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Cis Jasmone

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Jasmone is a natural organic compound extracted from the volatile portion of the oil fromjasmine 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.

An attempt to make Z jasmone – an important constituent of many perfumes

In fact one synthesis uses the following as carbon sources:

cis (Z) jasmone ,

cas no 488-10-8, 3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one

ref-(Can. J. Chem. 1978, Vol 56, p2301)

1    W. Theilheimer. Synthetic Methods of Organic Chemistry. Volume 31, 1977, p. 352 
2   Tetrahedron, 39 (24), p. 4127, 1983

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.

Predict NMR spectrum

Formula: C10H14O
CAS#: 488-10-8
MW: 150.22

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Recent Progress in the Use of Vilsmeier-Type Reagents

June 26, 2012

Recent Progress in the Use of Vilsmeier-Type Reagents

Organic Preparations and Procedures International: The New Journal for Organic Synthesis Volume 42, Issue 6, 2010                   

Weike Sua, Yiyi Wenga, Ling Jianga, Yanyan Yanga, Linyao Zhaoa, Zhiwei Chena, Zhenhua Lia & Jianjun Lia pages 503-555
Available online: 15 Nov 2010
a  Weike Su, Key Laboratory of Pharmaceutical Engineering of
Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology,
Hangzhou 310014, P. R. China. E-mail: Pharmlab@zjut.edu.cn


Vilsmeier-Haack reaction mechanism

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