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Chemical Structure| 6205-14-7 Chemical Structure| 6205-14-7
Chemical Structure| 6205-14-7

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Hydroxycitric acid, a natural product isolated and purified from the fruits of Garcinia atroviridis, can inhibit fat synthesis and reduces food intake, the primary mechanism of action of HCA appears to be related to its ability to act as a competitive inhibitor of the enzyme ATP-citrate lyase, which catalyzes the conversion of citrate and coenzyme A to oxaloacetate and acetyl coenzyme A (acetyl-CoA), primary building blocks of fatty acid and cholesterol synthesis, and ameliorate high-fructose-induced redox imbalance and activation of stress sensitive kinases in male Wistar rats through its hypolipidemic effects.

Synonyms: HCA; (±)-Hydroxycitric Acid

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Product Details of Hydroxycitric Acid

CAS No. :6205-14-7
Formula : C6H8O8
M.W : 208.12
SMILES Code : OC(C(C(O)=O)O)(C(O)=O)CC(O)=O
Synonyms :
HCA; (±)-Hydroxycitric Acid
MDL No. :MFCD02093093
InChI Key :ZMJBYMUCKBYSCP-UHFFFAOYSA-N
Pubchem ID :123908

Safety of Hydroxycitric Acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Hydroxycitric Acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 6205-14-7 ]

[ 6205-14-7 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 499-12-7 ]
  • [ 6205-14-7 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 12 (-)-threo-Hydroxycitric acid (-)-threo-Hydroxycitric acid ethylenediamine salt (26.8 g, 0.1 mole) was added in one portion to a stirred mixture of trifluoroacetic acid (130 ml) and water (5.0 ml) previously cooled to 5-10. Within several minutes the salt had essentially all dissolved and crystals of (-)-threo-hydroxycitric acid had begun to form in the mixture. After 30 minutes the solids were collected by filtration and were washed with trifluoroacetic acid (3*50 ml). The mother liquors were discarded and the solid was washed with ether and dried to give 20.1 g of the triacid, mp 154.5-155.5. This material was recrystallized by dissolving 20.1 g of triacid in 18 ml of water at 15 and diluting the solution in one portion with 100 ml trifluoroacetic acid. The mixture was chilled to -10 in an acetone ice bath and the resulting crystalline material was recovered to give 19.2 g of (-)-threo-hydroxycitric acid, mp 156.5-158; [alpha]D 25 -9.9 (C, 1.0, H2 O).
There may also be mentioned, alone or as a mixture, the following tricarboxylic and tetracarboxylic acids, and their anhydrides: ... 4-(3-carboxyphenyl)-2,5-pyridinedicarboxylic acid 3-(carboxymethyl)-2,4-quinolinedicarboxylic acid 3-(carboxymethyl)-1H-indole-2,5-dicarboxylic acid 3-C-carboxy-2-deoxy-D-threopentaric acid hydroxycitric acid D-glucopyranuronosyl-D-arabino-2-hexylofuranosidaric acid 2,3,5,6-pyridinetetracarboxylic acid N,N'-1,2-ethanediylbis[N-(carboxymethyl)-beta-alanine ...
Mention may also be made, alone or as a mixture, of the following tricarboxylic and tetracarboxylic acids, and also the anhydrides thereof: ... 4-(3-carboxyphenyl)-2,5-pyridinedicarboxylic acid 3-(carboxymethyl)-2,4-quinolinedicarboxylic acid 3-(carboxymethyl)-1H-indole-2,5-dicarboxylic acid 3-C-carboxy-2-deoxy-D-threo-pentaric acid hydroxycitric acid D-glucopyranuronosyl-D-arabino-2-hexulofuranosidaric acid 2,3,5,6-pyridinetetracarboxylic acid N,N'-1,2-ethanediylbis[N-(carboxymethyl)-beta-alanine ...
There may also be mentioned, alone or as a mixture, the following tricarboxylic and tetracarboxylic acids, and their anhydrides: ... 4-(3-carboxyphenyl)-2,5-pyridinedicarboxylic acid 3-(carboxymethyl)-2,4-quinolinedicarboxylic acid 3-(carboxymethyl)-1H-indole-2,5-dicarboxylic acid 3-C-carboxy-2-deoxy-D-threopentaric acid hydroxycitric acid D-glucopyranuronosyl-D-arabino-2-hexulofuranosidaric acid 2,3,5,6-pyridinetetracarboxylic acid N,N'-1,2-ethanediylbis[N-(carboxymethyl)-beta-alanine ...
EXAMPLE 3 (+)-Erythro-hydroxycitric acid, gamma lactone (Hibiscus acid) from (+)-threo-epoxyaconitic acid] A solution of the dextrarotatory epoxide prepared as in Example 2 (1.9 g.: 30 meq.) in 1N sodium hydroxide (30 ml.) was refluxed under nitrogen for three days. The reaction mixture was then cooled to ~ 80 and a solution of calcium chloride (2.6 g.) in water (5 ml.) was added rapidly with stirring. The resulting white precipitate was collected by filtration and washed well with water then was dissolved in the minimum amount of 1N hydrochloric acid (~ 15 ml.). The solution was passed through a column of cationic exchange resin (Amberlight IRA 120; 30 ml.). The acidic eluents were evaporated to dryness and then the residue was heated on a steam bath to induce crystallization to give essentially pure lactone. The residue was dissolved in ethyl acetate and the pale yellow solution was decolorized with charcoal. Two crystallizations from ethyl acetate-carbon tetrachloride furnished analytically pure hibiscus acid, mp 187-8; [alpha]D25 + 109 (c, 1.0, H2 O), identical with authentic material.

  • 3
  • [ 499-12-7 ]
  • [ 13898-47-0 ]
  • [ 6205-14-7 ]
  • 5
  • parasaccharate barium [ No CAS ]
  • [ 6205-14-7 ]
  • 6
  • [ 6205-14-7 ]
  • [ 75-36-5 ]
  • trimethyl ester [ No CAS ]
  • (+/-)-Threo-1,2-dihydroxy-1,2,3-propanetricarboxylic acid, trimethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; sodium chloride; In methanol; water; EXAMPLE 11 (+-)-Erythro-1,2-dihydroxy-1,2,3-propanetricarboxylic acid, trimethyl ester To a solution of (+-)-erythro-<strong>[6205-14-7]hydroxycitric acid</strong>, gamma lactone; (21 g.) in methanol (400 ml.) was added acetyl chloride (21 g.). The solution was brought to reflux and maintained at this temperature for 90 minutes, then was cooled and left overnight at room temperature. Enough pyridine (19 ml.) was added to neutralize the reaction mixture then the solvent was removed under reduced pressure. The resulting syrup was dissolved in water (350 ml.) and the solution was extracted with ether (5 * 100 ml.). The ether extracts were backwashed in turn with water (2 * 100 ml.). Sodium chloride (~ 125.g) was dissolved in the combined aqueous layers and the solution was extracted with methylene chloride (1 * 350 ml.; 3 * 125 ml.). The methylene chloride extracts were washed in turn with brine and with saturated sodium bicarbonate solution. The dried (MgSO4) methylene chloride extracts were concentrated in vacuo to give the trimethyl ester as a viscous oil.
  • 7
  • potassium (-)-hydroxycitrate [ No CAS ]
  • [ 6205-14-7 ]
YieldReaction ConditionsOperation in experiment
20% With hydrogenchloride; In water; Ingredients. (1) Tripotassium Hydroxycitrate Hydrate 34.0, (2) Deionized water 36.0, (3) Hydrochloric Acid (10 molar solution in water) 30.0. Procedure. Mix (1) and (2) with heating to a clear solution. Add (3) and mix. Upon cooling, potassium chloride precipitates out, which is then removed by filtration. A solution of hydroxycitric acid (20%) in water is thus obtained. This solution is useful for other compositions that may require hydroxycitric acid.
  • 8
  • calcium hydroxide [ No CAS ]
  • [ 6205-14-7 ]
  • [ 743369-26-8 ]
  • calcium and zinc double salt of HCA [ No CAS ]
YieldReaction ConditionsOperation in experiment
To an aqueous purified extract of garcinia solution (83 ml, 3.5 g) was added a solution of zinc carbonate (1.25 g) in water (20 mL) and stirred for 0.5 h. Charcoal (2.0 g) was added and stirred at 70-80 C for 1 h and filtered through celite. Then a solution of calcium hydroxide (1.8 g) in water (50 mL) was added and the solution was stirred at 70-80 C for 4 h. The solution was cooled and the precipitated solid was filtered and dried to give a colourless calcium and zinc double salt of <strong>[6205-14-7]HCA</strong> (5.0 g). The .analysis showed that (-) -<strong>[6205-14-7]HCA</strong> is 64.14%;'lactone is 0.42%; calcium is 10.09% and zinc is 9.69%.
  • 9
  • [ 6205-14-7 ]
  • [ 743369-26-8 ]
  • magnesium carbonate [ No CAS ]
  • magnesium and zinc double salt of HCA [ No CAS ]
YieldReaction ConditionsOperation in experiment
To an aqueous purified extract of garcinia solution (83 ml, 3.5 g) was added a solution of magnesium carbonate (3.6 g) in water (20 mL) and stirred for 0.5 h. Then a solution of zinc carbonate (2.0 g) in water (50 mL) was added and the solution was stirred at 70-80 C for 4 h. Charcoal (3.0 g) was added and stirred at 70-80 C for 1 h and filtered through celite. The solution was evaporated to give a colourless magnesium and zinc double salt of <strong>[6205-14-7]HCA</strong> (5.0 g). The analysis showed that (-) -<strong>[6205-14-7]HCA</strong> is 66.50%; lactone is 0.65%; magnesium is 8.5% and zinc is 9.5%.
  • 10
  • calcium hydroxide [ No CAS ]
  • [ 6205-14-7 ]
  • magnesium carbonate [ No CAS ]
  • calcium and magnesium double salt of HCA [ No CAS ]
YieldReaction ConditionsOperation in experiment
To an aqueous purified extract of garcinia solution (83 ml, 3.5 g) was added a solution of magnesium carbonate (0.9 g) in water (10 mL) and stirred for 0.5 h. Then a solution of calcium hydroxide (1.25 g) in water (50 mL) was added and after stirring for 1 h, the pH of the solution was adjusted to 9.4 using magnesium carbonate (0.5 g) and calcium hydroxide (0.5 g). The solution was stirred at 70-80 C for 4 h. The solution was cooled and filtered and the solid obtained was dried to give a colourless calcium and magnesium double salt of <strong>[6205-14-7]HCA</strong> (4.8 g). The analysis showed that (-) -<strong>[6205-14-7]HCA</strong> is 73.88%; lactone is 0.24%; calcium is 12.78% and magnesium is 2.50%. Example 2 Calcium and magnesum double salt of <strong>[6205-14-7]HCA</strong> To an aqueous purified extract of garcinia solution (332 ml, 14.0 g) was added a solution of magnesium carbonate (8.0 g) in water (50 mL) and stirred for 0.5 h. Then a solution of calcium hydroxide (4.8 g) in water (100 mL) was added and the solution was stirred at 70-80 C for 4 h. The pH of the solution was adjusted to 7.5 using garcinia solution. Charcoal (5.0 g) was added and stirred at.70-80 C for 1 h and filtered through celite. The solution was evaporated or spray dried to give a colourless calcium and magnesium double salt of <strong>[6205-14-7]HCA</strong> (13.0 g). The analysis showed that (-) -<strong>[6205-14-7]HCA</strong> is 73.17%; lactone is 0.43%; calcium is 11.88% and magnesium is 5.73%.
  • 11
  • magnesium hydrogencarbonate [ No CAS ]
  • [ 6205-14-7 ]
  • potassium hydroxide [ No CAS ]
  • HCA potassium/magnesium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
a. In a 500 ml glass beaker, pure acid form of <strong>[6205-14-7]HCA</strong> is diluted with distilled water. Calculate number of carboxylic group. Check mol. ratio of <strong>[6205-14-7]HCA</strong> free acid to <strong>[6205-14-7]HCA</strong> lactone. b. Add a solution of KOH using a half equivalent relative to <strong>[6205-14-7]HCA</strong> acid, and react for a period of 0.5, 1.0 or 1.5 h. Each reaction is analyzed using HPLC to obtain a molar ratio of <strong>[6205-14-7]HCA</strong> acid in the reaction mixture. c. The optimum condition gives the least amount of lactone, prior to adding Mg(HCO3)2 to the product mixture. The resulting product is highly soluble in water. By crystallization fractionation, monomer KMg<strong>[6205-14-7]HCA</strong> is recovered. d. The product is purified and characterized using x-ray diffraction (XRD) as compared to a pure monomeric KMg<strong>[6205-14-7]HCA</strong> sample.
  • 12
  • magnesium hydroxide [ No CAS ]
  • [ 6205-14-7 ]
  • potassium hydroxide [ No CAS ]
  • HCA potassium/magnesium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
86.2% The process of H3<strong>[6205-14-7]HCA</strong> making is repeated as described in section above and <strong>[6205-14-7]HCA</strong> free acid is obtained 200 ml of a solution consisting of 0.1 mol H3<strong>[6205-14-7]HCA</strong> is obtained The H3<strong>[6205-14-7]HCA</strong> is partially neutralized using a solution of KOH (5.6 g; 0.1 mol) in 10 ml demineral water. Into the solution, a Mg(OH)2 slurry (5.8 g; 0.1 mol) is added to form a white suspension. The mixture is heated at 60 C. for 1 hour, producing a clear solution The pH of the solution is adjusted to pH 9 by addition of a KOH solution. Then 20 ml of alcohol is added resulting in 2 layers. The top layer is separated and a further portion of ethanol added resulting in a solution of approximately 70% ethanol. This mixture forms 2 layers. The bottom layer is separated, then dried under vacuum, and then washed using dry methanol Dried insoluble material gave 35.5 g of white powder (86.2%) consisting Mg5.9% and K9.6%. This analysis is close to the formula of KMg<strong>[6205-14-7]HCA</strong>.8H2O
  • 13
  • calcium salt of (-)-hydroxycitric acid [ No CAS ]
  • [ 6205-14-7 ]
YieldReaction ConditionsOperation in experiment
With acid cation resin exchange column; In water; Take 100 gr of K3HCA (brix 74) consisting of 81% K3HCA Dilute with 250 ml of demineralized water (?DMW?) Add solution of CaCl2.2H2O (56.0 g; 0.38 mol) into 100 ml of DMW The precipitate is taken out, washed, dried and Ca3(HCA)2 white powder is obtained The amount of white powder Ca3(HCA)2 is 70.78 g with 20.9% of Ca Mix the powder and 500 ml of DMW, producing a slurry The slurry is then loaded onto an acid cation resin exchange column The soluble eluate/filtrate is then loaded onto a strong anion exchange column. The product soluble eluate/filtrate (420 ml) is cleaned using activated carbon 1 g at 60 C. to give a clean HCA free acid.
 

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