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

The 3,5-dimethylcyclohexanones

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(3R,5R)-3,5-Dimethylcyclohexanone - minty, resembling iospulegone in character

Ref: Charles S. Sell, Scent through the Looking Glass, Chemistry & Biodiversity, Volume 1, Issue 12, Date: December 2004, Pages: 1899-1920; Julius v. Braun, Wilhelm Teuffert, Geruch und molekulare Asymmetrie (II), Berichte der deutschen chemischen Gesellschaft (A and B Series), Volume 58, Issue 9, Date: 14. Oktober 1925, Pages: 2210-2215; Julius v. Braun, Werner Haensel, Geruch und molekulare Asymmetrie (III), Berichte der deutschen chemischen Gesellschaft (A and B Series), Volume 59, Issue 8, Date: 15. September 1926, Pages: 1999-2011; Julius v. Braun, Ernst Anton, Geruch und molekulare Asymmetrie, IV. Mitteilung: Die drei 1.3-Dimethylcyclohexanone-5 und die vier 1.3-Dimethyl-cyclohexanole-5, Berichte der deutschen chemischen Gesellschaft (A and B Series), Volume 60, Issue 11, Date: 7. Dezember 1927, Pages: 2438-2446; Absolute configuration from Rosalinde Imbos, Catalytic Asymmetric Conjugate Additions and Heck Reactions, Thesis, Rijksuniversiteit Groningen, October 2002, Chapter 4, p. 67; http://dissertations.ub.rug.nl/FILES/faculties/science/2002/r.imbos/thesis.pdf

 

(+)-(3S,5S)-3,5-dimethylcyclohexanone - fruity, ester like odor

Ref: Charles S. Sell, Scent through the Looking Glass, Chemistry & Biodiversity, Volume 1, Issue 12, Date: December 2004, Pages: 1899-1920; Julius v. Braun, Wilhelm Teuffert, Geruch und molekulare Asymmetrie (II), Berichte der deutschen chemischen Gesellschaft (A and B Series), Volume 58, Issue 9, Date: 14. Oktober 1925, Pages: 2210-2215; Julius v. Braun, Werner Haensel, Geruch und molekulare Asymmetrie (III), Berichte der deutschen chemischen Gesellschaft (A and B Series), Volume 59, Issue 8, Date: 15. September 1926, Pages: 1999-2011; Julius v. Braun, Ernst Anton, Geruch und molekulare Asymmetrie, IV. Mitteilung: Die drei 1.3-Dimethylcyclohexanone-5 und die vier 1.3-Dimethyl-cyclohexanole-5, Berichte der deutschen chemischen Gesellschaft (A and B Series), Volume 60, Issue 11, Date: 7. Dezember 1927, Pages: 2438-2446; Absolute configuration from Rosalinde Imbos, Catalytic Asymmetric Conjugate Additions and Heck Reactions, Thesis, Rijksuniversiteit Groningen, October 2002, Chapter 4, p. 67; http://dissertations.ub.rug.nl/FILES/faculties/science/2002/r.imbos/thesis.pdf

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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