Synthesis, structure elucidation, and olfactometric analysis of lilac aldehyde and lilac alcohol stereoisomers

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 9, 2003, Pages 2722-2726

  Kreck, Mirjam ^a   Mosandl, Armin ^a  

^a GOETHE UNIVERSITY   (Germany)

Author keywords

Enantioselective multidimensional gas chromatography; Lilac alcohol stereoisomers; Lilac aldehyde stereoisomers; Olfactometry

Indexed keywords

2 PHENYLPROPIONYL ESTER; ALCOHOL DERIVATIVE; ALDEHYDE; ESTER DERIVATIVE; LINALOOL; UNCLASSIFIED DRUG;

ANISOTROPY; ARTICLE; CAPILLARY GAS CHROMATOGRAPHY; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; ODOR; OLFACTOMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

ALCOHOLS; ALDEHYDES; MAGNETIC RESONANCE SPECTROSCOPY; ODORS; STEREOISOMERISM; SYRINGA;

EID: 0037462057     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf021140q     Document Type: Article

References (20)

1. Surburg, H.; Güntert, M. Headspace-Technik in der Parfümerie: Untersuchungen von Blütendüften. H & R, Contact 1991, 51, 12-17.
2. Mack, H.; Köpsel, M. Die Blüten des Maiglöckchens und des Flieders. Parfuem. Kosmet. 1973, 54, 233-237.
3. Wakayama, S.; Namba, S.; Hosoi, K.; Ohno, M. The synthesis and the absolute configurations of lilac alcohols, new naturally occurring odours ingredients of lilac flower. Bull. Chem. Soc. Jpn. 1973, 46, 3183-3187.
4. Wakayama, S.; Namba, S. Lilac aldehydes. Bull. Chem. Soc. Jpn. 1974, 47, 1293-1294.
5. Wakayama, S.; Namba, S.; Hosoi, K.; Ohno, M. The synthesis and absolute configurations of lilac alcohols. Bull. Chem. Soc. Jpn. 1971, 44, 5.
6. Kreck, M.; Püschel, S.; Wüst, M.; Mosandl, A. Biogenetic studies in Syringa vulgaris L.: Synthesis and bioconversation of deuterium-labeled precursors into lilac aldehydes and lilac alcohols. J. Agric. Food Chem. 2003, 51, 463-469.
7. Askari, C.; Mosandl, A. Stereoisomeric flavour compounds. LII: separation and structure elucidation of the furanoid linalool oxide stereoisomers using chirospecific capillary gas chromatography and nuclear magnetic resonance spectroscopy. Phytochem. Anal. 1991, 2, 211-214.
8. Weinert, B.; Wüst, M.; Mosandl, A.; Hanssum, H. Stereoisomeric flavour compounds. LXXVIII: Separation and sructure elucidation of the pyranoid linalool oxide stereoisomers using common gas chromatographic phases, modified cyclodextrin phases and nuclear magnetic resonance spectroscopy. Phytochem. Anal. 1998, 9, 10-13.
9. Bartschat, D. Chirale Lactone und Aldehyde - Struktur, Geruch, Analytik-. Dissertation, J. W. Goethe-University, Frankfurt a. M.; Herbert Utz Verlag Wissenschaft: München. Germany, 1997.
10. Helmchen, G.; Ott, R.; Sauber, K. Gezielte Trennung und absolute Konfiguration von enantiomeren Carbonsäuren und Aminen. Tetrahedron Lett. 1972, 37, 3873-3878.
11. 2HCCOOH. Tetrahedron Lett. 1977, 16, 1417-1420.
12. Dale, J. A.; Dull, D. L.; Mosher, H. S. α-Methoxy-α-trifluoromethyl-phenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines. J. Org. Chem. 1969, 34, 2543-2549.
13. Dale, J. A.; Mosher, H. S. Nuclear magnetic resonanceenantiomer reagents. Configurational correlation via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters. J. Am. Chem. Soc. 1973, 95, 512-519.
14. 1H NMR. J. Org. Chem. 1996, 61, 8569-8577.
15. Seco, J. M.; Quinoa, E.; Riguera, R. The assignment of absolute configuration by NMR of arylmethoxyacetate derivatives: is this methodology being correctly used? Tetrahedron: Asymm. 2000, 13, 2781-2791.
16. Latypov, S. K.; Seco, J. M.; Quinoa, E.; Riguera, R. Conformational structure and dynamics of arylmethoxyacetates: NMR spectroscopy and aromatic shielding effect. J. Org. Chem. 1995, 60, 1538-1545.
17. Latypov, S. K.; Ferreiro, M. J.; Quinoa, E.; Riguera, R. Assignment of the absolute configuration of β-chiral primary alcohols by NMR: Scope and limitations. J. Am. Chem. Soc. 1998, 120, 4741-4751.
18. Schetlick, K. Reaktionen von Carbonylverbindungen. In Organikum, 21 Aufl.; Wiley-VHC: Weinheim, Germany, 2001.
19. Corey, R.; Ensley, H. E.; Suggs, J. W. A convenient synthesis of (S)-pulegone from (-)-citronellol. J. Org. Chem. 1976, 41, 380-381.
20. Deger, W. Struktur-Wirkungsbeziehung und Analyse chiraler Carbonsäureester. Dissertation, Julius-Maximilians-University, Würzburg, Germany, 1988.