(1R,2R,4S)-2-butylfenchol (99:1 endo/exo) - main odor character - earthy, secondary odor character - camphor = (1R,2R,4S)-2-butyl-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol Ref: Barbara Finato, Roberto Lorenzi, Paolo Pelosi, Synthesis of new earthy odorants, J. Agric. Food Chem., 1992, 40 (5), pp 857–859 Note: Finato et al., inferred from the publication of E. Polak, D. Trotier and E.Baliguet, Odor similarities in structurally related odorants, Chemical Senses and Flavour, Volume 3, Number 4, 1978, 369-380, that the alcohol produced was in the exo position. However, P. Gosselin, D. Joulain, P. Laurin and F. Rouessac, Synthesis of earthy-mouldy smelling compounds - II ethyl alpha- and beta- fenchols, Tetrahedron Letters, Volume 31, Issue 22, 1990, Pages 3151-3154, have shown that alkyl-lithium as well as the alkyl grignard reagents produce the predominantly the endo alcohol on reaction with fenchone. This is consistent with the work of Vladimir Dimitrov, Svetlana Simova and Kalina Kostova, Highly effective and practical stereoselective synthesis of new homoallylic alcohols with (+)-camphor and (-)-fenchone skeleton , Tetrahedron. Volume 52, Issue 5, 29 January 1996, Pages 1699-1706, show the endo alcohol is predominately produced from fenchone. Similarly, Valentin Rautenstrauch, Endo-selectivity and kinetic control in alkali metal–NH3–NH4+ reductions of bicyclo[2.2.1]heptan-2-ones, J. Chem. Soc., Chem. Commun., 1986, 1558 - 1560, has shown that the lithium reduction of fenchone produces endo fenchol with high stereospecificity. For these reasons, we have corrected the hydroxy configuration to endo.

(1S,2S,4R)-2-butylfenchol (99:1 endo/exo) - main odor character - earthy, secondary odor character - camphor = (1S,2S,4R)-2-butyl-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol Ref: Barbara Finato, Roberto Lorenzi, Paolo Pelosi, Synthesis of new earthy odorants, J. Agric. Food Chem., 1992, 40 (5), pp 857–859 Note: Finato et al., inferred from the publication of E. Polak, D. Trotier and E.Baliguet, Odor similarities in structurally related odorants, Chemical Senses and Flavour, Volume 3, Number 4, 1978, 369-380, that the alcohol produced was in the exo position. However, P. Gosselin, D. Joulain, P. Laurin and F. Rouessac, Synthesis of earthy-mouldy smelling compounds - II ethyl alpha- and beta- fenchols, Tetrahedron Letters, Volume 31, Issue 22, 1990, Pages 3151-3154, have shown that alkyl-lithium as well as the alkyl grignard reagents produce the predominantly the endo alcohol on reaction with fenchone. This is consistent with the work of Vladimir Dimitrov, Svetlana Simova and Kalina Kostova, Highly effective and practical stereoselective synthesis of new homoallylic alcohols with (+)-camphor and (-)-fenchone skeleton , Tetrahedron. Volume 52, Issue 5, 29 January 1996, Pages 1699-1706, show the endo alcohol is predominately produced from fenchone. Similarly, Valentin Rautenstrauch, Endo-selectivity and kinetic control in alkali metal–NH3–NH4+ reductions of bicyclo[2.2.1]heptan-2-ones, J. Chem. Soc., Chem. Commun., 1986, 1558 - 1560, has shown that the lithium reduction of fenchone produces endo fenchol with high stereospecificity. For these reasons, we have corrected the hydroxy configuration to endo.

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants