马鞭草烯醇

马鞭草烯醇
	IUPAC名; 4,6,6-三甲基双环[3.1.1]庚-3-烯-2-醇; 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-ol
别名	2-蒎烯-4-醇
识别
CAS号	473-67-6
PubChem	61126
SMILES	CC1=CC(C2CC1C2(C)C)O;
InChIKey	WONIGEXYPVIKFS-UHFFFAOYSA-N
性质
化学式	C10H16O
摩尔质量	152.23 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

马鞭草烯醇（英语：verbenol），又称2-蒎烯-4-醇（英语：2-pine-4-ol）是一种双环单萜醇，化学式：C₁₀H₁₆O。是生物活性分子存在于植物精油和昆虫信息素中。

异构体

马鞭草烯醇已知有四种不同的立体异构体。通常情况下，马鞭草烯醇通常以它们的对映体的非外消旋混合物的形式存在^[1]。根据连接在同一个碳原子上的甲基与羟基的相对位置关系，存在顺式（两甲基与羟基同侧）和反式（两甲基与羟基异侧）两种构型。同时每种构型下又存在左旋体（-）和右旋体（+）两种对映异构体，因此一共有四种构型：

(+)-顺式马鞭草烯醇
(-)-顺式马鞭草烯醇
(+)-反式马鞭草烯醇
(-)-反式马鞭草烯醇

其不同的构型对于不同的昆虫，起到的作用不相同。反式马鞭草烯醇是山松甲虫（学名：Dendroctonus ponderosae）的信息素，能将昆虫吸引到树上^[2]。顺式马鞭草烯醇则是云杉八齿小蠹（学名：Ips typographus）'^[3] 和中欧山松大小蠹（学名：Dendroctonus ponderosae Hopkins.）的聚集信息素^[4]。

参考文献

^ Gambliel, H.; Croteau, R. Pinene cyclases I and II. Two enzymes from sage (Salvia officinalis) which catalyze stereospecific cyclizations of geranyl pyrophosphate to monoterpene olefins of opposite configuration. Journal of Biological Chemistry. 1984, 259 (2): 740–748. PMID 6693393. doi:10.1016/S0021-9258(17)43520-4 .
^ New pheromone insight may help predict mountain pine beetle outbreaks. [26 March 2018].
^ Jakus, R.; Blazenec, M. Influence of proportion of (4S)-cis-verbenol in pheromone bait on Ips typographus (Col., Scolytidae) catch in pheromone trap barrier and in single traps. Journal of Applied Entomology. 2002, 126 (6): 306–311. S2CID 83484064. doi:10.1046/j.1439-0418.2002.00659.x.
^ Miller, Daniel R. Cis-Verbenol: An aggregation pheromone for the mountain pine beetle, Dendroctonus ponderosae Hopkins (Coleoptera: Scolytidae). J. Entomol. Soc. Brit. Columbia 88: 34-38. 1991.

[1] Gambliel, H.; Croteau, R. Pinene cyclases I and II. Two enzymes from sage (Salvia officinalis) which catalyze stereospecific cyclizations of geranyl pyrophosphate to monoterpene olefins of opposite configuration. Journal of Biological Chemistry. 1984, 259 (2): 740–748. PMID 6693393. doi:10.1016/S0021-9258(17)43520-4 .

[physorg-2] New pheromone insight may help predict mountain pine beetle outbreaks. [26 March 2018].

[3] Jakus, R.; Blazenec, M. Influence of proportion of (4S)-cis-verbenol in pheromone bait on Ips typographus (Col., Scolytidae) catch in pheromone trap barrier and in single traps. Journal of Applied Entomology. 2002, 126 (6): 306–311. S2CID 83484064. doi:10.1046/j.1439-0418.2002.00659.x.

[4] Miller, Daniel R. Cis-Verbenol: An aggregation pheromone for the mountain pine beetle, Dendroctonus ponderosae Hopkins (Coleoptera: Scolytidae). J. Entomol. Soc. Brit. Columbia 88: 34-38. 1991.

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