7325. Phloionic Acid

Nomenclature

CAS number: 23843-52-9
(9R,10R)-rel-9,10-Dihydroxyoctadecanedioic acid; floionic acid.
C18H34O6; mol wt 346.46.
C 62.40%, H 9.89%, O 27.71%.

Description and references

Isoln from cork: Guillemonat, Cesaire, Bull. Soc. Chim. Fr. 1949, 792; Ribas, Seoane, An. R. Soc. Esp. Fis. Quim. 50B, 963 (1954), C.A. 50, 806f (1956); Brown, Rosen, US 2872464 (1959 to Crown Cork). Structure: Duhamel, Bull. Soc. Chim. Fr. 1965, 399. Synthesis: Ruzicka et al., Helv. Chim. Acta 25, 1086 (1942); Gensler, Schlein, J. Am. Chem. Soc. 77, 4846 (1955). Resolution of isomers: Gender, Mahadevan, ibid. 78, 169 (1956); Alvarez-Varquez, Ribas-Marques, An. Quim. 64, 783 (1968). Synthesis of (±), (+), and (-) forms: McGhie et al., Chem. Ind. (London) 1972, 536.

Chemical structure

Properties

Crystals from ethanol + water, mp 126°.

Derivative

Dimethyl ester.
C20H38O6; mol wt 374.51.
C 64.14%, H 10.23%, O 25.63%.

Properties

Crystals from ethanol, mp 77.5-78°.