Ocimene, trans

Chemically, all forms contain linalyl acetate, linalool and 1,8-cineole, along with many other compounds. Further analysis of each type reveals their differences in amounts of chemical components. The situation is illustrated by comparing published data for principal constituents and then seeing how these are reinforced by an actual GC chromatogram. This is shown in Table 7.1 the main figure is the published data while figures in brackets are those taken from the GC analysis of actual oil samples (cis- and trans-ocimene are minor hydrocarbon components, but are included as they are often used as markers for the authenticity of lavender oils). In all cases the amounts of compounds in the hybrid (Lavandula intermedia) are in between those of the true (Lavandula angustifolia) and the spike (Lavandula latifolia). 

True French lavender grows in Haute Provence at an altitude of 600-1500m. The plants are grown from seeds of the wild lavender ( population lavender). Lavender oil is produced in a yield of 10-25 kg/ha. It has the following typical composition (%) r/ .v-ocimcnc (4-10), trans-ocimene (1.5-6), 1,8-cineole (linalyl acetate (25-45), l-terpinen-4-ol (2-6), and lavan-dulyl acetate [25905-14-0] ( 2) [574-583b],... 

Alkenes (e.g. camphene) are readily prepared by the BF3,Et20-catalysed elimination of secondary borate esters.Terminal conjugated dienes may be prepared by Pd(OAc)2-PPh3-catalysed elimination from allyl phenyl ethers or allylic acetates [e.g. geranyl, neryl, and linalyl acetates to form similar mixtures of myrcene (60—74%), trans-ocimene (8—20%), and c -ocimene (14—20%)], and the complex [(i7-CsH5)Cr(NO)2]2 dehalogenates n/c-dihalides (e.g. limonene tetrabromide) without affecting other halides (except for benzyl halides). 

Composition Oil from French population lavender cis- ocimene 5-9% trans-ocimene 3-5% 1,8- cineole <1% camphor. <0.4% (-)- linalool 27-35% (-)-linalyl acetate (see linalool) 30-40% l+)-terpinen-4-ol (see p-menthenols) 3-4% (-)-la-vandulyl acetate (see lavandin [oil]) 3-4%. Bulgarian oil contains mostly 45-50% -)-linalyl acetate. Use L. has many uses in the perfume industry, e.g., in lavender waters, in masculine perfumes or perfumes with masculine notes, etc. in medicine in carminatives and balneotherapeutics. 

ISO standard 10115 shows character and data for this oil. Adulteration and blending are done by synthetic anethole, eugenol from cinnamon leaf oil, synthetic estragole, and cis- and trans ocimene... 

Takahashi, M., Urata,H., Suzuki, H., etal. (1984). Regioselective Introduction of 0-nucleophiles into Myrcene and trans-Ocimene Using Palladium(II) Complexes, J. Organomet Chem., 226, pp. 327-336. 

Essential oil components common to the aerial parts of E. pallida, E. purpurea, and E. angustifolia include bomeol, bornylace-tate, pentadeca-8-en-2-one, germacrene D, caryophyllene, caryophyllene epoxide, and palmitic acid. According to another report, the aerial parts contain P-myrcene, a- and P-pinene, limonene, camphene, tran -ocimene, 3-hexen-l-ol, and 2-methyl-4-pentenal. The same report lists dimethyl sulfide, 2- and 3-methylbutanal, 2-propanal, 2-methylpropa-nal, acetaldehyde, camphene, and limonene as the main volatile constituents of the roots, in addition to a-phellandrene that is present only in E. purpurea and E. angustifolia roots. ... 

Alloocimene Manufacture. a-Pinene (8) is converted thermally first to cis-ocimene (17), which rearranges to give about 40—50 wt % of the two alloocimene isomers, ie, alloocimene [7216-56-0] (53) and 4-trans-(i-trans-2S[oo[Pg.417]

The plant is strongly aromatic on account of an essential oil which comprises cis-a-ocimene (25.11%), 3,7-dimethyl-l,6-octadien-3 ol (16.85%), and trans-nerolidol (13.89%), hence the use of the plant in aromatherapy. A methanolic extract of bark of Litsea cubeba (Lour.) Pers. and its fractions (0.01 mg/mL) from bark inhibit NO and PGE2 production in LPS-activated RAW 264.7 macrophages without significant cytotoxicity at less than 0.01 mg/mL concentration. The methanol extract decreased the enzymatic activity of myeloperoxidase (0.05 mg/mL). These findings suggest that L. cubeba is beneficial for inflammatory conditions and may contain compound(s) with anti-inflammatory properties (63). Can we expect the vasorelaxant laurotetanine (64) isolated from the plant to exert such activity ... 

Although most consumers appreciate the fieriness of chile, capsaicinoids are not perceived through odor or taste receptors but through the nociceptive pain receptors described earlier. The compounds in chile fruit that create the flavor and aroma are produced in the fruit wall. Buttery et al. [90] generated vacuum steam distilled oil from green bell pepper macerate, with well over 40 peaks on subsequent GC/MS analysis. Of these peaks, the major flavor compound associated with bell pepper aroma was 2-methoxy-3-isobutylpyrazine (Fig. 8.1). They also reported several monoterpenoids in abundance, limonene, trans- 3-ocimene, and linalool as well as other aliphatic aldehydes and ketones. The flavor composition of dried red bell pepper powder (sweet paprika) extracted with ether identified 44 key peaks by GC/MS [91]. In these dried samples the key compounds were P-ionone and several furanones. The post-harvest processing and the different fruit maturities as well as possible varietal differences are all causes for the different aromatic profiles. 

Diels-Alder reaction of hemigossypolone with trans-B-ocimene. and heliocides Hp and H, are similarly formed from hemigossypol one and myrcene (Scheme 2)." Neither reaction requires an enzymatic catalyst, because they occur spontaneously at room temperature. The concentrations of H, and H2 are always two to three times those of H. 

There has been considerable activity in this area of monoterpenoid synthesis. Syntheses of [7- C]-, [7, 8- C]-, and [7, 8- H]-geraniol have been reported. The ocimene (42 X=H) has been synthesized again by Vig et ai, this time from trans-6,6-ethylenedioxy-2-methylhept-2-en-l-ol via Wittig reactions. Both (4iE )- and (4Z)-(6S)-2,6-dimethyloct-4-ene have been synthesized by known routes from 5-3-methylpent-l-yne. The addition of organohomocuprates (e.g. F. J. McQuillin, Chem. and Ind., 1976, 941. 

Cryptotaenia japonica Hasskarl C. canadensis (L.) DC Japan Liu Shan Ya Er Qin (whole plant) Cryptotaenen, kiganen, kiganol, petroselic acid, isomesityl oxide, mesityl oxide, methyl isobutyl ketone, tran.v-beta-ocimene, terpinolene.48-50 For diarrhea, dysmenorrhea, rheumatism, tubercular glands. 

Cyclization of allo-ocimene, using alkali metal amines, may give cycloheptadienes or acyclic dienes depending upon the conditions used 1,2,4-trimethylcyclohepta-1,3-diene may be obtained exclusively with sodium-piperidine, and 2,6-dimethylocta-2,4-diene (predominantly trans) is the major product using sodium-morpholine.129 The Prins formaldehyde reaction on myrcene (12), on the chelo-tropic adduct (42), and on the Diels-Alder adduct (43), has been investigated 130... 

Dimethyloctanes.— The full account of the synthetic work on achillene (see Vol. 1, p. 9) includes a technique for improvement of the yield of natural cfs-achillene (12) by irradiation of the trans-compound (11), in the presence of benzophenone, the equilibrium mixture containing 45 % ds-achillene. Thermal isomerization of cis-j8-ocimene (13) [= (16)] yields 6-cis-allo-ocimene (14) without any trans-isomer (15) this is presumably because the preferred conformer (16) has the bulky isobutenyl group in a pseudo-equatorial position (the 6-trans-... 

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