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Calcium diglutamate

Calcium diglutamate, sometimes abbreviated CDG and also called calcium biglutamate, is a compound with formula Ca(C<sub>5</sub>H<sub>8</sub>NO<sub>4</sub>)<sub>2</sub>. It is a calcium acid salt of glutamic acid. CDG is a flavor enhancer (E number E623)&mdash;it is the calcium analog of monosodium glutamate (MSG). Because the glutamate is the actual flavor-enhancer, CDG has the same flavor-enhancing properties as MSG but without the increased sodium content. Notably, only the <small>L</small> isomer is used in flavouring as <small>D</small>-glutamate does not have an umami/savoury flavour.

As a soluble source of calcium ions, this chemical is also used as a first-aid treatment for exposure to hydrofluoric acid.

Synthesis and reactions

Calcium di-glutamate can be prepared by reacting calcium carbonate with two molar equivalents of glutamic acid:

CaCO<sub>3</sub> + 2 HOOC(CH<sub>2</sub>)<sub>2</sub>CH(NH<sub>2</sub>)COOH → Ca(OOC(CH<sub>2</sub>)<sub>2</sub>CH(NH<sub>3</sub>)COO)<sub>2</sub> + H<sub>2</sub>O + CO<sub>2</sub>↑

Concentration of the solution to a syrup under reduced pressure, followed by gradual crystallisation, affords the monohydrate. Structurally, the glutamate anion is zwitterionic, with the amino group protonated (pK<sub>a</sub> = 9.47) and both carboxylic-acid groups (pK<sub>a</sub> = 2.10, 4.07) in their deprotonated carboxylate form.

Calcium di-<small>L</small>-glutamate can be used to prepare other glutamates through metathesis with a soluble sulfate, carbonate or hydroxide salt. For example, manganese(II) di-<small>L</small>-glutamate can be prepared through metathesis with manganese(II) sulphate:

Ca(OOC(CH<sub>2</sub>)<sub>2</sub>CH(NH<sub>3</sub>)COO)<sub>2</sub> + MnSO<sub>4</sub> → Mn(OOC(CH<sub>2</sub>)<sub>2</sub>CH(NH<sub>3</sub>)COO)<sub>2</sub> + CaSO<sub>4</sub>↓

References