Nutraceutical co-crystal compositions

Abstract

Co-crystals comprising at least one nutraceutical compound and at least one co-crystal former with or without impurities. These co-crystals may be included in compositions (optionally also including other components such as pharmaceutically acceptable excipients, other nutritional supplements, etc.) having utility as pharmaceuticals, nutraceuticals, nutritional supplements, and foodstuffs.

1 . A composition comprising a co-crystal of a nutraceutical and a co-crystal former, the co-crystal with or without impurities wherein
 (i) the nutraceutical and the co-crystal former are hydrogen bonded to each other,   (ii) the nutraceutical is selected from the group consisting of vitamin B2 (riboflavin), glucosamine HCl, chlorogenic acid, lipoic acid, catechin hydrate, creatine, acetyl-L-carnitine HCl, vitamin B6, pyridoxine, caffeic acid, naringenin, vitamin B1 (thiamine HCl), baicalein, luteolin, hesperedin, rosmarinic acid, epicatechin gallate, epigallocatechin, vitamin B9 (folic), genistein, methylvanillin, ethylvanillin, silibinin, diadzein, melatonin, rutin hydrate, vitamin A, retinol, vitamin D2 (ergocalciferol), vitamin E (tocopherol), diosmin, menadione (K3), vitamin D3 (caholecalciferol), phloretin, indole-3-carbinol, fisetin, glycitein, chrysin, gallocatechin, vitamin B4 (adenine), vitamin B5 (pantothenic acid), vitamin B7 (biotin), theobromine, quercetin, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid, and   (iii) a co-crystal former selected from the group consisting of pharmaceutically acceptable carbohydrates, amines, amides, sulfonamides, carboxylic acids, sulfonic acids, phenols, polyphenols, aromatic heterocycles, xanthines and alcohols.   
   
   
       2 . The composition of  claim 1  wherein the nutraceutical is selected from the group consisting of resveratrol, EGCG, quercetin, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid. 
   
   
       3 . The composition of  claim 2  wherein the co-crystal former is selected from the group consisting of 1,5-napthalene-disulfonic acid, 1-hydroxy-2-naphthoic acid, 4-aminobenzoic acid, 4-aminopyridine, 4-chlorobenzene-sulfonic acid, 4-ethoxyphenyl urea, 7-oxo-DHEA, acesulfame, acetohydroxamic acid, adenine, adipic acid, alanine, allopurinaol, arginine, ascorbic acid, asparagine, aspartic acid, benzenesulfonic acid, benzoic acid, caffeine, camphoric acid, capric acid, chrysin, cinnamic acid, citric acid, clemizole, cyclamic acid, cysteine, dimethylglycine, D-ribose, fumaric acid, galactaric acid, genistein, gentisic acid, glucamine N-methyl, gluconic acid, glucosamine, glucuronic acid, glutamic acid, glutamine, glutaric acid, glycine, glycolic acid, hippuric acid, histidine, hydroquinone, imidazole, ipriflavone, isoleucine, lactobionic acid, lauric acid, leucine, lysine, maleic acid, malic acid, malonic acid, mandelic acid, methionine, nicotinamide, nicotinic acid, orotic acid, oxalic acid, palmitic acid, pamoic acid, phenylalanine, piperazine, procaine, proline, p-toluenesulfonic acid, pyridoxamine, pyridoxine (4-pyridoxic acid), pyroglutamic acid, quercetin, resveratrol, saccharin, salicylic acid, salicylic acid 4-amino, sebacic acid, serine, stearic acid, succinic acid, tartaric acid, threonine, TRIS, tryptophan, tyrosine, urea, valine, Vitamin K5, xylitol, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       4 . The composition of  claim 1  wherein the co-crystal former is selected from the group consisting of 1,5-napthalene-disulfonic acid, 1-hydroxy-2-naphthoic acid, 4-aminobenzoic acid, 4-aminopyridine, 4-chlorobenzene-sulfonic acid, 4-ethoxyphenyl urea, 7-oxo-DHEA, acesulfame, acetohydroxamic acid, adenine, adipic acid, alanine, allopurinaol, arginine, ascorbic acid, asparagine, aspartic acid, benzenesulfonic acid, benzoic acid, caffeine, camphoric acid, capric acid, chrysin, cinnamic acid, citric acid, clemizole, cyclamic acid, cysteine, dimethylglycine, D-ribose, fumaric acid, galactaric acid, genistein, gentisic acid, glucamine N-methyl, gluconic acid, glucosamine, glucuronic acid, glutamic acid, glutamine, glutaric acid, glycine, glycolic acid, hippuric acid, histidine, hydroquinone, imidazole, ipriflavone, isoleucine, lactobionic acid, lauric acid, leucine, lysine, maleic acid, malic acid, malonic acid, mandelic acid, methionine, nicotinamide, nicotinic acid, orotic acid, oxalic acid, palmitic acid, pamoic acid, phenylalanine, piperazine, procaine, proline, p-toluenesulfonic acid, pyridoxamine, pyridoxine (4-pyridoxic acid), pyroglutamic acid, quercetin, resveratrol, saccharin, salicylic acid, salicylic acid 4-amino, sebacic acid, serine, stearic acid, succinic acid, tartaric acid, threonine, TRIS, tryptophan, tyrosine, urea, valine, Vitamin K5, xylitol, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       5 . The composition of  claim 1  wherein the co-crystal former is selected from the group consisting of L-ascorbic acid (vitamin C), salicylic acid, citric acid, gallic acid, maleic acid, malic acid, tartaric acid, nicotinamide, iso-nicotinamide, nicotinic acid, iso-nicotinic acid, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       6 . The composition of  claim 2  wherein the co-crystal former is selected from the group consisting of L-ascorbic acid (vitamin C), salicylic acid, citric acid, gallic acid, maleic acid, malic acid, tartaric acid, nicotinamide, iso-nicotinamide, nicotinic acid, iso-nicotinic acid, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       7 . The composition of  claim 5  wherein the nutraceutical is selected from the group consisting of EGCG, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid. 
   
   
       8 . A co-crystal composition comprising EGCG and a co-crystal former wherein EGCG and the co-crystal former are hydrogen bonded to each other, the co-crystal being with or without impurities. 
   
   
       9 . The co-crystal composition of  claim 8  wherein the co-crystal former is selected from the group consisting of pharmaceutically acceptable carbohydrates, amines, amides, sulfonamides, carboxylic acids, sulfonic acids, phenols, polyphenols, aromatic heterocycles, xanthines and alcohols. 
   
   
       10 . The composition of  claim 8  wherein the co-crystal former is selected from the group consisting of 1,5-napthalene-disulfonic acid, 1-hydroxy-2-naphthoic acid, 4-aminobenzoic acid, 4-aminopyridine, 4-chlorobenzene-sulfonic acid, 4-ethoxyphenyl urea, 7-oxo-DHEA, acesulfame, acetohydroxamic acid, adenine, adipic acid, alanine, allopurinaol, arginine, ascorbic acid, asparagine, aspartic acid, benzenesulfonic acid, benzoic acid, caffeine, camphoric acid, capric acid, chrysin, cinnamic acid, citric acid, clemizole, cyclamic acid, cysteine, dimethylglycine, D-ribose, fumaric acid, galactaric acid, genistein, gentisic acid, glucamine N-methyl, gluconic acid, glucosamine, glucuronic acid, glutamic acid, glutamine, glutaric acid, glycine, glycolic acid, hippuric acid, histidine, hydroquinone, imidazole, ipriflavone, isoleucine, lactobionic acid, lauric acid, leucine, lysine, maleic acid, malic acid, malonic acid, mandelic acid, methionine, nicotinamide, nicotinic acid, orotic acid, oxalic acid, palmitic acid, pamoic acid, phenylalanine, piperazine, procaine, proline, p-toluenesulfonic acid, pyridoxamine, pyridoxine (4-pyridoxic acid), pyroglutamic acid, quercetin, resveratrol, saccharin, salicylic acid, salicylic acid 4-amino, sebacic acid, serine, stearic acid, succinic acid, tartaric acid, threonine, TRIS, tryptophan, tyrosine, urea, valine, Vitamin K5, xylitol, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       11 . The composition of  claim 8  wherein the co-crystal former is selected from the group consisting of L-ascorbic acid (vitamin C), salicylic acid, citric acid, gallic acid, maleic acid, malic acid, tartaric acid, nicotinamide, iso-nicotinamide, nicotinic acid, iso-nicotinic acid, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       12 . A co-crystal comprising at least one nutraceutical compound and L-ascorbic acid wherein the nutraceutical compound and L-ascorbic acid are hydrogen bonded. 
   
   
       13 . The co-crystal of  claim 12  wherein the nutraceutical is selected from the group consisting of vitamin B2 (riboflavin), glucosamine HCl, chlorogenic acid, lipoic acid, catechin hydrate, creatine, acetyl-L-carnitine HCl, vitamin B6, pyridoxine, caffeic acid, naringenin, vitamin B1 (thiamine HCl), baicalein, luteolin, hesperedin, rosmarinic acid, epicatechin gallate, epigallocatechin, vitamin B9 (folic), genistein, methylvanillin, ethylvanillin, silibinin, diadzein, melatonin, rutin hydrate, vitamin A, retinol, vitamin D2 (ergocalciferol), vitamin E (tocopherol), diosmin, menadione (K3), vitamin D3 (caholecalciferol), phloretin, indole-3-carbinol, fisetin, glycitein, chrysin, gallocatechin, vitamin B4 (adenine), vitamin B5 (pantothenic acid), vitamin B7 (biotin), theobromine, quercetin, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid. 
   
   
       14 . The composition of  claim 12  wherein the nutraceutical is selected from the group consisting of resveratrol, EGCG, quercetin, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid. 
   
   
       15 . The composition of  claim 12  wherein the nutraceutical is selected from the group consisting of EGCG, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid. 
   
   
       16 . A co-crystal comprising: a nutraceutical and a co-crystal former, wherein the nutraceutical is a flavonoid and the co-crystal former is a xanthine. 
   
   
       17 . The co-crystal of  claim 16  wherein the flavonoid is epigallocatechin-3-gallate, quercetin, or hesperitin. 
   
   
       18 . A co-crystal, comprising: a nutraceutical and a co-crystal former, wherein the nutraceutical is epigallocatechin-3-gallate, quercetin, or hesperitin, and the co-crystal former is caffeine, theobromine, or theophylline 
   
   
       19 . A process for the preparation of a nutraceutical co-crystal, the process comprising combining at least one nutraceutical and at least one co-crystal former and inducing the nutraceutical(s) and the co-crystal former(s) to hydrogen bond with each other wherein:
 (i) the nutraceutical is selected from the group consisting of vitamin B2 (riboflavin), glucosamine HCl, chlorogenic acid, lipoic acid, catechin hydrate, creatine, acetyl-L-carnitine HCl, vitamin B6, pyridoxine, caffeic acid, naringenin, vitamin B1 (thiamine HCl), baicalein, luteolin, hesperedin, rosmarinic acid, epicatechin gallate, epigallocatechin, vitamin B9 (folic), genistein, methylvanillin, ethylvanillin, silibinin, diadzein, melatonin, rutin hydrate, vitamin A, retinol, vitamin D2 (ergocalciferol), vitamin E (tocopherol), diosmin, menadione (K3), vitamin D3   (caholecalciferol), phloretin, indole-3-carbinol, fisetin, glycitein, chrysin, gallocatechin, vitamin B4 (adenine), vitamin B5 (pantothenic acid), vitamin B7   (biotin), theobromine, quercetin, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid, and   (ii) a co-crystal former selected from the group consisting of pharmaceutically acceptable carbohydrates, amines, amides, sulfonamides, carboxylic acids, sulfonic acids, phenols, polyphenols, aromatic heterocycles, xanthines and alcohols.   
   
   
       20 . The process of  claim 19  wherein the nutraceutical is selected from the group consisting of resveratrol, EGCG, quercetin, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid. 
   
   
       21 . The process of  claim 20  wherein the co-crystal former is selected from the group consisting of 1,5-napthalene-disulfonic acid, 1-hydroxy-2-naphthoic acid, 4-aminobenzoic acid, 4-aminopyridine, 4-chlorobenzene-sulfonic acid, 4-ethoxyphenyl urea, 7-oxo-DHEA, acesulfame, acetohydroxamic acid, adenine, adipic acid, alanine, allopurinaol, arginine, ascorbic acid, asparagine, aspartic acid, benzenesulfonic acid, benzoic acid, caffeine, camphoric acid, capric acid, chrysin, cinnamic acid, citric acid, clemizole, cyclamic acid, cysteine, dimethylglycine, D-ribose, fumaric acid, galactaric acid, genistein, gentisic acid, glucamine N-methyl, gluconic acid, glucosamine, glucuronic acid, glutamic acid, glutamine, glutaric acid, glycine, glycolic acid, hippuric acid, histidine, hydroquinone, imidazole, ipriflavone, isoleucine, lactobionic acid, lauric acid, leucine, lysine, maleic acid, malic acid, malonic acid, mandelic acid, methionine, nicotinamide, nicotinic acid, orotic acid, oxalic acid, palmitic acid, pamoic acid, phenylalanine, piperazine, procaine, proline, p-toluenesulfonic acid, pyridoxamine, pyridoxine (4-pyridoxic acid), pyroglutamic acid, quercetin, resveratrol, saccharin, salicylic acid, salicylic acid 4-amino, sebacic acid, serine, stearic acid, succinic acid, tartaric acid, threonine, TRIS, tryptophan, tyrosine, urea, valine, Vitamin K5, xylitol, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       22 . The process of  claim 19  wherein the co-crystal former is selected from the group consisting of 1,5-napthalene-disulfonic acid, 1-hydroxy-2-naphthoic acid, 4-aminobenzoic acid, 4-aminopyridine, 4-chlorobenzene-sulfonic acid, 4-ethoxyphenyl urea, 7-oxo-DHEA, acesulfame, acetohydroxamic acid, adenine, adipic acid, alanine, allopurinaol, arginine, ascorbic acid, asparagine, aspartic acid, benzenesulfonic acid, benzoic acid, caffeine, camphoric acid, capric acid, chrysin, cinnamic acid, citric acid, clemizole, cyclamic acid, cysteine, dimethylglycine, D-ribose, fumaric acid, galactaric acid, genistein, gentisic acid, glucamine N-methyl, gluconic acid, glucosamine, glucuronic acid, glutamic acid, glutamine, glutaric acid, glycine, glycolic acid, hippuric acid, histidine, hydroquinone, imidazole, ipriflavone, isoleucine, lactobionic acid, lauric acid, leucine, lysine, maleic acid, malic acid, malonic acid, mandelic acid, methionine, nicotinamide, nicotinic acid, orotic acid, oxalic acid, palmitic acid, pamoic acid, phenylalanine, piperazine, procaine, proline, p-toluenesulfonic acid, pyridoxamine, pyridoxine (4-pyridoxic acid), pyroglutamic acid, quercetin, resveratrol, saccharin, salicylic acid, salicylic acid 4-amino, sebacic acid, serine, stearic acid, succinic acid, tartaric acid, threonine, TRIS, tryptophan, tyrosine, urea, valine, Vitamin K5, xylitol, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       23 . The process of  claim 19  wherein the co-crystal former is selected from the group consisting of L-ascorbic acid (vitamin C), salicylic acid, citric acid, gallic acid, maleic acid, malic acid, tartaric acid, nicotinamide, iso-nicotinamide, nicotinic acid, iso-nicotinic acid, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       24 . The process of  claim 20  wherein the co-crystal former is selected from the group consisting of L-ascorbic acid (vitamin C), salicylic acid, citric acid, gallic acid, maleic acid, malic acid, tartaric acid, nicotinamide, iso-nicotinamide, nicotinic acid, iso-nicotinic acid, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       25 . The process of  claim 23  wherein the nutraceutical is selected from the group consisting of EGCG, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid. 
   
   
       26 . A process for the preparation of a nutraceutical co-crystal, the process comprising combining at least one nutraceutical and at least one co-crystal former and inducing the nutraceutical(s) and the co-crystal former(s) to hydrogen bond with each other wherein the nutraceutical comprises EGCG. 
   
   
       27 . The process of  claim 26  wherein the co-crystal former selected from the group consisting of pharmaceutically acceptable carbohydrates, amines, amides, sulfonamides, carboxylic acids, sulfonic acids, phenols, polyphenols, aromatic heterocycles, xanthines and alcohols. 
   
   
       28 . The process of  claim 26  wherein the co-crystal former is selected from the group consisting of 1,5-napthalene-disulfonic acid, 1-hydroxy-2-naphthoic acid, 4-aminobenzoic acid, 4-aminopyridine, 4-chlorobenzene-sulfonic acid, 4-ethoxyphenyl urea, 7-oxo-DHEA, acesulfame, acetohydroxamic acid, adenine, adipic acid, alanine, allopurinaol, arginine, ascorbic acid, asparagine, aspartic acid, benzenesulfonic acid, benzoic acid, caffeine, camphoric acid, capric acid, chrysin, cinnamic acid, citric acid, clemizole, cyclamic acid, cysteine, dimethylglycine, D-ribose, fumaric acid, galactaric acid, genistein, gentisic acid, glucamine N-methyl, gluconic acid, glucosamine, glucuronic acid, glutamic acid, glutamine, glutaric acid, glycine, glycolic acid, hippuric acid, histidine, hydroquinone, imidazole, ipriflavone, isoleucine, lactobionic acid, lauric acid, leucine, lysine, maleic acid, malic acid, malonic acid, mandelic acid, methionine, nicotinamide, nicotinic acid, orotic acid, oxalic acid, palmitic acid, pamoic acid, phenylalanine, piperazine, procaine, proline, p-toluenesulfonic acid, pyridoxamine, pyridoxine (4-pyridoxic acid), pyroglutamic acid, quercetin, resveratrol, saccharin, salicylic acid, salicylic acid 4-amino, sebacic acid, serine, stearic acid, succinic acid, tartaric acid, threonine, TRIS, tryptophan, tyrosine, urea, valine, Vitamin K5, xylitol, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       29 . The process of  claim 26  wherein the co-crystal former is selected from the group consisting of L-ascorbic acid (vitamin C), salicylic acid, citric acid, gallic acid, maleic acid, malic acid, tartaric acid, nicotinamide, iso-nicotinamide, nicotinic acid, iso-nicotinic acid, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       30 . A process for the preparation of a nutraceutical co-crystal, the process comprising combining at least one nutraceutical compound and L-ascorbic acid and inducing the nutraceutical compound(s) and L-ascorbic acid to hydrogen bond with each other. 
   
   
       31 . The process of  claim 30  wherein the nutraceutical is selected from the group consisting of vitamin B2 (riboflavin), glucosamine HCl, chlorogenic acid, lipoic acid, catechin hydrate, creatine, acetyl-L-carnitine HCl, vitamin B6, pyridoxine, caffeic acid, naringenin, vitamin B1 (thiamine HCl), baicalein, luteolin, hesperedin, rosmarinic acid, epicatechin gallate, epigallocatechin, vitamin B9 (folic), genistein, methylvanillin, ethylvanillin, silibinin, diadzein, melatonin, rutin hydrate, vitamin A, retinol, vitamin D2 (ergocalciferol), vitamin E (tocopherol), diosmin, menadione (K3), vitamin D3 (caholecalciferol), phloretin, indole-3-carbinol, fisetin, glycitein, chrysin, gallocatechin, vitamin B4 (adenine), vitamin B5 (pantothenic acid), vitamin B7 (biotin), theobromine, quercetin, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid. 
   
   
       32 . The process of  claim 30  wherein the nutraceutical is selected from the group consisting of resveratrol, EGCG, quercetin, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid. 
   
   
       33 . The process of  claim 30  wherein the nutraceutical is selected from the group consisting of EGCG, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid. 
   
   
       34 . A process for the preparation of a nutraceutical co-crystal comprising a flavonoid and a xanthine, the process comprising combining the flavonoid and the xanthine and inducing the flavonoid and the xanthine to hydrogen bond with each other. 
   
   
       35 . The process of  claim 34  wherein the flavonoid is epigallocatechin-3-gallate, quercetin, or hesperitin. 
   
   
       36 . The process of  claim 34  wherein the flavonoid is epigallocatechin-3-gallate, quercetin, or hesperitin, and the xanthine is caffeine, theobromine, or theophylline 
   
   
       37 . A process for improving animal health or nutrition, the process comprising administering to the animal a composition comprising a nutraceutical co-crystal wherein
 (i) the nutraceutical co-crystal comprises a nutraceutical and a co-crystal former hydrogen bonded to each other, the nutraceutical co-crystal with or without impurities   (ii) the nutraceutical is selected from the group consisting of vitamin B2 (riboflavin), glucosamine HCl, chlorogenic acid, lipoic acid, catechin hydrate, creatine, acetyl-L-carnitine HCl, vitamin B6, pyridoxine, caffeic acid, naringenin, vitamin B1 (thiamine HCl), baicalein, luteolin, hesperedin, rosmarinic acid, epicatechin gallate, epigallocatechin, vitamin B9 (folic), genistein, methylvanillin, ethylvanillin, silibinin, diadzein, melatonin, rutin hydrate, vitamin A, retinol, vitamin D2 (ergocalciferol), vitamin E (tocopherol), diosmin, menadione (K3), vitamin D3 (caholecalciferol), phloretin, indole-3-carbinol, fisetin, glycitein, chrysin, gallocatechin, vitamin B4 (adenine), vitamin B5 (pantothenic acid), vitamin B7 (biotin), theobromine, quercetin, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid, and   (iii) the co-crystal former selected from the group consisting of pharmaceutically acceptable carbohydrates, amines, amides, sulfonamides, carboxylic acids, sulfonic acids, phenols, polyphenols, aromatic heterocycles, xanthines and alcohols.form of epigallocatechin-3-gallate to a person or animal having or predisposed to having a condition resulting from oxidative stress.   
   
   
       38 . The process of  claim 37  wherein the nutraceutical is selected from the group consisting of resveratrol, EGCG, quercetin, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid. 
   
   
       39 . The process of  claim 37  wherein the co-crystal former is selected from the group consisting of 1,5-napthalene-disulfonic acid, 1-hydroxy-2-naphthoic acid, 4-aminobenzoic acid, 4-aminopyridine, 4-chlorobenzene-sulfonic acid, 4-ethoxyphenyl urea, 7-oxo-DHEA, acesulfame, acetohydroxamic acid, adenine, adipic acid, alanine, allopurinaol, arginine, ascorbic acid, asparagine, aspartic acid, benzenesulfonic acid, benzoic acid, caffeine, camphoric acid, capric acid, chrysin, cinnamic acid, citric acid, clemizole, cyclamic acid, cysteine, dimethylglycine, D-ribose, fumaric acid, galactaric acid, genistein, gentisic acid, glucamine N-methyl, gluconic acid, glucosamine, glucuronic acid, glutamic acid, glutamine, glutaric acid, glycine, glycolic acid, hippuric acid, histidine, hydroquinone, imidazole, ipriflavone, isoleucine, lactobionic acid, lauric acid, leucine, lysine, maleic acid, malic acid, malonic acid, mandelic acid, methionine, nicotinamide, nicotinic acid, orotic acid, oxalic acid, palmitic acid, pamoic acid, phenylalanine, piperazine, procaine, proline, p-toluenesulfonic acid, pyridoxamine, pyridoxine (4-pyridoxic acid), pyroglutamic acid, quercetin, resveratrol, saccharin, salicylic acid, salicylic acid 4-amino, sebacic acid, serine, stearic acid, succinic acid, tartaric acid, threonine, TRIS, tryptophan, tyrosine, urea, valine, Vitamin K5, xylitol, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       40 . The process of  claim 37  wherein the co-crystal former is selected from the group consisting of 1,5-napthalene-disulfonic acid, 1-hydroxy-2-naphthoic acid, 4-aminobenzoic acid, 4-aminopyridine, 4-chlorobenzene-sulfonic acid, 4-ethoxyphenyl urea, 7-oxo-DHEA, acesulfame, acetohydroxamic acid, adenine, adipic acid, alanine, allopurinaol, arginine, ascorbic acid, asparagine, aspartic acid, benzenesulfonic acid, benzoic acid, caffeine, camphoric acid, capric acid, chrysin, cinnamic acid, citric acid, clemizole, cyclamic acid, cysteine, dimethylglycine, D-ribose, fumaric acid, galactaric acid, genistein, gentisic acid, glucamine N-methyl, gluconic acid, glucosamine, glucuronic acid, glutamic acid, glutamine, glutaric acid, glycine, glycolic acid, hippuric acid, histidine, hydroquinone, imidazole, ipriflavone, isoleucine, lactobionic acid, lauric acid, leucine, lysine, maleic acid, malic acid, malonic acid, mandelic acid, methionine, nicotinamide, nicotinic acid, orotic acid, oxalic acid, palmitic acid, pamoic acid, phenylalanine, piperazine, procaine, proline, p-toluenesulfonic acid, pyridoxamine, pyridoxine (4-pyridoxic acid), pyroglutamic acid, quercetin, resveratrol, saccharin, salicylic acid, salicylic acid 4-amino, sebacic acid, serine, stearic acid, succinic acid, tartaric acid, threonine, TRIS, tryptophan, tyrosine, urea, valine, Vitamin K5, xylitol, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       41 . The process of  claim 37  wherein the co-crystal former is selected from the group consisting of L-ascorbic acid (vitamin C), salicylic acid, citric acid, gallic acid, maleic acid, malic acid, tartaric acid, nicotinamide, iso-nicotinamide, nicotinic acid, iso-nicotinic acid, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       42 . The process of  claim 38  wherein the co-crystal former is selected from the group consisting of L-ascorbic acid (vitamin C), salicylic acid, citric acid, gallic acid, maleic acid, malic acid, tartaric acid, nicotinamide, iso-nicotinamide, nicotinic acid, iso-nicotinic acid, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       43 . The process of  claim 41  wherein the nutraceutical is selected from the group consisting of EGCG, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid. 
   
   
       44 . A process for improving animal health or nutrition, the process comprising administering to the animal a composition comprising a nutraceutical co-crystal comprising EGCG and a co-crystal former. 
   
   
       45 . The process of  claim 44  wherein the co-crystal former selected from the group consisting of pharmaceutically acceptable carbohydrates, amines, amides, sulfonamides, carboxylic acids, sulfonic acids, phenols, polyphenols, aromatic heterocycles, xanthines and alcohols. 
   
   
       46 . The process of  claim 44  wherein the co-crystal former is selected from the group consisting of 1,5-napthalene-disulfonic acid, 1-hydroxy-2-naphthoic acid, 4-aminobenzoic acid, 4-aminopyridine, 4-chlorobenzene-sulfonic acid, 4-ethoxyphenyl urea, 7-oxo-DHEA, acesulfame, acetohydroxamic acid, adenine, adipic acid, alanine, allopurinaol, arginine, ascorbic acid, asparagine, aspartic acid, benzenesulfonic acid, benzoic acid, caffeine, camphoric acid, capric acid, chrysin, cinnamic acid, citric acid, clemizole, cyclamic acid, cysteine, dimethylglycine, D-ribose, fumaric acid, galactaric acid, genistein, gentisic acid, glucamine N-methyl, gluconic acid, glucosamine, glucuronic acid, glutamic acid, glutamine, glutaric acid, glycine, glycolic acid, hippuric acid, histidine, hydroquinone, imidazole, ipriflavone, isoleucine, lactobionic acid, lauric acid, leucine, lysine, maleic acid, malic acid, malonic acid, mandelic acid, methionine, nicotinamide, nicotinic acid, orotic acid, oxalic acid, palmitic acid, pamoic acid, phenylalanine, piperazine, procaine, proline, p-toluenesulfonic acid, pyridoxamine, pyridoxine (4-pyridoxic acid), pyroglutamic acid, quercetin, resveratrol, saccharin, salicylic acid, salicylic acid 4-amino, sebacic acid, serine, stearic acid, succinic acid, tartaric acid, threonine, TRIS, tryptophan, tyrosine, urea, valine, Vitamin K5, xylitol, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       47 . The process of  claim 44  wherein the co-crystal former is selected from the group consisting of L-ascorbic acid (vitamin C), salicylic acid, citric acid, gallic acid, maleic acid, malic acid, tartaric acid, nicotinamide, iso-nicotinamide, nicotinic acid, iso-nicotinic acid, caffeine, paraxanthine, theobromine, theophylline, caprolactam, lactose, glucose and sucrose. 
   
   
       48 . A process for improving animal health or nutrition, the process comprising administering to the animal a composition comprising a nutraceutical co-crystal comprising at least one nutraceutical compound and L-ascorbic acid. 
   
   
       49 . The process of  claim 48  wherein the nutraceutical is selected from the group consisting of vitamin B2 (riboflavin), glucosamine HCl, chlorogenic acid, lipoic acid, catechin hydrate, creatine, acetyl-L-carnitine HCl, vitamin B6, pyridoxine, caffeic acid, naringenin, vitamin B1 (thiamine HCl), baicalein, luteolin, hesperedin, rosmarinic acid, epicatechin gallate, epigallocatechin, vitamin B9 (folic), genistein, methylvanillin, ethylvanillin, silibinin, diadzein, melatonin, rutin hydrate, vitamin A, retinol, vitamin D2 (ergocalciferol), vitamin E (tocopherol), diosmin, menadione (K3), vitamin D3 (caholecalciferol), phloretin, indole-3-carbinol, fisetin, glycitein, chrysin, gallocatechin, vitamin B4 (adenine), vitamin B5 (pantothenic acid), vitamin B7 (biotin), theobromine, quercetin, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid. 
   
   
       50 . The process of  claim 48  wherein the nutraceutical is selected from the group consisting of resveratrol, EGCG, quercetin, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid. 
   
   
       51 . The process of  claim 48  wherein the nutraceutical is selected from the group consisting of EGCG, ferulic acid, ellagic acid, hesperitin, and protocatechuic acid. 
   
   
       52 . A process for improving animal health or nutrition, the process comprising administering to the animal a composition comprising a nutraceutical co-crystal comprising a flavonoid and a xanthine. 
   
   
       53 . The process of  claim 52  wherein the flavonoid is epigallocatechin-3-gallate, quercetin, or hesperitin. 
   
   
       54 . The process of  claim 52  wherein the flavonoid is epigallocatechin-3-gallate, quercetin, or hesperitin, and the xanthine is caffeine, theobromine, or theophylline. 
   
   
       55 . (canceled) 
   
   
       56 . The co-crystal of  claim 12  wherein the nutraceutical compound is a zwitterion and/or has at least one carboxylate group. 
   
   
       57 . The co-crystal of  claim 12  wherein the nutraceutical compound is a vitamin, amino acid or derivative thereof, alkaloid, peptide, flavonoid, steroidal, terpenoid, pharmaceutical, hormone or prohormone. 
   
   
       58 . The cocrystal of  claim 12  wherein the nutraceutical is nicotinic acid or sarcosine. 
   
   
       59 . The cocrystal of  claim 12  wherein the molar ratio of the nutraceutical to L-ascorbic acid is about 1:1. 
   
   
       60 . The cocrystal of  claim 58  wherein the molar ratio of the nutraceutical to L-ascorbic acid is about 1:1. 
   
   
       61 . A pharmaceutical composition comprising a co-crystal comprising at least one nutraceutical compound and L-ascorbic acid wherein the nutraceutical compound and L-ascorbic acid are hydrogen bonded. 
   
   
       62 . The pharmaceutical composition of  claim 61  wherein the nutraceutical compound is a zwitterion and/or has at least one carboxylate group. 
   
   
       63 . The pharmaceutical composition of  claim 62  wherein the nutraceutical compound is a vitamin, amino acid or derivative thereof, alkaloid, peptide, flavonoid, steroidal, terpenoid, pharmaceutical, hormone or prohormone. 
   
   
       64 . The pharmaceutical composition of  claim 61  wherein the nutraceutical is nicotinic acid or sarcosine. 
   
   
       65 . The pharmaceutical composition of  claim 61  wherein the molar ratio of the nutraceutical to L-ascorbic acid is about 1:1. 
   
   
       66 . (canceled) 
   
   
       67 . A method of making a co-crystal, the method comprising: combining a nutraceutical compound and a first solvent to form a nutraceutical admixture; combining L-ascorbic acid and a second solvent to form an L-ascorbic acid admixture; combining the nutraceutical admixture and the L-ascorbic acid admixture under crystallization conditions to form a co-crystal in a solid phase, the co-crystal comprising the nutraceutical and L-ascorbic acid wherein the nutraceutical compound and L-ascorbic acid are hydrogen bonded; and optionally isolating the co-crystal. 
   
   
       68 . The method of  claim 67  wherein the first and second solvents are independently selected from water, alcohols, and mixtures thereof. 
   
   
       69 - 81 . (canceled)