13-05120. Isatropic Acid [Archived]

Nomenclature

CAS number: 596-56-5
1,2,3,4-Tetrahydro-1-phenyl-1,4-naphthalenedicarboxylic acid; 1-phenyltetrahydro-1,4-naphthalenedicarboxylic acid; 1-phenyltetralin-1,4-dicarboxylic acid; diatropic acid; α-isatropic acid; trans-isatropic acid.
C18H16O4; mol wt 296.32.
C 72.96%, H 5.44%, O 21.60%.

Description and references

Prepn: Staudinger, Ruzicka, Ann. 380, 296 (1911); Smith, Forsberg, C.A. 42, 7283 (1948). Structure: Voigtlander, Engelbert, Ann. 625, 196 (1959).

Chemical structure

Derivative

dl-Form.

Properties

Crystals from chloroform + petr ether, mp 238.5-239°. Sparingly sol in hot water; moderately sol in alcohol, acetic acid; practically insol in ether, benzene, ligroin, carbon disulfide.

Derivative

d-Form.

Properties

Crystals, sinters at 234°, dec at 230°. [α]D20 +9.44° (1 g/15 ml abs alc). K at 18° = 1.20×104. Soly in water 0.0047%.

Status

This monograph has been retired and is no longer subject to revision or update.