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Creatine hydroxycitric acids salts and methods for their production and use in individuals

Inactive Publication Date: 2006-08-31
IOVATE T & P +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0010] The present invention, according to various embodiments thereof, provides methods for the production and use in individuals, e.g. animals and humans, of organic salts formed via the reaction of creatine (as used herein, this term shall refer to any type of creatine and shall not be limited to any particular form or anion) with hydroxycitric acid (also referred to “HCA”), the principle acid occurring in the rind of fruits from plants of the Garcinia genus (including, but not limited to, Garcinia cambogia, Garcinia indica, and Garcinia atrovirids). These salts, e.g. monocreatine hydroxycitrate, dicreatine hydroxycitrate, and tricreatine hydroxycitrate (collectively referred to as “creatine hydroxycitrates”), may provide improved hydrosolubility and possess ameliorated stability in water and in acidic solutions compared to creatine monohydrate. The aforementioned creatine hydroxycitrates may be useful to increase muscle and exercise performance in individuals, athletes in particular, and to afford neuroprotective strategies addressing specific bioenergetic defects. In addition, by supplying biosignificant amounts of HCA, these creatine hydroxycitrates may contribute to reduce fatty acid synthesis by preventing the conversion of carbohydrate energy into triglycerides, thereby being particularly suitable to be used in conjunction with dietary and exercise regimens aimed at the reduction and / or prevention of excess adiposity leading to weight loss. Furthermore, the creatine hydroxycitrates, due to a stimulatory action of the HCA moiety on serotonergic output, may contribute to improved exercise recovery and suppress the appetite leading to weight loss.
[0011] Generally, the present invention, according to various embodiments thereof, provides stable hydrosoluble creatine hydroxycitric acid salts, e.g. creatine hydroxycitrates, and a method of producing same, that possess higher water solubility and stability in acidic solutions compared to creatine monohydrate. The present invention, according to various embodiments thereof, may also provide creatine hydroxycitrates, and a method of producing the same, that may be administered orally to a mammal with a bioavailability equal to or higher than creatine or hydroxycitric acid administered singularly or as a combination, wherein the salts may synergistically increase the physiological benefits afforded by the single creatine and the hydroxycitric acid components.

Problems solved by technology

Ingestion of creatine monohydrate thereof requires large amounts of water to also be ingested.

Method used

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  • Creatine hydroxycitric acids salts and methods for their production and use in individuals
  • Creatine hydroxycitric acids salts and methods for their production and use in individuals

Examples

Experimental program
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Effect test

example 1

Creatine Dipotassium Hydroxycitrate Monohydrate, Dicreatine Monopotassium Hydroxycitrate Monohydrate, and Tricreatine Hydroxycitrate Monohydrate

[0038] The fruits rinds of G. cambogia and G. indica may contain 20-30% (−)-HCA (Reference: Lewis, Y. S., and Neelakantan S. (−)-Hydroxycitric acids. The principle acid in the fruit is Garcinia cambogia. Pytochemistry 4:619-625, 1965). To provide reaction yields of not less than 50% (−)-HCA on anhydrous basis acid content, the fruit rinds of G. cambogia and G. indica may preferably contain a minimum of about 15% (−)-HCA.

[0039] Accordingly, it is estimated that 208.13g of (−)-HCA can be extracted from a starting amount of 1.3875 kg of Garcinia fruit rind. The extraction process may be similar to the process described by e.g. Majeed, M., et al. in U.S. Pat. No. 5,783,603, in which hydrosoluble (tri)potassium hydroxycitrate salts are described. That process involves the extraction of (−)-HCA from Garcinia fruit using an alkyl alcohol.

[0040] ...

example 2

Tricreatine Hydroxycitrate

[0053] Free (−)-HCA can easily be generated from calcium, sodium and potassium hydroxycitrate salts, by passing an aqueous solution of said salt through a cation exchange resin, e.g., Zeocarb® 225. (Reference: Singh, R. P., et al., (−)-Hydroxycitric acid from Garcinia cambogia. Biological Memoirs 21(1):27-33, 1995).

[0054] Hydroxycitric acid has a molecular weight of 208.13. Creatine monohydrate has a molecular weight of 149.13. Tricreatine hydroxycitrate may be manufactured as follows:

[0055] Step 1) Start with 10.84 l of anhydrous methyl alcohol;

[0056] Step 2) With stirring, an aqueous solution containing 1,084 g of hydroxycitric acid (5.2 moles), obtained after passing the (−)-HCA salt through a cation exchange resin, are added to the anhydrous methyl alcohol. The resulting mixture is stirred for approximately 45 minutes;

[0057] Step 3) 2,362 g (15.6 moles) or creatine monohydrate are added to the hydroxycitric acid / methyl alcohol mixture. This mixtur...

example 3

Preparation of Tricreatine Hydroxycitrate from Creatine Hydrochloride and (Tri)-Potassium Hydroxycitrate Monohydrate

[0064] Tripotassium hydroxycitrate monohydrate has a molecular weight of 340.41 g per mole. Creatine hydrochloride has a theoretical molecular weight of 167.57 g per mole.

[0065] The procedure is a follows:

[0066] Step 1) 3.5 g of tripotassium hydroxycitrate monohydrate (0.01 mol) is mixed in sufficient deionized water to a final volume of 300 ml;

[0067] Step 2) To the solution described above, creatine hydrochloride is added in an amount of 5.03 g (0.03 mol) and solution is stirred for 45 minutes;

[0068] Step 3) The resulting product is tricreatine hydroxycitrate (5.8-6%), having three creatine cations per hydroxycitrate (tri)-anion.

[0069] Step 4) Potassium chloride, also obtains via this reaction, can be precipitated with the addition of alcohol (ethanol, methanol) and removed by filtration.

[0070] Given that the described reaction mixture includes 0.01 moles of tr...

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Abstract

Methods of production for Tricreatine Hydroxycitrate are disclosed. Tricreatine hydroxycitrate can be used as supplemental dietary ingredient for the purposes of reducing adiposity, suppression of appetite, improvement of muscle and exercise performance and recovery. The salts are useful in the dietetic, food supplement and food industries.

Description

RELATED APPLICATIONS [0001] The application is related to and claims benefit of priority to U.S Provisional Patent Application Ser. No. 60 / 651,049, entitled “Creatine Hydroxycitric Acids Salts and Methods for their Production and Use in Individuals,” filed Feb. 7, 2005, the disclosure of which is hereby fully incorporated by reference.FIELD OF THE INVENTION [0002] The present invention relates to a supplemental dietary ingredient that promotes increased muscle and exercise performance in individuals, reduces and / or prevents adiposity, improves exercise recovery, and / or suppresses the appetite leading to weight loss. The present invention is also related to a method of promoting same by consuming the supplemental composition. The invention also relates to a method for producing a supplemental composition. BACKGROUND [0003] Creatine monohydrate is a commonly used supplement. Creatine monohydrate is soluble in water at a rate of 75 ml of water per gram of creatine. Ingestion of creatin...

Claims

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Application Information

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IPC IPC(8): A61K31/205C07C59/255A23L33/00
CPCA23L1/3051A23V2002/00C07C59/285C07C279/14A23V2250/306A23V2200/30A23V2200/332A23V2200/33A23L33/175A61P3/02A61P3/04A61P3/06A61P21/00A61P21/06
Inventor GARDINER, PAUL T.HEUER, MARVIN A.MOLINO, MICHELE
Owner IOVATE T & P
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