Water → 3-Glyceryl ascorbate

HRID 1698284Notes

Reaction equation

HRID 1698284 reaction equation
[O:1]=[C:2]1[O:8][C@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[C:5]([OH:6])=[C:3]1[OH:4].C(=O)([O-])O.[Na+].O.[CH2:19]1[O:21][CH:20]1[CH2:22][OH:23]>CO>[CH2:19]([O:6][C:5]1[C@@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[O:8][C:2](=[O:1])[C:3]=1[OH:4])[CH:20]([CH2:22][OH:23])[OH:21]

Participants

6

Reactant 4

HCID 962WaterHCID 11164GlycidolHCID 516892Sodium BicarbonateHCID 54670067L-Ascorbic Acid

Product 1

HCID 672677953-Glyceryl ascorbateYield 69.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Under an argon atmosphere, L-ascorbic acid (300 g) and sodium hydrogen carbonate (42.9 g) were added to water and the resultant mixture was stirred at room temperature for 30 minutes, then, glycidol (126 g) was added thereto. Thereafter, the mixture was heated up to 50° C. and stirred for 5 hours. Thereto, methanol was added and filtration was performed. The filtrate was concentrated under reduced pressure, and 457 g of the resultant residue was subjected to silica gel column chromatography. Elution was performed with chloroform/methanol/water(volume ratio:65/35/5), and concentration was performed under reduced pressure to obtain 3-O-glyceryl ascorbic acid (296 g).

Workup

  1. filtrationfiltration
  2. concentrationThe filtrate was concentrated under reduced pressure, and 457 g of the resultant residue
  3. washElution
  4. concentrationwas performed with chloroform/methanol/water(volume ratio:65/35/5), and concentration

Sources & evidence

ORD record
ord-3f0ed965065c4a64bb13a6817a4019e4
Source dataset
uspto-grants-2012_04
Patent number
US08163939B2

Reaction notes

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