Malic Acid → Malic Acid

HRID 1091224Notes

Reaction equation

[C:1]([OH:9])(=[O:8])[CH:2]([CH2:4][C:5]([OH:7])=[O:6])[OH:3].C1(=O)OC(=O)C=C1.[C:17]([OH:25])(=[O:24])[C@H:18]([CH2:20][C:21]([OH:23])=[O:22])O>>[C:1]([OH:9])(=[O:8])[CH:2]([CH2:4][C:5]([OH:7])=[O:6])[OH:3].[C:17]([O-:25])(=[O:24])/[CH:18]=[CH:20]/[C:21]([O-:23])=[O:22]

Participants

Reactant 3

HCID 525Malic Acid

HCID 7923Maleic Anhydride

HCID 222656L-Malic Acid

Product 2

HCID 525Malic Acid

HCID 5460307Fumarate

Procedure

Malic acid is used as an acidulant and taste enhancer in the beverage and food industry. Racemic malic acid is synthesized petrochemically from maleic anhydride whereas enantiometrically pure L-malic acid (used in pharmaceutical production) is produced from fumarate by hydration with fumarase.

Sources & evidence

ORD record: ord-40c0b11e53874c9ea24a43ac1c311227
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129154B2

Reaction notes

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