Jasmone

Jasmone

Names
Preferred IUPAC name 3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one
Other names cis-Jasmone
Identifiers
CAS Number	488-10-8 Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	1266012 N
PubChem CID	1549018
UNII	RC4W0G9YUK Y
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
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 [77 °F], 100 kPa). N verify (what is YN ?) 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. In perfume compositions, jasmone is used in small concentrations, where it enhances the naturalness of floral notes³.