Truxillic Acid
Structural Formula Vector Image
Title: Truxillic Acid
CAS Registry Number: 4462-95-7
CAS Name: 2,4-Diphenyl-1,3-cyclobutanedicarboxylic acid
Molecular Formula: C18H16O4
Molecular Weight: 296.32
Percent Composition: C 72.96%, H 5.44%, O 21.60%
Literature References: Cinnamic acid polymers obtained from the minor alkaloids of cocaine: Liebermann, Ber. 21, 2342 (1888). Five stereoisomers have been obtained: a-, g-, e-, peri- and epi-isomers. Stereochemical configurations: Stoermer, Bacher, Ber. 57B, 15-23 (1924).
Derivative Type: a-Isomer
Additional Names: g-Isatropaic acid; cocaic acid
Literature References: Prepd by irradiation of cinnamic acid in water: White, Dunathan, J. Am. Chem. Soc. 78, 6055 (1956).
Properties: Crystals from acetic acid, mp 284-285°. Sparingly sol in boiling water, in ether, benzene, carbon disulfide; sol in hot glacial acetic acid, hot alc; sparingly sol in acetone.
Melting point: mp 284-285°
Derivative Type: g-Isomer
Additional Names: e-Isatropaic acid
Literature References: g-Truxillic anhydride, obtained by heating a-truxillic acid with acetic anhydride and sodium acetate, was heated with alkali and the free acid pptd with HCl: Liebermann, Ber. 22, 124 (1889).
Properties: Needles from dil alc, mp 228°. Very slightly sol in hot water; sol in ether.
Melting point: mp 228°
Derivative Type: e-Isomer
Additional Names: b-Cocaic acid
Literature References: Prepd by fusion of a-truxillic acid with KOH: Hesse, Ann. 271, 180 (1892).
Properties: Needles from ether, mp 192°. Freely sol in glacial acetic acid, abs alcohol, chloroform; less sol in benzene. Practically insol in ligroin.
Melting point: mp 192°
Derivative Type: peri-Isomer
Additional Names: h-Truxillic acid
Literature References: Prepn: g-Truxillic anhydride heated at low pressure forms the peri-anhydride, converted to the acid by warming with alcoholic KOH: Stoermer, Bacher, loc. cit.
Properties: Crystals from benzene + ligroin, mp 266° (effervescence). Soluble in alcohol. Practically insol in ether, benzene.
Melting point: mp 266° (effervescence)
Derivative Type: epi-Isomer
Literature References: Prepd by boiling peri-truxillic acid with excess 10% NaOH: Stoermer, Bacher, loc. cit.
Properties: Crystals from dil alc, mp 285-287°. By melting or heating with acetic anhydride in a tube, e-isomer forms. Practically insol in ether, benzene.
Melting point: mp 285-287°

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