6052. Methyl Dihydrojasmonate
Nomenclature
Description and references
Fragrance compound identified as a natural product in flowers, tea, herbs, fruits and vegetables. Synthetic commercial formulations contain a racemic, near equilibrium mixture of ≈10% (±)-cis and ≈90% (±)-trans forms. The (+)-(1R,2S)-form is the most organoleptically active enantiomer. Prepn: E. Demole et al., Helv. Chim. Acta 45, 675, 685, 692 (1962). Fragrance monograph: Food Chem. Toxicol. 30, Suppl. 1, 85S (1992). Enantioselective synthesis of (+)- and ()-trans forms: T. Perrard et al., Org. Lett. 2, 2959 (2000). Review of sensory properties of stereoisomers and enantioselective distribution in plant sources: P. Werkhoff et al., Food Rev. Int. 18, 103-122 (2002).
Properties
Pale yellowish or almost colorless oil, bp0.2 109-112°; sweet, floral, jasmine-like odor. Flash point: >200°F (closed cup). Vapor pressure (20°): <0.001 mmHg. n20 1.457-1.462. d2020 0.998-1.006. LD50 (g/kg): >5 orally in rats; >5 dermally in rabbits (Food Chem. Toxicol.).Derivative
(+)-(1R,2S)-Form.Nomenclature
Description and references
Commercial formulations contain ≈90% ee of the (+)-(1R,2S)-form. Enantioselective synthesis: D. A. Dobbs et al., Angew. Chem. Int. Ed. 39, 1992 (2000); A. Porta et al., J. Org. Chem. 70, 4876 (2005).