| Beide Seiten der vorigen Revision
Vorhergehende Überarbeitung
Nächste Überarbeitung
|
Vorhergehende Überarbeitung
Letzte Überarbeitung
Beide Seiten der Revision
|
chrysopogon_zizanioides_l._roberty [2017/08/11 12:01]
andreas |
chrysopogon_zizanioides_l._roberty [2021/03/12 08:20]
andreas |
| 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... \\ |
| [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." \\ |
| [Vetivone and Khusimone: the Puzzling Vetiver Oil Components., Zviely, M., Perfumer & flavorist, 37(2), 2012, 46-50] | [Vetivone and Khusimone: the Puzzling Vetiver Oil Components., Zviely, M., Perfumer & flavorist, 37(2), 2012, 46-50] |
| |
| "The essential oils isolated from vetiver [Vetiveria zizanioides (L.) Nash.] roots collected from four locations in south India were analyzed by GC-FID and GC-MS. Eighty constituents, representing 94.5-97.8% of the oils, have been identified. The oils from Bangalore, Hyderabad, Kundapur, and Mettupalayam were rich in sesquiterpenes and oxygenated sesquiterpenes with cedrane, bisabolane, eudesmane, eremophilane, and zizaane skeletons. The main components of the four essential oils were: eudesma-4,6-diene (delta-selinene) + beta-vetispirene (3.9-6.1%), beta-vetivenene (0.9-9.4%), 13-nor-trans-eudesma-4(15),7-dien-11-one + amorph-4-en-10-ol (5.0-6.4%), trans-eudesma-4(15),7-dien-12-ol (vetiselinenol) + (E)-opposita-4(15),7(11)-dien-12-ol (3.7-5.9%), eremophila-1 (10),11-dien-2alpha-ol (nootkatol) + ziza-6(13)-en-12-ol (khusimol) (16.1-19.2%), and eremophila-1(10),7(11)-dien-2alpha-ol (isonootkatol) + (E)-eremophila-1(10),7(11)-12-ol (isovalencenol) (5.6-6.9%). The important compounds that impart the characteristic vetiver odor are: khusimene, delta-selinene, beta-vetivenene, cyclocopacamphan-12-ol (epimers A and B), vetiselinenol, khusimol, isovalencenol, khusimone, alpha-vetivone, and beta-vetivone. The chemical profiles of the oils are comparable to Haitian vetiver oil." \\ | "The main components of the... essential oils were: eudesma-4,6-diene (delta-selinene) + beta-vetispirene (3.9-6.1%), beta-vetivenene (0.9-9.4%), 13-nor-trans-eudesma-4(15),7-dien-11-one + amorph-4-en-10-ol (5.0-6.4%), trans-eudesma-4(15),7-dien-12-ol (vetiselinenol) + (E)-opposita-4(15),7(11)-dien-12-ol (3.7-5.9%), eremophila-1 (10),11-dien-2alpha-ol (nootkatol) + ziza-6(13)-en-12-ol (khusimol) (16.1-19.2%), and eremophila-1(10),7(11)-dien-2alpha-ol (isonootkatol) + (E)-eremophila-1(10),7(11)-12-ol (isovalencenol) (5.6-6.9%)... |
| | The characteristic components of south Indian vetiver oils are: ziza-6(13)-ene (khusimene), δ-selinene, β-vetivenene, cyclocopacamphan-12-ol (epimers A and B), vetiselinenol, khusimol, isovalencenol, khusimone, α-vetivone, and β-vetivone. The pleasant odor of the oil is highly complex. The primary alcohols cyclocopacamphanols A and B, khusimol, vetiselinenol, and isovalencenol contribute to the woody note. |
| | The norketone khusimone imparts a rhubarb-grapefruit like odor. The ketone α-vetivone possesses a strong grapefruit odor. β-Vetivone displays grapefruit and woody notes. Thus, the highly complex odor of vetiver oil is due to the presence of several organoleptically important compounds... The chemical profiles of the oils are comparable to Haitian vetiver oil." \\ |
| [Constituents of south Indian vetiver oils., Mallavarapu, G.R., Syamasundar, K.V., Ramesh, S., Rao, B.R., Natural product communications, 7(2), 2012, 223-225] | [Constituents of south Indian vetiver oils., Mallavarapu, G.R., Syamasundar, K.V., Ramesh, S., Rao, B.R., Natural product communications, 7(2), 2012, 223-225] |
| |
| "The characterization of the odour-active constituents of VEO [vetiver essential oil] is another example of a task that is particularly difficult when dealing with such complex materials. It obviously should be based on as complete as possible knowledge of the chemical composition, but it is also necessary that the sensorial analyses use samples of constituents at their highest state of olfactory purity. A good example of the difficulty of these determinations is furnished inter alia by the odorant activity of vetiselinenol. The Weyerstahl studies on essential oils are undoubtedly the most extensive analytical investigations ever conducted on complex oils, but despite his efforts to characterize the structures and the odour of many of VEO constituents, he attributed a ‘Woody, vetiver, cedar, ambra-like’ note to this ‘strong smelling component’ and reported that, with khusimol and (E)-isovalencol, it was ‘responsible for the base note’. When a high-resolution approach such as GC-O was used, vetiselenenol proved to be odourless for all of the panelists, and khusimol had apparently a much lower olfactory contribution to the whole oil than many other constituents, such as ziza-6(13)-ene-3-one and 2-epi-ziza-6(13)-ene-3-one." \\ | "The characterization of the odour-active constituents of VEO [vetiver essential oil] is another example of a task that is particularly difficult when dealing with such complex materials. It obviously should be based on as complete as possible knowledge of the chemical composition, but it is also necessary that the sensorial analyses use samples of constituents at their highest state of olfactory purity. A good example of the difficulty of these determinations is furnished inter alia by the odorant activity of vetiselinenol. The Weyerstahl studies on essential oils are undoubtedly the most extensive analytical investigations ever conducted on complex oils, but despite his efforts to characterize the structures and the odour of many of VEO constituents, he attributed a ‘Woody, vetiver, cedar, ambra-like’ note to this ‘strong smelling component’ and reported that, with khusimol and (E)-isovalencol, it was ‘responsible for the base note’. When a high-resolution approach such as GC-O was used, vetiselenenol proved to be odourless for all of the panelists, and khusimol had apparently a much lower olfactory contribution to the whole oil than many other constituents, such as ziza-6(13)-ene-3-one and 2-epi-ziza-6(13)-ene-3-one." \\ |
| [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]] |
| | |
| | "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." \\ |
| | [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. \\ |
| | [List, Benjamin, et al. "The Odorous Principle of Vetiver Oil, Unveiled by Chemical Synthesis." Angew. Chem. Int. Ed.2021, 60, 1-7] \\ |
| | [[https://onlinelibrary.wiley.com/doi/epdf/10.1002/anie.202014609]] |
| |
| {{chrysopogon_zizanoides.jpg?800}} \\ | {{chrysopogon_zizanoides.jpg?800}} \\ |
| 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]] |
