Hydrocarbons sesquiterpenic

Sesquiterpenic alcohol Sesquiterpene hydrocarbons Sesquiterpene lactones... 

Plectranthus tenuiflorus (Vatke) Agnew The partially dried leaves of P. tenuiflorus yielded oil (1.6%) that contained carvacrol (14%), a-terpinene (10%), p-cymene (11%) as the major constituents, while the hydrocarbon sesquiterpenes (a-cubenene, p-cubenene, 5-cardinol, y-cardinol, a-copaene) amounted to about 26% (67). 

Ch. II., The Constituents of Essential Oils and Synthetic Perfume Bodies. — Hydrocarbons—Sesquiterpenes —Alcohols—Terpene Alcohols—Esters— Aldehydes—Ketones— Phenols and Phenolic Compounds—Oxides and Lactones— Nitrogen Compounds — Sulphur Compound—Free Acids. 

Monoterpene hydrocarbon, sesquiterpene hydrocarbons, lactones, umbellic acid, umbelliferone, [2-methoxy-3-isobutyl pyrazine, 5-sec-butyl-3-methyl-2-butenethioate, 1,3,5-undecatriene as minor components]... 

Although the term terpene once referred only to hydrocarbons current usage includes functionally substituted derivatives as well grouped together under the general term isoprenoids Figure 26 6 (page 1086) presents the structural formulas for a number of representative examples The isoprene units m some of these are relatively easy to identify The three isoprene units m the sesquiterpene farnesol, for example are mdi cated as follows m color They are joined m a head to tail fashion... 

Amyris Oil. Obtained by steam distillation of the wood of y m hakamijera L., the so-called West Indian sandalwood which is indigenous to northern South America, Central America, and the West Indies, amyris oil [8015-65-4] is a pale yellow to brownish yellow viscous oil with a slightly oily-sweet and occasionally peppery balsamic woody note. It finds use as a blender and fixative for soap fragrances. The volatile constituents, which are primarily hydrocarbon and oxygenated sesquiterpenes, are shown in Table 22 and Figure 5 (63). 

Terpenes are characterized as being made up of units of isoprene in a head-to-tail orientation. This isoprene concept, invented to aid in the stmcture deterrnination of terpenes found in natural products, was especially useful for elucidation of stmctures of more complex sesquiterpenes, diterpenes, and polyterpenes. The hydrocarbon, myrcene, and the terpene alcohol, a-terpineol, can be considered as being made up of two isoprene units in such a head-to-tail orientation (1). 

The majority of the turpentine comes from the southeastern United States, which consists of 60—70% a-pinene, 20—25% P-pinene, and 6—12% other components. Because there is variation in components from different species of the pine tree as well as variation from the many paper pulp mills, there is obviously variation in the analysis of sulfate turpentines. Some of the other components consist of -menthadienes, alcohols, ethers such as anethole [104-46-1] and methylchavicol [104-67-0] and the sesquiterpene hydrocarbon, P-caryophyUene [87-44-5]. 

Important commercial sesquiterpenes mosdy come from essential oils, for example, cedrene and cedrol from cedarwood oil. Many sesquiterpene hydrocarbons and alcohols are important in perfumery as well as being raw materials for synthesis of new fragrance materials. There are probably over 3000 sesquiterpenes that have been isolated and identified in nature. 

Gedrene and Gedrol. Cedarwood oil is one of the essential oils whose production is large and provides a source for synthesizing a number of derivatives. Gedrene (91) and thujopsene (92) are the two main sesquiterpene hydrocarbons found in the oil, along with a number of minor components (187). Gedrol [77-53-2] (93) is the main alcohol component of the oil. 

Patchouli alcohol. Patchouli oil comes from Pogostemonpatchouli and the main constituent is patchouli alcohol [5986-55-0] (105) or patchoulol. Another component of the essential oil is norpatchoulenol (106), a norsesquiterpene derivative as a minor (3—5%) constituent, important ia determining the overall odor of the essential oil (197). The price of patchouli oil ia 1995 was 20.90/kg from Indonesia (69). Alarge proportion of the oil (40—60%) is comprised of sesquiterpene hydrocarbons that do not have much odor value. World production of the oil was at about 750 t ia 1984. It is valuable ia perfumery bases because of its characteristic woody, herbaceous odor (198). 

Guaiol and Bulnesol. The main constituents of guaicwood oil are the sesquiterpene alcohols guaiol [489-86-1] (107) and bulnesol (108). When the alcohols are dehydrated with acid, many of the hydrocarbons formed are also found ia patchouli oil. 

It is convenient to here mention the hydrocarbon verbenene, C,gH,4, on account of its relationship with pinene. It results from the action of acetic anhydride on verbenol, thei alcohol corresponding with the ketone, verbenone. So produced it is laevo-rotatory. The dextro-rotatory and racemic varieties are also known. The sesquiterpenes have the following characters when regenerated from their respective dibromides —... 

The above considerations indicate the complex nature of the hydrocarbons known as caryophyllene. For practical purposes, however, the compounds indicated are obtained of practically definite melting-points, and, in spite of the complicated isomerism existing amongst most of them, are useful for identification of the sesquiterpene or mixture of sesquiterpenes, occurring naturally and known as caryophyllene . 

When caryophyllene alcohol is dehydrated by means of zinc chloride or phosphorus pentoxide, a hydrocarbon results, which does not appear to be identical with any of the sesquiterpenes described under the name caryophyllene. It has therefore been named clovene . Clovene has the following characters —... 

Schimmel Co. attempted to acetylise the alcohol by means of acetic anhydride, but the reaction product only showed 5 per cent, of ester, which was not submitted to further examination. The bulk of the alcohol had been converted into a hydrocarbon, with loss of water. Ninety per cent, formic acid is most suitable for splitting off water. Gne hundred grams of the sesquiterpene alcohol were heated to boiling-point with three times the quantity of formic acid, well shaken, and, after cooling, mixed with water. The layer of oil removed from the liquid was freed fi-om resinous impurities by steam-distillation, and then fractionated at atmo.spheric pressure. It was then found to consist of a mixture of dextro-rotatory and laevo-rotatory hydrocarbons. By repeated fractional distillation, partly in vacuo, partly at ordinary pressure, it was possible to separate two isomeric sesquiterpenes, which, after treatment with aqueous alkali, and distillation over metallic sodium, showed the following physical constants —... 

One consequence of the shift from grassland to shrubland is the potential for significant increases in volatile hydrocarbons added to the atmosphere. The leaves of creosotebush, Larrea tridentata, yielded 0.1 to 0.2 percent of a complex mixture of volatile compounds. That mixture contains several hundred compounds of which 100 accounted for more than 90% of the total volatiles (23). The volatiles that were identified included four monoterpene hydrocarbons, four oxygenated monoterpenes, six sesquiterpene hydrocarbons, eight aromatics like benzyl acetate and ethyl benzoate, plus... 

Longifolene is a tricyclic sesquiterpene. It is a typical terpene hydrocarbon in terms of the structural complexity. The synthetic challenge lies in construction of the bicyclic ring system. Schemes 13.24 through 13.33 describe nine separate syntheses of longifolene. We wish to particularly emphasize the methods for carbon-carbon bond formation used in these syntheses. There are four stereogenic centers in longifolene,... 

In a search for allelopathic agents from common weeds, Amaranthus palmerl S. Wats (Palmer amaranth) and Ambrosia artemisiifolia L. (Louisiana annual ragweed) have been analysed for their organic natural products. From A. palmerl phytol, chondrlllasterol, vanillin, 3-methoxy-4-hydroxynitrobenzene and 2,6-dimethoxy- benzoquinone were isolated. From the roots of Ambrosia artemisiifolia four polyacetylenes, a mixture of sesquiterpene hydrocarbons, methyl caffeate, and a mixture of 8-sitosterol and stlgmasterol were obtained. 

Fraction 2 and 3 (P.E.) provided, besides the sesquiterpene hydrocarbon mixture, a compound which on the basis of H NMR and MS spectral evidence was shown to be the acetylenic hydrocarbon pentayneene (9) C,Ht> previously isolated from A. artemisiifolia... 

Resins older than 40 000 years are considered to be fossil resins. The fossilization of resins begins with polymerisation and forms ambers and copals. Most of the ambers are derived from components of diterpenoid resins with a labdanoid structure other ambers are based on polymers of sesquiterpene hydrocarbons such as cadinene, and may include triterpenoids less common ambers from phenolic resins derive from polymers of styrene. Figure 1.4 shows the skeletal structures of the components which make up the polymers occurring in fossil resins [141]. 

D. Joulain and W. A. Konig, The Atlas of Spectral Data of Sesquiterpene Hydrocarbons, E. B. Verlag, Hamburg, 1998. 

Natural hydrocarbon products such as terpenes and steroids have been subjected successfully to MM calculations. Sesquiterpenes... 

Because a-copaene is a sesquiterpene, a hydrocarbon, and because of very early reports that kerosene is a Hedfly attractant (17). hydrocarbons in kerosene were re-investigated. Also, in the Hawaiian 1950-1955 survey (6), 2-methylnaphthalene was indicated as active. This compound was found in kerosene and was tested for activity again. The positional isomer, 1-methylnaphthalene, has very little activity, but 2-methylnaphthalene did exhibit activity in olfactometer tests by Gothilf and in field trials by Cunningham. Although the activity of 2-methylnaphthalene is somewhat less than... 

Capnellane is the generic name applied to a group of sesquiterpene alcohols and the hydrocarbon isolated from the soft coral Capnella imbricata A < >-Capnellene (667), the presumed biosynthetic precursor of the capnellenols, was first synthesized in 1981 by Stevens and Paquette Their synthetic plan called for the construction of bicyclic ketone 668 and its appropriate annulation. The latter event was achieved by application of the Rupe rearrangement to 668, conjugate addition of a vinyl group to 669, ozonolysis, and cyclization (Scheme LXVIII). Hydrogenation and olefination completed the sequence. 

The first naturally occurring tricyclo[6.3.0.0 ]undecane to be synthesized was isocomene (757), a colorless oily sesquiterpene hydrocarbon isolated from several plant sources. In 1979, Paquette and Han reported an efficient, stereospecific approach starting with a preformed bicyclic enone, to which the third five-membered ring was appended with proper attention to stereochemistry and position of unsaturation (Scheme LXXX) The pivotal steps are seen to be the stannic chloride-induced cyclization of aldehyde 732 and the conjugate addition of lithium dimethylcuprate to 733 which sets the stereochemistry of the last methyl group. 

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