Chirospecific analysis

Figure 10.1 Analysis of racemic 2,5-dimethyl-4-hydroxy-3[2H]-furanone (1) obtained from a strawbeny tea, flavoured with the synthetic racemate of 1 (natural component), using an MDGC procedure (a) dichloromethane extract of the flavoured strawbeny tea, analysed on a Carbowax 20M pre-column (60 m, 0.32 mm i.d., 0.25 p.m film thickness earner gas H2, 1.95 bar 170 °C isothermal) (b) chirospecific analysis of (1) from the sti awbeny tea exti act, ti ansfened foi stereoanalysis by using a pemiethylated /3-cyclodextrin column (47 m X 0.23 mm i.d. canier gas H2, 1.70 bar 110 °C isothemial). Reprinted from Journal of High Resolution Chromatography, 13, A. Mosandl et al., Stereoisomeric flavor compounds. XLIV enantioselective analysis of some important flavor molecules , pp. 660-662, 1990, with permission from Wiley-VCH.

Werkhoff P, Brennecke S, Bretschneider W, Giintert M, Hopp R, Surburg H, Chirospecific analysis in essential oil, fragrance and flavor research, Z Lebensm Unters Forsch 196 307-328, 1993. 

Kopke X Mosandl A, Stereoisomeric flavor compounds. Part LIV 8-Mercapto-p-menthane-3-one -optically pure stereoisomers and chirospecific analysis, Z Lebensm Unters Forsch 194 372—376, 1992. 

Ferreira V, Jarauta I, Ortega L, Cacho J (2004) Simple strategy for the optimization of solid-phase extraction procedures through the use of solid-liquid distribution coefficients—application to the determination of aliphatic lactones in wine. J Chromatogr A 1025 147 Rettinger K, Karl V, Schmarr HG, Dettmar F, Hener U, Mosandl A (1991) Chirospecific analysis of 2-alkylbranched alcohols, -acids, and -esters chirality evaluation of 2-methylbutanoates from apples and pineapples. Phytochem Anal 2 184... 

Werkhoff P, Bretschneider W, Giintert M, Hopp R, Surburg H (1991) Chirospecific analysis in flavor and essential oil chemistry. Part B. Direct enantiomer resolution of trans-a-ionone and trans-a-damascone by inclusion gas chromatography. Z Lebensm Unters Forsch 192 111 Larsen M, Poll L (1990) Odour thresholds of some important aroma compounds in raspberries. Z Lebensm Unters Forsch 191 129... 

A. Mosandl, K. Fischer, U. Hener, P. Kreis, K. Rettinger, V. Schubert and H.-G. Schmarr, Stereoisomeric flavor compounds. 48. Chirospecific analysis of natural flavors and essential oils using multidimensional gas chromatography , J. Agric. Food Chem. 39 1131-1134(1991). 

K. Rettinger, V. Karl, H.-G. Schmarr, F. Dettmar, U. Hener and A. Mosandl, Chirospecific analysis of 2-alkyl-branched alcohols, acids and esters chirality evaluation of 2-methylbutanoates from apples and pineapples , Phytochem. Anal. 2 184-188 (1991). 

V. Karl, J. Gutser, A. Dietrich, B. Maas and A. Mosandl, Stereoisomeric flavour compounds. LXVIII. 2-, 3- and 4-alkyl-branched acids. Part 2 chirospecific analysis and sensory evaluation , Chirality 6 427-434 (1994). 

D. Bartschat, D. Lehmann, A. Dietrich, A. Mosandl and R. Kaiser, Chiral compounds of essential oils. XIX. 4-methyl-5 decanolide chirospecific analysis, structure and properties of the stereoisomers , Phytochem. Anal. 6 130-134 (1995). 

H.-G. Schmarr, A. Mosandl and K. Grob, Stereoisomeric flavour compounds. XXXVIII direct chirospecific analysis of y-lactones using on-line coupled LC-GC with a chiral separation column , Chromatographia 29 125-130 (1990). 

M. Glintert, R. Emberger, R. Hopp, M. Kbpsel, W. SUberzahn and P. Werkhoff. Chirospecific analysis in flavor and essential oil chemistry Part A. Filbertone - the character impact compound of hazel-nuts. Z. Lebensm. Unters. Forsch., 192. 108-110 (1991). 

V. Karl, A. Dietrich and A. Mosandl. Stereoisomeric Flavour Compounds LXIV The chirospecific analysis of 2-alkyl-branched flavour compounds from headspace extracts and their sensory evaluation. Phytochem. Anal., 4, 158-164 (1993). 

Chirospecific analysis can only be applied to a minority of coffee flavor constituents, most of them being aromatic and planar heterocyclic compounds. Nevertheless, Werkhoff et al. (1993) published a review on chirospecificity in essential oil, fragrance and flavor research. 

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