Nerolidol

Nerolidol and Farnesol. The alcohols nerohdol [7212-44-4] (96) and famesol [4602-84-0] (97) are isomeric and are both important perfumery products. Nerohdol has been isolated from neroH oil, jasmine, citroneUa oil, and pepper oil. It has a mild and woody-floral, slightly green odor with excellent tenacity and good blending and fixative properties (190). 

Determination of the enantiomeric distribution of a-pinene, /3-pinene, limonene, terpinen-4-ol and nerolidol in neroli and petitgrain oils... 

The next group of alcoholic bodies to be studied are those which, although open-chaini alcohols, show considerable tendency to easily pass into closed-chain compounds, so that they occupy a definite position of their own, midway between the ordinary aliphatic series and the closed-chain series. The principal members of this important group are geraniol, nerol, linalol, and citronellol, together with the so-called aliphatic sesquiterpene alcohols, farnesol and nerolidol. 

Nerolidol is an aliphatic sesquiterpene alcohol of the formula CjjHjjO, which has been isolated from the higher boiling fractions of orange-flower oil. It has the following characters —... 

In 1899 Thoms isolated an alcohol from Peru balsam oil, which he termed peruviol. This body was stated to have powerful antiseptic properties, but has not been further investigated until Schimmel Co. took up the subject. The oil after saponification was fractionated, and after benzyl alcohol had distilled over, a light oil with characteristic balsamic odour passed over. It boiled at 125° to 127° at 4 mm., and had a specific gravity 0 8987, optical rotation -1- 12° 22, and refractive index 1-48982. This body appeared to be identical with Hesse s nerolidol, whilst in physical and chemical properties it closely resembles peruviol. The characters of the various preparations were as follows —... 

It appeared that the impure alcohol isolated from balsam of Peru was, in fact, identical with nerolidol. When allowed to stand for three to four weeks with phenyl-isocyanate both alcohols yielded a phenyl-urethane, melting at 37" to 38°. A mixture of the two bodies suffered no depression in melting-point. The alcohols have the formula 15 260-The alcohol from balsam of Peru is therefore mixed with a small quantity -of an alcohol of higher specific gravity, the nature of which is still undetermined. Traces of benzyl alcohol were found in it, but not in sufficient quantity to account for the differences observed. Oxidation experiments did not throw any light on the question. It may therefore be safely assumed that the peruviol of Thoms consisted in the main of nerolidol, but contaminated with a substance of the same boiling-point to such an extent that its combustion figures pointed to the formula CjjH. jO instead of... 

Scheme 9.37 Vanadium-dependent bromoperoxidase (VBPO)-mediated conversion of nerolidol to a-, fl-, and y-snyderols.

In vanadium-dependent haloperoxidases, the metal center is coordinated to the imidazole system of a histidine residue, which is similarly responsible for creating hypochlorite or hypobromite as electrophilic halogenating species [274]. Remarkably, a representative of this enzyme class is capable of performing stereoselective incorporation of halides, as has been reported for the conversion of nerolidol to various snyderols. The overall reaction commences through a bromonium intermediate, which cyclizes in an intramolecular process the resulting carbocation can ultimately be trapped upon elimination to three snyderols (Scheme 9.37) [275]. 

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 ... 

Nernst-Einstein equatioon, 5 587 Nernst equation, 9 571 12 206 19 206 Nernst-Planck equation, 9 612-613 Nerol, 3 233 24 479, 501, 503-506 grades of, 24 505 hydrogenation of, 24 506 price of, 24 505 Nerolidol, 24 546-547 Neroliodyl acetate, 24 547 Nerve agents, 5 815, 818-821 Neryl, 24 479 Neryl esters, 24 505 Nesmeyanov reaction, 3 75 Nested fullerenes, 12 231 Nested situations, amount of coverage in experimental design texts compared, S 395t... 

Synthetic nerolidol, 24 547 Synthetic oligonucleotides, 17 621 Synthetic organic chemicals industry, 24 253-254... 

Nezara antennata males produce similar volatile compounds, including Z-a-bisabolene, trans-Z-BAE, czs-Z-BAE, and E-nerolidol, as do males of four Acrosternum species [17,72]. In three of these species (A. aseadum, A. hilare, and A. marginatum), the transxis ratio strongly favors cz s-BAE, whereas in A. pennsylvanicum, the ratio is about equal. For all species except A. hilare, the absolute configurations of the compounds and their biological roles remain unknown. 

Arabidopsis thaliana Roots, JA Leaves, Pieris rapae [59] Plutella xylostella [58] (it, )-geranyllinalool synthase Root-expressed ( )-nerolidol synthases Root- and leaf-expressed P450s GES/TPS04 (Atlg61120) [58] Unpublished results Unpubhshed results... 

Zea mays Leaves, Spodoptera littoralis [31] Leaves, Spodoptera littoralis [31] (35)-( )-nerolidol synthase (3/ )-(it)-nerolidol/(ii)-f - famesene/( , )-famesol synthase tpsl [62] [64]... 

Nerolidol synthases of non-homoterpene emitting plants are not shown. JA, jasmonic acid. 

Table 11.1). In both cases, (ii)-nerolidol was not detected or found only in traces in the volatile blend, indicating a rapid conversion of this terpene alcohol into DMNT. Despite finding nerolidol synthase activities, the identification of the respective genes involved in DMNT formation has lagged behind. Schnee et al. 

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