Misplaced Pages

Jasmone

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Jasmone
Ball-and-stick model of jasmone
Names
Preferred IUPAC name 3-methyl-2-cyclopent-2-en-1-one
Other names cis-Jasmone
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
InChI
  • 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-Key: XMLSXPIVAXONDL-PLNGDYQASA-N
SMILES
  • CC\C=C/CC1=C(CCC1=O)C
  • O=C1\C(=C(/CC1)C)C\C=C/CC
Properties
Chemical formula 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
Solubility in water in water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Jasmone is produced by some plants by the metabolism of jasmonic acid, via a decarboxylation. 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 (18): 2281–2285. doi:10.1002/cbic.200700464. PMID 18033720.

External links

  • Media related to Jasmone at Wikimedia Commons
Categories: