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chrysopogon_zizanioides_l._roberty [2018/06/14 14:07]
andreas
chrysopogon_zizanioides_l._roberty [2021/05/27 09:47] (aktuell)
andreas
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 contribute to the total sensory impression. The main descriptor of the odour is undoubtfully precious //woody//. Three primary alcohols, all of them major constituents, are responsible for the base note, at first the strong smelling allyl alcohol [[http://webbook.nist.gov/cgi/cbook.cgi?ID=R341194&Mask=2000|isovalencenol]], but also [[http://webbook.nist.gov/cgi/cbook.cgi?ID=R199314&Mask=2000|vetiselinenol]] and [[http://pubchem.ncbi.nlm.nih.gov/compound/167519|khusimol]]. The complex woody note of these three alcohols is slightly reminiscent of cedarwood, but there is also an ambery tonality (vetiselinenol) and a grapefruit note (khusimol)... In contrast, the major constituent β-vetivone according contribute to the total sensory impression. The main descriptor of the odour is undoubtfully precious //woody//. Three primary alcohols, all of them major constituents, are responsible for the base note, at first the strong smelling allyl alcohol [[http://webbook.nist.gov/cgi/cbook.cgi?ID=R341194&Mask=2000|isovalencenol]], but also [[http://webbook.nist.gov/cgi/cbook.cgi?ID=R199314&Mask=2000|vetiselinenol]] and [[http://pubchem.ncbi.nlm.nih.gov/compound/167519|khusimol]]. The complex woody note of these three alcohols is slightly reminiscent of cedarwood, but there is also an ambery tonality (vetiselinenol) and a grapefruit note (khusimol)... In contrast, the major constituent β-vetivone according
 to Spreitzer et al., is not an important compound from the point of view of odour, although it displays to Spreitzer et al., is not an important compound from the point of view of odour, although it displays
-grapefruit and woody notes... The mixture of [[http://webbook.nist.gov/cgi/inchi/InChI=1S/C15H22O/c1-9-12-7-13%2816%2910%282%2915%2812%296-5-11%288-15%2914%289,3%294/h10-12H,1,5-8H2,2-4H3|zizaenones]], ziza(6,13)-en-3-one (2-β methyl group) and 2-epi-ziza(6,13)-en-3-one (2-α methyl group), smells like khusimone but weaker. The aldehydes zizaenal (exhibiting also aldehydic melon and floral notes) and eremophiladienal are valuable typical vetiver-like +grapefruit and woody notes... The mixture of [[http://webbook.nist.gov/cgi/inchi/InChI=1S/C15H22O/c1-9-12-7-13%2816%2910%282%2915%2812%296-5-11%288-15%2914%289,3%294/h10-12H,1,5-8H2,2-4H3|zizaenones]], ziza(6,13)-en-3-one (2-β methyl group) and 2-epi-ziza(6,13)-en-3-one (2-α methyl group), smells like khusimone but weaker. The aldehydes zizaenal (exhibiting also aldehydic melon and floral notes) and eremophiladienal are valuable typical vetiver-like elements..." \\
-elements..." \\+
 [Constituents of Haitian vetiver oil., Weyerstahl, P., Marschall, H., Splittgerber, U., Wolf, D., Surburg, H., Flavour and fragrance journal, 15(6), 2000, 395-412] [Constituents of Haitian vetiver oil., Weyerstahl, P., Marschall, H., Splittgerber, U., Wolf, D., Surburg, H., Flavour and fragrance journal, 15(6), 2000, 395-412]
 +
 +"The bourbon quality (10% of total production) possesses an additional rosy tonality with sulfury aspects,   while vetiver oil from Haiti (50% of total production) shows additional aspects reminiscent of jute and roasted peanuts, and the Java and China qualities (together 35% of total production) have harsh and smoky bynotes. All vetiver oils share, however, a characteristic and distinctive suave and sweet woody-earthy odor with green, grapefruit- and rhubarb-type facets that is much appreciated in perfumery." \\
 +(–)-Khusimone as one of the most important constituents for the odor of vetiver oils shows an odor threshold of 4.7 ng/L (air). \\
 +[Kraft, Philip, and Riccardo Cadalbert. "Design, synthesis and structure-odor correlation of novel spiro [4.5]-decan-2-ones." Synthesis 2002.15 (2002): 2243-2253] see also [Ellena, J.C., H & R Contact 2000, 82, 27]
  
 "Vetiver oil consists of a highly complex mixture of over 150 sesquiterpenoid constituents, and the composition as well as its odor quality depend decisively upon its origin...  the sesquiterpenes (+)-α-vetivone, (-)-β-vetivone, and khusimol always occur in amounts up to 35%, and considered fingerprints, even though they do not contribute much to the typical odor characteristics associated with vetiver oil. Most decisive for the characteristic odor of vetiver oil are, according to Maurer, //(-)-(3aR,6R,8aR)-khusimone// and two dimethylnaphtalenones... \\ "Vetiver oil consists of a highly complex mixture of over 150 sesquiterpenoid constituents, and the composition as well as its odor quality depend decisively upon its origin...  the sesquiterpenes (+)-α-vetivone, (-)-β-vetivone, and khusimol always occur in amounts up to 35%, and considered fingerprints, even though they do not contribute much to the typical odor characteristics associated with vetiver oil. Most decisive for the characteristic odor of vetiver oil are, according to Maurer, //(-)-(3aR,6R,8aR)-khusimone// and two dimethylnaphtalenones... \\
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 [Meaningful Scents around the World, Roman Kaiser, Zürich 2006, 291-295] [Meaningful Scents around the World, Roman Kaiser, Zürich 2006, 291-295]
  
-|{{:khusimone.jpg|}} \\ khusimone \\ //(vetiver-like, grapefruit, flowery)// | {{:vetivone_alpha.jpg| α-vetivone }} \\ α-vetivone \\ //(vetiver, grapefruit-like, fruity)// | {{:vetivone_beta.jpg| β-vetivone }} \\ β-vetivone \\ //(woody-vetiver or lime-like, hesperidic, rosy, exotic fruit)// |+|{{:khusimone.jpg|}} \\ khusimone \\ //(vetiver-like, grapefruit, flowery)// | {{:vetivone_alpha.jpg| α-vetivone }} \\ α-vetivone (isonootkatone) \\ //(vetiver, grapefruit-like, fruity)// | {{:vetivone_beta.jpg| β-vetivone }} \\ β-vetivone \\ //(woody-vetiver or lime-like, hesperidic, rosy, exotic fruit)// |
  
 "Although it originates in India, vetiver is widely cultivated in the tropical regions around the world. The world’s major producers include Haiti, India, Indonesia’s Java and the French island Réunion. α-Vetivone (CAS# 15764-04-2; (4R,4aS)-4,4a-dimethyl-6-propan-2-ylidene-4,5,7,8-tetrahydro-3H-naphthalen-2-one) has a warm pleasant powerful odor while β-vetivone (CAS# 18444-79-6; (5R,10R)-6,10-dimethyl-2-(1-methyl-ethylidene)-spiro[4.5]dec-6-en-8-one) has a quinolinelike, fruity (cassis, grapefruit) aroma with a woody by-note." \\ "Although it originates in India, vetiver is widely cultivated in the tropical regions around the world. The world’s major producers include Haiti, India, Indonesia’s Java and the French island Réunion. α-Vetivone (CAS# 15764-04-2; (4R,4aS)-4,4a-dimethyl-6-propan-2-ylidene-4,5,7,8-tetrahydro-3H-naphthalen-2-one) has a warm pleasant powerful odor while β-vetivone (CAS# 18444-79-6; (5R,10R)-6,10-dimethyl-2-(1-methyl-ethylidene)-spiro[4.5]dec-6-en-8-one) has a quinolinelike, fruity (cassis, grapefruit) aroma with a woody by-note." \\
Zeile 50: Zeile 53:
 [Volatile constituents of vetiver: a review., Belhassen, E., Filippi, J.J., Brévard, H., Joulain, D., Baldovini, N., Flavour and Fragrance Journal, 30(1), 2015, 26-82] [[http://onlinelibrary.wiley.com/doi/10.1002/ffj.3227/pdf]] [Volatile constituents of vetiver: a review., Belhassen, E., Filippi, J.J., Brévard, H., Joulain, D., Baldovini, N., Flavour and Fragrance Journal, 30(1), 2015, 26-82] [[http://onlinelibrary.wiley.com/doi/10.1002/ffj.3227/pdf]]
  
-{{chrysopogon_zizanoides.jpg?800}} \\+"The manufacture of vetiveryl acetate modulates the initial scent of vetiver essential oil by suppressing the notes brought by the main fragrant alcohols. While the impact of undesired odorant molecules such as phenol derivatives and geosmin is lowered, the major odour-active ketones such as khusimone, ziza-6(13)-en-3-ones, and the two vetivones develop their own odor characters in vetiveryl acetate." \\ 
 +Main components of vetiveryl acetate preparations were β-vetivenene (~0-1%), ylangen-15-yl acetate (~0-1%), cyclocopacamphan-12-yl acetate A (~1-3%), cyclocopacamphan-12-yl acetate B (~1-3%), khusian-2-yl acetate (~1-2%), ziza-6(13)en-3α-yl acetate (~1-2%), β-funebren-14-yl acetate (~1-2%), β-vetivone (~2-3%), ziza-6(13)en-3β-yl acetate (~1-2%), isokhusimyl acetate (~0-2%), vetiselinenyl acetate (~3-10%), α-vetivone (~1-4%), khusimyl acetate (~11-27%), α-isonootkatyl acetate (~1-7%), and (E)-isovalencenyl acetate (~3-28%). \\ 
 +[Tissandié, Loïc, et al. "Integrated comprehensive two-dimensional gas-chromatographic and spectroscopic characterization of vetiveryl acetates: Molecular identifications, quantification of constituents, regulatory and olfactory considerations." Journal of Chromatography A 1573 (2018): 125-150] 
 + 
 +The citrusy grapefruit character of vetiver oil originates from α-vetivone, β-vetivone, and nootkatone, earthy aspects are due to geosmine and nor-acorenone, and the creamy santal character mainly results from (E)-isovalencenol. The typical transparent woody-ambery character of vetiver is contributed by ziza-6(13)en-3-one (th 0.13 ng/L air) and 2-epi-ziza-6(13)en-3-one (th 0.029 ng/L air), now proved by synthesis of all (1R)-configured ziza-6(13)-en-3-one stereoisomers. \\ 
 +[Ouyang, Jie, et al. "The Smelling Principle of Vetiver Oil, Unveiled by Chemical Synthesis." Angewandte Chemie (International Ed. in English) 60.11 (2021): 5666] \\ 
 +[[https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7986879/]] 
 + 
 +{{chrysopogon_zizanoides.jpg}} \\
 Chrysopogon zizanioides-seeding habit-Kokomo Haiku (2009) \\ Chrysopogon zizanioides-seeding habit-Kokomo Haiku (2009) \\
  [[https://commons.wikimedia.org/wiki/File:Chrysopogon_zizanioides-seeding_habit-Kokomo_Haiku.jpg|Wikimedia Commons]], Author: Forest and Kim Starr  [[https://creativecommons.org/licenses/by/2.0/deed.en|CC BY-SA 2.0]]  [[https://commons.wikimedia.org/wiki/File:Chrysopogon_zizanioides-seeding_habit-Kokomo_Haiku.jpg|Wikimedia Commons]], Author: Forest and Kim Starr  [[https://creativecommons.org/licenses/by/2.0/deed.en|CC BY-SA 2.0]]
chrysopogon_zizanioides_l._roberty.1528978079.txt.gz · Zuletzt geändert: 2018/06/14 14:07 von andreas