Abstract
The enantiomeric distributions of δ- and γ-lactones from dairy products are determined by enantioselective multidimensional gas chromatography. By using heptakis(2,3-di-O-acetyl-6-O-TBDMS)-β-cyclodextrin as the chiral main column, the simultaneous stereodifferentiation of the δ- and γ-lactones C13–C18 is reported for the first time. Genuine lactones of dairy products preferably occur as (R)-enantiomers. Flavoured margarine and coconut are analysed and discussed. Reference compounds are synthesized as racemates and separated by enantioselective HPLC into the enantiomers. Chiral compounds of characteristic enantiomeric ratios are detected irrespective of the manufacturing processes used.
Similar content being viewed by others
References
Maga JA (1976) Crit Rev Food Sci Nutr 8: 1–56
Werkhoff P, Brennecke S, Bretschneider W (1991) Chem Mikrobiol Technol Lebensm 13: 129–152
Mick S, Mick W, Schreier P (1982) Milchwissenschaft 37: 661–665
Widder S, Sen A, Grosch W (1991) Z Lebensm Unters Forsch 193: 32–35
Siek TJ, Albin IA, Sather LA, Lindsay RC (1971) J Dairy Sci 54: 1–4
Palm U, Askari C, Hener U, Jakob E, Mandler C, Geßner M, Mosandl A, König WA, Evers P, Krebber R (1991) Z Lebensm Unters Forsch 192: 209–213
Günther C (1988) Doctoral Thesis, University of Würzburg, Germany
Geßner M (1988) Doctoral Thesis, University of Würzburg, Germany
Barco A, Benetti S, Pollini GP (1973) Synthesis 316
Elsinger F (1965) Org Synth 45: 7–11
Fries SL (1949) J Am Chem Soc 71: 2571–2575
Corey EJ, Suggs JW (1975) Tetrahedron Lett 2647–2650
Boxer SE, Linstead RP (1931) J Chem Soc 740–751
Boormann EJ, Linstead RP (1933) J Chem Soc 577–580
Huffer M, Schreier P (1989) J Chromatogr 469: 137–141
Vandeweghe P, Reineccius GA (1990) J Agric Food Chem 38: 1549–1552
Maarse H, Visscher CA (1989) Volatile compounds in food, qualitative and quantitative data, vol 1–6. TNO-CIVO Food Analysis Institute, Zeist, The Netherlands
Wadhawa BK, Jain MK (1984) Indian J Dairy Sci 37: 137–144
Keeney PG, Patton S (1956) J Dairy Sci 39: 1114–1119
Dimick PS, Patton S, Kinsella JE, Walker NJ (1966) Lipids 1: 387–390
Dimick PS, Walker NJ, Patton S (1969) J Agric Food Chem 17: 649–655
Dimick PS, Walker HM (1968) J Dairy Sci 51: 478–482
Thijs L, Waanders PP, Stokkingreef EHM, Zwanenburg B (1986) Reel Trav Chim Pays-Bas 105: 332–337
Utaka M, Watabu H, Takeda A (1985) Chem Lett 1475–1476
Servi S (1983) Tetrahedron Lett 24: 2023–2024
Nawar WW, Yoo YJ, Bradley MS, Morin O, Potter T, Whiteman RC (1988) Rev Fr Corps Gras 35: 117–122
Boldingh J, Taylor RJ (1962) Nature 194: 909–913
Karg JE (1983) Seifen Fette Öle Wachse 109: 327–330
Nago H, Matsumoto M (1993) Biosci Biotech Biochem 57: 427–432
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Lehmann, D., Maas, B. & Mosandl, A. Stereoisomeric flavour compounds LXIX: stereodifferentiation of δ(γ)-lactones C8–C18 in dairy products, margarine and coconut. Z Lebensm Unters Forch 201, 55–61 (1995). https://doi.org/10.1007/BF01193201
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01193201