Jasmone
{{Chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 415361066
|Name = Jasmone
|ImageFile = Jasmon structural formation V1.svg
|ImageSize = 180
|ImageFile1 = Jasmone molecule ball.png
|ImageAlt1 = Ball-and-stick model of jasmone
|PIN = 3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one
|OtherNames = cis-Jasmone
|Section1={{Chembox Identifiers
|SMILES = CC\C=C/CC1=C(CCC1=O)C
|PubChem = 1549018
|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
|ChemSpiderID = 1266012
|SMILES2 = O=C1\C(=C(/CC1)C)C\C=C/CC
|StdInChI_Ref = {{stdinchicite|changed|chemspider}}
|StdInChI = 1S/C11H16O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h4-5H,3,6-8H2,1-2H3/b5-4-
|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
|StdInChIKey = XMLSXPIVAXONDL-PLNGDYQASA-N
|CASNo_Ref = {{cascite|correct|CAS}}
|CASNo = 488-10-8
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = RC4W0G9YUK
}}
|Section2={{Chembox Properties
|Formula = C11H16O
|MolarMass = 164.246 g/mol
|Appearance = colorless to pale yellow liquid
|Density = 0.94 g/mL, liquid
|Solubility = in water
|MeltingPtC = 203 to 205
| BoilingPtC = 146
| BoilingPt_notes = at 27 mmHg
}}
}}
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.{{cite journal
| title = Über Jasminriechstoffe I. Die Konstitution des Jasmons | trans-title = On Jasmine Perfumes I. The Composition of Jasmone
|first1=L. |last1=Ruzicka |first2=M. |last2=Pfeiffer | journal = Helvetica Chimica Acta
| year = 1933
| volume = 16
| issue =
| pages = 1208–1214
| doi = 10.1002/hlca.193301601153
}}
Jasmone is produced by some plants by the metabolism of jasmonic acid, via a decarboxylation.{{cite journal|first1=P. |last1=Dąbrowska |first2=W. |last2=Boland |title=iso-OPDA: An Early Precursor of cis-Jasmone in Plants? |journal= ChemBioChem |date=2007 |volume=8 |issue=18 |pages=2281–2285 |doi=10.1002/cbic.200700464|pmid=18033720 }} It can act as either an attractant or a repellent for various insects. Commercially, jasmone is used primarily in perfumes and cosmetics.
References
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