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salvia_sclarea_l [2016/07/21 15:44]
andreas 		salvia_sclarea_l [2018/08/30 15:34]
andreas
Zeile 2: Zeile 2:
  
 Biennial or perennial herb, 0.50-1.10m high, native from South Europe to Central Asia; leaves simple, up to 30cm long, heart-shaped; flowers white to mauve or violet. Biennial or perennial herb, 0.50-1.10m high, native from South Europe to Central Asia; leaves simple, up to 30cm long, heart-shaped; flowers white to mauve or violet.
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 +{{:1methoxyhexan3thiol.png| 1-methoxyhexane-3-thiol }} 1-methoxyhexane-3-thiol 
  
 "The peculiar and highly diffusive odor signal of flowering clary-sage plants (Salvia sclarea L.) was identified to derive from trace amounts of 1-methoxyhexane-3-thiol (1) by mass-spectrometry analysis and confirmed by comparison with synthetic racemic thiol (±)-1. The enantiomers (S)- and (R)-1 were prepared by enantioselective synthesis, and the absolute configuration of (S)-1 was fully corroborated by X-ray-diffraction analysis of the crystalline thioester (1′S,1S)-2. Compound (S)-1 is one of the most powerful odorants known, with a detection threshold of 0.04⋅10−3 ng/l air, and is, with its herbaceous-green, alliaceous, and perspiration profile, key to the fragrance of clary-sage flowers and of the freshly distilled essential oil. As a consequence of its unique odor, 1 was also suspected to be part of the volatiles of a Ruta species where it was subsequently identified together with its homologue, 1-methoxyheptane-3-thiol (3), 1-methoxy-4-methylpentane-3-thiol (4), and the known 4-methoxy-2-methylbutane-2-thiol (5). The syntheses of (±)-3 and (±)-4 as well as of the enantiomer (R)-4 are described. In both natural fractions, the ratio (S)-1/(R)-1 was slightly in favor of the (S)-enantiomer. Natural 4 has (R)-configuration." \\ "The peculiar and highly diffusive odor signal of flowering clary-sage plants (Salvia sclarea L.) was identified to derive from trace amounts of 1-methoxyhexane-3-thiol (1) by mass-spectrometry analysis and confirmed by comparison with synthetic racemic thiol (±)-1. The enantiomers (S)- and (R)-1 were prepared by enantioselective synthesis, and the absolute configuration of (S)-1 was fully corroborated by X-ray-diffraction analysis of the crystalline thioester (1′S,1S)-2. Compound (S)-1 is one of the most powerful odorants known, with a detection threshold of 0.04⋅10−3 ng/l air, and is, with its herbaceous-green, alliaceous, and perspiration profile, key to the fragrance of clary-sage flowers and of the freshly distilled essential oil. As a consequence of its unique odor, 1 was also suspected to be part of the volatiles of a Ruta species where it was subsequently identified together with its homologue, 1-methoxyheptane-3-thiol (3), 1-methoxy-4-methylpentane-3-thiol (4), and the known 4-methoxy-2-methylbutane-2-thiol (5). The syntheses of (±)-3 and (±)-4 as well as of the enantiomer (R)-4 are described. In both natural fractions, the ratio (S)-1/(R)-1 was slightly in favor of the (S)-enantiomer. Natural 4 has (R)-configuration." \\
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 Sibthrop, J., Smith, J.E., Flora Graeca (drawings), vol.1, t.25 (1806) \\ Sibthrop, J., Smith, J.E., Flora Graeca (drawings), vol.1, t.25 (1806) \\
 [[http://plantgenera.org/species.php?id_species=903766]] [[http://plantgenera.org/species.php?id_species=903766]]
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 +{{http://www.botanische-spaziergaenge.at/Bilder/Konica_3/PICT1755.JPG}} \\
 +Salvia sclarea\\ © Rolf Marschner (2006),  
 +[[http://botanische-spaziergaenge.at/viewtopic.php?f=95&t=2136| www.botanische-spaziergaenge.at]]
salvia_sclarea_l.txt · Zuletzt geändert: 2024/01/07 10:56 von andreas

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