4486. Glycerophosphoric Acid

Nomenclature

CAS number: 57-03-4 (dl-α-form); 17181-54-3 (β-form)
Phosphoric acid glycerol esters.
C3H9O6P; mol wt 172.07.
C 20.94%, H 5.27%, O 55.79%, P 18.00%.

Description and references

Three isomers exist: β-glycerophosphoric acid, the d(+)- and l()-forms of α-glycerophosphoric acid. The l-α-acid is the naturally occurring form; the β-acid, present in hydrolyzates of lecithins from natural sources, arises from migration of the phosphoryl group from the α-carbon atom. See review: Dawson, Annu. Rep. Prog. Chem. 55, 365 (1958). Prepn by phosphorylation of glycerol results in a mixture of the α- and β-acids: Cherbuliez, Weniger, Helv. Chim. Acta 29, 2006 (1946). Prepn and configuration of l-α-acid: Baer, Fischer, J. Biol. Chem. 128, 491 (1939). Prepn of d-α-acid: eidem, ibid. 135, 321 (1940). Separation of α-acid from β- and polyglycerophosphoric acids: Carrara, IT 460219 (1950), C.A. 46, 5077a (1952).

Chemical structure

Properties

Absolute acid (commercial mixture of α- and β-acids); clear syrupy liq, mp 25°. d414 1.59. Tends to dec during concn; hence, usually marketed as a 25-50% soln. Soluble in water, alcohol.

Derivative

α-Acid l-form.

Nomenclature

CAS number: 5746-57-6
(2S)-1-(Dihydrogen phosphate)-1,2,3-propanetriol.

Properties

Syrup. Readily sol in water, methanol, ethanol. Practically insol in ether. [α]D 1.45° (barium salt, c = 10.3 in 2N HCl).

Note

Phosphatidic acids are fatty acid diesters of glycerophosphoric acid.

Use

Absolute acid used to manuf certain glycerophosphates or to impart taste to solns of glycerophosphates which are generally used medicinally. See also: Calcium Glycerophosphate.