英文Coumarins.pptVIP

Coumarins(香豆素) Coumarins I. Overview Ⅱ. Classification Ⅲ. Chemical characteristics Ⅳ. Isolation Ⅴ. Spectroscopic methods of Identification I. Overview Coumarin is 5,6-benzo-2-pyrone and it along with its various derivatives occurs abundantly in plant families such as Umbelliferae, Rutaceae, Leguminaceae, Otchidaceae, Asteraceae, Guttiferae, Melastomaceae, Thymelaceae and Solanaceae. The name coumarine is derived from the Caribbean word “Coumarou” for the tonka tree from which coumarin with the characteristic aroma of new- mown hay was isolated. Unsubstituted coumarin is widespread in nature. Furocoumarins containing linear or angular types with substituent on benzene nucleus or pyrone ring including dihydrofuranocoumarins. 3. Pyranocoumarins containing linear or angular type with substituents on benzene and pyrone rings.  3. Bis- and Tri-coumarins. (Figure 5) Ⅲ. Chemical characteristics Alkali Degradation Coumarin on treatment with hot dilute aqueous alkali hydrolyses to yield sodium coumarinate by lactone ring opening and retaining the cis configuration of the cinn-amic acid salt. This stereochemistry enables to re-lactonize to couma-rin on acidification with mineral acid or even a mild a-cid like carbon dioxide (H2CO3). However when coumar-in is subjected to prolonged treatment with hot dilute aqueous alkali the cis-coumarinate converts to the more stable trans-coumarinate. (Figure 6) Fig. 6 Chemical Methods of Degradation 2. Acid reaction 1) Cyclization reaction 2) The dehiscence of ether linkage 3) Double bond imbitition Ⅳ. Isolation The advancement in the sophisticated separation an disolation techniques as exemplified by capillary electrophoresis, centrif-ugal partition, different chromatographic techniques including two dimensional planar chromatography and the most versatile high pressure liquid chromatography have simplified the otherwise tedious Similarly the powerful modern spectroscopic techniques espec-ially the high fie