Jasmone

Jasmone is an organic compound, which is a volatile portion of the oil from jasmine flowers. It is a colorless to pale yellow liquid. 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 of both, with the cis form predominating. Both forms have similar odors and chemical properties. Its structure was deduced by Lavoslav Ružička.[1]

Jasmone
Ball-and-stick model of jasmone
Names
Preferred IUPAC name
3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one
Other names
cis-Jasmone
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C11H16O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h4-5H,3,6-8H2,1-2H3/b5-4- ☒N
    Key: XMLSXPIVAXONDL-PLNGDYQASA-N ☒N
  • CC\C=C/CC1=C(CCC1=O)C
  • O=C1\C(=C(/CC1)C)C\C=C/CC
Properties
C11H16O
Molar mass 164.246 g/mol
Appearance colorless to pale yellow liquid
Density 0.94 g/mL, liquid
Melting point 203 to 205 °C (397 to 401 °F; 476 to 478 K)
Boiling point 146 °C (295 °F; 419 K) at 27 mmHg
in water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Jasmone is produced by some plants by the metabolism of jasmonic acid, via a decarboxylation.[2] It can act as either an attractant or a repellent for various insects. Commercially, jasmone is used primarily in perfumes and cosmetics.

References
  1. Ruzicka, L.; Pfeiffer, M. (1933). "Über Jasminriechstoffe I. Die Konstitution des Jasmons" [On Jasmine Perfumes I. The Composition of Jasmone]. Helvetica Chimica Acta. 16: 1208–1214. doi:10.1002/hlca.193301601153.
  2. Dąbrowska, P.; Boland, W. (2007). "iso-OPDA: An Early Precursor of cis-Jasmone in Plants?". ChemBioChem. 8: 2281–2285. doi:10.1002/cbic.200700464.
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