Glyceric Acid
Title: Glyceric Acid
CAS Registry Number: 473-81-4
CAS Name: 2,3-Dihydroxypropanoic acid
Additional Names: a,b-dihydroxypropionic acid
Molecular Formula: C3H6O4
Molecular Weight: 106.08
Percent Composition: C 33.97%, H 5.70%, O 60.33%
Line Formula: CH2OHCH(OH)COOH
Literature References: Prepn from a,b-dibromopropionic acid by treatment with silver oxide: Karrer, Klarer, Helv. Chim. Acta 7, 931 (1924); from isoserine and nitrous acid: Fischer, Jacobs, Ber. 40, 1069 (1907); from glycerol and nitrous acid: Mulder, Ber. 9, 1902 (1876); Beilstein, Ann. 120, 229 (1861). Dextrorotatory glyceric acid is obtained by the action of Penicillia or Aspergilli on the DL-form: McKenzie, Harden, J. Chem. Soc. 83, 431 (1903). Levorotatory glyceric acid has been obtained by the oxidation of D(+)-glyceric aldehyde: Wohl, Schellenberg, Ber. 55, 1408 (1922).
 
Derivative Type: DL-Form
Properties: Syrup, dec on distn. pK (25°): 3.55. Miscible with water, alcohol, acetone. Nearly insol in ether.
pKa: pK (25°): 3.55
 
Derivative Type: L(+)-Form
Properties: Syrup. Its esters and salts are levorotatory and its salts are much more sol in water than those of the DL-form.
 
Derivative Type: L-Form calcium salt
Molecular Formula: Ca(C3H5O4)2.2H2O
Molecular Weight: 286.25
Percent Composition: Ca 14.00%, C 25.18%, H 4.93%, O 55.89%
Properties: Monoclinic sphenoidal crystals, mp 137°. One gram dissolves in 10 ml water. [a]D20 -14.6° (c = 5).
Melting point: mp 137°
Optical Rotation: [a]D20 -14.6° (c = 5)
 
Derivative Type: D(-)-Form
Properties: Syrup. Its salts are dextrorotatory.
 
Derivative Type: D-Form calcium salt
Molecular Formula: Ca(C3H5O4)2.2H2O
Molecular Weight: 286.25
Percent Composition: Ca 14.00%, C 25.18%, H 4.93%, O 55.89%
Properties: Prisms, mp 138°. [a]D20 +14.5° (c = 5).
Melting point: mp 138°
Optical Rotation: [a]D20 +14.5° (c = 5)

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