Lesquerolic acid

Hydroxy-cis-9-octadecenoic (ricinoleic) acid, physical properties, 5 35t 14-Hydroxy-cis-ll-eicosenoic (lesquerolic) acid, physical properties, 5 35t Hydroxycitronellal, 24 489, 490, 533—534 Hydroxy-containing organics, 20 794-795 3-Hydroxycyclohexanecarboxylic acid, 22 21... 

Lesquerolic acid, physical properties, 5 35t Lessing rings, 7 28 Lethal agents, 5 815—822 Lethal concentration (LC50), 23 112-113. See also LC50... 

The Lesquerella seed yields roughly 20-25 % oil by weight. The functional fatty acid from the profile is mainly the 20-carbon lesquerolic acid, or 14-hydroxy-ll-eicosenoic acid (Fig. 9). 

Ricinoleic acid (i -12-hydroxy-9-cw-octadecenoic acid) (Fig. 6) accounts for 80-90% of fatty acids in castor oil (from Ricinus communis). It is found in other plant species and in the sclerotia of the ergot fungus Claviceps purpurea). Lesquerolic acid (i -14-hydroxy-ll-cw-eicosenoic acid), which is a C20 homolog of ricinoleic acid, occurs in Lesquerella species (up to 70% of total fatty acids). Isoricinoleic acid (i -9-hydroxy-12-cw-octadecenoic acid, or 9-OH 18 2 12c) is a major acid in the Wrightia species. In plants, several C16 and C18 mono, di, and trihydroxy fatty acids are stmctural components of cutin (a polyester constituent of plant cuticle). 

Plants of the Lesquerella species are characterized by the presence of the C20 bis-homologue of ricinoleic acid—lesquerolic acid—sometimes accompanied by other acids of the same type at lower levels ... 

Ricinoleic acid Densipolic acid Lesquerolic acid Auricolic acid... 

A typical analysis of L. fendleri seed oil showed the presence of 16 0 (1%), 18 0 (2%), 18 1 (15%), 18 2 (7%), 18 3 (14%), lesquerolic (54%), and auricolic (4%) acids. As lesquerolic acid is the C20 homologue of ricinoleic with the same p-hydroxy alkene unit, it undergoes similar chemical reactions but produces (some) different products. For example, pyrolysis should give heptanal and 13-tri-decenoic acid (in place of 11-undecenoic acid). This could be converted to 13-ami-notridecanoic acid, the monomer required to make nylon-13. Similarly, alkali-fusion will give 2-octanol and dodecanedioic acid in place of decanedioic (sebacic) acid. This C12 dibasic acid is aheady available from petrochemical products and has a number of applications. A recent account of the status of this oil is available (126). 

Plant species of the genus Lesquerella are being developed as an alternative erop for the southwestern region of the U.S. The seed oil of Lesquerella contains 55-60% of 14-hydroxy-cw-11 -eicosenoic acid (lesquerolic acid), a homologue of ricinoleic acid obtained from castor oil (19). Chemical modifications of lesquerolic acid, thus far, have nearly duplicated derivatizations of ricinoleic acid. 

Lesquerolic Acid carbon chain, one double bond) OH I CHj(CHj)i-CH-CHr-CH=CH-(CH2),CO,H... 

Lauryl sulfate, see D-00286 Lesquerolic acid, in H-00303 Leukotriene 4, in E-00007 Leukotriene B4, L-OOOl 1 Leukotriene B4, in L-OOOl 1 14,15-Lcukotriene 44, in E-00009 Leukotriene B, in L-OOOl 1 Lichesterol, in M-00013 Lichesterylic acid, see M-00094 Lignoccrane, see T-00004 Lignoceric acid, see T-00007 Lignoceryl alcohol, see T-00008 Linderic acid, in D-00260... 

Lesquerolic acid, A7.15 4-Cembrene-15,19,20-triol, T"31.7 C20H39NO2 Spectaline, K"6.4 C20H40O... 

Members of the genus Lesquerella produce seed oils containing a high proportion of hydroxy fatty acids. There are three types of Lesquerella which are distinguished by the most abundant seed oil fatty acid - lesquerolic acid (20 1 OH), densipolic acid (18 20H) or auricolic acid (20 2OH), as represented by L. fendleri, L. kathryn and L. auriculata, respectively. We have investigated the conversion of radiolabelled intermediates of hydroxy fatty acid biosynthesis in the above three species. 

The major fatty acid component of lesquerella oil (LO) is lesquerolic acid (55%), a C20 hydroxy fatty acid with an isolated double bond. Other than castor oil lesquerella is the only commercially available oil with a hydroxyl functional fatty acid. Two types of LO methacrylates, methacrylated lesquerella oil (MALO) and hydroxyethyl methacrylate modified lesquerella oil (HEMALO), were synthesized by reacting the oil with methacryloyl chloride and an methacrylic functional isocyanate, respectively (Scheme 2). 

Other examples of the direct use of ricinoleic or lesquerolic acid, or their TAG, have been reported. Polyesters of castor oil and succinic acid, a bio-refinery platform chemical, have potential utility in personal care products (O Lenick and LaVay, 2002). Copolymers of lactic acid and ricinoleic acid, and castor oil esterified to polylactic acid have utility in drug delivery systems (Sokolsky-Papkov et al., 2009). Thames and co-workers prepared alkyds containing lesquereolic acid-trimethylolethane monoester and phthahc acid as comonomers through performing glycerolysis of lesquereUa oil, followed by the addition of phthalic anhydride, with the resultant material used in the preparation of polyurethanes (Thames et al., 1994). 

Wang, W., Wang, C., Huang, B.-L., Huang, B., 2008. Agrobacterium-tumefaciens-mediiAed transformation of Lesquerella fendleri L., a potential new oil crop with rich lesquerolic acid. Plant Cell Tissue Organ Cult. 92, 165-171. 

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