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α-葎草烯

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葎草烯
IUPAC名
(1E,4E,8E)-2,6,6,9-Tetramethylcycloundeca-1,4-8-triene
別名 蛇麻烯、α-石竹烯
識別
CAS號 6753-98-6  checkY
PubChem 5281520
ChemSpider 4444853
SMILES
 
  • C\1=C/C(C)(C)C/C=C(/CC/C=C(/C/1)C)C
InChI
 
  • 1/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6-7,10-11H,5,8-9,12H2,1-4H3/b11-6+,13-7+,14-10+
InChIKey FAMPSKZZVDUYOS-HRGUGZIWBF
ChEBI 5768
性質
化學式 C15H24
摩爾質量 204.35 g·mol−1
外觀 淡黃綠色的透明液體
密度 0.886 g/cm3
熔點 25 °C(298 K)
沸點 106 - 107 °C(272 K)
危險性
致死量或濃度:
LD50中位劑量
>48 mg/kg
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

α-葎草烯(英語:Humulene[註 1],又名蛇麻烯α-石竹烯,是天然存在的單環倍半萜,分子式C15H24,可看作三個異戊二烯單元構成,分子有三個非共軛雙鍵

葎草烯最早從啤酒花(葎草屬,學名:Humulus精油發現,因此得名[1]。葎草烯有個雙環的同分異構體β-石竹烯,在很多有香氣植物中,都能提取出兩者的混合物。

發現

蛇麻

葎草烯是蛇麻花精油成分之一,其濃度根據品種不同而變,最高可占精油40%[2]。釀啤酒過程中會產生多種葎草烯的環氧化物,根據GC-MS及氣味分析研究,葎草烯環氧衍生物水解會散發出啤酒花香氣[3][4]

分布

葎草烯與β-石竹烯在各大洲的許多植物中都能找到,能釋放葎草烯的植物有松樹[5]、橘園[6]煙草 [7]向日葵[8]。在芳香氣氛的植物精油中也能找到葎草烯,如藥用鼠尾草 [9]烏藥人參屬三七花旗參 [10]留蘭香(可占精油29.9 %)[11]姜科植物[12]、霧社木姜子(一種中國月桂樹)[13]、erva baleeira(馬鞭草科一種灌木,位於南美洲沿海)的葉片提取物中可達4 %,另有25%反式石竹烯[14]越南香菜大麻屬植物的香氣成分[15]

合成

葎草烯衍生自法尼基焦磷酸(FPP),FPP合成葎草烯過程由倍半萜合成酶催化[16],FPP脫焦磷酸基團後產生烯丙基陽離子[16]


實驗室合成葎草烯的方法有很多,如模擬生物合成從法尼醇合成葎草烯(Corey合成);閉合大環化合物不同位置的碳-碳鍵;催化羰基偶聯反應(McMurry合成);烯丙基鹵化物和受保護羥腈陰離子內烷基化(Takahashi合成)等[17]。有研究報道了更簡單構建碳-碳鍵和環結構的方法,用四部份組裝和介導環化兩步合成[18]

葎草烯上兩個已取代雙鍵更活潑,計算結果顯示有四種不同構象[19]

應用

有研究報道植物精油的葎草烯有潛在抗炎作用[20][21]。2015年,巴西研究員用氣相色譜法證明鼠尾草葉油的葎草烯可抑制埃及伊蚊繁殖[22][23]

備註

  1. ^ 下文中如無說明,皆以葎草烯指代α-葎草烯。

參考文獻

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