Enantiomer analysis of linalool in commercial bergamot (Citrus bergamia Risso) essential oils
The purity of commercial bergamot (Citrus bergamia Risso) essential oils was assessed by analyzing the enantiomers of linalool and linalyl acetate. The study included 34 cold-pressed oils and one steam-distilled oil obtained from peels. Additionally, laboratory-prepared samples comprised a cold-pres...
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| Published in | Japan Journal of Aromatherapy Vol. 26; no. 1; pp. 42 - 49 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | Japanese |
| Published |
Aroma Environment Association of Japan
07.02.2025
公益社団法人 日本アロマ環境協会 |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1346-3748 2189-5147 |
| DOI | 10.15035/aeaj.260105 |
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| Abstract | The purity of commercial bergamot (Citrus bergamia Risso) essential oils was assessed by analyzing the enantiomers of linalool and linalyl acetate. The study included 34 cold-pressed oils and one steam-distilled oil obtained from peels. Additionally, laboratory-prepared samples comprised a cold-pressed oil and a hexane-extracted oil from bergamot fruit. The analysis also included three aged cold-pressed oils and a racemic reagent of linalool. The enantiomeric analysis was performed using gas chromatography-mass spectrometry with a chiral column in the selected-ion monitoring mode. The mass units were set at m/z 71.0, 93.0, 80.0 and 121.0 for linalool and linalyl acetate. Results demonstrated that the enantiomer excess % of (R)-(−)-linalool over (S)-(+)-linalool exceeded 98.0% in most commercial cold-pressed and steam-distilled bergamot oils, as well as in the lab-prepared and aged samples. These findings indicate that the enantiomeric composition was unaffected by the experimental conditions. In conclusion, based on the enantiomeric excess of (R)-(−)-linalool, the high enantiomeric purity of 29 of commercial bergamot essential oils was confirmed, while the remaining 9 oils did not meet the verification criteria. |
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| AbstractList | The purity of commercial bergamot (Citrus bergamia Risso) essential oils was assessed by analyzing the enantiomers of linalool and linalyl acetate. The study included 34 cold-pressed oils and one steam-distilled oil obtained from peels. Additionally, laboratory-prepared samples comprised a cold-pressed oil and a hexane-extracted oil from bergamot fruit. The analysis also included three aged cold-pressed oils and a racemic reagent of linalool. The enantiomeric analysis was performed using gas chromatography-mass spectrometry with a chiral column in the selected-ion monitoring mode. The mass units were set at m/z 71.0, 93.0, 80.0 and 121.0 for linalool and linalyl acetate. Results demonstrated that the enantiomer excess % of (R)-(−)-linalool over (S)-(+)-linalool exceeded 98.0% in most commercial cold-pressed and steam-distilled bergamot oils, as well as in the lab-prepared and aged samples. These findings indicate that the enantiomeric composition was unaffected by the experimental conditions. In conclusion, based on the enantiomeric excess of (R)-(−)-linalool, the high enantiomeric purity of 29 of commercial bergamot essential oils was confirmed, while the remaining 9 oils did not meet the verification criteria. The purity of commercial bergamot (Citrus bergamia Risso) essential oils was assessed by analyzing the enantiomers of linalool and linalyl acetate. The study included 34 cold-pressed oils and one steam-distilled oil obtained from peels. Additionally, laboratory-prepared samples comprised a cold-pressed oil and a hexane-extracted oil from bergamot fruit. The analysis also included three aged cold-pressed oils and a racemic reagent of linalool. The enantiomeric analysis was performed using gas chromatography-mass spectrometry with a chiral column in the selected-ion monitoring mode. The mass units were set at m/z 71.0, 93.0, 80.0 and 121.0 for linalool and linalyl acetate. Results demonstrated that the enantiomer excess % of (R)-(−)-linalool over (S)-(+)-linalool exceeded 98.0% in most commercial cold-pressed and steam-distilled bergamot oils, as well as in the lab-prepared and aged samples. These findings indicate that the enantiomeric composition was unaffected by the experimental conditions. In conclusion, based on the enantiomeric excess of (R)-(−)-linalool, the high enantiomeric purity of 29 of commercial bergamot essential oils was confirmed, while the remaining 9 oils did not meet the verification criteria. 市販のベルガモット（Citrus bergamia Risso）精油に含まれるLinaloolとLinalyl acetateのエナンチオマー分析を行うことによって，ベルガモット精油の純度の検証を行った。市販試料としては，34種類が果皮圧搾油，1種類が果皮水蒸気蒸留油であった。また，ベルガモット果実から実験室レベルの圧搾油およびヘキサン抽出油を調製し試料とした。これらに加えて，長期室温保蔵した3種類の圧搾油およびラセミ体のLinalool標準試薬についても分析した。分析は選択的イオンモニタリング（SIM）モードを使ったガスクロマトグラフィー－質量分析計によりキラルカラムを用いて行った。設定質量はLinalool, Linalyl acetateに共通して，m/z 71.0, 93.0, 80.0, 121.0とした。（S）-（＋）-Linaloolに対する（R）-（－）-Linaloolのエナンチオマー割合は，（R）-（－）-Linaloolが多くの市販の圧搾油，蒸留油，そして実験室レベルの調製試料および長期室温保蔵試料においても98.0％ee以上と圧倒的に高いことが明らかとなった。このことはエナンチオマー割合が種々の因子によって影響されず変化しないことを示唆している。結論として，（R）-（－）-Linaloolのエナンチオマー割合から判断して，市販ベルガモット精油にはエナンチオマー純度の高い精油と判断されたものが29種類，残りの9種類の精油は純正な精油とは判断できなかった。 |
| Author | ASHIZAWA, Honami KITAOKA, Yuichi ASANO, Kimito SAWAMURA, Masayoshi NAGANO, Momota |
| Author_FL | 芦澤 穂波 北岡 雄一 浅野 公人 沢村 正義 長野 桃太 |
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| References | 13） Yamamoto N., Fujiwara S., Saito-Izumi K., Kamei A., et al: Effects of inhalated （S）-linalool on hypothalamic gene expression in rats under restraint stress, Biosci. Biotechnol. Biochem., 77, 2413–2418 （2013 18） Verzera A., Lamonica G., Mondello L., Trozzi A., et al: The composition of bergamot oil, Perfumer and Flavorist, 21, 19–34（1996）. 21） 沢村正義，鈴木 悟，浅野公人，佐藤美夢，他：数種の精油およびユズ種子油のフロクマリン類分析，アロマテラピー学雑誌，19, 1–9（2018 11） 熊谷千津，川口光倫，齋藤 碧：精油の香りを纏うライフスタイルが女子大学生の魅力に与える影響，アロマテラピー学雑誌，19, 10–21（2018 5） 井上重治：香りの抗菌作用―アロマセラピーへの応用，化学と生物，39, 475–481（2001 25） Jäger W., Buchbauer G., Jirovertz L., Fritzer M., et al: Percutaneous adsorption of lavender oil from a massage oil, J. Soc. Cosmet. Chem., 43, 49–54 （1992）. 22） Giacomo A. D., Mincione B.: “Olio Essenziale di Bergamotto Citrus bergamia, Risso”, pp. 1–31, Laruffa Editore, Reggio Calabria （1995）. 3） 沢村正義：イタリアのベルガモット精油について，aromatopia, 8, 22–25（1999 20） 沢村正義，鈴木 悟，小原典子，佐藤美夢，他：精油中のフロクマリン類分析，アロマテラピー学雑誌，17, 39–47（2016 19） 公益社団法人日本アロマ環境協会編：“アロマテラピー検定公式テキスト1級・2級”，p. 14, 公益社団法人日本アロマ環境協会，東京（2020 14） 山本直人：香料によるストレス調節効果を遺伝子科学から検証する―（S）-リナロールの効果を例にして，香料，（268）, 53–61（2015 17） Cotroneo A., Stagno d’Alcontres I., Trozzi A.: On the genuineness of citrus essential oils. Part XXXIV. Detection of added reconstituted bergamot oil in genuine bergamot essential oil by high resolution gas chromatography with capillary columns, Flavour Fragr. J., 7, 15–17 （1992）. 9） 渡邉映理，木村真理，ケニークフタ，亀井 勉，他：ベルガモット精油による芳香浴の自律神経系および情動に及ぼす効果，Aroma Research, 14, 150–154（2013 1） 日本アロマ環境協会：好きな香りランキング，AEAJ,（75）, 68（2015 16） Dugo G., Giacomo A. D. （Eds.）: “Citrus: The Genus Citrus”, pp. 461–495, Taylor & Francis, Florida（2002）. 10） 桑波田日香里：アロマセラピーの疼痛ケアへの有効性を検証する：ベルガモット精油，リナロール，酢酸リナリル，aromatopia, 22, 116–121（2013 4） 沢村正義，芦澤穂波，長野桃太，赤須治郎，他：和紅茶アールグレイの機能性関連成分および付香されたベルガモット精油の検証について，日本食品化学学会誌，30, 82–90（2023 8） 武田ひとみ：アロマテラピーの嗅覚刺激と触刺激が睡眠の質に及ぼす影響，アロマテラピー学雑誌，17, 24–30（2016 12） Höferl M., Krist S., Buchbauer G.: Chirality influences the effects of linalool on physiological parameters of stress, Planta Med., 72, 1188–1192 （2006 23） Sawamura M., Poiana M., Kawamura A., Itoh T., et al: Volatile components of peel oils of Italian and Japanese lemon and bergamot, Ital. J. Food Sci., 11, 121–130 （1999）. 24） Spanier A. M., Shahidi F., Parliment T. H., Mussinan C., et al: “Food Flavors and Chemistry, Advances of the New Millenium”, pp. 216–231, The Royal Society of Chemistry, Cambridge （2001）. 2） 岩政正男：柑橘の品種，p. 182, 静岡県柑橘農業協同組合連合会，清水市（1976 6） 枝 伸彦，伊藤大永，清水和弘，赤間高雄：エッセンシャルオイルによる香り刺激が口腔内免疫能に及ぼす影響についての生理心理学的研究，アロマテラピー学雑誌，20, 28–37（2019 15） Sawamura M., Kuriyama T.: Quantitative determination of volatile constituents in the pummelo（Citrus grandis Osbeck forma Tosa-buntan）, J. Agric. Food. Chem., 36, 567–569 （1988）. 7） 武田ひとみ：ベルガモット精油の芳香および精油を用いたトリートメントが心身に及ぼす影響―その効果と特性不安レベルについて―，生理心理学と精神生理学，33, 92（2015 |
| References_xml | – reference: 3） 沢村正義：イタリアのベルガモット精油について，aromatopia, 8, 22–25（1999）． – reference: 4） 沢村正義，芦澤穂波，長野桃太，赤須治郎，他：和紅茶アールグレイの機能性関連成分および付香されたベルガモット精油の検証について，日本食品化学学会誌，30, 82–90（2023）． – reference: 5） 井上重治：香りの抗菌作用―アロマセラピーへの応用，化学と生物，39, 475–481（2001）． – reference: 23） Sawamura M., Poiana M., Kawamura A., Itoh T., et al: Volatile components of peel oils of Italian and Japanese lemon and bergamot, Ital. J. Food Sci., 11, 121–130 （1999）. – reference: 19） 公益社団法人日本アロマ環境協会編：“アロマテラピー検定公式テキスト1級・2級”，p. 14, 公益社団法人日本アロマ環境協会，東京（2020）． – reference: 21） 沢村正義，鈴木 悟，浅野公人，佐藤美夢，他：数種の精油およびユズ種子油のフロクマリン類分析，アロマテラピー学雑誌，19, 1–9（2018）． – reference: 6） 枝 伸彦，伊藤大永，清水和弘，赤間高雄：エッセンシャルオイルによる香り刺激が口腔内免疫能に及ぼす影響についての生理心理学的研究，アロマテラピー学雑誌，20, 28–37（2019）． – reference: 15） Sawamura M., Kuriyama T.: Quantitative determination of volatile constituents in the pummelo（Citrus grandis Osbeck forma Tosa-buntan）, J. Agric. Food. Chem., 36, 567–569 （1988）. – reference: 13） Yamamoto N., Fujiwara S., Saito-Izumi K., Kamei A., et al: Effects of inhalated （S）-linalool on hypothalamic gene expression in rats under restraint stress, Biosci. Biotechnol. Biochem., 77, 2413–2418 （2013）． – reference: 18） Verzera A., Lamonica G., Mondello L., Trozzi A., et al: The composition of bergamot oil, Perfumer and Flavorist, 21, 19–34（1996）. – reference: 12） Höferl M., Krist S., Buchbauer G.: Chirality influences the effects of linalool on physiological parameters of stress, Planta Med., 72, 1188–1192 （2006）． – reference: 7） 武田ひとみ：ベルガモット精油の芳香および精油を用いたトリートメントが心身に及ぼす影響―その効果と特性不安レベルについて―，生理心理学と精神生理学，33, 92（2015）． – reference: 20） 沢村正義，鈴木 悟，小原典子，佐藤美夢，他：精油中のフロクマリン類分析，アロマテラピー学雑誌，17, 39–47（2016）． – reference: 10） 桑波田日香里：アロマセラピーの疼痛ケアへの有効性を検証する：ベルガモット精油，リナロール，酢酸リナリル，aromatopia, 22, 116–121（2013）． – reference: 16） Dugo G., Giacomo A. D. （Eds.）: “Citrus: The Genus Citrus”, pp. 461–495, Taylor & Francis, Florida（2002）. – reference: 9） 渡邉映理，木村真理，ケニークフタ，亀井 勉，他：ベルガモット精油による芳香浴の自律神経系および情動に及ぼす効果，Aroma Research, 14, 150–154（2013）． – reference: 14） 山本直人：香料によるストレス調節効果を遺伝子科学から検証する―（S）-リナロールの効果を例にして，香料，（268）, 53–61（2015）． – reference: 8） 武田ひとみ：アロマテラピーの嗅覚刺激と触刺激が睡眠の質に及ぼす影響，アロマテラピー学雑誌，17, 24–30（2016）． – reference: 17） Cotroneo A., Stagno d’Alcontres I., Trozzi A.: On the genuineness of citrus essential oils. Part XXXIV. Detection of added reconstituted bergamot oil in genuine bergamot essential oil by high resolution gas chromatography with capillary columns, Flavour Fragr. J., 7, 15–17 （1992）. – reference: 25） Jäger W., Buchbauer G., Jirovertz L., Fritzer M., et al: Percutaneous adsorption of lavender oil from a massage oil, J. Soc. Cosmet. Chem., 43, 49–54 （1992）. – reference: 1） 日本アロマ環境協会：好きな香りランキング，AEAJ,（75）, 68（2015）． – reference: 22） Giacomo A. D., Mincione B.: “Olio Essenziale di Bergamotto Citrus bergamia, Risso”, pp. 1–31, Laruffa Editore, Reggio Calabria （1995）. – reference: 2） 岩政正男：柑橘の品種，p. 182, 静岡県柑橘農業協同組合連合会，清水市（1976）． – reference: 11） 熊谷千津，川口光倫，齋藤 碧：精油の香りを纏うライフスタイルが女子大学生の魅力に与える影響，アロマテラピー学雑誌，19, 10–21（2018）． – reference: 24） Spanier A. M., Shahidi F., Parliment T. H., Mussinan C., et al: “Food Flavors and Chemistry, Advances of the New Millenium”, pp. 216–231, The Royal Society of Chemistry, Cambridge （2001）. |
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| Title | Enantiomer analysis of linalool in commercial bergamot (Citrus bergamia Risso) essential oils |
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