Title: Jasmone
CAS Registry Number: 488-10-8
CAS Name: 3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one
Molecular Formula: C11H16O
Molecular Weight: 164.24
Percent Composition: C 80.44%, H 9.82%, O 9.74%
Literature References: Found in the volatile portion of oil from jasmine flowers. Natural jasmone is the
cis-ketone. Isoln and structure: Ruzicka, Pfeiffer,
Helv. Chim. Acta 16, 1208 (1933). Stereochemistry: Crombie, Harper,
J. Chem. Soc. 1952, 869. Synthesis of
cis-jasmone: H. Hunsdiecker,
Ber. 75, 447 (1942); Stork, Borch,
J. Am. Chem. Soc. 86, 936 (1964); Büchi, Wuest,
J. Org. Chem. 31, 977 (1966); Sakan
et al., Chem. Lett. 1973, 713; P. Bakuzis, M. L. F. Bakuzis,
J. Org. Chem. 42, 2362 (1977). Synthesis of dihydrojasmone and
cis-jasmone: C. S. Subramaniam
et al., J. Chem. Soc. Perkin Trans. 1 1979, 2346; T. Kato
et al., Chem. Pharm. Bull. 28, 349 (1980). Synthesis of
trans-jasmone: Sisido
et al., J. Org. Chem. 29, 2290 (1964). Comprehensive synthetic reviews: R. A. Ellison,
Synthesis 1973, 397; T. L. Ho,
Synth. Commun. 4, 265 (1974).
Derivative Type: cis-Form
Properties: Oil, odor of jasmine, bp27 146°.
nD20 1.4978. uv max: 235 nm (e 12,000).
Boiling point: bp27 146°
Index of refraction: nD20 1.4978
Absorption maximum: uv max: 235 nm (e 12,000)
Derivative Type: trans-Form
Properties: Oil, odor of jasmine, bp23 142°.
nD20 1.4974. uv max: 234 nm (e 12,300).
Boiling point: bp23 142°
Index of refraction: nD20 1.4974
Absorption maximum: uv max: 234 nm (e 12,300)
Use: In perfumery.
