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香茅醇

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香茅醇
Skeletal formula of (+)-citronellol and (−)-citronellol
Ball-and-stick model of the (+)-citronellol molecule
Ball-and-stick model of the (-)-citronellol molecule
IUPAC名
3,7-Dimethyloct-6-en-1-ol
别名 (±)-β-Citronellol;
3,7-Dimethyl-6-octen-1-ol
识别
CAS号 106-22-9  checkY
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
性质
化学式 C10H20O
摩尔质量 156.27 g·mol−1
密度 0.855 g/cm3
沸点 225 °C（498 K）
危险性
NFPA 704
2
1
0
 
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

香茅醇（Citronellol）是一种天然有机化合物，存在于多种植物精油以及一些水果中，属于类萜。其两种对映异构体在自然界中均有分布：R-(+)-香茅醇, 存在于香茅油 (50%)；而S-(−)-香茅醇存在于蔷薇属植物精油中(18–55%)，以及天竺葵属植物等。[1]

制备

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每年生产数百万公斤的香茅醇。 香茅醇主要由香叶醇或橙花醇在亚铬酸铜催化剂上加氢化合成[2]。均相催化剂用于生产对映异构体[3][4]。

应用

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香茅醇用于香水和驱虫剂，[5]农业害螨引诱剂。[6]香茅醇在短距离内是一种很好的驱蚊剂，但保护性能随距离增加大大降低。[7]与环糊精结合能增强驱蚊效用，有效时间提升至1.5小时。[8]

香茅醇是生产玫瑰醚的原料。[9]

健康和安全性

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美国食品药品监督管理局(FDA)将香茅醇归入“公认安全”(GRAS)的分类，[6]在食物中仅限作为香料用途添加。[10]有报道称一些人群可能对香茅醇敏感，但其作为食品添加剂时的剂量是否足以使人过敏则尚不清楚。[11][12]

就皮肤安全性而言，香茅醇已被评估为一种驱虫剂[13]，市面上多用作螨虫引诱剂。[6]香茅醇在短距离内是一种很好的驱蚊剂，但当目标距离源头稍远时，保护作用就会大大降低。[14]当与β-环糊精混合时，它对蚊子叮咬的平均保护时间为90分钟。[15]

参见

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参考资料

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  1. ^ Lawless, J. The Illustrated Encyclopedia of Essential Oils. ISBN 1-85230-661-0. 
  2. ^ Kirk-Othmer (编). Terpenoids. Kirk-Othmer Encyclopedia of Chemical Technology 1. Wiley. 2001-01-26. ISBN 978-0-471-48494-3. doi:10.1002/0471238961.2005181602120504.a01.pub2 （英语）. 
  3. ^ Morris, Robert H. Ruthenium and Osmium. De Vries, J. G.; Elsevier, C. J. (编). 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. 1995-02-01, 6 (2): 369. ISSN 0957-4166. doi:10.1016/0957-4166(95)00015-H. 
  5. ^ Taylor, Wesley G.; Schreck, Carl E. Chiral-Phase Capillary Gas Chromatography and Mosquito Repellent Activity of Some Oxazolidine Derivatives of (+)- and (−)-Citronello1. Journal of Pharmaceutical Sciences. 1985-05-01, 74 (5): 534-539. ISSN 0022-3549. PMID 2862274. doi:10.1002/jps.2600740508 （英语）. 
  6. ^ 6.0 6.1 6.2 Citronellol (167004) Fact Sheet (PDF). epa.gov. [12 May 2017]. （原始内容存档 (PDF)于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. ISSN 0001-706X. 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. 2012-04, 72 (3-4): 339. ISSN 0923-0750. doi:10.1007/s10847-011-9985-7 （英语）. 
  9. ^ Alsters, Paul L.; Jary, Walther; Nardello-Rataj, Véronique; Aubry, Jean-Marie. “Dark” Singlet Oxygenation of β-Citronellol: A Key Step in the Manufacture of Rose Oxide. Organic Process Research & Development. 2010-01-15, 14 (1). ISSN 1083-6160. doi:10.1021/op900076g. 
  10. ^ Standards Restricted. IFRA International Fragrance Association. [2025-03-12]. （原始内容存档于2012-01-06）. 
  11. ^ Cropwatch Report April 2008 (PDF). [2017-05-12]. （原始内容 (PDF)存档于2014-02-10）. 
  12. ^ Survey and health assessment of chemical substances in massage oils 互联网档案馆的存档，存档日期2007-09-27.
  13. ^ Taylor, Wesley G.; Schreck, Carl E. Chiral-Phase Capillary Gas Chromatography and Mosquito Repellent Activity of Some Oxazolidine Derivatives of (+)- and (−)-Citronello1. Journal of Pharmaceutical Sciences. 1985-05-01, 74 (5): 534-539. ISSN 0022-3549. PMID 2862274. doi:10.1002/jps.2600740508 （英语）. 
  14. ^ 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): 63–68. ISSN 0001-706X. PMID 23545129. doi:10.1016/j.actatropica.2013.03.011. 
  15. ^ 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. 2012-04, 72 (3-4): 339. ISSN 0923-0750. S2CID 93566912. doi:10.1007/s10847-011-9985-7 （英语）. 
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