代谢
松香油烃 (+)-, (-)-, 和 (+/-)-α-蒎烯，(-)-β-蒎烯（诺蒎烯），(-)-顺-蒎烷，(+)-3-蒈烯，(-)-顺-荜澄茄烷，香叶烯和对-伞花烃在家兔中的生物转化进行了研究。主要代谢物如下：来自 (+)-, (-)-, 和 (+/-)-α-蒎烯的 (-)-反-香叶醇；来自 (-)-β-蒎烯的 (-)-10-蒎醇和 (-)-1-p-薄荷烯-7,8-二醇；来自 (-)-顺-蒎烷的 (-)-α-松油醇和 (-)-反-苏合香醇；来自 (+)-3-蒈烯的 (-)-m-薄荷-4,6-二烯-8-醇，3-蒈烯-9-醇，(-)-3-蒈烯-9-羧酸和3-蒈烯-9,10-二羧酸；来自 (-)-顺-荜澄茄烷的荜澄茄烷-9,10-二羧酸；以及来自对-伞花烃的香叶烯-3(10)-乙二醇，香叶烯-1,2-乙二醇，尿松油醇和对-伞花烃-9-羧酸。这些代谢过程包括烯丙基氧化，环氧化，对映选择性二甲基羟基化及其氧化，通过环氧化开裂共轭双键以及区域选择性氧化，其中一些在化学反应中通常不会发现，由此确定了各种新的化合物。这种单萜烃的生物转化产生了一些高收率的昆虫信息素。
The biotransformation of (+)-, (-)-, and (+-)-alpha-pinenes, (-)-beta-pinene (nopinene), (-)-cis-pinane, (+)-3-carene, (-)-cis-carane, myrcene, and p-cymene in rabbits was investigated. The major metabolites were as follows: (-)-trans-verbenol from (+)-, (-)-, and (+/-)-alpha-pinenes; (-)-10-pinanol and (-)-1-p-menthene-7,8-diol from (-)-beta-pinene; (-)-alpha-terpineol and (-)-trans-sobrerol from (-)-cis-pinane; (-)-m-mentha-4,6-dien-8-ol, 3-caren-9-ol, (-)-3-carene-9-carboxylic acid, and 3-carene-9,10-dicarboxylic acid from (+)-3-carene; carane-9,10-dicarboxylic acid from (-)-cis-carane; and myrcene-3(10)-glycol, myrcene-1,2-glycol, uroterpenol, and p-cymene-9-carboxylic acid from p-cymene. These metabolisms include allylic oxidation, epoxidation, stereoselective gem-dimethyl hydroxylation and its oxidation, cleavage of a conjugated double bond by epoxidation, and regioselective oxidation, some of which are not found usually in chemical reactions, and due to which various new compounds were determined. This biotransformation of the monoterpene hydrocarbons gave some insect pheromones in high yield.
来源:Hazardous Substances Data Bank (HSDB)
