Light-induced transformation of asarone

Autor: Vera Lander, Peter Schreier
Rok vydání: 1991
Předmět:
Zdroj: Flavour and Fragrance Journal. 6:21-28
ISSN: 1099-1026
0882-5734
DOI: 10.1002/ffj.2730060104
Popis: The stability of α- (1) and β-asarone (2) in ethanolic solutions (30 %; 100 %; pH 7; pH3) was studied under daylight conditions over a period of six months. After rapid initial light-induced isomerization of 1 to 2, a number of (i) oxidation products, i.e. 2,4,5-trimethoxybenzaldehyde (4); l-(2,4,5-trimethoxyphenyl) propan-2-one (5); 2,4,5-trimethoxypropiophenone (6); and (ii) addition products, i.e. l-ethoxy-l-(2,4,5-trimethoxyphenyl) propane (3); (1R, 2R; 1S, 2S)-l-ethoxy-l-(2,4,5-trimethoxyphenyl) propan-2-ol (7A); (1R, 2S; 1S, 2R)-l-ethoxy-l-(2,4,5-trimethoxy-phenyl propan-2-ol (7B); (1R, 2R; 1S, 2S)-l-(2,4,5-trimethoxyphenyl) propan-1, 2-diol (8A); (1R, 2S; 1S 2R)-1-(2,4,5-trimethoxyphenyl) propan-1,2-diol (8B); as well as (iii) the dimers l-(2′,4′,5′-trimethoxyphenyl)-2-methyl-3-(2,4,5-trimethoxyphenyl)-lE-pentene (9) and l-(2′,4′,5′-trimethoxyphenyl)-2-methyl-3-ethyl-lα, 2β, 3α (H)-4,6,7-trimethoxyindane (13) were detected after extractive sample preparation. In addition, three dimers, l-(2′,4′,5′-trimethoxyphenyl)-2-methyl-3(2,4,5-trimethoxyphenyl)-penta-1E, 4-diene (10); 1 -(2′,4′,5′-trimethoxyphenyl)-2-(2,4,5-trimethoxyphenyl)-3,4-dimethylcyclobutane (11) and l-(2′,4′,5′-trimethoxyphenyl)-2-rnethyl-3-(2,4,5-trimethoxyphenyl) prop-l-en-3-one (12) were tentatively identified. Identifications were carried out by capillary gas chromatography (HRGC) and on-line HRGC techniques, i.e. HRGC-mass spectrometry (HRGC-MS) and HRGC-Fourier transform infrared spectroscopy (HRGC-FTIR) as well as 1H-NMR spectroscopy.
Databáze: OpenAIRE
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