Glycerophosphoric Acid
Title: Glycerophosphoric Acid
CAS Registry Number: 57-03-4 (DL-a-form); 17181-54-3 (b-form)
Additional Names: Phosphoric acid glycerol esters
Molecular Formula: C3H9O6P
Molecular Weight: 172.07
Percent Composition: C 20.94%, H 5.27%, O 55.79%, P 18.00%
Literature References: Three isomers exist: b-glycerophosphoric acid, the D(+)- and L(-)-forms of a-glycerophosphoric acid. The L-a-acid is the naturally occurring form; the b-acid, present in hydrolyzates of lecithins from natural sources, arises from migration of the phosphoryl group from the a-carbon atom. See review: Dawson, Annu. Rep. Prog. Chem. 55, 365 (1958). Prepn by phosphorylation of glycerol results in a mixture of the a- and b-acids: Cherbuliez, Weniger, Helv. Chim. Acta 29, 2006 (1946). Prepn and configuration of L-a-acid: Baer, Fischer, J. Biol. Chem. 128, 491 (1939). Prepn of D-a-acid: eidem, ibid. 135, 321 (1940). Separation of a-acid from b- and polyglycerophosphoric acids: Carrara, IT 460219 (1950), C.A. 46, 5077a (1952).
Properties: Absolute acid (commercial mixture of a- and b-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.
Melting point: mp -25°
Density: d414 1.59
Derivative Type: a-Acid L-form
CAS Registry Number: 5746-57-6
CAS Name: (2S)-1-(Dihydrogen phosphate)-1,2,3-propanetriol
Properties: Syrup. Readily sol in water, methanol, ethanol. Practically insol in ether. [a]D -1.45° (barium salt, c = 10.3 in 2N HCl).
Optical Rotation: [a]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.

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