马鞭草烯酮

马鞭草烯酮
	Verbenone
	IUPAC名; (1R,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one
别名	马鞭烯酮
识别
CAS号	80-57-9
PubChem	65724
ChemSpider	59147
SMILES	CC1=CC(=O)[C@@H]2C[C@H]1C2(C)C;
InChI	1/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3/t7-,8+/m1/s1;
InChIKey	DCSCXTJOXBUFGB-SFYZADRCBG
ChEBI	9955
KEGG	C09913
性质
化学式	C10H14O
摩尔质量	150.22 g·mol−1
密度	0.978 g/cm3
熔点	6.5 °C（280 K）
沸点	227—228 °C（441—442 °F；500—501 K）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

马鞭草烯酮（verbenone）是一种天然单萜衍生物，存在于许多植物中，有一种令人愉快的气味。除了是植物中的天然成分外，它与它的类似物也是昆虫信息素的成分之一。特别是用马鞭草烯酮配制长效基质后，在防治树皮甲虫，如山松甲虫和南方松甲虫（英语：dendroctonus frontalis）方面十分重要。

化学性质

马鞭草烯酮是一种重要的双环单萜类酮，是马鞭草油的主要成分，因此得名；它同样是迷迭香油的成分之一。马鞭草烯酮几乎不溶于水，可以与大多数有机溶剂混溶^[1]。

马鞭草烯酮可以由α-蒎烯选择性烯丙位氧化而来^[2]：

马鞭草烯酮在紫外线照射下会重排为菊油环酮^[3]：

用途

昆虫防治

南方松甲虫的生殖周期受到化学物质（包含马鞭草烯酮）不同程度的控制。树皮甲虫在繁殖时会在宿主松树中大量聚集，在最开始甲虫产生的化学物质会吸引同种甲虫。当成虫与幼虫的数量过多时，便会开始产生抗聚集的信号素，如马鞭草烯酮，进而阻止更多的甲虫进攻松树。曾经护林员通过砍伐、焚烧寄生的松树与其邻近树木来防止树皮甲虫的侵扰，随后他们将马鞭草烯酮制剂放置在附近易感的树木上，来阻止甲虫对其的伤害^[4] 。马鞭草烯酮也被用于山松甲虫^[5]、红湾鳄梨材小蠹（英语：redbay ambrosia beetle）^[6]的防治。

其他用途

马鞭草烯酮被用于香水、香料、草药茶、芳香疗法之中，它的左旋异构体可以用于止咳剂，马鞭草烯酮也被认为有一定的抗菌性^[7]。

参考文献

^ Merck Index, 11th Edition, 9862.
^ Glidden, U.S. Patent 2,911,442 (1959)
^ Erman, William F. Photochemical transformations of unsaturated bicyclic ketones. Verbenone and its photodynamic products of ultraviolet irradiation. Journal of the American Chemical Society. 1967, 89 (15): 3828–3841. doi:10.1021/ja00991a026.
^ U.S. Environmental Protection Agency Pesticide Fact Sheet #128986 （页面存档备份，存于互联网档案馆）.
^ Mafra-Neto, Agenor; de Lame, Frédérique M.; Fettig, Christopher J.; Perring, Thomas M.; Stelinski, Lukasz L.; Stoltman, Lyndsie L.; Mafra, Leandro E. J.; Borges, Rafael; Vargas, Roger I. Manipulation of Insect Behavior with Specialized Pheromone and Lure Application Technology (SPLAT®). John Beck; Joel Coats; Stephen Duke; Marja Koivunen (编). Natural Products for Pest Management 1141. American Chemical Society. 2013: 31–58.
^ Martini, X., Sobel, L., Conover, D., Mafra‐Neto, A., & Smith, J. (2020). Verbenone reduces landing of the redbay ambrosia beetle, vector of the laurel wilt pathogen, on live standing redbay trees. Agricultural and Forest Entomology, 22(1), 83-91.
^ Santoyo, S; Cavero, S; Jaime, L; Ibañez, E; Señoráns, FJ; Reglero, G. Chemical composition and antimicrobial activity of Rosmarinus officinalis L. Essential oil obtained via supercritical fluid extraction. Journal of Food Protection. 2005, 68 (4): 790–5. PMID 15830672. doi:10.4315/0362-028x-68.4.790.

[1] Merck Index, 11th Edition, 9862.

[2] Glidden, U.S. Patent 2,911,442 (1959)

[3] Erman, William F. Photochemical transformations of unsaturated bicyclic ketones. Verbenone and its photodynamic products of ultraviolet irradiation. Journal of the American Chemical Society. 1967, 89 (15): 3828–3841. doi:10.1021/ja00991a026.

[4] U.S. Environmental Protection Agency Pesticide Fact Sheet #128986 （页面存档备份，存于互联网档案馆）.

[5] Mafra-Neto, Agenor; de Lame, Frédérique M.; Fettig, Christopher J.; Perring, Thomas M.; Stelinski, Lukasz L.; Stoltman, Lyndsie L.; Mafra, Leandro E. J.; Borges, Rafael; Vargas, Roger I. Manipulation of Insect Behavior with Specialized Pheromone and Lure Application Technology (SPLAT®). John Beck; Joel Coats; Stephen Duke; Marja Koivunen (编). Natural Products for Pest Management 1141. American Chemical Society. 2013: 31–58.

[6] Martini, X., Sobel, L., Conover, D., Mafra‐Neto, A., & Smith, J. (2020). Verbenone reduces landing of the redbay ambrosia beetle, vector of the laurel wilt pathogen, on live standing redbay trees. Agricultural and Forest Entomology, 22(1), 83-91.

[7] Santoyo, S; Cavero, S; Jaime, L; Ibañez, E; Señoráns, FJ; Reglero, G. Chemical composition and antimicrobial activity of Rosmarinus officinalis L. Essential oil obtained via supercritical fluid extraction. Journal of Food Protection. 2005, 68 (4): 790–5. PMID 15830672. doi:10.4315/0362-028x-68.4.790.

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