R-cadinene

Juniperus rigida Sieb. et Zucc. J. rigida Sieb. et Zucc. f. modesta (Nakai) Y. C. Chu Tu Soon (Juniper) (fruit) Alpha-pinene, myrcene, carene, limonene, p-cymene, beta-elemene, caryophyllene, humulene, bomeol, r-cadinene, terpinene, citronellol, anethole.48 Hemorrhage, treat hemoptysis, inflammation, kidney infection, arthritis joint infection. 

Quinene Quinic acid Quinochalone Quinonic substance Quinonoid Quinoric acid Quinquenosides Quisqualic acid r-cadinene... 

Six male specific compounds were isolated from the crucifer flea beetle, Phyllotreta cruciferae, and the same compounds plus two additional compounds were isolated from males of Aphthona flava, A. czwalinae, and A. cyparissiae. Three of the compounds were identified as (-F)-i r-himachalene, (-F)- ra w-a-himachalene (-F)-y-cadinene. Two other compounds were identified as new enantiomers of himachalene hydrocarbons that were previously identified from the fir trees, Abies alba and Abies nordmanniana. Finally, there were two himachalene alcohols and one nonsesquiterpene ketone that is a himachalene analog that were identified. The chemical and electrophysiological patterns are consistent with, but do not prove, a pheromonal function. 

China Valeriana altemifolia Bunge. V. amurensis R Smira. ex Kom. V. fauriei Briq. V.fauriei Briq. var. dasycarpa V. subbipinnatifolia A. Baranow Bomyl isovalerate, isovaleric acid, bomeol, camphene, pinene, d-terpineol, 1-limonene, pyrryl-a-methyl ketone, alpha-fenchene, myrcene, phellandrene, 1-caryophyllene, erpinene, terpinolene, eremophilene, selinene, cadinene, valerianol, valerenone, myrtenol, bisabolene, chatinine, caffeic acid.48 Antispasmodic, aphrodisiac, emmenagogue, stimulant, sudorific, backache, cramps, influenza, nausea, numbness. 

Fig. 5-3. Examples of mono- and sesquiterpenes and their derivatives in softwood. 1, a-Pinene 2, /3-pinene 3, 3-carene 4, camphene 5, borneol (R = H), bornyl acetate (R = COCH3) 6, limonene 7, a-terpineol 8, dipentene 9, a-muurolene 10, 8-cadinene 11, a-cadinol 12, a-cedrene 13, longifolene 14, juniperol.

Chen, X.Y., Wang, M.S., Chen, Y, Davisson, V.J. and Heinstein, R (1996) Cloning and heterologous expression of a second (-l-)-delta-cadinene synthase from Gossypium arboreum. ]. Nat. Prod., 59, 944—51. 

The dihydroxy-ketal (240), previously prepared from ( —)-santonin, has been used to synthesize a number of related sesquiterpenoids. Thus the diacetate of (240) was converted in six steps into (241), which was then treated with iso-propenyl acetate-sulphuric acid the derived enol-acetate was cleaved to the triol (242) by ozonolysis and lithium aluminium hydride reduction. The triol (242) was then converted into the di-iodo acetate (243) in a number of steps and thence to shyobunone (244) by dehydroiodination, reduction, and oxidation. Thermolysis of shyobunone at 160—180 °C gave preisocalamendiol (245) in about 30% yield. More recently, Iguchi et al. have shown that preisocalamendiol (245) can be cyclized to isocalamendiol (246) in aqueous acetic acid no trace of calamendiol (247) was found. A number of other interesting acid-catalysed cyclizations have been observed in this area, e.g. the formation of (248 R = OH) and (248 R = OAc) from (249) and the formation of (250) from (251). Finally, e-cadinene (252) has been obtained from (253), the lithium aluminium hydride product of preisocalamendiol (245). 

Additional remark The not sharp tasting fruits of another pepper species, cubeb (R cubeba L.), are also used for seasoning purposes (ingredient of curry). Apart from starch, protein and fatty oil, they contain 6-11% essential oil with 5-cadinene, P-cubebene, a-copaene, cubebol and germacrene D as main components. Origin and Output Indonesia (essential oil less than 1 t). 

Both (+)- -cadinene (71) and ( )-y2-cadinene (72) have been synthesised from the previously known intermediates (73, R = Et, optically active) and (73, R = Me, racemic). (— )-y2-Cadinene is one example of the relatively small... 

All samples are characterized by a prominent brown ester zone at R, 0.75 due to bornyl and/or terpinyl acetate and the violet zone.s of terpcne.s (e.g. cadinene) at the solvent front. The pattern and amount of blue and violet-blue zones in the R, range 0.4-0.6 and the zones of terpene alcohols (e.g. borneol T2, terpineol) in the R, range 0.25-0.4 varies in the commercial oil samples 1 --5. 

B Cubebin and the essential oil compounds, such as cadinol, a tricyclic sequiterpene alcohol, a mixture of isomer cadinenes, 1,4-dneol and terpineol-4, give prominent blue to violet-blue zones (B) with the VS reagent in the R, range 0.5 up to the solvent front. 

Oil Of Juniper, Juniperberry oil. Volatile oil from dried ripe fruit (harries) of Juniperus communis L., Cupressa-ceae, Constit, Pinene, cadinene, camphene, terpineo], juniper camphor, Analysis by GLC of the oil of six western North American species F, C. Vasec, R. W, Scora, Am. J. Bot. 54, 781 (1962). 

The soldier secretions of the North American species, Reticulitermes flavipes and R. virginicus contain none of the above compounds, but two sesquiterpenes, y-cadinene and its aldehyde (Fig. 16.11), have been isolated from both species (Zalkow et a/., 1981). These compounds, or attack by soldiers, apparently... 

The liquid chlorides freed by suction from the cadinene hydrochloride of fraction I were examined for the presence of other chlorides. As they could not be distilled in r>acuo they were boiled with their own weight of sodium acetate in glacial acetic acid solution, for the purpose of eliminating the hydrochloric acid, and the resulting oil was fractionated in vacuo. Of three equal fractions thus obtained—... 

Lavender oil has been reported to contain more than 100 components, including linalool, linalyl acetate, lavandulyl acetate, terpinen-l-ol-4, 1,8-cineole, camphor, 3-phellandrene, terpinolene, a-thujene, n-hexanal, n-heptanal, methyl amyl ketone, ethyl amyl ketone, perillaldehyde, perillyl alcohol, r/-bomeol, a-terpineol, a-pinene, limonene, lactones (4-butanolide, dihydrocoumarin, 4-methyl-4-vinyl-4-butanolide, 5-pentyl-5-pentanolide, 4,4-dimethyl-2-buten-4-olide, etc.), sesquiterpenes (caryophyllene, cadinene, etc.), fatty acids (propionic acid, isobutyric acid, caproic acid, p-coumaric acid, etc.), and others (list and horhammer). " ... 

Dwarf pine needle oil has been reported to contain mostly monoterpene hydrocarbons (ca. 70%), including bomyl acetate and other esters aldehydes (e.g., hexanal, cuminaldehyde, and anisaldehyde) r/-ciyp-tone small amounts of sesquiterpenes (e.g., cadinene) and alcohols among others (list and horhammer martindale merck remington). 

---