Parasorbic Acid
Title: Parasorbic Acid
CAS Registry Number: 10048-32-5
CAS Name: (6S)-5,6-Dihydro-6-methyl-2H-pyran-2-one
Additional Names: 5-hydroxy-2-hexenoic acid lactone; d-Da,b-hexenolactone; 2-hexen-5,1-olide; sorbic oil
Molecular Formula: C6H8O2
Molecular Weight: 112.13
Percent Composition: C 64.27%, H 7.19%, O 28.54%
Literature References: The sole constituent of "Vogelbeeröl", 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).
Properties: Oily liquid, sweet aromatic odor. bp14 104-105°; bp22 119-123°. nD25 1.4682. d418 1.079. [a]D18 +49.3°; [a]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).
Boiling point: bp14 104-105°; bp22 119-123°
Optical Rotation: [a]D18 +49.3°; [a]D19 +210° (c = 2 in alc)
Index of refraction: nD25 1.4682
Density: d418 1.079
Toxicity data: LD50 in mice (mg/kg): 420 ±6.3 i.p.; 195 ±13.6 i.v. (Meyer, Kretzschmar)

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