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--- salvia_sclarea_l [2019/11/09 12:37]
andreas
+++ salvia_sclarea_l [2024/01/07 10:56] (aktuell)
andreas
@@ Zeile 3: / Zeile 3: @@
 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.
-{{:1methoxyhexan3thiol.png| 1-methoxyhexane-3-thiol }} 1-methoxyhexane-3-thiol
+Clary sage oil and concrete are important in the flavour and fragrance industry. The concrete contains 38-45% of the diterpenediol sclareol "...that is used either as natural fixative or as raw material for the oxidative conversion to a mixture of ethers and unsaturated alcohols, possessing an ambergris-like aroma. In flavour industry, clary sage is used in alcoholic beverages, liqueurs and as a modifier in spices." \\
+Main components of the essential oil are linalool and linalyl acetate. Hydrodistillation at low pH drastically increased the amount of myrcene, cis-β-ocimene, trans-β-ocimene, α-terpineol, nerol, geraniol, neryl acetate and geranyl acetate. \\
-"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." \\
+[Schmaus, G., and K-H. Kubeczka. "The influence of isolation conditions on the composition of essential oils containing linalool and linalyl acetate." Essential Oils and Aromatic Plants: Proceedings of the 15th International Symposium on Essential Oils, held in Noordwijkerhout, The Netherlands, July 19–21, 1984. Dordrecht: Springer Netherlands, 1985]
-[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]
 "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] \\
+{{:1methoxyhexan3thiol.png| 1-methoxyhexane-3-thiol }} 1-methoxyhexane-3-thiol
-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%). \\
+"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." \\
-[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]]
+[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]
 "... 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." \\
@@ Zeile 22: / Zeile 21: @@
 [Chemical composition and antifungal activity of //Salvia sclarea// (Lamiaceae) essential oil. Džamić, A., Soković, M., Ristić, M., Grujić-Jovanović, S., Vukojević, J., Marin, P. D., Archives of Biological Sciences, Vol.60(2), 2008, 233-237] \\
 [[http://www.doiserbia.nb.rs/img/doi/0354-4664/2008/0354-46640802233D.pdf]]
+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]]
 | {{:linalool_r.jpg| (R)-(-)-linalool }} \\ (R)-(-)-linalool | {{:linalylacetate_r.jpg| linalyl acetate }} \\ (R)-(-)-linalyl acetate | {{:spathulenol_plus.jpg|(+)-spathulenol}} \\ (+)-spathulenol | {{:ambrox.jpg|(-)-ambrox}} \\ (-)-ambrox | {{:sclareol.jpg|sclareol}} \\ sclareol |
@@ Zeile 31: / Zeile 33: @@
 Sibthrop, J., Smith, J.E., Flora Graeca (drawings), vol.1, t.25 (1806) \\
 [[http://plantgenera.org/species.php?id_species=903766]]
 {{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]]

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