A Chemical Study of  Virginia  Tobacco Flavour ( Nicotiana tabacum  L.) II. Isolation and synthesis of  cis ‐2‐isopropenyl‐8‐methyl‐1,2,3,4‐tetrahydro‐1‐naphthalenol and 3‐isopropenyl‐5‐methyl‐1,2‐dihydronaphthalene | Zendy

Demole Edouard | Zendy; Enggist Paul | Zendy

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A Chemical Study of Virginia Tobacco Flavour ( Nicotiana tabacum L.) II. Isolation and synthesis of cis ‐2‐isopropenyl‐8‐methyl‐1,2,3,4‐tetrahydro‐1‐naphthalenol and 3‐isopropenyl‐5‐methyl‐1,2‐dihydronaphthalene

Author(s) -

Demole Edouard,

Enggist Paul

Publication year - 1978

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19780610416

Subject(s) - chemistry , nicotiana tabacum , biogenesis , tobacco product , alcohol , flavour , organic chemistry , stereochemistry , biochemistry , food science , gene , medicine , environmental health

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 these norsesquiterpenes were identified on spectral grounds and synthesized from 1‐methylnaphthalene in a way (9 steps) that also afforded the «non‐natural», trans ‐alcohol A ′. The possible biogenesis of A and B in tobacco is briefly outlined.

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