香茅醇

香茅醇
	IUPAC名; 3,7-Dimethyloct-6-en-1-ol
別名	(±)-β-Citronellol; ; 3,7-Dimethyl-6-octen-1-ol
識別
CAS號	106-22-9
ChemSpider	13850135
SMILES	OCC[C@@H](CC/C=C(/C)C)C;
InChI	1/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3/t10-/m1/s1;
InChIKey	QMVPMAAFGQKVCJ-SNVBAGLBBU
ChEBI	50462
KEGG	C09849
性質
化學式	C10H20O
摩爾質量	156.27 g·mol−1
密度	0.855 g/cm3
沸點	225 °C（498 K）
危險性
NFPA 704	2 1 0
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

香茅醇（Citronellol）是一種天然有機化合物，存在於多種植物精油以及一些水果中，屬於類萜。其兩種對映異構體在自然界中均有分布：R-(+)-香茅醇, 存在於香茅油 (50%)；而S-(−)-香茅醇存在於薔薇屬植物精油中(18–55%)，以及天竺葵屬植物等。^[1]

製備[編輯]

每年生產數百萬公斤的香茅醇。香茅醇主要由香葉醇或橙花醇在亞鉻酸銅催化劑上加氫化合成^[2]。均相催化劑用於生產對映異構體^[3]^[4]。

應用[編輯]

香茅醇用於香水和驅蟲劑，^[5]農業害蟎引誘劑。^[6]香茅醇在短距離內是一種很好的驅蚊劑，但保護性能隨距離增加大大降低。^[7]與環糊精結合能增強驅蚊效用，有效時間提升至1.5小時。^[8]

香茅醇是生產玫瑰醚（英語：rose oxide）的原料。^[9]

健康和安全性[編輯]

美國食品藥品監督管理局(FDA)將香茅醇歸入「公認安全」(GRAS)的分類，^[6]在食物中僅限作為香料用途添加。^[10]有報道稱一些人群可能對香茅醇敏感，但其作為食品添加劑時的劑量是否足以使人過敏則尚不清楚。^[11]^[12]

就皮膚安全性而言，香茅醇已被評估為一種驅蟲劑^[13] 。

參見[編輯]

參考資料[編輯]

^ Lawless, J. The Illustrated Encyclopedia of Essential Oils. ISBN 1-85230-661-0.
^ Sell, Charles S. Terpenoids. Kirk-Othmer Encyclopedia of Chemical Technology. 2006. ISBN 0471238961. doi:10.1002/0471238961.2005181602120504.a01.pub2.
^ Morris, Robert H. Ruthenium and Osmium. De Vries, J. G.; Elsevier, C. J. (編). The Handbook of Homogeneous Hydrogenation. Weinheim: Wiley-VCH. 2007. ISBN 978-3-527-31161-3.
^ Ait Ali, M.; Allaoud, S.; Karim, A.; Roucoux, A.; Mortreux, A. Catalytic Synthesis of (R)- and (S)-citronellol by homogeneous hydrogenation over amidophosphinephosphinite and diaminodiphosphine rhodium complexes. Tetrahedron: Asymmetry. 1995, 6 (2): 369. doi:10.1016/0957-4166(95)00015-H.
^ Taylor WG, Schreck CE. Chiral-phase capillary gas chromatography and mosquito repellent activity of some oxazolidine derivatives of (+)- and (−)-citronellol. J Pharm Sci. 1985, 74 (5): 534–539. PMID 2862274. doi:10.1002/jps.2600740508.
^ ^6.0 ^6.1 Citronellol (167004) Fact Sheet (PDF). epa.gov. [12 May 2017]. （原始內容存檔 (PDF)於2017-04-30）.
^ Revay, Edita E.; Kline, Daniel L.; Xue, Rui-De; Qualls, Whitney A.; Bernier, Ulrich R.; Kravchenko, Vasiliy D.; Ghattas, Nina; Pstygo, Irina; Müller, Günter C. Reduction of mosquito biting-pressure: Spatial repellents or mosquito traps? A field comparison of seven commercially available products in Israel. Acta Tropica. 2013, 127 (1): 63–8. PMID 23545129. doi:10.1016/j.actatropica.2013.03.011.
^ Songkro, Sarunyoo; Hayook, Narissara; Jaisawang, Jittarat; Maneenuan, Duangkhae; Chuchome, Thitima; Kaewnopparat, Nattha. Investigation of inclusion complexes of citronella oil, citronellal and citronellol with β-cyclodextrin for mosquito repellent. Journal of Inclusion Phenomena and Macrocyclic Chemistry. 2011, 72 (3–4): 339. doi:10.1007/s10847-011-9985-7.
^ “Dark” Singlet Oxygenation of β-Citronellol: A Key Step in the Manufacture of Rose Oxide. Organic Process Research & Development.
^ 存档副本. [2012-07-19]. （原始內容存檔於2012-01-06）.
^ Cropwatch Report April 2008 (PDF). [2017-05-12]. （原始內容 (PDF)存檔於2014-02-10）.
^ Survey and health assessment of chemical substances in massage oils 網際網路檔案館的存檔，存檔日期2007-09-27.
^ Taylor, W. G.; Schreck, C. E. Chiral-phase capillary gas chromatography and mosquito repellent activity of some oxazolidine derivatives of (+)- and (−)-citronellol. Journal of Pharmaceutical Sciences. 1985, 74 (5): 534–539 [2023-05-21]. PMID 2862274. doi:10.1002/jps.2600740508. （原始內容存檔於2022-12-01）.

[1] Lawless, J. The Illustrated Encyclopedia of Essential Oils. ISBN 1-85230-661-0.

[KO-2] Sell, Charles S. Terpenoids. Kirk-Othmer Encyclopedia of Chemical Technology. 2006. ISBN 0471238961. doi:10.1002/0471238961.2005181602120504.a01.pub2.

[3] Morris, Robert H. Ruthenium and Osmium. De Vries, J. G.; Elsevier, C. J. (編). The Handbook of Homogeneous Hydrogenation. Weinheim: Wiley-VCH. 2007. ISBN 978-3-527-31161-3.

[4] Ait Ali, M.; Allaoud, S.; Karim, A.; Roucoux, A.; Mortreux, A. Catalytic Synthesis of (R)- and (S)-citronellol by homogeneous hydrogenation over amidophosphinephosphinite and diaminodiphosphine rhodium complexes. Tetrahedron: Asymmetry. 1995, 6 (2): 369. doi:10.1016/0957-4166(95)00015-H.

[5] Taylor WG, Schreck CE. Chiral-phase capillary gas chromatography and mosquito repellent activity of some oxazolidine derivatives of (+)- and (−)-citronellol. J Pharm Sci. 1985, 74 (5): 534–539. PMID 2862274. doi:10.1002/jps.2600740508.

[usepa-6] 6.0 ^6.1 Citronellol (167004) Fact Sheet (PDF). epa.gov. [12 May 2017]. （原始內容存檔 (PDF)於2017-04-30）.

[7] Revay, Edita E.; Kline, Daniel L.; Xue, Rui-De; Qualls, Whitney A.; Bernier, Ulrich R.; Kravchenko, Vasiliy D.; Ghattas, Nina; Pstygo, Irina; Müller, Günter C. Reduction of mosquito biting-pressure: Spatial repellents or mosquito traps? A field comparison of seven commercially available products in Israel. Acta Tropica. 2013, 127 (1): 63–8. PMID 23545129. doi:10.1016/j.actatropica.2013.03.011.

[8] Songkro, Sarunyoo; Hayook, Narissara; Jaisawang, Jittarat; Maneenuan, Duangkhae; Chuchome, Thitima; Kaewnopparat, Nattha. Investigation of inclusion complexes of citronella oil, citronellal and citronellol with β-cyclodextrin for mosquito repellent. Journal of Inclusion Phenomena and Macrocyclic Chemistry. 2011, 72 (3–4): 339. doi:10.1007/s10847-011-9985-7.

[9] “Dark” Singlet Oxygenation of β-Citronellol: A Key Step in the Manufacture of Rose Oxide. Organic Process Research & Development.

[10] 存档副本. [2012-07-19]. （原始內容存檔於2012-01-06）.

[11] Cropwatch Report April 2008 (PDF). [2017-05-12]. （原始內容 (PDF)存檔於2014-02-10）.

[12] Survey and health assessment of chemical substances in massage oils 網際網路檔案館的存檔，存檔日期2007-09-27.

[13] Taylor, W. G.; Schreck, C. E. Chiral-phase capillary gas chromatography and mosquito repellent activity of some oxazolidine derivatives of (+)- and (−)-citronellol. Journal of Pharmaceutical Sciences. 1985, 74 (5): 534–539 [2023-05-21]. PMID 2862274. doi:10.1002/jps.2600740508. （原始內容存檔於2022-12-01）.

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