Jasmone

Jasmone
Names


IUPAC name 3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one
Other names cis-jasmone
Identifiers
CAS Registry Number	488-10-8^Y
ChemSpider	1266012^N
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-^N Key: XMLSXPIVAXONDL-PLNGDYQASA-N^N InChI=1/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-PLNGDYQABD
Jmol-3D images	Image Image
PubChem	1549018
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 mm Hg
Solubility in water	in water
Related compounds
Related compounds	jasmonate
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
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.

References

Thomas Koch, Katja Bandemer, Wilhelm Boland (1997). "Biosynthesis of cis-Jasmone: a pathway for the inactivation and the disposal of the plant stress hormone jasmonic acid to the gas phase?". Helvetica Chimica Acta 80 (3): 838–850. doi:10.1002/hlca.19970800318.
L. Ruzicka, M. Pfeiffer (1933). "Über Jasminriechstoffe I. Die Konstitution des Jasmons". Helvetica Chimica Acta 16: 1208–1214. doi:10.1002/hlca.193301601153.