Chirality & Odour Perception
John C. Leffingwell, Ph.D.

The Patchoulols

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(1R,3R,6S,7S,8S)-patchoulol - a strong, typical patchouli scent with an earthy, slightly camphoraceous, powdery cellar note which was indistinguishable from natural patchoulol; deep woody like patchouli oil

= (-)-(1R,3R,6S,7S,8S)-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-3-ol

Also known as (-)-(1R,3S,4S,7R,8S)-4,8,11,11-tetramethyltricyclo[5.3.1.03,8 ]undecan-7-ol

Ref: F. Naf, R. Decorzant, W. Giersch & G. Ohloff, A Stereocontrolled Access to (+/-)-, (-)-, and (+)-Patchouli Alcohol, Helv. Chim. Acta, 64, 1387-1397, 1981; Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993; see also Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

(+)-(1S,3S,6R,7R,8R)-patchoulol - much weaker, less characteristic, nearly indefinable and by no means reminiscent of patchouli. It might have a beta-santalol odour with a green undertone; woody with underlying green notes

= (+)-(1S,3S,6R,7R,8R)-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-3-ol

Also known as (+)-(1S,3R,4R,7S,8R)-4,8,11,11-tetramethyltricyclo[5.3.1.03,8 ]undecan-7-ol

Ref: F. Naf, R. Decorzant, W. Giersch & G. Ohloff, A Stereocontrolled Access to (+/-)-, (-)-, and (+)-Patchouli Alcohol, Helv. Chim. Acta, 64, 1387-1397, 1981; Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993; see also Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

Cyclic Terpenoid Odorants

Bicyclic Terpenoid Odorants

Acyclic Terpenoid Odorants

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants

Steroid Urine Type Odorants

Sandalwood Type Odorants

Musk Odorants

Miscellaneous

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