Tagetones

Tagetes meal and extract Tagetes oil Tagetone [6752-80-3] Tagonis... 

The branched-chain polyunsaturated ketones tagetone and ocimenone, the odor impact compounds ia tagettes, are unstable and presumably responsible for the resiniftcation of the oil. 

Methyl-5-hepten-2-one is an important intermediate in the synthesis of terpenoids. Its odor properties are not impressive. It occurs in nature as a decomposition product of terpenes. Tagetone [6752-80-3] is a major component of tagetes oil. Solanone [1937-45-8] and pseudoionone [141-10-6] are acyclic Cn ketones with a terpenoid skeleton. Solanone is one of the flavor-determining constituents of tobacco, pseudoionone is an intermediate in the synthesis of ionones. 

Tagetes erecta L. Chou Fu Yong (Marigold) (leaf, flower) Alpha-terthienyl, d-limonene, 1-linalool, tagetone, n-nonyl aldehyde.50 Treat sores and ulcers, cold, conjuctivitis, cough, mastitis, mumps. 

N.A. Essential oils, tagetone, limonene, linalool, ocimene, linalyl acetate, thiophenes.171 Treat rheumatism, externally for boils, carbuncles, earache. 

Sumaresinolic acid esters Swertiamarin Syringaldehyde Syringic acid Tagetone... 

Z-Tagetone (82a) -Tagetone (82b) Z-Ocimenone (83a) -Ocimenone (83b) Fig. (13). Acyclic monoterpene ketones tagetone and ocimenone... 

Analysis of Tagetes minuta. L. (Compositae) revealed the presence of cis- (40a) and trans- (40b) -ocimenones (= tagetenones), in addition to the previously known tagetones and dihydrotagetones. The new compounds were synthesized by treatment of a mixture of 3-methylbut-2-enoyl chloride and isoprene with a Lewis acid, e.g. SbClg. ... 

An interesting variant of these Michael-type additions is the 1,6-addition of the anion of type (29) to a dienyl sulfone as a route to tagetones and 1,4-addition to nitrostyrene to form 3-nitro ketones. A key step in a synthesis of 11-deoxyanthracyclinone involves the regioselective reaction of complexed styrene with lithiated protected acetddehyde cyanohydrin. ... 

The full paper on Cookson s syntheses of ocimenones, filifolene, and the tagetones has appeared (Vol. 5, p. 8). ° One-pot syntheses of the predominantly trans-isomers (>80%) of (12 X = CH2OH) and (13 named lavandurol), (12 X = CO2H), and (12 X = CHO) result from [(77 -C5Hs)2TiCl2]-catalysed regioselective isoprene... 

Lippia dauensis (Chiov.) Chiov. L. dauensis oil was obtained from plants collected in the north-eastern arid region of the country. The semi-dried leaves and flowering tops of the plant produced 2.4% oil contaiiung p-ocimene (24.7%), 2-methyl-6-methylene-7-octen-4-one (15.7%), myrcene (12.9%), cis-tagetone (11.0%), and 2-methyl-6-methylene-2,7-octadien-4-ol (9.4%). The... 

Lippia grandifolia A. Rich. Leaves SD 0.7 octen-4-one, myrcene, cA-tagetone linalol, thymol, P-cubenene, />cymene 79,81... 

D. 4-Oxygenated 2,6-Dimethyloctanes Ipsenol, Ipsdienol, Tagetones, and Ocimenones... 

The original method by Cookson et al. for the preparation of the ocimenones (89) has been reexamined by Weyerstahl et al., who foimd that the proportion of ( )-89 to (Z)-89 is 3 1 rather than 9 1, as originally reported. This C5 + C5 coupling which Cookson (and de Villiers et al. ) carried out with isoprene and the acid chloride of senecioic acid (59) (cf. Vol. 4, p. 47, Refs. 160 and 161), has also been realized by Julia (cf. Vol. 4, p. 473, Refs. 158 and 159), who has published more recent developments. A Russian patent claims that the oxidation of the allene 99 with pyridnium chlorochromate followed by isomerization with powdered potassium hydroxide gives (Z)-tagetone [(Z)-88] stereoselectively. 

This oil also contains tagetonal, (+)-3,7-dimethyl-3-hydroxy-l-octen-5-onc. ... 

Many functional groups are tolerated during the Friedel-Crafts acylation of allylsilanes, giving rise to a wide variety of functionalized ketones, some of which are shown in Scheme 13. The stability of a sulfone group under conditions required for acylation has potential for the formation of dienones, as demonstrated in the synthesis of ( )- and (Z)-tagetones (11) shown in Scheme 13. ... 

Chloro ketones have been observed in tin(IV) chloride catalyzed acylations of isopiene as part of high-yielding synthetic approaches to tagetones (12) and ocimenones (13 Scheme 15). Typically, it was not necessary to isolate these, dehydrohalogenation to mixtures of cis- and rran -dienones being accomplished using lithium fluoride and lithium carbonate in DMF. 

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