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Vorhergehende Überarbeitung
Nächste Überarbeitung
Beide Seiten der Revision
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salvia_sclarea_l [2016/07/21 15:43]
andreas |
salvia_sclarea_l [2018/08/30 15:34]
andreas |
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| 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 |
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| "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." \\ |
| [[http://www.doiserbia.nb.rs/img/doi/0354-4664/2008/0354-46640802233D.pdf]] | [[http://www.doiserbia.nb.rs/img/doi/0354-4664/2008/0354-46640802233D.pdf]] |
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| | {{:linalool_r.jpg| (R)-(-)-linalool }} \\ (R)-(-)-linalool | {{:linalylacetate_r.jpg| linalyl acetate }} \\ (R)-(-)-linalyl acetate | {{:spathulenol_plus.jpg|(+)-spathulenol}} \\ (+)-spathulenol \\ //(ambergris)// | {{:ambrox.jpg|(-)-ambrox}} \\ (-)-ambrox \\ //(ambergris)// | | | {{:linalool_r.jpg| (R)-(-)-linalool }} \\ (R)-(-)-linalool | {{:linalylacetate_r.jpg| linalyl acetate }} \\ (R)-(-)-linalyl acetate | {{:spathulenol_plus.jpg|(+)-spathulenol}} \\ (+)-spathulenol | {{:ambrox.jpg|(-)-ambrox}} \\ (-)-ambrox | |
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| Of the ca. 250 constituents identified in clary sage oil, (R)-linalyl acetate (67%) and (R)-linalool (16%) represent the main part of the oil, but the odor of the oil is based on trace compounds. Some cyclic ethers (pyranes) possess camphoraceous odors. Sesquiterpene derivatives play an important role: (3R,6E)-3,15-epoxy-caryophyll-6-ene (woody), β-caryophyllene oxide (woody), (+)-spathulenol (aromatic earthy), (+)-isospathulenol (aromatic earthy), 1,5-epoxy-salvial-(4,14)-ene (spicy floral, stronger than its thia analog mint sulfide), α-bisabolol (floral), 10-epi-ɣ-eudesmol (woody), salvial-4(14)-ene-1-one (woody), (-)-ambrox (ambergris), and ɣ-bicyclohomofarnesal (ambergris). The labdanoid diterpenediol (-)-sclareol (2% in clary sage oil, 70% in its absolute) is isolated from oil or absolute on industrial scale as starting material for the synthesis of (-)-ambrox. \\ | Of the ca. 250 constituents identified in clary sage oil, (R)-linalyl acetate (67%) and (R)-linalool (16%) represent the main part of the oil, but the odor of the oil is based on trace compounds. Some cyclic ethers (pyranes) possess camphoraceous odors. Sesquiterpene derivatives play an important role: (3R,6E)-3,15-epoxy-caryophyll-6-ene (woody), β-caryophyllene oxide (woody), (+)-spathulenol (aromatic earthy), (+)-isospathulenol (aromatic earthy), 1,5-epoxy-salvial-(4,14)-ene (spicy floral, stronger than its thia analog mint sulfide), α-bisabolol (floral), 10-epi-ɣ-eudesmol (woody), salvial-4(14)-ene-1-one (woody), (-)-ambrox (ambergris), and ɣ-bicyclohomofarnesal (ambergris). The labdanoid diterpenediol (-)-sclareol (2% in clary sage oil, 70% in its absolute) is isolated from oil or absolute on industrial scale as starting material for the synthesis of (-)-ambrox. \\ |
| 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]] |
