyuki Ishizone, Koichi Naito, and Toshio Honda (1992) Concise Enantiospecific Syntheses of (+)-Eldanolide and (-)-cis-Whisky Lactone. Tetrahedron letters, volume 33, pages 4931-4932 doi:10.1016/S0040-4039(00)61237-6
- ^ Masuda and Nishimura (1971), Branched nonalactones from some Quercus species. Phytochemistry, volume 10, pages 1401-1402.
- ^ Hisashi Nishikori, Katsuji Ito, and Tsutomu Katsuki (1998) A short-step synthesis of trans-whisky lactone by an asymmetric Michael reaction. Tetrahedron: Asymmetry, volume 9, pages 1165–1170.
- ^ Katsuji Ito, Miwa Yoshitake and Tsutomu Katsuki (1995), Enantioselective Synthesis of trans-Whisky Lactone by Using Newly Developed Asymmetric Ring Expansion Reaction of Oxetane as a Key Step. Chemistry Letters, volume 24, issue 11, page 1027 doi:10.1246/cl.1995.1027