Process for the production of alpha-tocotrienol and derivatives

Abstract

The invention discloses novel processes for production, enrichment and/or isolation of alpha-tocotrienol from source material comprising at least one non-alpha-tocotrienol, such as natural extracts comprising mixed tocotrienols.

What is claimed is: 
     
         1 . A process for the production, enrichment and/or isolation of d-alpha-tocotrienol from a plant extract that comprises at least one non-alpha tocotrienol and that optionally comprises alpha-tocopherol and optionally comprises other tocols, non-tocols and/or organic impurities, comprising the steps of:
 1a.) reacting the plant extract with suitable reagents which react with the one or more non-alpha-tocols to introduce a functional group in the free 5 and/or 7 position of the one or more non-alpha-tocols;   1b.) separating the one or more non-alpha-tocols that have been functionalized in step (1a) from the alpha-tocotrienol and optional alpha tocopherol and other non-tocol compounds that may be present;   1c.) optionally further separating the alpha-tocotrienol in the mixture separated in step (1b), from the optional alpha tocopherol and from optional other non-tocols;   1d.) chemically reacting the separated one or more non-alpha-tocols that have been functionalized from step (1b) to give alpha-tocotrienol; and   1e.) optionally combining the alpha-tocotrienol from step (1c) with the alpha-tocotrienol from step (1d) to give alpha-tocotrienol.   
     
     
         2 . The process of  claim 1 , wherein the plant extract is selected from a palm oil extract, a palm fruit extract, a rice extract, a rice bran extract, a barley extract, an annatto extract, or a mixture thereof. 
     
     
         3 . The process of  claim 2 , wherein the plant extract is a palm oil extract. 
     
     
         4 . The process of  claim 2 , wherein the plant extract is Tocomin®. 
     
     
         5 . The process of  claim 1 , where the reaction in step (1a) is amino-alkylation followed by acidification. 
     
     
         6 . The process of  claim 5 , where the amino-alkylation is performed with paraformaldehyde and a cyclic amine selected from 1-methylpiperazine, piperidine or morpholine. 
     
     
         7 . The process of  claim 5 , where the amino-alkylation is performed with paraformaldehyde and 1-methylpiperazine. 
     
     
         8 . The process of  claim 1 , where the reducing agent is a hydride reagent, a borane complex or an electron donor in the presence of a suitable proton source. 
     
     
         9 . The process of  claim 8 , where the reducing agent is sodium cyano borohydride. 
     
     
         10 . A process for the production, enrichment and/or isolation of d-alpha-tocotrienol from an extract of palm oil which comprises at least non-alpha tocotrienol and that optionally comprises alpha-tocopherol and optionally comprises other tocols, non-tocols and/or organic impurities, comprising the steps of:
 2a.) reacting the extract with amino-alkylating agents which react with the one or more non-alpha-tocols to introduce a functional group in the free 5 and/or 7 position of the one or more non-alpha tocotrienols and converting the products into acid salts;   2b.) separating the one or more non-alpha-tocotrienol acid salts of the products in step (2a) from the alpha-tocotrienol, the optional alpha tocopherol and the other optional non-tocol compounds that may be present; and   2c.) reducing the one or more non-alpha-tocotrienol functionalized homologues with a reducing agent to give alpha-tocotrienol.   
     
     
         11 . The process of  claim 10 , wherein the extract from palm oil is Tocomin®. 
     
     
         12 . The process of  claim 10 , wherein the amino-alkylation is performed with paraformaldehyde and a cyclic amine selected from 1-methylpiperazine, piperidine or morpholine. 
     
     
         13 . The process of  claim 10 , where the amino-alkylation is performed with paraformaldehyde and 1-methylpiperazine. 
     
     
         14 . The process of  claim 10 , where the reducing agent is a hydride reagent, a borane complex or an electron donor in the presence of a suitable proton source. 
     
     
         15 . The process of  claim 14 , where the reducing agent is sodium cyano borohydride. 
     
     
         16 . The process of  claim 10 , comprising an additional step wherein the alpha-tocotrienol from step (2b) is recovered. 
     
     
         17 . The process of  claim 1 , additionally comprising an additional last step wherein the alpha-tocotrienol (from steps 1d and/or 1e) is oxidized to alpha-tocotrienol quinone. 
     
     
         18 . The process of  claim 10 , additionally comprising an additional last step wherein the alpha-tocotrienol (from step 2c) is oxidized to alpha-tocotrienol quinone. 
     
     
         19 . The process of  claim 1 , additionally comprising a step 1b1) after step 1b), wherein a solution of the non-alpha-tocols homologues that have been functionalized is filtered. 
     
     
         20 . The process of  claim 10 , additionally comprising a step 2b1) after step 2b), wherein a solution of the non-alpha-tocols homologues that have been functionalized is filtered. 
     
     
         21 . The process of  claim 17 , additionally comprising a step 1b1) after step 1b), wherein a solution of the non-alpha-tocols homologues that have been functionalized is filtered. 
     
     
         22 . The process of  claim 18 , additionally comprising a step 2b1) after step 2b), wherein a solution of the non-alpha-tocols homologues that have been functionalized is filtered. 
     
     
         23 . The process of  claim 1 , additionally comprising a step 1d1) after step 1d) wherein a solution of the alpha-tocotrienol produced by the reduction is mixed with silica gel, followed by removal of the silica gel by filtration. 
     
     
         24 . The process of  claim 10 , additionally comprising a step 2d1) after step 2d) wherein a solution of the alpha-tocotrienol produced by the reduction is mixed with silica gel, followed by removal of the silica gel by filtration. 
     
     
         25 . The process of  claim 17 , additionally comprising a step 1d1) after step 1d) wherein a solution of the alpha-tocotrienol produced by the reduction is mixed with silica gel, followed by removal of the silica gel by filtration. 
     
     
         26 . The process of  claim 18 , additionally comprising a step 2d1) after step 2d) wherein a solution of the alpha-tocotrienol produced by the reduction is mixed with silica gel, followed by removal of the silica gel by filtration. 
     
     
         27 . The process of  claim 17 , additionally comprising placing the alpha-tocotrienol quinone on a silica gel column and eluting the alpha-tocotrienol quinone off of the column. 
     
     
         28 . The process of  claim 18 , additionally comprising placing the alpha-tocotrienol quinone on a silica gel column and eluting the alpha-tocotrienol quinone off of the column.