| Identification | More | [Name]
(+)-5,6-O-Isopropylidene-L-ascorbic acid | [CAS]
15042-01-0 | [Synonyms]
5,5-ISOPROPYLIDENE-L-ASCORBIC ACID
5,6-ISOPROPYLIDENE-L-ASCORBIC ACID
(+)-5,6-O-ISOPROPYLIDENE-L-ASCORBIC ACID
5,6-O-ISOPROPYLIDENE-L-ASCORBIC ACID
ASCORBIC ACID ACETONIDE
5,6-0,0-ISOPROPYLIDENE-L-ASCORBIC ACID
L-Ascorbicacidacetonide
L-Ascorbic acid, 5,6-O-(1-methylethylidene)-
(+)-5,6-O-ISOPROPYLIDENE-L-ASCORBIC ACID 99+%
(+)-5,6-O-Isopropylidene-L-ascorbic acid
5-O,6-O-Isopropylidene-L-ascorbic acid
Iasa
Isopropylidene ascorbic acid | [Molecular Formula]
C9H12O6 | [MDL Number]
MFCD00010552 | [Molecular Weight]
216.19 | [MOL File]
15042-01-0.mol |
| Chemical Properties | Back Directory | [Appearance]
White Powder | [Melting point ]
217 °C (dec.) | [alpha ]
10.5 º (c=5%, MeOH) | [Boiling point ]
395.2±42.0 °C(Predicted) | [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 Rotation]
[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 Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [F ]
10-21 | [HS Code ]
2932990090 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [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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