7032. Parasorbic Acid

Nomenclature

CAS number: 10048-32-5
(6S)-5,6-Dihydro-6-methyl-2H-pyran-2-one; 5-hydroxy-2-hexenoic acid lactone; δ-Δα,β-hexenolactone; 2-hexen-5,1-olide; sorbic oil.
C6H8O2; mol wt 112.13.
C 64.27%, H 7.19%, O 28.54%.

Description and references

The sole constituent of “Vogelbeer"ol”, an oil obtained by steam distillation of the acidified juice of the ripe berries of the mountain ash, Sorbus aucuparia L., Rosaceae: Hofmann, Ann. 110, 129 (1859); Doebner, Ber. 27, 344 (1894); Kuhn, Jerchel, Ber. 76, 413 (1943). Structure: eidem, ibid. Synthesis: Haynes, Jones, J. Chem. Soc. 1946, 954; Lamberti et al., Recl. Trav. Chim. Pays-Bas 86, 504 (1967). Pharmacology and acute toxicity: H. J. Meyer, R. Kretzschmar, Arzneim.-Forsch. 19, 617 (1969).

Chemical structure

Properties

Oily liquid, sweet aromatic odor. bp14 104-105°; bp22 119-123°. nD25 1.4682. d418 1.079. [α]D18 +49.3°; [α]D19 +210° (c = 2 in alc). Soluble in water; freely sol in alcohol, ether. Aq solns are neutral and turn acid on storage. LD50 in mice (mg/kg): 420 ±6.3 i.p.; 195 ±13.6 i.v. (Meyer, Kretzschmar).