馬鞭草烯醇

馬鞭草烯醇
	IUPAC名; 4,6,6-三甲基雙環[3.1.1]庚-3-烯-2-醇; 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-ol
別名	2-蒎烯-4-醇
識別
CAS號	473-67-6
PubChem	61126
SMILES	CC1=CC(C2CC1C2(C)C)O;
InChIKey	WONIGEXYPVIKFS-UHFFFAOYSA-N
性質
化學式	C10H16O
摩爾質量	152.23 g·mol−1
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

馬鞭草烯醇（英語：verbenol），又稱2-蒎烯-4-醇（英語：2-pine-4-ol）是一種雙環單萜醇，化學式：C₁₀H₁₆O。是生物活性分子存在於植物精油和昆蟲信息素中。

異構體

馬鞭草烯醇已知有四種不同的立體異構體。通常情況下，馬鞭草烯醇通常以它們的對映體的非外消旋混合物的形式存在^[1]。根據連接在同一個碳原子上的甲基與羥基的相對位置關係，存在順式（兩甲基與羥基同側）和反式（兩甲基與羥基異側）兩種構型。同時每種構型下又存在左旋體（-）和右旋體（+）兩種對映異構體，因此一共有四種構型：

(+)-順式馬鞭草烯醇
(-)-順式馬鞭草烯醇
(+)-反式馬鞭草烯醇
(-)-反式馬鞭草烯醇

其不同的構型對於不同的昆蟲，起到的作用不相同。反式馬鞭草烯醇是山松甲蟲（學名：Dendroctonus ponderosae）的信息素，能將昆蟲吸引到樹上^[2]。順式馬鞭草烯醇則是雲杉八齒小蠹（學名：Ips typographus）'^[3] 和中歐山松大小蠹（學名：Dendroctonus ponderosae Hopkins.）的聚集信息素^[4]。

參考文獻

^ 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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