L-Threonic acid calcium salt Chemical Properties

Melting point:

>300 °C(lit.)

alpha 

16 º (c=1, H2O)

refractive index 

15 ° (C=1, H2O)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Water (Slightly, Heated)

form 

Powder

color 

Pale Brown

optical activity

[α]20/D +16°, c = 1 in H2O

Water Solubility 

Soluble in water. Sparingly soluble in methanol.

BRN 

5166008

InChI

InChI=1/2C4H8O5.Ca.H2O/c2*5-1-2(6)3(7)4(8)9;;/h2*2-3,5-7H,1H2,(H,8,9);;1H2/q;;+2;/p-2/t2*2-,3+;;/s3

InChIKey

ZJXGOFZGZFVRHK-BALCVSAKSA-L

SMILES

[C@@H](O)([C@@H](O)CO)C(=O)O[Ca]OC(=O)[C@H](O)[C@@H](O)CO.O |&1:0,2,13,15,r|

CAS DataBase Reference

70753-61-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-37/39-26

WGK Germany 

3

HS Code 

2918195000

MSDS

• Language:English Provider:SigmaAldrich

L-Threonic acid calcium salt Usage And Synthesis

Uses

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 (A786990).

Synthesis

L-ascorbic acid (52.8 g, 0.3 mol) was dissolved in deionized water (410 mL). Calcium carbonate (60.06 g, 0.6 mol) was added to this solution and the reaction mixture was cooled to 0-5 °C. Under stirring, 50% (w/w) hydrogen peroxide solution (61.2 mL, 0.9 mol) was slowly added dropwise, controlling the reaction temperature at 5-20 °C. After the dropwise addition, the reaction mixture was continued to be stirred at room temperature for 16 hours. Subsequently, the reaction mixture was heated to 70-75 °C and maintained for 1 h until no oxygen was released. The reaction mixture was filtered while hot and the filter cake was washed with hot water at 50-60 °C (30 mL × 2). The filtrates were combined and concentrated under reduced pressure to about 20 mL at 55 °C. Methanol (250 mL) was added slowly and dropwise to the warmed concentrate (about 50 °C) until the solution became turbid, and then stirred for 12 h at room temperature. The precipitate was filtered and washed with methanol (30 mL × 3). The resulting solid was dried to constant weight at 60 °C (about 3 h) to give calcium L-threonate 45.2 g in 94.6% yield. The product was characterized by IR (KBr) and 1H-NMR (D2O, 400 MHz), and the data were consistent with those reported in the literature.

References

[1] Canadian Journal of Chemistry, 2003, vol. 81, # 8, p. 937 - 960
[2] Patent: US2003/232820, 2003, A1. Location in patent: Page 16
[3] Journal of Organic Chemistry, 2016, vol. 81, # 6, p. 2302 - 2307
[4] Journal of Organic Chemistry, 1985, vol. 50, # 19, p. 3462 - 3467
[5] Helvetica Chimica Acta, 2002, vol. 85, # 12, p. 4111 - 4153

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