(+)-5,6-O-Isopropylidene-L-ascorbic acid Chemical Properties

Melting point:

217 °C (dec.)

Boiling point:

395.2±42.0 °C(Predicted)

alpha 

10.5 º (c=5%, MeOH)

Density 

1.518±0.06 g/cm3(Predicted)

refractive index 

10 ° (C=5, MeOH)

storage temp. 

2-8°C

solubility 

Acetone, DMSO, Ethanol, Methanol

form 

Solid

pka

3.99±0.10(Predicted)

color 

Off-White

optical activity

[α]19/D +25.3°, c = 1 in H2O

BRN 

86893

InChI

InChI=1S/C9H12O6/c1-9(2)13-3-4(15-9)7-5(10)6(11)8(12)14-7/h4,7,10-11H,3H2,1-2H3/t4-,7+/m0/s1

InChIKey

POXUQBFHDHCZAD-MHTLYPKNSA-N

SMILES

OC1=C(O)C(=O)O[C@@H]1[C@@H]1COC(O1)(C)C

CAS DataBase Reference

15042-01-0(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

F 

10-21

HS Code 

2932990090

MSDS

• Language:English Provider:SigmaAldrich

(+)-5,6-O-Isopropylidene-L-ascorbic acid Usage And Synthesis

Chemical Properties

White Powder

Uses

5,6-O-Isopropylidene-L-ascorbic acid (L-Ascorbic acid 5,6-acetonide) is an organic compound. 5,6-O-Isopropylidene-L-ascorbic acid is a derivative of L-Ascorbic acid (vitamin C). Ascorbic acid has antioxidant properties.

Synthesis

General procedure for the synthesis of 5,6-O-isopropylidene-L-ascorbic acid from vitamin C: Vitamin C (1.76 g, 10 mmol) and acetone (9 mL) were added to a reaction flask fitted with a magnetic stirrer and stirred until dissolved. Subsequently, phosphoryl chloride (0.5 mL) was added slowly and dropwise to the above solution. The reaction mixture was stirred continuously for 4 hours at room temperature. After completion of the reaction, the mixture was filtered, and the filter cake was washed with cold acetone-water (volume ratio adjusted according to the actual situation), and finally dried under vacuum to obtain the target compound 5,6-O-isopropylidene-L-ascorbic acid (1.92 g, 89% yield) as a colorless granular solid. The product was detected by IR (KBr press method) and the main absorption peaks were: νmax 3242.6, 2993.3, 2907.6, 2741.6, 1755.5, 1665.4 cm-1. 1H NMR (600 MHz, CD3COCD3) data: δ 4.71-4.73 (m, 1H, C4-H), 4.37-4.39 ( m, 1H, C5-H), 4.16-4.21 (m, 1H, C6-H), 3.99-4.03 (m, 1H, C6-H), 1.29 (s, 6H, Me).

References

[1] Pappenberger G, et al. Industrial production of L-ascorbic Acid (vitamin C) and D-isoascorbic acid. Adv Biochem Eng Biotechnol. 2014;143:143-88. DOI:10.1007/10_2013_243

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