Stereoisomeric Flavour Compounds. Part LVII: The Stereoisomers of 3-Oxo-p-menthane-8-thiol acetate, Simultaneously Stereoanalysed with their Corresponding Thiols

被引:19
作者
Koepke, Thomas [1 ]
Schmarr, Hans-Georg [1 ]
Mosandl, Armin [1 ]
机构
[1] Univ Frankfurt, Inst Lebensmittelchem, D-6000 Frankfurt 11, Germany
关键词
Buchu leaf oil; Cassis flavour; 3-Oxo-p-menthane-8-thiol acetate stereoisomers; Sensory properties; 8-Mercapto-p-menthan-3-one and its S-acetate; Simultaneous chirospecific analysis;
D O I
10.1002/ffj.2730070407
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The stereoisomers of 3-oxo-p-menthane-8-thiol acetate have been synthesized by acetylation of optically pure stereoisomers of 8-mercapto-p-menthan-3-one. The stereoisomers were identified by H-1/C-13-NMR spectroscopy and CGC-MS. Their sensory properties are described. Their chirospecific analysis is reported simultaneously with the stereoisomers of their corresponding thiols using selectivity adjusted enantioselective capillary gas chromatography with octakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl)-gamma-cyclodextrin as the chiral stationary phase.
引用
收藏
页码:205 / 211
页数:7
相关论文
共 8 条
[1]   SOLVENT EFFECTS IN NUCLEAR MEGNETIC RESONANCE .6. CONFORMATIONS OF SUBSTITUTED CYCLOHEXANONES [J].
FETIZON, M ;
GORE, J ;
LASZLO, P ;
WAEGELL, B .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) :4047-&
[2]  
Grob K., 1986, MAKING MANIPULATING
[3]   STEREOISOMERIC FLAVOR COMPOUNDS .54. 8-MERCAPTO-PARA-MENTHAN-3-ONE - OPTICALLY PURE STEREOISOMERS AND CHIROSPECIFIC ANALYSIS [J].
KOPKE, T ;
MOSANDL, A .
ZEITSCHRIFT FUR LEBENSMITTEL-UNTERSUCHUNG UND-FORSCHUNG, 1992, 194 (04) :372-376
[4]  
LAMPARSKY D, 1971, Tetrahedron Letters, V36, P3323
[5]  
Ludwig H., 1972, DBP, V2, P221
[6]  
NOWOTNY HP, 1989, HRC-J HIGH RES CHROM, V12, P383
[7]   INFLUENCE OF DERIVATIZATION ON THE CHIRAL SELECTIVITY OF CYCLODEXTRINS - ALKYLATED ACYLATED CYCLODEXTRINS AND GAMMA/DELTA-LACTONES AS AN EXAMPLE [J].
SCHMARR, HG ;
MOSANDL, A ;
KAUNZINGER, A .
JOURNAL OF MICROCOLUMN SEPARATIONS, 1991, 3 (05) :395-402
[8]   ORGANOLEPTIC PRINCIPLE OF CASSIS FLAVOR IN BUCHU OIL [J].
SUNDT, E ;
WILLHALM, B ;
CHAPPAZ, R ;
OHLOFF, G .
HELVETICA CHIMICA ACTA, 1971, 54 (07) :1801-&