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

The Santalols

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(1'S,2'R,4'R)-(Z)-beta-santalol - Typical sandalwood scent, identical to the natural product (Krotz & Helmchen); very strong, woody to animal, typical sandalwood (Brunke); sandalwood, natural, woody, milky (Chapuis)

Ref: A. Krotz, G. Helmchen, "Total Syntheses, Optical Rotations and Organoleptic Properties of Sandalwood Fragrances, (Z)- and (E)-b-Santalol and their Enantiomers, ent-b-Santalene". Liebigs Ann. Chem. 1994, 601-609; A. Krotz, G. Helmchen, "Total Syntheses of Sandalwood Fragrances, (Z)- and (E)-Santalol and their Enantiomers, ent-b-Santalene". Tetrahedron Asymmetry 1990, 537-540; E.-J. Brunke, Dragoco Report, 1983, No. 2, 35-40; Christian Chapuis, In the Quest for a Virtual Pseudo Receptor for Sandalwood-Like Odorants, Part I, Chemistry & Biodiversity, Volume 1, Issue 7, Date: July 2004, Pages: 980-1021

(+)-(1'R,2'S,4'S)-(Z)-beta-santalol - No scent (odorless)

Ref: A. Krotz, G. Helmchen, "Total Syntheses, Optical Rotations and Organoleptic Properties of Sandalwood Fragrances, (Z)- and (E)-b-Santalol and their Enantiomers, ent-b-Santalene". Liebigs Ann. Chem. 1994, 601-609; A. Krotz, G. Helmchen, "Total Syntheses of Sandalwood Fragrances, (Z)- and (E)-Santalol and their Enantiomers, ent-b-Santalene". Tetrahedron Asymmetry 1990, 537-540

(-)-(1'S,2'R,4'R) -(E)-beta-santalol - Scent similar to (-)-(1'S,2'R,4'R) -(Z)-beta-santalol but less intense (Krotz & Helmchen); woody, medicinal, phenolic, very weakly sandalwood (Brunke).

Ref: A. Krotz, G. Helmchen, "Total Syntheses, Optical Rotations and Organoleptic Properties of Sandalwood Fragrances, (Z)- and (E)-b-Santalol and their Enantiomers, ent-b-Santalene". Liebigs Ann. Chem. 1994, 601-609; A. Krotz, G. Helmchen, "Total Syntheses of Sandalwood Fragrances, (Z)- and (E)-Santalol and their Enantiomers, ent-b-Santalene". Tetrahedron Asymmetry 1990, 537-540; E.-J. Brunke, Dragoco Report, 1983, No. 2, 35-40

(+)-(1'R,2'S,4'S)- (E)-beta-santalol - No scent (odorless).

Ref: A. Krotz, G. Helmchen, "Total Syntheses, Optical Rotations and Organoleptic Properties of Sandalwood Fragrances, (Z)- and (E)-b-Santalol and their Enantiomers, ent-b-Santalene". Liebigs Ann. Chem. 1994, 601-609; A. Krotz, G. Helmchen, "Total Syntheses of Sandalwood Fragrances, (Z)- and (E)-Santalol and their Enantiomers, ent-b-Santalene". Tetrahedron Asymmetry 1990, 537-540

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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