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citrus_x_aurantium_l [2016/06/15 15:38]
andreas |
citrus_x_aurantium_l [2021/11/12 09:33] (aktuell)
andreas |
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| Bitter orange peel oils exhibited a very high content of limonene (87.6-95.1%). The minor components β-pinene (tr-2.4%), myrcene (1.3-1.8%), linalool (tr-1.5%), linalyl acetate (0-3.9%), α-pinene (0-0.6%) were found in almost all samples. \\ | Bitter orange peel oils exhibited a very high content of limonene (87.6-95.1%). The minor components β-pinene (tr-2.4%), myrcene (1.3-1.8%), linalool (tr-1.5%), linalyl acetate (0-3.9%), α-pinene (0-0.6%) were found in almost all samples. \\ |
| [Chemical variability of peel and leaf essential oils of sour orange. Marie-Laure Lota, Dominique de Rocca Serra, Camille Jacquemond, Felix Tomi, Joseph Casanova, Flavour Fragr. J. 2001; 16: 89–96] | [Chemical variability of peel and leaf essential oils of sour orange. Marie-Laure Lota, Dominique de Rocca Serra, Camille Jacquemond, Felix Tomi, Joseph Casanova, Flavour Fragr. J. 2001; 16: 89-96] |
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| | "... dividing the concentration (ppm) by the threshold (ppm) for bitter orange [peel oil], it can be seen that the most important odour characters in the oil are octanal, decanal, linalool, nonanal and linalyl acetate... the odour characters of petitgrain and neroli are obviously linalool and linalyl acetate; however, the odour character of lesser importance in these oils are nonanal, α-terpineol, geranial, and nerol for petigrain oils and methyl N-methylanthranilate, indole, geranial, (E)-nerolidol, methyl anthranilate and α-terpineol in neroli oil." \\ |
| | [Swift, Karl AD, ed. Advances in flavours and fragrances: From the sensation to the synthesis. Royal Society of Chemistry, 2007, 79-80] |
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| | Flavour components of C.aurantium essential oil (EO) were characterized by GC-MS and GC-O. Potent odour contributors were α-pinene (floral), octanal (green), limonene (citrus), linalool (floral), α-terpineol (indeterminate: ‘ND’, green), linalyl acetate (floral), (E,E) or (E,Z)-2,4-decadienal (frying), dodecanal (ND), caryophyllene (green) and an unknown compound (IT = 1678, plastic note). "Interestingly, the EO odour was also characterized by five volatile compounds (FD: 6/9 to 7/9) responsible for fresh, plastic notes in trace amounts not allowing identification. These compounds with a high IT (IT >1630) were smelled but not detected in GC conditions." \\ |
| | [Deterre, Sophie, et al. "Identification of key aroma compounds from bitter orange (Citrus aurantium L.) products: essential oil and macerate–distillate extract." Flavour and fragrance journal 27.1 (2012): 77-88] |
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| **Neroli** oil is the essential oil steam distilled from the flowers of C. x aurantium. \\ | **Neroli** oil is the essential oil steam distilled from the flowers of C. x aurantium. \\ |
| "Main volatile constituents are linalool, nerolidol and farnesol. Etymology: It. neroli, from the French-born Anna Maria de la Trémoille (1670-1722), princess of Nerola, a village near Rome. She loved the fragrance of the orange flowers, and was the first person to have them distilled. The tertiary sesquiterpene alcohol 3,7,11-trimethyl-1,6,10-dodecatriene-3-ol was first identified in neroli oil, hence the name nerolidol. Somewhat later, the isomeric alcohol 3,7,11-trimethyl-2,6,10-dodecatriene-1-ol was also identified. It was correspondingly named farnesol, from Villa Farnese, another village near Rome. " [[http://www.bojensen.net/EssentialOilsEng/EssentialOils21/EssentialOils21.htm]] | The distillaton water is //Orange Flower Water// as by-product. Orange Flower Water is extracted with solvent to leave a dark orange-brown product known as //Orange Flower Water Absolute//. Two other materials are //Orange Flower Concrete// (extracted from the flowers with solvent) and further //Orange Blossom Absolute// (concrete extracted with ethanol). |
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| | "Main volatile constituents are linalool, nerolidol and farnesol. Etymology: It. neroli, from the French-born Anna Maria de la Trémoille (1670-1722), princess of Nerola, a village near Rome. She loved the fragrance of the orange flowers, and was the first person to have them distilled. The tertiary sesquiterpene alcohol 3,7,11-trimethyl-1,6,10-dodecatriene-3-ol was first identified in neroli oil, hence the name [[http://www.thegoodscentscompany.com/data/rw1053991.html|nerolidol]]. Somewhat later, the isomeric alcohol 3,7,11-trimethyl-2,6,10-dodecatriene-1-ol was also identified. It was correspondingly named [[http://www.thegoodscentscompany.com/data/rw1290201.html|farnesol]], from Villa Farnese, another village near Rome. " [[http://www.bojensen.net/EssentialOilsEng/EssentialOils21/EssentialOils21.htm]] |
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| | "As most synthetic linalool contains dihydrolinalool (0.5-2.0%), this impurity can be used to determine adulteration of neroli oil with synthetic linalool. Frey (1988) showed that using the selective ion monitoring mode in GC/MS he could detect down to 50 ppm of dihydrolinalool in neroli oil, which corresponds to the addition of 0.5-1.0% synthetic linalool in the oil... Konig et al. (1992) proved through chiral GC analysis that the (R)-(-)-linalool enantiomer was predominant in neroli oil. They also found that (S)-(+)-(E)-nerolidol |
| | was the main (>98%) enantiomer found in this same oil" \\ |
| | [Lawrence, Brian M. "Progress in Essential Oils-Neroli Oil, Savory Oil, Yarrow Oil and Star Anise Oil." Perfumer and Flavorist 28.6 (2003): 56-75] [[http://media.allured.com/documents/PF_28_06_056_18.pdf]] |
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| "The major compounds within the hydrolate [of Citrus aurantium L. (Rutaceae) flowers (neroli) grown in Iran] obtained in the laboratory were geraniol (26.6%), α-terpineol (20.7%), linalool (15.4%) and benzene acetaldehyde (5.5%). Linalool (44.1%), methyl anthranilate (11.8%) and cis-linalool oxide (6.1%) were found in high percentages in the Hydrolate from the obtained traditional sample. 1,8-Cineol (15.9%), linalool (13.8%) and α-terpineol (6.6%) were more than other constituents in the industrially obtained hydrolate." \\ | "The major compounds within the hydrolate [of Citrus aurantium L. (Rutaceae) flowers (neroli) grown in Iran] obtained in the laboratory were geraniol (26.6%), α-terpineol (20.7%), linalool (15.4%) and benzene acetaldehyde (5.5%). Linalool (44.1%), methyl anthranilate (11.8%) and cis-linalool oxide (6.1%) were found in high percentages in the Hydrolate from the obtained traditional sample. 1,8-Cineol (15.9%), linalool (13.8%) and α-terpineol (6.6%) were more than other constituents in the industrially obtained hydrolate." \\ |
| Hajimehdipour, Mohammad Ali Faramarzi, Iranian Journal of Pharmaceutical Research (2004) 3: 177 -179] [[http://ijpr.sbmu.ac.ir/pdf_597_e28bb6bcb662fee9994b1a06bb9f7ab0.html ]] | Hajimehdipour, Mohammad Ali Faramarzi, Iranian Journal of Pharmaceutical Research (2004) 3: 177 -179] [[http://ijpr.sbmu.ac.ir/pdf_597_e28bb6bcb662fee9994b1a06bb9f7ab0.html ]] |
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| | {{:linalool.jpg| linalool}} \\ linalool | {{:methylnmethylanthranilate.jpg| methyl N-methylanthranilate}} \\ [[http://www.thegoodscentscompany.com/data/rw1004392.html|methyl N-methylanthranilate]] | | | {{:linalool.jpg| linalool}} \\ linalool | {{:methylnmethylanthranilate.jpg| methyl N-methylanthranilate}} \\ methyl N-methylanthranilate \\ //(sweet fruity)// | {{:nerolidol_e.jpg| (E)-nerolidol}} \\ (E)-nerolidol \\ //(floral green)// |{{:farnesol_2e6e.jpg| (E,E)-farnesol}} \\ (E,E)-farnesol \\ //(floral muguet)// | {{:pyrazine_2meo3isopropyl.png| 2-methoxy-3-isopropylpyrazine}} \\ 2-methoxy-3-isopropylpyrazine \\ //(green pea earthy)// | |
| {{:nerolidol_e.jpg| (E)-nerolidol}} \\ (E)-nerolidol //(floral green)// | | |
| {{:farnesol_2e6e.jpg| (E,E)-farnesol}} \\ (E,E)-farnesol //(floral muguet)// | | |
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| "The combination of these two sesquiterpene alcohols [(+)-(E)-nerolidol 3% and (E,E)-farnesol 1%], a considerable amount of methyl N-methylanthranilate (0.1%), which resembles the odor of concord grapes, and 1H-indole (0.1%), which, on high dilution posesses a distinct exotic jasmine note, differentiate neroli from petitgrain oil. Other nitrogen-containing compounds such as 2-phenylacetonitrile (0.1%) and (2-nitroethyl)-benzene (0.15%) have been identified by Maurer. With its low treshold of 2 ng/l water (0.002ppb), 2-isopropyl-3-methoxypyrazine (1 ppm) is also important and imparts neroli with an interesting green note." \\ | "The combination of these two sesquiterpene alcohols [(+)-(E)-nerolidol 3% and (E,E)-farnesol 1%], a considerable amount of [[http://www.thegoodscentscompany.com/data/rw1004392.html|methyl N-methylanthranilate]] (0.1%), which resembles the odor of concord grapes, and 1H-indole (0.1%), which, on high dilution posesses a distinct exotic jasmine note, differentiate neroli from petitgrain oil. Other nitrogen-containing compounds such as 2-phenylacetonitrile (0.1%) and (2-nitroethyl)-benzene (0.15%) have been identified by Maurer. With its low treshold of 2 ng/l water (0.002ppb), 2-isopropyl-3-methoxypyrazine (1 ppm) is also important and imparts neroli with an interesting green note." \\ |
| [Scent and Chemistry, Günther Ohloff, Wilhelm Pickenhagen, Philip Kraft, Wiley-VCH, 2012, 240-241] | [Scent and Chemistry, Günther Ohloff, Wilhelm Pickenhagen, Philip Kraft, Wiley-VCH, 2012, 240-241] |
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| [Italian Citrus Petitgrain Oils. Part I. Composition of Bitter Orange Petitgrain Oil. Luigi Mondello, Giovanni Dugo, Paola Dugo, Keith D. Bartle, Journal of Essential Oil Research, Vol.8 (6) 1996, 597-609] | [Italian Citrus Petitgrain Oils. Part I. Composition of Bitter Orange Petitgrain Oil. Luigi Mondello, Giovanni Dugo, Paola Dugo, Keith D. Bartle, Journal of Essential Oil Research, Vol.8 (6) 1996, 597-609] |
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| "In addition to linalool, the other important alcohols are geraniol (2.5%), nerol (0.4%), α-terpineol (5.6%), (+)-(R,E)-nerolidol (0.05%) and the intensly woody smelling (+)-spathulenol and (+)-isospathulenol (0.03%)... Although more than 100 carbonyl compounds found in petitgrain oils account for only 0.37%, their importance is unquestioned, among them high-impact compounds as β-ionone (5 ppm) and β-damascenone (2 ppm) that occur in concentrations way above their odor tresholds (0.009 and 0.007 ppb, resp.)...\\ | Enantiomerically pure or nearly pure (R)(-)-linalyl acetate was detected in petitgrain oil of Citrus aurantium L. using a chiral capillary column. \\ |
| Another important constituent is 2-isopropyl-3-methoxypyrazine with its typical galbanum-like, green note that can be found together with ten other substituted pyrazines. The concentration of [it] in petitgrain oil is 1 ppm, which exceeds its odor treshold by a million times." \\ | [Ravid, Uzi, Eli Putievsky, and Irena Katzir. "Chiral gc analysis of enantiomerically pure (R)(-)‐linalyl acetate in some lamiaceae, myrtle and petitgrain essential oils." Flavour and fragrance journal 9.5 (1994): 275-276] see also \\ |
| | [Dugo, Giovanni, et al. "Characterization of oils from the fruits, leaves and flowers of the bitter orange tree." Journal of Essential Oil Research 23.2 (2011): 45-59] |
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| | | {{:linalool.jpg| linalool}} \\ linalool |{{:linalylacetate_r.jpg|linalyl acetate}} \\ (R)-(-)-linalyl acetate | {{geraniol.jpg| geraniol }} \\ geraniol | {{:nerolidol_e.jpg| (E)-nerolidol}} \\ (E)-nerolidol | {{:spathulenol_plus.jpg|(+)-spathulenol}} \\ (+)-spathulenol | {{:pyrazine_2meo3isopropyl.png| 2-methoxy-3-isopropylpyrazine}} \\ 2-methoxy-3-isopropylpyrazine | |
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| | "In addition to linalool, the other important alcohols are geraniol (2.5%), nerol (0.4%), α-terpineol (5.6%), (+)-(R,E)-nerolidol (0.05%) and the intensely woody smelling (+)-spathulenol and (+)-isospathulenol (0.03%)... Although more than 100 carbonyl compounds found in petitgrain oils account for only 0.37%, their importance is unquestioned, among them high-impact compounds as β-ionone (5 ppm) and β-damascenone (2 ppm) that occur in concentrations way above their odor tresholds (0.009 and 0.007 ppb, resp.)...\\ |
| | Another important constituent is [[http://www.thegoodscentscompany.com/data/rw1107761.html|2-isopropyl-3-methoxypyrazine]] with its typical galbanum-like, green note that can be found together with ten other substituted pyrazines. The concentration of [it] in petitgrain oil is 1 ppm, which exceeds its odor treshold by a million times." \\ |
| [Scent and Chemistry, Günther Ohloff, Wilhelm Pickenhagen, Philip Kraft, Wiley-VCH, 2012, 238] | [Scent and Chemistry, Günther Ohloff, Wilhelm Pickenhagen, Philip Kraft, Wiley-VCH, 2012, 238] |
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| {{:citrus_vulgaris.jpg?500}} \\ | {{:citrus_vulgaris.jpg?600}} \\ |
| Köhler,F.E., Medizinal Pflanzen, vol.1, t.2 (1887) [W.Müller] \\ | Köhler,F.E., Medizinal Pflanzen, vol.1, t.2 (1887) [W.Müller] \\ |
| [[http://plantgenera.org/species.php?id_species=249703]] | [[http://plantgenera.org/species.php?id_species=249703]] |
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| | {{:citrus_aurantium.jpg}}\\ |
| | Citrus ×aurantium L. © Dipartimento di Scienze della Vita, Università di Trieste \\ |
| | pictures by Andrea Moro [[https://creativecommons.org/licenses/by-sa/4.0/|CC BY-SA 4.0]], [[http://dbiodbs.univ.trieste.it/carso/chiavi_pub26?spez=8441]] |
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| | VIDEO: [[https://www.youtube.com/watch?v=xGWCxZjW8jU|Orange flowers from Tunisia]] (IFF-LMR) |
