Jasmone

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.
Jasmonic Acid Jatrorrhizine Javanicin Jerusalem Artichoke Jesaconitine

Jasmone
Jasmone.png
Identifiers
CAS number 488-10-8 YesY
PubChem 1549018
ChemSpider 1266012 N
Jmol-3D images Image 1
Properties
Molecular formula C11H16O
Molar mass 164.246 g/mol
Appearance colorless to pale yellow liquid
Density 0.94 g/mL, liquid
Melting point 203-205 C
Boiling point 146 °C at 27 mm Hg
Solubility in water in water
Related compounds
Related compounds jasmonate
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Jasmone is a natural organic compound extracted from the volatile portion of the oil from jasmine flowers. It is a colorless to pale yellow liquid that has the odor of jasmine. Jasmone can exist in two isomeric forms with differing geometry around the pentenyl double bond, cis-jasmone and trans-jasmone. The natural extract contains only the cis form, while synthetic material is often a mixture containing both forms, with the cis form predominating. Both forms have similar odors and chemical properties.

Jasmone is produced within plants by the metabolism of jasmonate, from linolenic acid by the octadecanoid pathway. It can act as either an attractant or a repellent for various insects. Commercially jasmone is used primarily in perfumes and cosmetics.