Jasmone

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Jasmone
Jasmone.png
Ball-and-stick model of jasmone
Names
IUPAC name
3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one
Other names
cis-jasmone
Identifiers
488-10-8 YesY
ChemSpider 1266012 N
Jmol 3D model Interactive image
Interactive image
PubChem 1549018
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 mm Hg
in water
Related compounds
Related compounds
jasmonate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

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 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]

  1. ^ L. Ruzicka; M. Pfeiffer (1933). "Über Jasminriechstoffe I. Die Konstitution des Jasmons". Helvetica Chimica Acta. 16: 1208–1214. doi:10.1002/hlca.193301601153. 
  2. ^ Paulina Dąbrowska, Wilhelm Boland "iso-OPDA: An Early Precursor of cis-Jasmone in Plants?" ChemBioChem 2007, Volume 8, pages 2281–2285. doi:10.1002/cbic.200700464