Terpinolene aldehyde

Scheme 6.31 Synthesis of terpinolene aldehyde from different precursors and under different hydroformylation conditions.

Coriandrum sativum L. Hu Sui (Coriander) (leaf) Acetone, bomeol, coriandrol, cymene, decanal, decanol, decylic aldehyde, dipentene, geraniol, rutin, limonene, linalool, malic acid, nonanal, oxalic acid, phellandrene, tannic acid, terpinene, terpinolen, umbelliferone, scopoletun, coumarins, quercetin, kaepferal, aflatoxins.50-450 Eruptions of pox and measles. 

Although, chemically, all products belonging to these two series are correctly described as terpenes, in perfumery (just to make matters even more complicated ) the word is often used in a narrower sense to describe only the hydrocarbon members of the series. These include limonene and terpinolene with 10 carbon atoms, and cedrene and caryophyllene with 15. Materials belonging to the series but containing oxygen are then described as terpenic alcohols, aldehydes, and so on. 

In ethanol solutions under the same hydroformylation conditions [Rh(COD) (OMe)]2, P(O-0-fBuPh)3, CO/H2 (1 1, 80bar, 80 C), terpinolene and y-terpinene gave mixtures of fragrance acetals in 60 - 70% combined yields (along with the aldehydes themselves) [115]. 

The aroma of apricots (Armeniaca vulgaris, syn. Prunus armeniaca, Rosaceae) is composed of a large number of different substances. Important components are monoterpenic hydrocarbons, alcohols and aldehydes (myrcene, hmonene, p-cymene, terpinolene, a-terpineol, geranial, geraniol and hnalool in particular) and aldehydes with green flavour, such as (Z)-hex-3-enal and acetaldehyde. Other volatile components include products of oxidation of fatty acids, such as (2 ,6Z)-nona-2,6-dienal, (Z)-octa-l,5-dien-3-one, lactones (y-hexalactone, y-octalactone, y-decalactone, y-dodecalactone, 8-decalactone and 8-dodecalactone), carboxylic acids (especially, 2-methylbutanoic and acetic acids) and degradation products of carotenoids, such as P-ionone. 

The aroma of carrots root Daucus carota, Apiaceae) is very complex. It consists of various aldehydes, ketones, mono- and sesquiterpenic hydrocarbons and other compounds. The important hydrocarbons are myrcene, sabinene, terpinolene, P-caryophyUene, y-bisabolene and a-pinene, which are present in the largest quantities. The significant carbonyl compounds are acetaldehyde and (2 ,6Z)-nona-2,6-dienal. One of the typical aromatic substances determining the basic odour of carrots is 2-sec-butyl-3-methoxypyrazine. During the cooking of carrots, the contents of methanal, ethanal, propanal, octanal, (Z)-dec-2-enal and some sulfur compounds, such as dimethylsulfide and ethanethiol, increase. At the same time, the contents of monoterpenes and P-caryophyUene decrease. 

According to Walbaum, the oil contains about 50 per cent, of linalol,. but bis results were obtained by a direct acetylation. If the method of Boulez be used, which is necessary in the case of linalol, from 65 to 70 per cent, of linalol is indicated. JDextro-a--pvaene, i-a-pinene, y3-pinene, dipentene, cymene, terpinene, geraniol, borneol, acetic esters, and decy) aldehyde are also present in the oil, with, possibly, phellandrene and terpinolene. 

Figure 28 Comparison of chromatograms of soft drink extracted from both the aqueous (top) and gaseous phase (middle). Combined sampling technique SBSE (bottom). Peak identities are as follows 1, terpinolene 2, nonanal 3, linalool 4, 1-terpinen-4-ol 5, a-terpineol 6, geranyl acetate 7, safrol 8, cinnamic aldehyde 9, cinnamyl acetate 10, a-bisabolol 11, myiisticin 12, campherenol 13, 2-methoxycinnamic aldehyde 14, myristic acid 15, pentadecanoic acid 16, palmitic acid 17, squalene 18, caffeine.

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