WO2007010838A1

WO2007010838A1 - Process for producing alkaline earth metal salt of (-)-hydroxycitric acid

Info

Publication number: WO2007010838A1
Application number: PCT/JP2006/314024
Authority: WO
Inventors: Shinji Yoshikawa; Shoichi Komai
Original assignee: Nippon Shinyaku Co., Ltd.
Priority date: 2005-07-15
Filing date: 2006-07-14
Publication date: 2007-01-25
Also published as: JP4998264B2; JPWO2007010838A1

Abstract

A novel process for producing alkaline earth metal salts of (-)-hydroxycitric acid (hereinafter referred to as “compounds (1)”)represented by the general structural formula: (1) wherein M is an alkaline earth metal. There is provided a process for producing compounds (1), comprising the steps of reacting with an extract of garcinia cambogia an alkaline earth metal oxide or alkaline earth metal hydroxide or hydroxide thereof amounting in molar ratio to 0.5 to less than 0.9 foldness of (-)-hydroxycitric acid contained in the garcinia cambogia, preferably followed by cooling, and collecting resultant deposit; and reacting the collected deposit with an alkaline earth metal salt and a base and separating the compounds (1).

Description

(1) —Method for producing alkaline earth metal salt of hydroxyquenate

Technical field

[0001] The present invention relates to an alkaline earth metal salt (hereinafter referred to as "compound (1)") represented by the following general structural formula (1): (1) -hydroxyquenic acid (hereinafter referred to as "HCA") Or a new method for producing the hydrate.

[Chemical 1]

[Wherein M represents an alkaline earth metal. ]

Background art

[0002] For example, HCA is known as a substance abundant in the skin of Garcinia, and inhibits ATP citrate lyase, one of the enzymes on the pathway to synthesize citrate fat. It is known to be useful in the treatment of obesity because it suppresses the increase in fat mass (see, for example, Patent Document 1).

[0003] Generally, HCA can be obtained by extraction from the skin of Garcinia by the method of Lewis, YS, and the like, and its salt can be obtained from HCA by a conventional method (for example, , Non-Patent Document 1, Non-Patent Document 2, and Patent Document 2;). HCA and its salts can be produced according to the method described in Patent Documents 3, 4, 5, 6, 7 in addition to the method of Lewis, Y. S. et al. However, these methods cannot remove all impurities such as bectin and organic acids such as citrate, malic acid and tartaric acid, and it is difficult to produce high-purity HCA and the like.

In particular, the calcium salt of HCA can be produced by reacting an excess amount of calcium hydroxide with garcinia extract. At the same time, pectin contained in the extract forms a hard gel with calcium hydroxide. It is also known to obtain a high-purity substance because citrate and maleic acid form calcium salts that are sparingly soluble in water. It is difficult with the manufacturing method.

Patent Document 1: US Patent No. 3764692

Patent Document 2: Indian Patent No. 160753

Patent Document 3: Pamphlet of International Publication No. 99Z03464

Patent Document 4: US Patent No. 6875891

Patent Document 5: International Publication No. 2004Z100682 Pamphlet

Patent Document 6: US Pat. No. 6,160,172

Patent Document 7: European Patent No.866866

Non-patent literature l: "Phytochemistry, 1965, 4 卷, p. 619—625

Non-Patent Document 2: Lewis, Y. S. et al., “Methods In Enzymology”, 1969, 13 卷, p. 613-617

Disclosure of the invention

Problems to be solved by the invention

[0004] An object of the present invention is mainly to provide a novel production method for obtaining a highly pure compound (1).

Here, “high purity” means 96% or more, preferably 98% or more, and more preferably 99% or more.

Means for solving the problem

[0005] As a result of intensive studies, the present inventors have found a production method that can achieve the above object, and have completed the present invention. Fortunately, it is an alkaline earth metal salt (hereinafter referred to as “compound (2)”) of a rataton HCA represented by the following general structural formula (2), which is an intermediate of compound (1). Or a production method for easily obtaining the hydrate thereof with high purity.

[Chemical 2]

M is as defined above. J [0006] Examples of the present invention include a method for producing compound (1) or a hydrate thereof having at least the following steps a to e.

Process a: Garcinia extract and alkaline earth metal hydroxide or alkaline earth metal hydroxide in a molar ratio of 0.5 to 0.9 times the HCA contained in Garcinia Reacting the product or its hydrate,

Step b: A step of depositing a product by leaving or cooling the reaction solution of Step a, Step c: A step of obtaining the precipitate,

Step d: a step of reacting the obtained precipitate with an alkaline earth metal salt or hydrate thereof and a base,

Step e: A step of obtaining an alkaline earth metal salt of HCA or a hydrate thereof from the reaction solution in step d.

[0007] Further, the present invention can include a method for producing compound (2) or a hydrate thereof having at least the following steps a 'to c'.

Step a ,: Alkaline earth metal oxide or alkaline earth metal hydroxide in a range of 0.5 times or more and less than 0.9 times in molar ratio to Garcinia extract and HCA contained in Garcinia Reacting the product or its hydrate,

Step b ′: a step of depositing a product by leaving or cooling the reaction liquid in step a ′, step c ′: a step of acquiring the precipitate and recrystallizing the acquired precipitate.

Brief Description of Drawings

[0008] Fig. 1 shows a chromatogram obtained by HPLC analysis. In the figure, the vertical axis represents time (minutes) and the horizontal axis represents absorption intensity.

[Figure 2] Shows the chromatogram obtained by HPLC analysis. In the figure, the vertical axis represents time (minutes) and the horizontal axis represents absorption intensity.

[Fig. 3] Shows a chromatogram obtained by HPLC analysis. In the figure, the vertical axis represents time (minutes) and the horizontal axis represents absorption intensity.

[FIG. 4] A chromatogram obtained by HPLC analysis is shown. In the figure, the vertical axis represents time (minutes) and the horizontal axis represents absorption intensity.

[FIG. 5] A chromatogram obtained by HPLC analysis is shown. In the figure, the vertical axis represents time (minutes) and horizontal The axis indicates the absorption intensity.

[Fig. 6] A chromatogram obtained by HPLC analysis is shown. In the figure, the vertical axis represents time (minutes) and the horizontal axis represents absorption intensity.

FIG. 7 shows a chromatogram obtained by HPLC analysis. In the figure, the vertical axis represents time (minutes) and the horizontal axis represents absorption intensity.

FIG. 8 shows a chromatogram obtained by HPLC analysis. In the figure, the vertical axis represents time (minutes) and the horizontal axis represents absorption intensity.

BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the present invention will be described in detail.

L Lee ^^ (1) and the end of 7k 禾 D)

(1) About process a

Ganorescinia extract is an extract that contains a large amount of HCA. It can be obtained by performing an extraction operation.

Garcinia extract contains a small amount of strength, for example, polysaccharides such as pectin, and organic acids such as citrate, lingoic acid and tartaric acid. Even a garshi layer containing such impurities can be used in the present invention.

Currently, Garcinia extract is marketed as an aqueous solution containing HCA in the range of 10% to 70% by weight. Examples of such commercial products include Garcinia Extract S (manufactured by Nippon Shinyaku Co., Ltd.), Garcitric Gold (registered trademark) (manufactured by Renaissance Herb (USA), Citrin (registered trademark) (manufactured by Sabinsa (USA)). Citrimax (registered trademark) (manufactured by Interhealth (USA)).

The concentration of HCA contained in the garcinia extract is suitably within the range of 5% to 90% by weight, preferably within the range of 7% to 80% by weight, more preferably 10% to 70% by weight. Is within the range. If necessary, water may be added to adjust the concentration of HCA contained in the Garcinia extract.

[0010] Garcinia extract and alkaline earth metal hydroxide or alkaline earth metal hydroxide The reaction with the hydrate is carried out by, for example, stirring the garcinia extract and the alkaline earth metal oxide or alkaline earth metal hydroxide or hydrate in an aqueous solution while heating and stirring. Can be performed. At that time, if necessary, an appropriate amount of activated carbon may be added. Examples of the “alkaline earth metal oxides” include acid calcium. Examples of the “alkaline earth metal hydroxide or hydrate thereof” include calcium hydroxide or a hydrate thereof. Among these, calcium hydroxide dihydrate is particularly preferable.

[0011] The amount of the alkaline earth metal oxide or alkaline earth metal hydroxide or hydrate thereof is not particularly limited as long as the reaction solution does not show basicity. The molar ratio with respect to HCA contained in the Garcinia extract is suitably in the range of 0.5 times or more and less than 0.9 times, preferably in the range of 0.7 times or more and less than 0.9 times, more preferably 0.

It is within the range of 8 times or more and less than 0.9 times.

[0012] The amount of activated carbon used varies depending on the garcinia extract used, but is suitably in the range of 1 to 10% by weight with respect to the HCA contained in the garcinia extract, preferably 2 It is in the range of 7% by weight to 7% by weight, more preferably in the range of 3% to 4% by weight.

[0013] The reaction temperature varies depending on the concentration of HCA contained in the Garcinia extract and the amount of alkaline earth metal oxide or alkaline earth metal hydroxide used. Usually 20 ° C to 10 ° C

The range of 0 ° C is suitable, preferably within the range of 40 ° C to 95 ° C, more preferably 60 ° C.

Within the range of ~ 90 ° C.

Although the reaction time varies depending on the reaction temperature, etc., it is suitable within the range of 1 minute to 24 hours.

, Preferably within the range of 5 minutes to 12 hours, more preferably within the range of 10 minutes to 1 hour.

[0014] (2) About step b

This step can be performed, for example, by leaving the reaction solution of step a as it is at room temperature after completion of the reaction of step a. It can also be carried out by cooling the reaction solution in step a, and it is preferable to cool it rather than leaving it at room temperature. The effective cooling temperature is usually in the range of 10 ° C to 30 ° C, preferably in the range of 5 ° C to 25 ° C. Within the range, more preferably within the range of 0 ° C to 20 ° C. The cooling time is suitably in the range of 1 minute to 48 hours, preferably in the range of 10 minutes to 36 hours, and more preferably in the range of 20 minutes to 24 hours.

[0015] (3) About step c

This step can be performed by performing a filtration operation by a conventional method. The precipitates that can be produced in this step c are substantially free of impurities such as bectin, which is a polysaccharide, citrate, malic acid, tartaric acid, which are organic acids, which have been difficult to remove completely until now. Contained in a way.

[0016] (4) Step d

This step can be carried out, for example, by dissolving the precipitate obtained in step c with heating in water, adding an alkaline earth metal salt or hydrate thereof and a base, and stirring with heating. If necessary, a filtering operation can be performed after adding the alkaline earth metal salt.

[0017] The amount of water used is, for example, suitably in the range of 5 to 100 times by weight with respect to the precipitate, preferably in the range of 10 to 70 times, more preferably 20 to 40 times. Within double range.

Examples of alkaline earth metal salts include calcium salts. Examples of the “calcium salt” include calcium chloride, calcium sulfate, calcium carbonate, and calcium bromide. Of these, calcium chloride dihydrate is particularly preferred.

The amount of the alkaline earth metal salt or hydrate thereof used is, for example, suitably in the range of 0.40 times to 0.70 times, preferably 0.45 times the molar ratio to the precipitate. Within the range of ~ 0.65 times, more preferably within the range of 0.50 times to 0.660 times.

Examples of the “base” include amines such as aqueous ammonia, pyridine, and trimethylamine.

The amount of base used is, for example, suitably in the range of 0.5 to 2.0 times in molar ratio to the precipitate, preferably in the range of 0.9 to 1.5 times, More preferably, it is in the range of 1.0 times to 1.2 times.

The reaction temperature is usually within the range of 20 ° C to 100 ° C, preferably 30 ° C to 9 ° C. It is within the range of 5 ° C, more preferably within the range of 40 ° C to 90 ° C.

The reaction time varies depending on the reaction temperature and the like, but is suitably in the range of 1 minute to 12 hours, preferably in the range of 5 minutes to 7 hours, and more preferably in the range of 10 minutes to 2 hours.

[0018] (5) Process e

The compound (1) in the reaction liquid in the step d can be obtained by performing a known solid-liquid separation operation. When performing the solid-liquid separation operation, the compound (1) can be washed with water. Examples of the solid-liquid separation operation include a filtration operation, a dehydration operation using a centrifuge, or a juicer.

If necessary, the compound (1) can be further purified. Specifically, the purity can be further increased by, for example, stirring the water of 10 to 20 times by weight with respect to the obtained compound (1) and performing the above solid-liquid separation operation. it can. If necessary, the mixture may be heated and stirred within a range of 40 ° C to 60 ° C.

[0019] Since the compound (1) obtained by performing the solid-liquid separation operation contains a large amount of water, it is preferable to perform a drying operation.

Examples of the drying operation include drying under reduced pressure. The vacuum force, for ^{^{example, 1. 0xl0 _13 Pa~l. 0xl0 5}} Pa and is suitably within the range of, the good Mashiku 1. 0xl0 ^_9 Pa~l. 0xl0 ⁴ within the Pa, more preferably 1. 0xl0 " ⁵ Pa ~ l. Within the range of 0xl0 ³ Pa.

The drying temperature is, for example, suitably in the range of 50 ° C to 140 ° C, preferably in the range of 60 ° C to 130 ° C, more preferably in the range of 70 ° C to 120 ° C. .

The drying time is suitably in the range of 1 hour to 96 hours, preferably in the range of 12 hours to 72 hours, more preferably in the range of 24 hours to 48 hours.

[0020] For the production of compound (1), the precipitate produced in step c from which impurities such as bectin, a polysaccharide, and organic acids such as citrate, malic acid, and tartaric acid are removed is used. Therefore, the highly pure compound (1) can be easily obtained.

Further, the compound (1) produced in the present invention uses only water as a reaction solvent and a washing solvent used in the production process, methanol, ethanol, butanol, chloroform, methylene chloride, acetonitrile, Dimethylformamide, acetone, dimethyl Since organic solvents such as til sulfoxide are not used, there is no concern about residual solvents that are harmful to humans and animals.

[0021] II. Method for producing compound (2) and hydrates thereof

(1) About process a '

This step is the same as step a in I above.

(2) About step b

This process is the same as the process b in I above.

(3) About process c '

This step can be carried out by recrystallizing the precipitate after performing a filtration operation by a conventional method to obtain the precipitate.

To the obtained precipitate, for example, water in the range of 1 to 10 times by weight is added and heated in the range of 50 ° C to 100 ° C to dissolve the precipitate and left as it is at room temperature or The compound (2) can be produced by cooling and recrystallization. The effective cooling temperature is usually in the range of 10 ° C to 30 ° C, preferably in the range of 5 ° C to 25 ° C, more preferably in the range of 0 ° C to 20 ° C. Within range. The cooling time is suitably in the range of 1 minute to 48 hours, preferably in the range of 10 minutes to 36 hours, and more preferably in the range of 20 minutes to 24 hours.

[0022] The compound (2) that can be produced in this step has been difficult to completely remove until now, such as polysaccharides bectin, organic acids such as citrate, malic acid, tartaric acid, etc. Contain substantially no impurities.

In addition, the compound (2) produced in the present invention uses only water as the reaction solvent and washing solvent used in the production process, methanol, ethanol, butanol, chloroform, methylene chloride, acetonitrile, Since organic solvents such as dimethylformamide, acetone, and dimethyl sulfoxide are not used, there is no concern about residual solvents that are harmful to humans and animals.

[0023] Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited thereto.

[0024] Example 1 While stirring 30 mL of water in 20 g of Garcinia Extract (Garcitric Gold (registered trademark) Liquid; made in Renaissance Herbnet (USA); containing 60.75 wt% as HCA), 3.03 g, 3.46 g, 3. Add 89g, 4.33g or 4.76g of calcium hydroxide and 85. Each reaction solution stirred for 30 minutes at C was allowed to stand at 5 ° C for 2 days, and the resulting precipitate was collected by filtration. The results are shown in Table 1.

[table 1]

The purity of the precipitate deposited under each condition was confirmed using a high performance liquid chromatography (hereinafter referred to as “H PLCJ”) apparatus.

0.1 g of the precipitate precipitated under each condition was diluted with water so that the total amount became lOOmL, and HPLC measurement was performed under the following conditions.

[Measurement condition]

HPLC system: Liquid feed: LC-7A (manufactured by Shimadzu Corporation)

Detector: SPD—10AV (manufactured by Shimadzu Corporation)

Organic acid analysis column: ULTRON PS-80H

<8mm φ x30cm> 1 (made by Shinwa Kako Co., Ltd.)

<8mm φ x5cm> 1 piece (Shinwa Kako Co., Ltd.)

Column temperature: 50 ° C

Mobile phase: water (adjusted to pH 2. 20 using perchloric acid)

Flow rate: 0.81mlZ min

UV-visible spectrometer detection wavelength: 210nm

Injection volume: 20 μ 1

The results are shown in Figs.

In FIGS. 1 to 8, peak 1 represents impurities contained in the mobile phase, peak 2 represents HCA ratatones, peak 3 represents HCA, and peak 4 represents the organic acid citrate.

In Example 1, only the mobile phase used was analyzed by HPLC. Mouth matogram was obtained.

As a result of HPLC analysis of the garcinia extract used in Example 1, a chromatogram as shown in FIG. 2 was obtained. It was confirmed that the garcinia extract contained at least citrate (a substance having a retention time of about 8 minutes) as an impurity.

In Example 1, the results of using 0.9% molar ratio of calcium hydroxide to HCA contained in the Garcinia extract used in Fig. 5 are used in Example 1. Fig. 6 shows the results when calcium hydroxide is used at a molar ratio of HCA contained in Garcinia extract. In Example 1,! /, The precipitate obtained when using 0.9 times the molar ratio of calcium hydroxide and calcium hydroxide with respect to the HCA contained in the Garcinia extract used, It was confirmed that the impurity citrate (peak 4 in Figs. 5 and 6) was included.

In Example 1, the result of using 0.7% molar ratio of calcium hydroxide with respect to HCA contained in the Garcinia extract used in FIG. 3 is used in Example 1. Figure 4 shows the results of using 0.8 times the molar ratio of calcium hydroxide relative to the HCA contained in Garcinia extract. In Example 1! / Precipitates obtained when calcium hydroxide with a molar ratio of 0.8 times or less with respect to HCA contained in the used Garcinia extract has been difficult to remove completely until now. It was also confirmed that impurities such as polysaccharides such as bectine, organic acids such as citrate, malic acid and tartaric acid were not included.

Further, in Example 1, each precipitate obtained when 0.7 times and 0.8 times the molar ratio of calcium hydroxide was used with respect to the HCA contained in the Garcinia extract used in Example 1. 10 mL of water was added, dissolved by heating at 90 ° C, and then the precipitate obtained by standing was subjected to HPLC measurement and measurement of the amount of calcium contained in the precipitate. The amount of calcium contained in the precipitate was measured according to a known method using 0.05M ethylenediamine tetraacetic acid aqueous solution. It was confirmed that the recrystallized precipitates were only HCA rataton calcium salts (peak 2 in Figs. 7 and 8) (see Figs. 7 and 8).

Example 2

4kg Garcinia Extract (Garcitric Gold (registered trademark) Liquid; Renaissance herb Co. (USA); HCA containing 64.0% by weight) While stirring 6L of water, 0.664 kg of calcium hydroxide (8.64 mol; molar ratio to HCA is 0. 70 times calcium hydroxide) and 100 g activated carbon were added and stirred at 85 ° C for 30 minutes. The reaction mixture was then filtered while washing with hot water at 80 ° C.

The filtrate was allowed to stand overnight at 5 ° C, and 1.5 kg of the deposited precipitate (HCA rataton calcium salt) was collected by filtration.

7.7 L of water was added to the calcium salt of the resulting HCA rataton body, dissolved by heating at 90 ° C., stirred as it was for 5 minutes, and then filtered. The obtained filtrate was heated again to 85 ° C, cooled to 20 ° C or lower, and allowed to stand for 30 minutes.The resulting precipitate was collected by filtration, and purified HCA ratatotone calcium salt 1. 0 kg was obtained (yield: 51%).

The amount of calcium contained in the precipitate was measured according to a known method using 0.05 M ethylenediamine tetraacetic acid aqueous solution.

Melting point: 250 ° C or higher

Elemental analysis value (as C H O Ca-4H O)

6 4 7 2

Theoretical values: H: 4.0.3%, C: 24. 0%

Actual value: H: 3. 88%, C: 23.9%

Calcium content:

Theoretical value: Ca: 13. 35%

Actual value: Ca: 13. 40%

Specific rotation: [α] ² ° = 67. 0 ° (c = 0. 2, HO)

D 2

'Η NMR (D O)

2

4.84 (s, 1H), 3.18 (d, 1H), 2.83 (d, 1H)

Example 3 Production of calcium salt of HCA

20 L of water was added to 1.0 kg (4.4 mol) of HCA ratatotone calcium salt obtained in Example 2 and stirred at 80 ° C. for 5 minutes. Then, 0.35 kg of salty calcium dihydrate (2.4 mol) and 0.5 L of water were added and dissolved, and then the reaction solution was filtered. The obtained filtrate was heated again to 80 ° C., stirred as it was for 5 minutes, and then cooled to 50 ° C. to 60 ° C. 0.29 kg of 28% aqueous ammonia was added dropwise to the reaction solution and stirred at 85 ° C for 60 minutes. The precipitate was subjected to solid-liquid separation with a centrifuge (manufactured by Sakuma Seisakusho) for 10 minutes. The obtained solid was collected to obtain 0.55 kg of crude HCA calcium salt.

The obtained crude calcium salt of HCA was charged with 8.25 L of water, heated to 50 ° C. and stirred for 5 minutes, and then subjected to solid-liquid separation with a centrifuge for 10 minutes. The obtained solid was collected and the same purification operation was performed again. The obtained solid was dried at 100 ° C for 1 hour, and then the solid was pulverized, and then dried at 80 ° C for 41 hours and 115 ° C for 7 hours to obtain 0.62 kg of the target compound (yield: 53% ).

Melting point: 250 ° C or higher

Elemental analysis value (as C H O Ca '5H O)

12 10 16 3 2

Theoretical values: H: 3.25%, C: 23.23%

Actual value: H: 3.40%, C: 23.11%

Calcium content:

Theoretical value: Ca: 19.38%

Actual value: Ca: 19.60%

Specific rotation: [α] ^2G = — 26.0 ° (c = 0.2, HO)

D 2

'Η NMR (D O)

2

4.ll (s, 2H), 2.84 (d, 2H), 2.64 (d, 2H)

Industrial applicability

Since no organic solvent is used in the production process of compound (1), compound (1) can be produced safely and at low cost, and there is no concern about residual organic solvent. In addition, since a precipitate from which impurities such as citrate, malic acid, tartaric acid, etc., which are organic acids, such as bectin, which is a polysaccharide contained in Garcinia extract, is removed, a high-purity compound ( 1) can be manufactured.

Claims

Claims Represented by the following general structural formula (1) having at least the following steps a to e (a method for producing an alkaline earth metal salt of citrate or a hydrate thereof.

[Chemical 1]

[Wherein M represents an alkaline earth metal. ]

Process a: Garcinia extract and (1) Alkaline earth metal oxide or alkali earth within a molar ratio of 0.5 times or more and less than 0.9 times the molar ratio of hydroxycienic acid contained in Garcinia extract Reacting with metal hydroxide or its hydrate,

Step e: A step of obtaining (1) -alkaline earth metal salt of hydroxy quenoic acid or a hydrate thereof from the reaction solution of the reaction of Step d.

[2] (1) -Hydroxycene according to claim 1, wherein the ganoressin extract is obtained by extracting from the skin of goraka (Garcinia cambogia), indomangosteen (Garcinia inrovica) or garguru (Garcinia atroviridis). A method for producing an alkaline earth metal salt of an acid or a hydrate thereof.

[3] The alkaline earth metal salt of (1) -hydroxycenoic acid or a hydrate thereof according to any one of claims 1 and 2, wherein the base used in step d is ammonia water, pyridine or trimethylamine. Manufacturing method.

[4] The alkaline earth metal salt of (1) -hydroxyquenic acid according to any one of claims 1 to 3, wherein the alkaline earth metal oxide used in step a is calcium carbonate Hydrate manufacturing method.

The alkaline earth metal hydroxide or hydrate used in step a is a calcium hydroxide or calcium hydrate. 4. The method for producing an alkaline earth metal salt of (1) -hydroxyquenic acid or a hydrate thereof according to any one of claims 1 to 3, wherein is a hydrate thereof.

6. The alkaline earth metal salt of (1) -hydroxyquenic acid according to any one of claims 1 to 5, wherein the alkaline earth metal salt or hydrate thereof used in step d is a calcium salt or a hydrate thereof. For producing a metal salt or a hydrate thereof.

7. The process for producing an alkaline earth metal salt of (1) -hydroxyquenoic acid or a hydrate thereof according to claim 6, wherein the calcium salt is calcium chloride.

[8] A process for producing an alkaline earth metal salt of a latathon body of hydroxy acid represented by the following general structural formula (2) having at least the following steps a ′ to c ′ or a hydrate thereof:

(2)

[Wherein M represents an alkaline earth metal. ]

Step a ,: Garcinia extract and (1) Alkaline earth metal oxide or alkali within a range of 0.5 times or more and less than 0.9 times in molar ratio with respect to monohydroxy quenate Reacting with an earth metal hydroxide or a hydrate thereof,

Step b ': a step of depositing a product by leaving or cooling the reaction solution of step a', step c ': a step of obtaining the precipitate and recrystallizing the obtained precipitate.

[9] The (1) -hydroxycend according to claim 8, wherein the ganoressin extract is obtained by extracting from the peel of goraka (Garcinia cambogia), indomangosteen (Garcinia inrovica) or gurugur (Garcinia atroviridis). A method for producing alkaline earth metal salts or hydrates of acid ratatones.

[10] The alkaline earth metal of the ratatones of (1) hydroxychenic acid according to any one of claims 8 or 9, wherein the alkaline earth metal oxide used in step a 'is acid calcium. A method for producing a metal salt or a hydrate thereof.

[11] Alkaline earth metal hydroxide or its hydrate used in step a 'is calcium hydroxide Or (1) a method for producing an alkaline earth metal salt of an acid ratatotone or a hydrate thereof according to any one of claims 8 and 9, which is a hydrate thereof.