以α-蒎烯(1)为原料,合成了8-羟基别二氢葛缕醇(3)及其甲酸酯(4)、乙酸酯(5)和丙酸酯(6),并用IR、MS、^1H NMR及^13C NMR分析对它们的结构进行了表征。按照国家标;隹GB 17322.10—1998测定了这4个化合物对白纹伊蚊的驱避活性。结果显示:化合物3对白纹伊蚊没有驱避活性,与之结构及其类似的对盖烯二醇等已被以往的研究证明具有驱避活性,因此极性官能团和手性碳原子位置可能是影响驱避活性的重要因素;衍生物6对白纹伊蚊没有驱避活性,这可能与其羰基部分太大有关,在目前的萜类驱避剂中尚极少见丙酸酯类;衍生物5具有一定的驱避活性,质量分数为20%时,对白纹伊蚊的驱避时间接近4h;衍生物4的驱避效果最好。质量分数为20%时,对白纹伊蚊的驱避时间可以达到7~8h,与避蚊胺(DETA)的驱避效果相同。
8-Hydroxylcarveol (3) and its ester derivatives were synthesized from α-pinene (1), and their structures had been identified by IR, MS, IH NMR and ^13C NMR analysis. The repellent activity against mosquito (Aedes albopictus ) of the 4 compounds has been determined by the methods of GB 17322. 10 - 1998. The results are as follows: compound (3) has no repellent against mosquito. On the other hand, it has been reported that compounds having structure simlar to 8-hydroxylcarveol have mosquito-repellent activity, such as p-menthendiol, etc. Perhaps the position of polar functional groups and chiral C atoms are important factors for mosquito-repellent activity. 8-Hydroxylcarveol propionate (6) has no mosquito-repellent activity mosquito, perhaps its carbonyl part is too large. There is few report of propionate used as terpenoid repellent currently. 8-Hydroxylcarveol acetate(5) has some repellent activity against mosquito, when its mass fraction is 20 % , which can exhibit repelling time close to 4 h. 8-Hydroxylcarveol formate (4) has the longest repelling time of upto 7-8 h against mosquito, when its mass fraction is 20 % , which is similar to the repellent activity of N, N-diethyl-m-toluamide (DETA).