Genipin-rich material and its use

Abstract

A method of preparing genipin-rich materials from the fruit of Genipa americana fruit for their use as a cross-linking agent and as a raw material to produce colors is disclosed. The genipin-rich materials can be used in a broad range of applications including personal care, cosmetics, dietary supplements, packaging, textiles, beverages, foodstuffs, drugs, and animal feeds.

What is claimed is: 
     
       1. A method of preparing a genipin-rich red colorant from Genipa americana comprising:
 (a) extracting a Genipa americana fruit source selected from the group consisting of Genipa americana whole fruit, fruit juice, fruit puree, fruit juice concentrate, dried powder forms of the fruit and juice, water-insoluble parts of the fruit, and mixtures thereof, with a solvent selected from water, organic solvents, and mixtures thereof, to produce a genipin-rich extract;   (b) hydrolyzing the genipin-rich extract for 30 minutes to 24 hours to produce a hydrolyzed extract;   (c) adjusting the pH of the hydrolyzed extract to about 3.5-5.0, to produce an acidified solution;   (d) heating the acidified solution to 65 to 85° C. for about 5 to 120 minutes to produce a brown-colored precipitate and removing the precipitate to produce a clear solution,   (e) adjusting the pH of the clear solution to about 4-4.6,   (f) mixing the solution of step (e) with one or more compounds having a primary amine group in the presence of an organic acid or salt thereof, under anaerobic conditions, for a sufficient time and temperature to produce the genipin-rich red colorant.   
     
     
       2. The method according to  claim 1  wherein the colorant is further purified and concentrated using an ion exchange column and/or a membrane filter. 
     
     
       3. The method according to  claim 1  wherein the one or more compounds having a primary amine group is an amino acid selected from alanine, arginine, lysine, glutamic acid, and mixtures thereof. 
     
     
       4. The method of  claim 1  wherein the organic solvent is selected from ethyl acetate, butyl acetate, n-butanol, diethyl ether, hexane, 2-butanone, chloroform, 1,2-dichloroethane, xylene, methyl-t-butyl ether, toluene, carbon tetrachloride, trichloroethylene, cyclohexane, pentane, heptane and mixtures thereof. 
     
     
       5. A method of preparing a genipin-rich red colorant from Genipa americana comprising:
 (a) extracting a Genipa americana fruit source selected from the group consisting of Genipa americana whole fruit, fruit juice, fruit puree, fruit juice concentrate, dried powder forms of the fruit and juice, water-insoluble parts of the fruit, and mixtures thereof, with a solvent selected from water, organic solvents, and mixtures thereof, to produce a genipin-rich extract;   (b) hydrolyzing the genipin-rich extract for 30 minutes to 24 hours to produce a hydrolyzed extract;   (c) adjusting the pH of the hydrolyzed extract to about 3.5-5.0, to produce an acidified solution;   (d) heating the acidified solution to 65 to 85° C. for about 5 to 120 minutes to produce a brown-colored precipitate and removing the precipitate to produce a clear solution,   (e) adjusting the pH of the clear solution to about 4-4.6,   (f) mixing the solution of step (e) with one or more compounds having a primary amine group in the presence of an organic acid or salt thereof, under anaerobic conditions, for about 60 to 120 minutes at about 70 to 95° C. to produce the genipin-rich red colorant.    
     
     
       6. The method according to claim 5 wherein the colorant is further purified and concentrated using an ion exchange column and/or a membrane filter.  
     
     
       7. The method according to claim 5 wherein the one or more compounds having a primary amine group is an amino acid selected from alanine, arginine, lysine, glutamic acid, and mixtures thereof.  
     
     
       8. The method of claim 5 wherein the organic solvent is selected from ethyl acetate, butyl acetate, n-butanol, diethyl ether, hexane, 2-butanone, chloroform, 1,2-dichloroethane, xylene, methyl-t-butyl ether, toluene, carbon tetrachloride, trichloroethylene, cyclohexane, pentane, heptane and mixtures thereof.  
     
     
       9. The method according to claim 5 wherein the one or more compounds having a primary amine group is an amino acid selected from alanine, arginine, lysine, asparagine, aspartic acid, glutamine, glutamic acid, glycine, histidine, valine, leucine, serine, and mixtures thereof.  
     
     
       10. A method of preparing a genipin-rich colorant from Genipa americana comprising:
 (a) blending water and a Genipa americana fruit source selected from the group consisting of Genipa americana whole fruit, fruit pulp, fruit juice, fruit puree, fruit juice concentrate, dried powder forms of the fruit or juice, water-insoluble parts of the fruit, and leaves from Genipa americana L., and mixtures of any thereof to produce a water and Genipa americana fruit source mixture;   (b) mixing the water and Genipa americana fruit source mixture to produce a puree;   (c) removing at least a portion of insoluble solid material from the puree to obtain a filtrate of the insoluble solid material;   (d) adjusting the pH of filtrate to a pH of 3.5-5.0;   (e) extracting the filtrate using an organic solvent to obtain a solvent extract layer, wherein the organic solvent is either polar or non-polar, wherein when the organic solvent is polar, it is selected from the group consisting of acetic acid, ethanol, n-propanol, iso-propanol, methanol, or acetic, citric, and phosphoric acid buffer solutions, and mixtures thereof, and when the organic solvent is non-polar, it is selected from the group consisting of ethyl acetate, butyl acetate, and n-butanol, and mixtures thereof;   (f) removing at least some of the organic solvent from the layer to obtain a genipin-rich extract comprising at least 70% w/w of genipin; and   (g) mixing the genipin-rich extract of step (f) with one or more compounds having a primary amine group to produce the genipin-rich colorant, the genipin-rich colorant having a different color than the genipin-rich extract, wherein the primary amine group is an amino acid.    
     
     
       11. The method according to claim 10 wherein the Genipa americana fruit source comprises peeled and cut fruit.  
     
     
       12. The method according to claim 10 wherein in step (a), the water is deionized water.  
     
     
       13. The method of claim 10 wherein in step (a), the blending comprises blending the water and Genipa americana fruit source in ratio in the range of about 1.0:0.67 to about 1.0:0.86 by weight.  
     
     
       14. The method of claim 10 wherein in step (b), the puree is allowed to stand for at least about 15 minutes.  
     
     
       15. The method of claim 10 wherein step (c) comprises a first filtering step to form a first filtrate, followed by adding water to the first filtrate, mixing the water and first filtrate, and then a second filtering step to form a second filtrate, and step (d) comprises adjusting the pH of the second filtrate.  
     
     
       16. The method of claim 15 wherein the water added to the first filtrate is deionized water.  
     
     
       17. The method of claim 15 wherein the mixing of the water and the first filtrate is performed for a period of at least about 15 minutes.  
     
     
       18. The method of claim 10 wherein the acid is selected from the group consisting of acetic acid, formic acid, lactic acid, citric acid, tartaric acid, adipic acid, oxalic acid, succinic acid, fumaric acid, malic acid, and phosphoric acid, and mixtures thereof.  
     
     
       19. The method of claim 10 wherein the acid is selected from citric acid and tartaric acid, and mixtures thereof.  
     
     
       20. The method of claim 10 wherein after step (d) and prior to step (e), further comprising concentrating the filtrate.  
     
     
       21. The method of claim 10 wherein step (e) comprises extracting the filtrate using the organic solvent in a ratio of about 1:1 by weight.  
     
     
       22. The method of claim 10 wherein the removing in step (f) comprises evaporating at least a portion of the organic solvent from the layer.  
     
     
       23. The method of claim 22 wherein the evaporating is performed using rotary evaporation.  
     
     
       24. The method of claim 10 wherein step (e) comprises repeating the liquid-liquid extraction to obtain more than one solvent extract layer.