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Clinical pharmacy PharmD program                     Third level                          Phytochemistry-1 (PG-504)


              5- Terpineols            OH                                          OH       OH

                                               -H 2 O                  +            +


                                       OH                         OH

                                  Terpin     5% H 2 SO 4  -Terpineol         ----    ----

                                                                                 HCOOH
                                     60%H 2 SO 4                        H 3 PO 4

                                                                         +
                                                KHSO 3               O

                                                                    Cineol

                                                                            Terpinene  Terpinolene
                                         Dipentene     -Pinene          + Terpinolene




              2) Bicyclic monoterpene alcohol           e.g. Borneol & Isoborneol


                 •  Odour: camphor-like odour

                 •  N.B Isoborneol: is not a natural compound but probably a synthetic
                     product from reduction of camphor

                 •  Uses: Antiseptic, diuretic and prevent calculi formation.




                                                                                      H
                                                                                                         OH

                                                                                       OH                  H
              Chemical reactions of Borneol & Isoborneol

                                                                          Borneol             Isoborneol

              1) Borneol is readily oxidized to camphor using CuO but isoborneol is not

              oxidized

                                           H      CuO/                 O                    OH
                                                Oxidation               Reduction
                                           OH

                                                              Camphor               Borneol
                                   Borneol                                         Isoborneol


              2) Isoborneol is more readily dehydrated to camphene, but borneol is not
              dehydrated




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