Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Food or edible as carrier for pharmaceutical
Reexamination Certificate
2000-08-11
2002-05-28
Killos, Paul J. (Department: 1623)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Food or edible as carrier for pharmaceutical
C562S584000, C514S574000
Reexamination Certificate
active
06395296
ABSTRACT:
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.
BACKGROUND
(−) Hydroxycitric acid (HCA) occurs in the fruit rind of Garcinia species (
G. cambogia, G. indica
and
G. atroviridis
). The first two species grow abundantly in India and the third occurs mostly in South East Asian countries. The success of this natural food product derived from Garcinia fruit has been documented and been in use since several centuries BC. Also known as “Kokum”, the extracts of the fruit have been used as a tart flavoring in meat and seafood dishes, turned into a refreshing beverage that serves as a unique flavor enhancer, gourmet spice and a digestive after a heavy meal. In Ayurveda, the traditional ancient system of herbal medicine in India, Garcinia is also considered to be one of the prime herbs that are beneficial for the heart.
In more recent times, Garcinia has received worldwide attention as a nutriceutical for effective obesity control. Several scientists including at Hoffman-La Roche have established that HCA, the active ingredient in the fruit, prevents the conversion of excess carbohydrates to fat in animals. The energy released by the excess carbohydrate is converted into and stored as glycogen, a readily usable form of energy. Interestingly, it has been shown to inhibit ATP dependent citrate-lyase, a key enzyme in diverting carbohydrate to fatty acids and cholesterol synthesis. (Sullivan et al. Lipids, 9:121 and 129 (1973), Sergio, W., Medical Hypotehsis 27:39 (1988)).
The age-old practice of consuming Garcinia rind as a food additive by inhabitants of Malabar and Konkan coast of the Indian peninsula has established the safety of HCA. The isolation and chemical nature of (−) hydroxycitric acid from Garcinia rind are described in the publication of Lewis Y. S., et al. (Methods in Enzymology, 13:613 (1967) and in the patents (Indian patents 160753 & 178298 and U.S. Pat. Nos. 5,536,516 & 5,656,314).
It is believed that consumption of HCA influences the body metabolism leading to the saturation of glycogen receptors in the liver and a consequent transmission of signals of satiation to brain. Even as a food supplement, (−) HCA helps a person to lose/control weight in a natural way without affecting normal physical activities.
In view of its unique property, several health care formulations incorporating HCA are being sold across the counter in the Western markets. These include tablets, capsules, herbal teas, chocolate bars, milk shakes and other beverages. The active ingredient (HCA) from this insoluble HCA salt is released upon contact with hydrochloric acid in the stomach and absorbed through the intestine to exert its metabolic effect.
There is prior art on the preparation of a soluble tri-potassium salt of (−) HCA (Lewis Y. S., et al (Methods in Enzymology, 13:613 (1967), International Patent WO 96/36585, U.S. patent Ser. No. 08/440,968 filed). However, its alkaline nature and risks associated with the consumption of high potassium (~36%) makes this product unsuitable for HCA-based formulations.
In our earlier patents (Indian patent No. 178298 &.U.S. Pat. Nos. 5,536,516, 5,656,314) which describes preparation of a concentrate of (−) hydroxycitric acid and its lactone in liquid form, comprising of several steps like water extraction of Garcinia rind containing (−) hydroxycitric acid and its concentration, acetone refinement of this concentrated water extract, evaporation of acetone, loading thus obtained refined extract on ion-exchange columns containing an anion exchange resin followed by a cation exchange resin, and finally evaporation of the free acid liberated from the ion-exchange process to said concentration. This liquid form of (−) hydroxycitric acid has problems of stability and half-life.
In addition, its highly acidic nature poses problems in formulating into beverage and various other food products without affecting their flavor and properties.
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.
To achieve the said objective, this invention provides a new soluble double metal salt of group IA and II A of (−) hydroxycitric acid of general formula I and more particularly formula II as given below:
Where X is IA group metal: Li or Na or K or Rb or Cs or Fr
Where Y is 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%,
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 IA metal salt of (−) hydroxycitric acid,
ii) displacing completely the said group IA 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 (−) hydroxycitri
Balasubramanyam Karanam
Chandrasekhar Bhaskaran
Ramadoss Candadai Seshadri
Rao Pillarisetti Venkata Subba
Jain Mishrilal
Killos Paul J.
Nirmel C.
Nirmel & Associates
Tucker Zachary C.
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