Meadowfoam oil

Katengam S, Crane JM, Slabaugh MB, Knapp SJ (200J) Genetic mapping of a macromutation and quantitative trait loci underlying fatty acid composition differences in meadowfoam oil. Crop Sci 41 1927-1930... 

Olefin metathesis can be very useful in the CM mode, as shown in the synthesis of insect phere-mones.46 In the first example for the synthesis of the peach twig borer pheromone 23, an excess of 1-hexene was used to increase the yield of the desired product. However, both of the other products could be recycled (Scheme 28.17). In the second example, CM was used to change the ester groups of meadowfoam oil (24) through cleavage of the alkenes rather than ester bonds. The sequence resulted in the synthesis of the mosquito pheromone (25) (Scheme 28.18). 

Meadowfoam oil from Limnanthes alba seed oil is unusual in that over 95% of its component acids are C20 or C22 and include 5-20 1 (63-67%), 5-22 1 (2-4%), 13-22 1 (16-18%), and 5,13-22 2 (5-9%). It is being grown in the United States, and its potential uses thoroughly examined. The crop yields 1000-1500 kg of seed per hectare and contains 25% oil. Potential uses of this oil include cosmetic applications, production of dimer acid, as a lubricant, and via a wide range of novel derivatives based on reaction at the A5 double bond (134-138). 

Cahoon, E.B. E.F. Marrillia K.L. Stecca S.E. Hall D.C. Taylor A.J. Kinney. Production of fatty acid components of meadowfoam oil in somatic soybean embryos. Plant Physiol 2000, 124, 243-251. 

With A5 acids (such as the C20 acids in meadowfoam oil), the 8 lactone is formed in high yield when the acid is refluxed for 3 h with perchloric acid in dichloromethane. The proportion of 8 to y lactone depends on the reaction solvent. In hexane, the ratio is 6 1 and in dichloromethane almost 40 1. The 8-lactone is much more reactive than its y isomer. It can be converted to hydroxy amides (amines), hydroxy acids (alkali), and alkoxy esters (alcohol and acid) wifli the reagents indicated in parentheses. 

Another aspect of the 8-lactone chemistry is the interconversion between 8-lac-tone and 5-hydroxy fatty acid. Under basic aqueous conditions, the equilibrium favors the formation of the 5-hydroxy fatty acids. In contrast, catalytic amounts of acid will cause rapid cyclization/dehydration of the 5-hydroxy fatty acid into the 8-lactone. By utilizing the equilibrium between these two species, 5-hydroxy fatty acids were synthesized directly from meadowfoam oil (Scheme 13). 

Meadowfoam oil has been cross-linked with sulfur (39) to form factice (vulcanized oil). The Shore hardness of meadowfoam factice was superior to factices prepared from other vegetable oils, giving materials that had little to no stickiness. 

IsbeU, T.A., T.P. Ahhott, and K.D. Carlson, Oxidative Stability Index of Vegetable Oils in Binary Mixtures with Meadowfoam Oil, Ind. Crop, and Prod. 9 115-123 (1999). 

Erhan, S.M., and R. Kleiman, Meadowfoam Oil Factice and Its Performance in Natural Rubber Mixes, Rubber World 203 33-36 (1990). 

Trade Name Synonyms Cropure Meadowfoam [Croda Oleochems.] EmCon Limnanthes Alba t[Fanning http //www.fanncorp.com], Fancor Meadowfoam Seed Oil [Fanning http //www.fanncorp.com], Nikkol Meadowfoam Oil [Nikko Chems. Co. Ltd http //WWW. nikkol. co.jp/index. html]... 

Bis (4-vinylthiophenyl) sulfide 153065-40-8 Cropure Meadowfoam EmCon Limnanthes Alba Fancor Meadowfoam Seed Oil Meadowfoam (Limnanthes alba) seed oil Nikkol Meadowfoam Oil... 

Gunstone, F. D. (1993b) The C-NMR spectra of six oils containing petroselinic acid and of aquilegia oil and meadowfoam oil which contain A5 acids. Chemistry and Physics of Lipids, 58, 159-67. 

Another example of organic synthesis via cross-metathesis is the synthesis of biologically active compounds such as insect pheromones. Use of such pheromones offers an effective and selective pest control method. Thus, cross-metathesis of ethyl oleate with 5-decene results in a cis-trans mixture of ethyl 9-tetradecenoate, an insect pheromone precursor [15]. Cross-metathesis of methyl d.y-5-eicosenoate (obtained from meadowfoam oil) with excess 5-decene gives methyl tm 5-decenoate, which can be transformed into a 83 17 mixture of trani -5-decenylacetate and tran.y-5-decenol (in total 90% trans), the sex pheromone of the Peach Twig Borer moth, a major pest in Northern Hemisphere fruit orchards. The isomeric mixture was active in mating disruption [16]. Other examples of organic synthesis via cross-metathesis are summarised elsewhere [17 18]. 

The effect of vegetable oil concentration on the COF of the Fantesk starch-oil composite is illustrated in fig. 13.14, where the concentration of oil in the starch matrix is expressed in parts per hundred (pph), which is the ratio of oil to dry-starch weights multiplied by 100. The data in fig. 13.14 are for a composite of meadowfoam oil in PFGS and display a number of interesting features. First, the composite without vegetable oil (pure steam-jet cooked starch) displays a very high COF, on the order of 0.8. Second, incorporation of even a small quantity of vegetable oil into the composite causes a sharp reduction in the COF. The COF continues to decrease with... 

FIGU RE 13.14 Effect of meadowfoam oil concentration in purified food-grade starch (pfgs) on the coefficient of friction of Fantesk starch-oil composite dry-film lubricant. 

FIG U RE 13.20 Langmuir analysis of adsorption isotherm derived from steel-steel friction due to meadowfoam oil in hexadecane. 

Chinese tallow Crambe oil Crepsis foetida oil Croton oil Cuphea oil Jojoba oil Lesquerella seed oil Linseed oil Meadowfoam oil Neatsfoot oil Oitica oil Rapeseed ... 

Long-chain fatty acids generally are undesirable for food and feed use, but have been in demand for production of lubricants and polymers (Nylon 1313), and as plasticizers. Potential sources include Crambe abyssinica oil containing over 60 percent C22 Limnanthes alba (Meadowfoam) oil with 95 percent C20 and C22 Lunaria annua oil wth 40 percent C22 and 20 percent C24 Selenia grandis oil with 58 percent C22 Leavenworthia alabamica oil with 50 percent C22 and Marshallia caespitosa oil with 44 percent C22. ... 

Plant oils (eg, soybean, rapeseed, crambe, jojoba, and meadowfoam oils, or their mixtures) react with sulfur (or S2CI2), producing materials known as factices. Sulfur atoms serve as cross-linking agents between double bonds located on different TAG molecules. This process has been used for over a century (Erhan and Kleiman, 1990a,b, 1993). Factices are used as processing aids and property modifiers in rubber, and impart enhanced ozone resistance. 

Erhan, S.M., Kleiman, R., 1990a. Meadowfoam oil factice and its performance in natural rubber... 

The erucic acid content of meadowfoam wild-type cultivars ranges from 8 to 24% (Gandhi et al., 2009). While oil containing erucic acid >3% is considered unfit for human consumption, the cosmetic and industrial applications of meadowfoam oil would most likely supersede its use for food. Nevertheless,... 

The wholesale price of meadowfoam oil described by Burden (2012) is as high as 33/kg. It is thus best suited for use in cosmetics and hair care products due to its stability and ability to act as a carrier for other oils. In this way, it is very similar to jojoba. Numerous applications for meadowfoam oil have been proposed, including use as a lubricant additive, source... 

Hayes, D.G., Kleiman, R., 1993. The isolation and recovery of fatty adds with A5 unsaturation from meadowfoam oil using lipase-catalyzed hydrolysis and esterilication. J. Am. Oil Chem. Soc. 70, 555-560. 

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