Title: Methyl Dihydrojasmonate
CAS Registry Number: 24851-98-7
CAS Name: 3-Oxo-2-pentylcyclopentaneacetic acid methyl ester
Additional Names: methyl 2-pentyl-3-oxocyclopentyl-1-acetate
Trademarks: Hedione (Firmenich)
Molecular Formula: C13H22O3
Molecular Weight: 226.31
Percent Composition: C 68.99%, H 9.80%, O 21.21%
Literature 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.).
Boiling point: bp0.2 109-112°
Flash point: Flash point: >200°F (closed cup)
Index of refraction: n20 1.457-1.462
Density: d2020 0.998-1.006
Toxicity data: LD50 (g/kg): >5 orally in rats; >5 dermally in rabbits (Food Chem. Toxicol.)
Derivative Type: (+)-(1R,2S)-Form
CAS Registry Number: 39647-11-5
Additional Names: (+)-Methyl dihydroepijasmonate; (+)-cis-methyl dihydrojasmonate
Trademarks: Paradisone (Firmenich)
Literature 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).
Properties: Colorless oil; intense floral, jasmine-like, bright, fatty odor. [a]D20 +78° (c = 1.1 in CH2Cl2).
Optical Rotation: [a]D20 +78°
Derivative Type: (-)-(1R,2R)-Form
CAS Registry Number: 2630-39-9
Additional Names: (-)-trans-Methyl dihydrojasmonate
Properties: Faint, slightly floral, sweet, jasmine-like odor, bp0.03 100°. nD20 1.4583. d421 0.9968. [a]D -33.8° (c = 2.9 in CHCl3).
Boiling point: bp0.03 100°
Optical Rotation: [a]D -33.8° (c = 2.9 in CHCl3)
Index of refraction: nD20 1.4583
Density: d421 0.9968
Derivative Type: (+)-(1S,2S)-Form
CAS Registry Number: 151716-36-8
Additional Names: (+)-trans-Methyl dihydrojasmonate
Properties: Colorless oil, bp0.3 108°. Faint, slightly floral, fatty, lemon peel-like odor. [a]D20 +33.8° (c = 0.9 in CHCl3).
Boiling point: bp0.3 108°
Optical Rotation: [a]D20 +33.8° (c = 0.9 in CHCl3)
Use: Fragrance ingredient in perfumes, toilette and laundry products. Flavor ingredient producing fruit, tea, tobacco, and floral flavors.