9-Octadecen acid

Ricinic (castor) oil is a special oil which is of significant use in the emulsifier industry. This consists of 85% of esters of c/5-12-hydroxy-9-octadecenic acid. The free hydroxy group is used as a starting point for the formation of chemical derivatives such as esters or ethers, for instance, in polyethoxylated or polyglycerol surfactants. 

CARBOXYLICACIDS-SURVEY] (Vol 5) trans-ll-Octadecene-9-ynoic acid [557-58-4]... 

Aldrich 90%) of oleic acid were dissolved in 200 g of 1-octadecene at room temperature. The reaction mixture was heated to 320 °C with a heating rate of 3.3 C/min, and then kept at that temperature for 30 min. When the reaction temperature reached 320 °C, a severe reaction occurred and the initial transparent solution became turbid and brownish black. The resulting solution... 

Polar-substituted alkenes where the functionality is not attached to a strained ring are considerably more discriminating in their compatibility with metathesis catalysts and as a rule require relatively high catalyst charges. In the aliphatic series, unsaturated esters have received the most attention. Boelhouwer reported in 1972 the metathesis of the ester methyl oleate and its trans isomer, methyl elaidate, with a homogeneous catalyst based on a 1/1.4 molar combination of WCl6/(CH3)4Sn (23). At 70°C and an ester/W molar ratio of 33, near-thermodynamic equilibrium was attained, and 49 and 52% of the respective esters were converted to equal amounts of 9-octadecene and the dimethyl ester of 9-octadecene-1,18-dioic acid. 

These reactions, which are believed to occur predominantly inter-molecularly, are capable of producing intermediates which hold some potential as precursors for important chemical products. For example, metathesis of olive oil, which consists chiefly of triglycerides of oleic acid, produces the glyceride of 9-octadecene-l,l8-dioic acid from which can be obtained, after saponification, acidification, and low-temperature crystallization, the free acid, which can be transformed by intramolecular condensation to civetone. 

Hydroxy-17-octadecene-9,11 -diynoic (isanolic) acid, physical properties, 5 35t... 

OCTADECYNE OLEIC ACID DIBUTYL SEBACATE DI HEXYL ADIPATE 1-CYCOPENTYLTRIDECANE 1-CYCLOHEXYLDOOECANE 1-OCTADECENE STEARIC ACID n-OCTADECANE DINONYL ETHER 1-OCTADECANOL BUTYL-TETRADECYL-SULFIDE ETHYL-HEXADECYL-SULFIDE HEPTADECYL-HETHYL-SULFIDE NONYL-SULFIDE PENTADECYL-PROPYL-SULFIDE 1-OCTADECANETHIOL NONYL-DISULFIDE 1-n-NONYLNAPHTHALENE n-TRIDECYLBENZENE... 

Octadecane has 18 carbon atoms, as does oleic acid, and enoic imphes a double bond (octadecane is the saturated hydrocarbon while octadecene has a double bond somewhere). The 9 indicates that the carbon atom closest to the carboxyl end that is involved in the double bond is number 9. Finally, cis establishes the stereochemistry at the double bond. 

A few other oxidations involve no C=C bond cleavage. Cti-9-octadecene gave 9.10-diketo-octadecane with RuO /aq. Na(C10)/( Bu N)Br/CHjCl2 [324], while cyclo-octene was oxidised by RnCyaq. Na(10 )/DCE to 8-oxo-octanal [325]. Oxidation of A -, and A - steroids using RuO /aq. Na(10 )/acetone gave cis-diols, diones and acids [303] while RuO /aq. Na(10 )/CHjCyCH3CN oxidised 2,3-dichlorodecene to decane-2,3-dione [326]. 

The indole 22 was previously isolated from the sponge Dysidea etheria [110] and has now been obtained from the Antarctic ice bacterium ARK 13-2-437. The lipid phase of Hel45 delivered additionally N-(2-hydroxyethyl)-ll-octadecen-amide and the new natural products 17-methyl-16-octadecenoic acid [95] and indole-3-carboxylic acid thiomethyl ester (23). 

Institut fur allgemeine Botanik Universitat Mainz SaarstraBe 21 D-55122 Mainz Telefon (06131) 39-3326 Telefax (06131) 39-3787 9,12-Octadecadien-6-ynoic acid 9,12,15-Octadecatrien-6-ynoic acid 9-Octadecen-6-ynoic acid... 

Octadecen-6-ynoic acid (Z-isomer) 2.3- Dihydro-5 -hydroxyamentoflavone (S-isomer) 2.3- Dihydro-5, 3" -dihydroxyamentoflavone (S-isomer)... 

Octadecene Propanal 10-Oxoundecanoic acid Dodecanoic acid methylester... 

The property of the polymers in question to form nonspherical nanostructures was confirmed in experimental studies. Shih et al. [29] synthesized alternating copolymers of 1-alkenes with maleic anhydride. The maleic anhydride units were hydrolyzed to maleic acid units. Fully hydrolyzed macromolecules associated into microstructures of cylindrical and ellipselike shape. The cylindrical shape was characteristic of copolymers with octadecene and hexadecene moieties, while the copolymers with lower alkene copolymers (tetradecene, dodecene, decene, octene) formed ellipsoidal structures. Wataoka et al. [30] investigated the formation of nonspherical helices in a system of maltopentaose-carrying polystyrene (PS). The polymer was synthesized via the homopolymerization of vinylbenzyl maltopentaose amide (Scheme 3). 

The application of olefin metathesis to fatty acids and related compounds has its starting point in 1972 with the selective transformation of methyl oleate into equimolar amounts of 9-octadecene and dimethyl 9-octadecene-l,18-dioate by Van Dam, Mittelmeijer, and Boelhouwer (Scheme 1) [29]. In this early work, 1-2 mol% of a... 

CdMe2 = dimethylcadmium, ZnEt2 = diethylzinc, TMS = trimethylsilyl, (BDMS)2Te = bis(tert-butyldimethylsilyl) telluride, TDPA = tetradecylphosphonic acid, ODPA = octadecylphosphonic acid, SA = stearic acid, LA = lauric acid, OA = oleic acid, MA = myristic acid, ac = acetate, my = myristate, st = stearate, hdx = hexadecylxanthate, ex = ethylxanthate, dx = decylxanthate, TOPO = trioctylphos-phine oxide, HDA = hexadecylamine, DA = dodecylamine, ODA = octadecylamine, TOP = trioctylphosphine, TBP = tributylphosphine, ODE = 1-octadecene, HH = hexadecyl hexadecanoate,... 

Male moths and butterflies have proven to be an especially rich source of interesting natural products. The sex pheromone produced in the wing glands of the lesser waxmoth, Achroia grisella, is composed of n-undecanal and (Zj-ll-octadecenal (98), whereas that of the greater waxmoth also contains n-undecanal (.99) but is dominated by n-nonanal (100). The scent brushes of male noctuid moths produce large amounts of aromatic compounds and terpenes which are believed to function as aphrodisiacs (101). Benzaldehyde, 2-phenyl ethanol, benzyl alcohol, 6-methyl-5-hepten-2-one, pinocarvone, and isobutyric acid have been identified in the secretions of different noctuid species (102), and it appears that these pheromones may possess some chemotaxonomic value. 

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