Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
  • C07C59/235—Saturated compounds containing more than one carboxyl group
  • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P3/00—Drugs for disorders of the metabolism
  • A61P3/04—Anorexiants; Antiobesity agents
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
  • C07C51/42—Separation; Purification; Stabilisation; Use of additives
  • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
  • C07C51/42—Separation; Purification; Stabilisation; Use of additives
  • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
  • C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
  • C07C51/42—Separation; Purification; Stabilisation; Use of additives
  • C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
  • C07C51/42—Separation; Purification; Stabilisation; Use of additives
  • C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification

Definitions

• This invention relates to a new soluble double metal salt of group IA and II A of (-) hydroxycitric acid, process of preparing the same and its use in beverages and other food products without effecting their flavor and properties.
• This product with >98% purity can be used safely not only as a food supplement in various nutriceutical formulations and beverages but also for effecting obesity control.
• HCA Hydroxycitric acid
• HCA active ingredient
• Patent WO 96/36585 US patent 08/440,968 filed.
• high potassium high potassium
• the object of this invention is to overcome the above drawbacks by developing a new soluble double metal salt of (-) hydroxycitric acid which will not pose any problem in formulating with beverages and various other food products without affecting their flavor and properties.
• this invention provides a new soluble double metal salt of group IA and II A of (-) hydroxycitric acid of general fonnula I and more particularly formula II as given below:
• X is IA group metal: Li or Na or K or Rb or Cs or Fr
• Y IIA group metal: Be or Mg or Ca or Sr or Ba or Ra where concentration of X in the salt varies from 1.5 - 51.0%, the concentration of Y in the salts varies from 2.0 - 50.9%, the concentration of HCA in the salts varies from 31.0 - 93.0%) depending on the nature of X and Y. concentration of sodium in the salt : 8.58%, concentration of calcium in the salt: 14.92% concentration of (-) hydroxycitric acid : 76.50%o,
• This invention further relates to a process for preparing the said soluble metal salt of group IA and IIA of (-) hydroxycitric acid of general formula I or more particularly formula II comprising:
• Step 1 preparing (-) hydroxycitric acid liquid concentrate/solid lactone of hydroxycitric acid from Garcinia extract,
• Step 2 neutralizing the free (-) hydroxycitric acid present in the said hydroxycitric acid liquid concentrate/solid lactone present (-) hydroxycitric acid with group IA metal hydroxides
• Step 3 displacing partially group IA metal ions in the above salt solutions by adding group IIA metal chlorides to form soluble double metal salt of group IA and IIA of (-) hydroxycitric acid,
• Step 4 precipitating the said solubilised group IIA metal salts of (-) hydroxycitric acid by adding aqueous polar solvent to get soluble IIA metal salt of (-) hydroxycitric acid
• the free (-) hydroxycitric acid present in the step 2 is neutralized by three equivalents of group IA metal hydroxides.
• Partial displacement of group IA metal ion in step 3 is carried out with one equivalent of group IIA metal chloride.
• the soluble metal salt of hydroxycitric acid is obtained in powder from by spray drying prior to the solvent addition or spray drying water solubilised solvent precipitated material.
• the said polar solvents are methanol, ethanol, propanol, isopropanol and acetone.
• the (-) hydroxycitric acid concentrate in step 1 is prepared from the Garcinia extract by: i) treating the said Garcinia extract with group IA metal hydroxide to obtain soluble group LA metal salt of (-) hydroxycitric acid, ii) displacing completely the said group LA metal ions with group IIA metal ion by adding group IIA metal chlorides solution to precipitate insoluble group IIA metal salts of (-) hydroxycitric acid, iii) collecting the said precipitate of insoluble group IIA metal salt of (-) hydroxycitric acid and washing it with water, iv) adding a water soluble organic acid to the said precipitated insoluble group II A metal salt of HCA to form a stronger salt of group IIA metal and release (-) hydroxycitric acid, v) repeating the steps (iii) and (iv) to form concentrate of (-) hydroxycitric acid, vi) decolorizing the said (-) hydroxycitric acid concentrate, if desired.
• the water soluble organic acid used in step (iv) is an oxalic acid.
• the (-) hydroxycitric acid concentrate in step 1 is also prepared from the Garcinia by: i) extracting Garcinia rind with aqueous polar solvent and filtering, ii) heating the filtrate in vacuum at 50-80° C to evaporate the said polar solvent, iii) removing the water insoluble substances to get the (-) hydroxycitric acid concentrate, iv) decolorizing the said (-) hydroxycitric acid concentrate, if necessary.
• the aqueous polar solvent used in step 1 is 80% acetone in water.
• the (-) hydroxycitric acid concentrate in step 1 is also prepared from the
• Garcinia extract by: i) loading the Garcinia extract containing free (-) hydroxycitric acid on anion exchange resin column, ii) washing the said column with group IA metal hydroxide solution to get group IA metal salt of (-) hydroxycitric acid, iii) loading the said group LA metal salt solution of (-) hydroxycitric acid on cation exchange resin to get free (-) hydroxycitric acid, iv) heating the said free (-) hydroxycitric acid in vacuum to evaporate water and get the (-) hydroxycitric acid concentrate. v) decolorizing the said (-) hydroxycitric acid concentrate, if necessary.
• the said (-) hydroxycitric acid concentrate is decolorized by heating with 2- 5% activated charcoal, if desired.
• the said lactone of (-) hydroxycitric acid in step 1 is prepared by: i) heating the (-) hydroxycitric acid concentrate at 67° C to form syrup of (-) hydroxycitric acid lactone, ii) drying and desiccating the said syrup to get solid mass of (-) hydroxycitric acid lactone.
• a process for the preparation of soluble double metal salt of group IA and IIA of (-) hydroxycitric acid comprising: i) loading Garcinia extract containing free (-) hydroxycitric acid on an anion exchange resin column, ii) washing the said anion exchange resin column with Group IA metal hydroxide to obtain group IA metal salt of (-) hydroxycitric acid solution. iii) treating the said group IA metal salt of (-) hydroxycitric acid partially with group IIA metal chloride to get soluble double metal salt of group IA and IIA of (-) hydroxycitric acid.
• Group IA metal hydroxides used are LiOH, NaOH, KOH, RbOH, CsOH and FrOH.
• Group IIA metal chlorides BeCl 2 , MgCI 2 , CaCI 2 , SrCl 2 , BaCl 2 and RaC12.
• the soluble double metal salt of group IA and IIA of (-) hydroxycitric acid is soluble sodium calcium salt of (-) hydroxycitric acid.
• Example 1 The process will now be described with reference to the following examples.
• Example 1 Example 1 :
• Water extract of Garcinia rind is obtained by counter current extraction, this is carried out in three vessels more specifically each time fresh Garcinia rind each time lKg is loaded into vessel 3 and treated with 1.5 liters of water, the rind is moved from V 3 to V 2 then to Vj. On the other hand the extract was moved from V ! to V 2 then to V 3 .
• the extract obtained starting from 3Kgs of rind was 3.6 litres containing 620gms of acid along with the other water-soluble substances.
• the total soluble constituents in the extract i.e. brix was found to be 43 degrees.
• the extraction efficiency was found to be 90%.
• This acid was transferred to a vessel and neutralized by addition if 358 gm of sodium hydroxide. After cooling this solution to room temperature, 500 ml of solution containing 490 gm of calcium chloride was added to it and resultant insoluble calcium salt was centrifuged and washed thoroughly to removed the color and water soluble impurities.
• the salt obtained was dried and weight is found to be 693 gm.
• the solution of hydroxycitric acid thus obtained was found to contain 202 gm of acid in 450 ml of extract. This was neutralized by 117 gm of sodium hydroxide and the solution was cooled to room temperature. To this sodium salt solution of hydroxycitric acid, 200 ml of solution containing 81 gm of calcium chloride was added drop wise with vigorous stirring. The soluble calcium salt of hydroxycitric acid was then precipitated by addition of ethanol. Then precipitated salt was filtered, washed with ethanol and dried to obtain 234 gm of the soluble calcium salt of hydroxycitric acid (yield: 91.2%).
• An anion exchange resin (bed volume IL) was loaded onto a glass column and washed thoroughly with 10% aqueous sodium hydroxide to remove the chloride present in the resin. The column was then washed with water till the eluate pH was neutral. Three hundred milliliters of an aqueous solution containing 108 gm of (-) hydroxycitric acid was loaded onto the column and washed with water to remove the colored materials. The column was eiuted with 1 liter of an aqueous solution containing 63 gm of sodium hydroxide followed by 0.5 L of water. The combined eluate (1.5 liters) containing sodium salt of hydroxycitric acid was divided into two parts (750 ml each) and the soluble calcium salt was prepared as follows.
• a portion of the sodium salt of hydroxycitric acid (750 ml) was concentrated to 200 ml. Fifty milliliters of a solution containing 20.25 gm of calcium chloride was added drop wise with vigorous stirring. The soluble salt of hydroxycitric acid thus formed was precipitated by the addition of ethanol, collected by filtration, washed with ethanol and dried to obtain 60.3 gm of the soluble calcium salt of hydroxycitric acid (yield: 91.8%). b) The remaining portion of the eluate (750-ml) from the anion exchange column was passed through a column of cation exchange resin (bed volume 750 ml). The column was washed with water until the pH of the eluent reached neutral.
• This invention also provides the use of the said soluble double metal salt of group IA and IIA of (-) hydroxycitric acid of formula I and particularly formula II in beverages and other food products.
• the said beverage is a Pilsner, beer containing alcohol content 3.0-3.8 weight % or Dortmund beer containing alcohol content 2.5-4.0 weight % or Kunststoff beer containing alcohol content 2.0-5.0 weight % or Kunststoff Ale or Porter beer containing alcohol contents 2.0-5.0 weight % or Stout beer containing alcohol content 5.0-6.5 weight %, each said beer includes the soluble double metal salt of group IA or IIA of formula I or II in the proportion 0.01-0.5 % w/v.
• the said beverage is aerated or non-aerated beverage/colas and the syrups are either processed or naturally occurring like honey including soluble double metal salt of group IA and IIA of (-) hydroxycitric acid of formula I or II in the proportion 0.01-10 % w/v.
• Soluble double metal salt of group IA and IIA of (-) hydroxycitric acid of formula I or formula II in the proportion 0.01-10 % w/v is added at any stage during the production of the beverage or processed syrups.

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• 1999
  • 1999-02-18 EP EP99909175A patent/EP1154978A1/de not_active Withdrawn
  • 1999-02-18 IL IL14482799A patent/IL144827A0/xx unknown
  • 1999-02-18 WO PCT/IN1999/000004 patent/WO2000048983A1/en not_active Application Discontinuation
  • 1999-02-18 JP JP2000599724A patent/JP2002542152A/ja not_active Withdrawn
  • 1999-02-18 CA CA2364245A patent/CA2364245C/en not_active Expired - Fee Related
  • 1999-02-18 AU AU28517/99A patent/AU2851799A/en not_active Abandoned

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