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 Number	488-10-8 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	1266012 ;
PubChem CID	1549018;
UNII	RC4W0G9YUK ;
	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 ; 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;
	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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	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

L. Ruzicka; M. Pfeiffer (1933). "Über Jasminriechstoffe I. Die Konstitution des Jasmons". Helvetica Chimica Acta. 16: 1208–1214. doi:10.1002/hlca.193301601153.
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

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[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