5717. Mandelic Acid

Nomenclature

CAS number: 90-64-2
α-Hydroxybenzeneacetic acid; dl-mandelic acid; racemic mandelic acid; α-hydroxy-α-toluic acid; α-hydroxyphenylacetic acid; phenylhydroxyacetic acid; phenylglycolic acid; amygdalic acid; amygdalinic acid; paramandelic acid; Uromaline.
C8H8O3; mol wt 152.15.
C 63.15%, H 5.30%, O 31.55%.

Description and references

Prepd by the action of warm, dil alkali upon dichloroacetophenone: Org. Synth. 23, 48 (1943); by hydrolysis of mandelonitrile (prepd from benzaldehyde and hydrogen cyanide or from benzaldehyde, sodium bisulfite, and sodium cyanide): Org. Synth. coll. vol. I, 336 (1941); ibid. coll. vol. III, 538 (1955); L. F. Fieser, Organic Experiments (Boston, 1964) p 109. May be prepd by boiling amygdalin with HCl.

Chemical structure

Properties

Orthorhombic plates from water, mp 119°. Darkens and dec on prolonged exposure to light. d 1.30. Can be distilled rapidly in vacuo at 2 mm without much decompn. Acid to litmus. pK (25°) 3.37. One gram dissolves in 6.3 ml water, 1 ml alc; freely sol in ether, isopropyl alcohol.

Derivative

Calcium salt.

Nomenclature

CAS number: 134-95-2
Calcium mandelate; Camdelate.
C16H14CaO6; mol wt 342.36.
C 56.13%, H 4.12%, Ca 11.71%, O 28.04%.

Properties

Contains 88.88% mandelic acid. White powder. One gram dissolves in 80 ml boiling water. Slightly sol in cold water. Insol in alc. The aq soln is slightly acid.

Derivative

Sodium salt.

Nomenclature

CAS number: 114-21-6
Sodium mandelate.
C8H7NaO3; mol wt 174.13.
C 55.18%, H 4.05%, Na 13.20%, O 27.56%.

Properties

Cryst powder; slight aromatic odor. Very sol in water; sol in alcohol; the aq soln is neutral or slightly alkaline to litmus.

Therapeutic Category

Antiseptic (urinary).