Compounds and methods of their manufacturing

1. A method for producing an extract composition of Entandrophragma caudatum prepared from seeds of Entandrophragma caudatum , said extract composition of Entandrophragma caudatum comprising a compound according to Formula IIa, wherein the extract composition of Entandrophragma caudatum is produced by the steps of:

i) mixing ground seeds of Entandrophragma caudatum with methanol, filtering, collecting and concentrating to obtain a concentrated methanol extract;

ii) mixing the concentrated methanol extract with a less polar solvent and a more polar solvent to obtain a two-phase composition and discarding the more polar solvent phase to eliminate polar impurities and concentrating the less polar solvent phase, thereby obtaining the extract composition of Entandrophragma caudatum

wherein R 1 is a straight, branched or cyclic alkyl group with 1 to 6 carbon atoms that is unsubstituted or substituted with OH or a halogen, and

wherein R 2 and R 3 independently are selected from straight, branched or cyclic, substituted or unsubstituted alkyl groups with 1 to 6 carbons or from a nicotinyl group.

2. The method according to claim 1 , wherein the less polar solvent in step (ii) forms an azeotrope with water.

3. The method according to claim 2 , wherein the less-polar solvent comprises ethyl acetate and the polar solvent comprises water.

4. The method according to claim 3 , wherein the less polar solvent is ethyl acetate and the more polar solvent is water, and wherein ethyl acetate and water are present in a volume ratio of 2:1.

5. The method according to claim 1 , wherein the extract composition comprises phragmalin-3,30-di-isobutyrate, phragmalin-3-isobutyrate-30-proprionate, or phragmalin-3-nicotinate-30-isobutyrate, or a combination thereof.

6. The method according to claim 1 , wherein the less polar solvent phase is concentrated by distillation.