## Abstract Gas liquid chromatography allowed isolation of the novel __cis__‐2‐isopropenyl‐8‐methyl‐1,2,3,4‐tetrahydro‐1‐naphthalenol (**A**) and its dehydration product, 3‐isopropenyl‐5‐methyl‐1,2‐dihydronaphthalene (**B**), from two small subfractions of __Virginia__ tobacco condensate. Both thes
A Chemical Study of Virginia Tobacco Flavour (Nicotiana Tabacum L.). I. Isolation and Synthesis of Two Bicyclodamascenones
✍ Scribed by Edouard Demole; Paul Enggist
- Publisher
- John Wiley and Sons
- Year
- 1976
- Tongue
- German
- Weight
- 403 KB
- Volume
- 59
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
Aged Virginia tobacco was steam‐distilled and the resulting condensate investigated by chromatographic methods. This allowed identification of the bicyclodamascenones A and B in a small subfraction from this condensate. Both these ketones, which are novel tobacco constituents, were also synthesized and a possible mechanism is proposed for their formation via acid‐catalysed cyclization of β‐damascenone (1).
📜 SIMILAR VOLUMES
A 0.4 x 250 cm column packed with 5% of 'Carbowax' 20 M (Varian Aerogrdph .4G) on C'hromosorh W5) was used for this second set of separations.
## Abstract Two novel constituents of __Burley__ tobacco condensate were shown to be 5‐(4‐methyl‐2‐furyl)‐6‐methylheptan‐2‐one (__solanofuran__, **4**) and 3,4,7‐trimethyl‐1,6‐dioxa‐spiro[4.5]‐dec‐3‐en‐2‐one (__spiroxabovolide__, **6**). These structures were deduced from spectral data and confirme
The principal axes of the 50%-thermal vibration ellipsoids for C-and 0-atoms vary between 0.18 and 0.35 8. A qualitative impression of the relative orientation of the ellipsoids can be obtained from the stereoscopic drawing of the molecule in Fig. 2 ) , which also shows the overall conformation of