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salvia_sclarea_l [2018/02/24 10:00] andreas |
salvia_sclarea_l [2019/08/07 10:09] 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." \\ |
[1‐Methoxyhexane‐3‐thiol, a Powerful Odorant of Clary Sage (//Salvia sclarea L.//). van de Waal, M., Niclass, Y., Snowden, R. L., Bernardinelli, G., Escher, S., Helvetica chimica acta, Vol.85(5), 2002, 1246-1260] | [1‐Methoxyhexane‐3‐thiol, a Powerful Odorant of Clary Sage (//Salvia sclarea L.//). van de Waal, M., Niclass, Y., Snowden, R. L., Bernardinelli, G., Escher, S., Helvetica chimica acta, Vol.85(5), 2002, 1246-1260] |
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"The analysis of the volatile components in the essential oil of Salvia sclarea L. (Labiatae) by GC and GC-MS demonstrated the presence of at least 72 compounds. They correspond to 97.2% of the oil. The major compounds were linalool, linalyl acetate, terpineol, neryl acetate, geraniol, geranyl acetate, nerol, and [[http://de.wikipedia.org/wiki/Sclareol|sclareol]]." \\ | "The analysis of the volatile components in the essential oil of Salvia sclarea L. (Labiatae) by GC and GC-MS demonstrated the presence of at least 72 compounds. They correspond to 97.2% of the oil. The major compounds were linalool, linalyl acetate, terpineol, neryl acetate, geraniol, geranyl acetate, nerol, and [[http://de.wikipedia.org/wiki/Sclareol|sclareol]]." (The diterpene sclareol is a valued starting material for semisynthesis of Ambrox® and related ambergris substitutes.) \\ |
[Constituents of the essential oil of Salvia sclarea growing wild in Greece. Souleles, C., Argyriadou, N. , Pharmaceutical Biology, Vol.35(3), 1997, 218-220] \\ | [Constituents of the essential oil of Salvia sclarea growing wild in Greece. Souleles, C., Argyriadou, N. , Pharmaceutical Biology, Vol.35(3), 1997, 218-220] \\ |
(The diterpene sclareol is a valued starting material for semisynthesis of Ambrox® and related ambergris substitutes.) | |
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| Major constituents of the essential oil of fresh inflorescences were linalyl acetate (39.6%), linalool (28.8%), α-terpineol (5.6%), sclareol (2.4%), geraniol (2.1%), geranyl acetate (2.3%), (E)-β-ocimene (2.5%), myrcene (1.7%), neryl acetate (1.1%) and limonene (1.0%). Mminor constituents were e.g. camphor (0.1%), (Z)-linalool oxide (0.1%) and terpinen-4-ol (0.6%). \\ |
| [Verma, Ram Swaroop, et al. "Aroma Profile of Clary Sage (Salvia sclarea L.): Influence of Harvesting Stage and Post Harvest Storage in Uttarakhand Hills." Medicinal and Aromatic Plant Science and Biotechnology 5.2 (2011): 139-142] [[http://www.globalsciencebooks.info/Online/GSBOnline/images/2011/MAPSB_5(2)/MAPSB_5(2)139-142o.pdf]] |
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"... the essential oil of S. sclarea L. is dominated by two monoterpenes, linalool and linalylacetate, which mostly determine the oil quality in all the tested phases of development; they constitute 86.07% from total oil mass." \\ | "... the essential oil of S. sclarea L. is dominated by two monoterpenes, linalool and linalylacetate, which mostly determine the oil quality in all the tested phases of development; they constitute 86.07% from total oil mass." \\ |