温州大学：《有机化学 Organic Chemistry》课程教学资源（PPT课件讲稿）第十八章 萜类和甾族化合物 Terpenes and Steroids

第章萜^族化合物 rones

第十八章 萜类和甾族化合物 Terpenes and Steroids

181萜类 Terpenes

18.1 萜类 Terpenes

t has been known for centuries that codistillation of many plant materials with steam(called steam distillation produces a fragrant mixture of liquids known as plant essential oils These compounds have had a variety of uses, particularly in early medicine and in the making of perfumes

◼ It has been known for centuries that codistillation of many plant materials with steam (called steam distillation) produces a fragrant mixture of liquids known as plant essential oils. ◼ These compounds have had a variety of uses, particularly in early medicine and in the making of perfumes

Chemically, the essential oils of plants consist largely of mixtures of lipids called terpenes a Terpenes are small organic molecules that have an immense diversity of structure. Thousands of different terpenes are known; some are hydrocarbons and others contain oxygen; some are open chain molecules, and others contain rings

◼ Chemically, the essential oils of plants consist largely of mixtures of lipids called terpenes. ◼ Terpenes are small organic molecules that have an immense diversity of structure. Thousands of different terpenes are known; some are hydrocarbons, and others contain oxygen; some are open￾chain molecules, and others contain rings

Some terpenes isolated from essential oils Myrcene(oil of bay)a-Pinene(oil of turpentine) 月桂烯 α-蒎烯 Carvone(oil of spearmint) 香芹酮

Some terpenes isolated from essential oils Myrcene (oil of bay) -Pinene (oil of turpentine) O Carvone (oil of spearmint) 月桂烯 -蒎烯 香芹酮

According to the isoprene rule proposed by Ruzicka, terpenes can be considered to arise from head-to-tail joining of simple five-carbon Isoprene unIts. CH3 CH2-C-CH-CH Head Isoprene Tail 2-Methyl-1, 3-butadiene Tail Head rene Head Pinene

◼ According to the isoprene rule proposed by Ruzicka, terpenes can be considered to arise from head-to-tail joining of simple five-carbon isoprene units. CH2 C CH CH3 CH2 1 2 3 4 Isoprene 2-Methyl-1,3-butadiene Head Tail Tail Head Myrcene Tail Head -Pinene

Classification of Terpenes Carbon atoms I Isoprene units Classification 10 Monoterpenes 15 Sesquiterpenes 20 25 30 234568 Diterpenes Sesterterpenes Triterpenes 40 Tetraterpenes

Classification of Terpenes Carbon atoms Isoprene units Classification 10 2 Monoterpenes 15 3 Sesquiterpenes 20 4 Diterpenes 25 5 Sesterterpenes 30 6 Triterpenes 40 8 Tetraterpenes

β- Pinene Camphene Limonene β-蒎烯 莰烯 苧烯 β- Caryophyllene β-石竹烯

-Pinene Camphene Limonene -蒎烯 莰烯 苧烯 -Caryophyllene -石竹烯

OH CHOH CH2OH CH2OH analog Nerol Geraniol Citronellol 芳樟醇橙花醇 香叶醇 香茅醇

OH CH2 OH CH2 OH CH2 OH Linalool Nerol Geraniol Citronellol 芳樟醇 橙花醇 香叶醇 香茅醇

CHO HOCH? CHO OH Citral a Citral b My lycrenol Lavandulyl 柠檬醛α柠檬醛b月桂烯醇薰衣草醇

OH HOCH2 Mycrenol Lavandulol 月桂烯醇 薰衣草醇 CHO CHO 柠檬醛 a 柠檬醛 b Citral a Citral b