9779. Tropic Acid

Nomenclature

CAS number: 529-64-6
α-(Hydroxymethyl)benzeneacetic acid; 2-phenylhydracrylic acid; α-phenyl-β-hydroxypropionic acid; tropaic acid; tropeic acid.
C9H10O3; mol wt 166.17.
C 65.05%, H 6.07%, O 28.88%.

Description and references

Degradation product of tropane alkaloids, esp atropine: Lossen, Ann. 133, 351, 370 (1865). Resolution of isomers: McKenzie, Wood, J. Chem. Soc. 115, 828 (1919). Absolute config of isomers: Fodor, Csepreghy, ibid. 1961, 3222; Watson, Youngson, J. Chem. Soc. Perkin Trans. 1 1972, 1597. Prepn: Sletzinger, Paulsen, US 2390278 (1945 to Merck & Co.); Blicke, US 2716650 (1955 to U. of Michigan); DE 923426 (1955 to Sterling Drug). Biosynthetic studies: Louden, Leete, J. Am. Chem. Soc. 84, 1510, 4507 (1962).

Chemical structure

Derivative

(±)-Form.

Properties

Needles or plates from water or benzene, mp 118°. K at 25° = 7.5×10-5. Absorption spectrum: Dobbie, Fox, J. Chem. Soc. 103, 1194 (1913). 1 gram dissolves in 50 ml water; freely sol in boiling water; sol in alcohol, ether, slightly in benzene; practically insol in petr ether.

Derivative

(+)-Form.

Properties

mp 107°. [α]D20 +72° (c = 0.5 in water).

Derivative

(-)-Form.

Properties

mp 126-128°. [α]D20 -72° (c = 0.5 in water).