Cardanol 8 -monoene

Pharm.-Chem. Institut der Universitat D-69120 Heidelberg Cardanol, Diene Cardanol, Monoene Cardanol, saturated Cardanol, Triene Cardol, Diene Cardol, Monoene Cardol, saturated Cardol, TYiene... 

Cardanol 15 0 Cardanol 15 1 (n-7) Cardanol 15 2 (n-4) Cardanol, saturated Cardanol, Monoene Cardanol, Diene... 

Cardanol 15 3 (n-1) Cardanol, Diene Cardanol, Monoene Cardanol, TViene... 

Cardanol-monoolefin Cardanol-triolefin Cardol Cardanol, Monoene Cardanol, Driene Cardol, saturated... 

Cardol, Monoene Cardanol, Monoene Cardol, Monoene... 

The skin irritancy of cardanol monoene isolated from the fruits of the spice pink pepper, Schinus terebinthifolius, has been examined. However, it was supposed that the irritative effect, which was manifested after a long latency period, was also contributed to by ingredients of the essential oil, for example, by phellandrene and delta-3 carene [255]. Accordingly, it was indicated that experimental tests with animals were necessary before the spice can be forbidden for sale . 

The oligomerization of cardanol with boron trifluoride etharate as the initiator was studied in detail by Antony et al. [171]. The reaction conditions were optimized by using gel permeation chromatography as 140°C with an initiator concentration of 1%. GPC data indicate conversion of all monoene, diene, and triene components into polymer except the saturated component, indicating participation of all the unsaturated components in polymerization. It is possible that the initiation of po-... 

Figure 10.5 SEM images of self-assembled gel from cardanol glycolipids. (a) GLY-2 in cyclohexane (b) EtOH-HjO gel of the monoene derivative I (c) EtOH-H20 gel of GLY-2. Reprinted with permission from [71] (2006) American Chemical Society.

In a similar manner to the fatty acids, monohydric, dihydric and phenolic members invariably exists as a mixture of saturated, monoene, diene and triene constituents and rarely in the pure form as one of these four. In the nomenclature of this series a comprehensive system which takes account of the chain length, double bond position and its stereochemistry has not been widely agreed and accepted. Trivial and systematic names thus both abound and because of their dual functional nature as aromatic and acyclic these compounds have remained relatively unclassified. For example, cardanol is a well-known member consisting of saturated, monoene, diene... 

In procedures based on alkyne chemistry directed towards compounds with unsaturation commencing at the 8-position, the ArC7 intermediates are the same essentially as used for monoene syntheses, while the ArCg unit contains a terminal alkyne grouping and the ArC.,o is an aryl dec-2-yn-1-ol. In the cardanol and cardol series this latter synthon was obligatory since it was found that in the formation of 3-(non-8-ynyl)phenol from 3-(7-bromoheptyl)phenol and lithium acetylide a partial isomerisation occurred (refs. 146, 147) giving the 2-yne. 

Long-chain alkylphenols have been investigated extensively (33) by both adsorption and reversed-phase partition methods (34). The cashew phenols (from Anacardium occidentale) comprise cardanol (1), cardol (2), 2-methylcardol (3), and anacardic acid (4), each existing as a mixture of the saturated, 8 -monoene, 8 ,11 -diene, and 8 ,1 l ,14 -trieneconstituents. In ammoniated solvent [light petroleum-diethyl ether-ammonia (60 40 2)] the acidic compound anacardic acid remained practically on the baseline, whereas in an acidic solvent [light petroleum-diethyl ether-formic acid (70 30 1)] it migrated toward the solvent front as an intramolecularly bonded substance. In natural cashew nut shell liquid the phenols and their unsaturated constituents have the values 0.20 (cardol). 

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