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]
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| Names | |
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| Preferred IUPAC name
3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one | |
| Other names
cis-Jasmone
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| Identifiers | |
3D model (JSmol)
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| 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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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
edit- ^ 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.
- ^ Dąbrowska, P.; Boland, W. (2007). "iso-OPDA: An Early Precursor of cis-Jasmone in Plants?". ChemBioChem. 8 (18): 2281–2285. doi:10.1002/cbic.200700464. PMID 18033720.