Calcium L-threonate
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Calcium L-threonate
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CAS No:
70753-61-6
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Formula:
C4H8O5.1/2Ca
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Chemical Name:
Calcium L-threonate
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Synonyms:
Butanoic acid,2,3,4-trihydroxy-,calcium salt (2:1),(2R,3S)-;Butanoic acid,2,3,4-trihydroxy-,calcium salt (2:1),[R-(R*,S*)]-;Calcium L-threonate;Calcium (2R,3S)-2,3,4-trihydroxybutanoate;159837-98-6;1241674-41-8
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CAS No:
Description
Calcium L-Threonate is an anti-osteoporosis agent, and widely used as a calcium supplement[1]. Calcium L-Threonate also stimulates the uptake of ascorbic acid[2].
Calcium L-threonate Use and Manufacturing
L-Ascorbic acid (52.8 g, 0.3 mol) was dissolved in water (410 mL). To the solution was added calcium carbonate (60.06 g, 0.6 mol) and the slurry was cooled to 05° C. Hydrogen peroxide (50percent w/w, 61.2 ml, 0.9 mol) was added dropwise at 520° C. over a period of 60 minutes, and the mixture was then stirred at room temperature for sixteen hours. The reaction mixture was heated at 7075° C. for one hour until no more oxygen was evolved. The suspension was filtered at 7075° C., and the filter cake was washed with 50-60° C. hot water (30 mL.x.2). The combined filtrate was concentrated to about 20 mL at 55° C. under reduced pressure. Methanol (250 ml) was added dropwise to the warm concentrate (about 50° C.) until the solution became cloudy, and the mixture was then stirred at room temperature for twelve hours, filtered, and the precipitate was washed with methanol (30 mL.x.3). The solid was dried to a constant weight at 60° C. (3 hours) to give 45.2 grams (Yield: 94.6percent) of Calcium L-threonate (Bock et al. Acta Chem. Scand. Ser. B, 37, 342-344 (1983)). IR (KBr) 1600 (s) cm-1; 1H-NMR (D2O, 400 MHz): δ4.02 (2 1H, Hc, Jbc=2.3 Hz), 3.94 (ddd, 1H, Hb, Jab=7.7 Hz, Jab=5.2 Hz, Jbc=2.2 Hz), 3.65 (ABX, 1H, Ha, Jaa=11.6 Hz, Jab=5.2 Hz), 3.58 (ABX, 1H, Ha, Jaa=11.6 Hz, Jab=7.7 Hz).This compound was synthesized according to a known procedure (Schoning, K. U.; Scholz, P.; Wu, X. L.; Guntha, S.; Delgado, G.; Krishnamurthy, R.; Eschenmoser, A. Helv. Chim. Acta 2002, 85, 4111). To a solution of 200 g (1.14 mol) of L-ascorbic acid dissolved in 1.6 L of distilled water, 227 g (2.27 mol) of CaCO
L-Threonic acid calcium salt is the salt of L-Threonic acid, a naturally occurring compound that can be found in the leaves of Pelargonium crispum. L-Threonic acid is also the degradation product of Dehydroascorbate (DHA), a metabolite of Vitamin C.
Computed Properties
Molecular Weight:176.18
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:175.9997642
Monoisotopic Mass:175.9997642
Topological Polar Surface Area:98
Heavy Atom Count:10
Complexity:101
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
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