Magnesium Hydroxide → Magnesium ascorbyl phosphate

HRID 1447988Notes

Reaction equation

HRID 1447988 reaction equation
[P:1]([O:5][C:6]1[C:7]([O:9][C@H:10]([C@H:13]([CH2:15][OH:16])[OH:14])[C:11]=1[O-:12])=[O:8])([OH:4])([OH:3])=[O:2].[OH-].[Mg+2:18].[OH-]>>[P:1]([O:5][C:6]1[C:7]([O:9][C@H:10]([C@H:13]([CH2:15][OH:16])[OH:14])[C:11]=1[O-:12])=[O:8])([O-:4])([O-:3])=[O:2].[Mg+2:18].[O:8]=[C:7]1[O:9][C@H:10]([C@H:13]([CH2:15][OH:16])[OH:14])[C:11]([O-:12])=[C:6]1[O:5][P:1]([O-:4])([O-:3])=[O:2].[Mg+2:18].[Mg+2:18]

Participants

3

Reactant 2

HCID 73981Magnesium HydroxideHCID 131711663HCID 131711663, compound

Product 1

HCID 71587428Magnesium ascorbyl phosphate

Procedure

The remainder (247 ml) of the reaction mixture which had been analyzed by uv and HPLC, was passed through a column of strongly acidic cation exchange resin (600 ml) in the hydrogen ion form. The column was washed until the total effluent was 2000 ml. The absorbance of the column effluent at pH 10 and 264 nm showed a 93.4% recovery (53.1 mmoles) of the theoretical amount (57 mmoles) of L-ascorbate 2-phosphate expected for stoichiometric 2-phosphorylation of IAA. The column effluent (which was at pH 1.0), was allowed to stand 2 hr. at 25° C., and solid magnesium hydroxide (about 11 g) was added to adjust the pH to about 9.0. The mixture was then allowed to stand overnight at 5° C., and was filtered. Recovery of L-ascorbate 2-phosphate in the filtrate was 91.7%. The filtrate was next concentrated under reduced pressure to a volume of 50 ml, and the concentrate added to absolute ethanol (300 ml). The precipitated magnesium L-ascorbate 2-phosphate was collected by centrifugation and was washed with 95% ethanol (2×100 ml). High pressure liquid chromatographic examination of the ethanol washings showed that magnesium bis-(L-ascorbyl) 2,2'-phosphate was concentrated in the ethanolic washings, and that the solid residue contained only traces of the bis compound. The insoluble material was dried under vacuum to give 19.5 g of practically pure magnesium L-ascorbate 2-phosphate as a freeflowing powder (approximately 86% yield).

Workup

  1. washThe column was washed until the total effluent
  2. waitto stand overnight at 5° C.
  3. filtrationwas filtered
  4. concentrationThe filtrate was next concentrated under reduced pressure to a volume of 50 ml
  5. additionthe concentrate added to absolute ethanol (300 ml)
  6. customThe precipitated magnesium L-ascorbate 2-phosphate was collected by centrifugation
  7. washwas washed with 95% ethanol (2×100 ml)
  8. concentrationwas concentrated in the ethanolic washings
  9. customThe insoluble material was dried under vacuum

Sources & evidence

ORD record
ord-2ccbbc8786b64b22805c0b9fbb9b56e5
Source dataset
uspto-grants-1979_12
Patent number
US04179445

Reaction notes

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