Structure d'une lactone odorante présente dans l'essence de jasmin (Jasminum grandiflorum L.)

Abstract

The isolation of a new lactonic component from jasmine waxes and jasmine oil is described. This odoriferous compound is shown to be (‐)‐cis‐5‐pent‐2′‐enyl‐pentanolide‐(5,1).

Jasminum grandiflorum flowers—Phytochemical complexity and its capture in extracts: a review

“…It was identified as its methyl ester prepared with CH 2 N 2 , by HRMS, 13 C NMR, mp 162‐6℃ and j +50° (c 3, CHCl 3 ). It is possible that ursolic acid corresponds to the unidentified crystalized product observed during the isolation of jasmine lactone 191 . In general, this acid is accompanied by oleanolic acid, which has not been characterized yet in jasmine flower concrete.…”

“…It is possible that ursolic acid corresponds to the unidentified crystalized product observed during the isolation of jasmine lactone. 191 In general, this acid is accompanied by oleanolic acid, which has not been characterized yet in jasmine flower concrete.…”

“…This is the main delta‐lactone present in JA (Figure 5), as the pure ( Z )‐isomer 13 , 191 along with the bicyclic lactone 15, which occurs in trace 121 . Unlike 13 , the latter is biogenetically linked to 6‐ epi ‐7‐isocucurbic acid (not found yet in JA), which is formally a reduction product of trans‐ jasmonic acid, the precursor of methyl trans ‐jasmonate 8a (Figure 3).…”

Preparation of Optically Active γ- and δ-Lactones by Microbiological Reduction of the Corresponding Keto Acids

“…The 5-lactones appeared to have a slightly higher [a]D than did the y-lactones. Winter et al (1962) reported that (-)5-pentyl-pentanelactone obtained from the unsaturated lactone isolated from jasmine oil by hydrogenation had [aID20 = -49.7°(without solvent), and nD25 1.4544.…”

“…Parasorbic acid [(+)5-methylpentene-2-lactone] is present in rowan berries (Doebner, 1894; Kuhn and Jerchel, 1943;Diemair and Franzen, 1959), and massoia lactone [(-)5-pentyl-pentene-2-lactone] has been extracted from the bark of the New Guinea massoia tree, Cryptocaria massoia (Meyer, 1940). Recently, Winter et al (1962) reported the isolation of a levorotatory unsaturated lactone, 5-(penten-2 cis-yl)-pentanelactone, from jasmine oil. Dextrorotatory -y-lactones can be prepared from the antibiotics nemotin and odyssine Leeming, 1955, 1957;Bu'Lock et al, 1956) or from (+)4dodecen-8-yl)-butanelactone (Friinkel, 1939), but a limiting factor is that these natural compounds can only be isolated in minute quantities.…”