title: The (+)-cis- and (+)-trans-Olibanic Acids: Key Odorants of Frankincense.
abstract: Frankincense (olibanum) is one of the oldest aromatic materials used by humans, but the key molecular constituents contributing to its characteristic odor remained unknown. Reported herein is the discovery that (1S,2S)-(+)-trans- and (1S,2R)-(+)-cis-2-octylcyclopropyl-1-carboxylic acids are highly potent and substantive odorants occurring in ppm amounts in all of the frankincense samples analyzed, even those showing radically different volatile compositions. These cyclopropyl-derived acids provide the very characteristic old churchlike endnote of the frankincense odor.
authors.affiliation: Albert Vieille SA, 629, route de Grasse, 06227, Vallauris, France.
authors.forename: Céline
authors.initials: C
authors.lastname: Cerutti-Delasalle
authors.affiliation: Institut de Chimie de Nice, Université Nice Sophia Antipolis, CNRS, UMR 7272, Parc Valrose, 06108, Nice, France.
authors.forename: Mohamed
authors.initials: M
authors.lastname: Mehiri
authors.affiliation: Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, Via Pietro Giuria, 9-, 10125, Torino, Italy.
authors.forename: Cecilia
authors.initials: C
authors.lastname: Cagliero
authors.affiliation: Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, Via Pietro Giuria, 9-, 10125, Torino, Italy.
authors.forename: Patrizia
authors.initials: P
authors.lastname: Rubiolo
authors.affiliation: Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, Via Pietro Giuria, 9-, 10125, Torino, Italy.
authors.forename: Carlo
authors.initials: C
authors.lastname: Bicchi
authors.affiliation: Institut de Chimie de Nice, Université Nice Sophia Antipolis, CNRS, UMR 7272, Parc Valrose, 06108, Nice, France.
authors.forename: Uwe J
authors.initials: UJ
authors.lastname: Meierhenrich
authors.affiliation: Institut de Chimie de Nice, Université Nice Sophia Antipolis, CNRS, UMR 7272, Parc Valrose, 06108, Nice, France. baldovin@unice.fr.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Baldovini
keywords: density functional calculations; fragrances; natural products; small-ring systems; structure elucidation