Eleostearic acid

Z,Z,Z,)-9,12,15-octadecatrienoic acid). Fish oils contain esters of eicosanoic and docosanoic acids with four to six double bonds separated by single methylene groups, eg, (i7//-Z)-4,7,10,13,16,19-docosahexaenoic acid [6217-54-5] in menhaden oil (4). The fatty acid with conjugated double bonds in tung oil is a-eleostearic acid [506-23-0] ((F,Z,F)-9,ll,13-octadecatrienoic acid) the predominant fatty acid in oiticica oil is licanic acid [17699-20-6] (4-oxo-(F,Z,F)-9,ll,13-octadecatrienoic acid). In all oils, other fatty acids including palmitic acid [57-10-3] (hexadecanoic acid), stearic acid [57-11-4] (octadecanoic acid), and oleic acid [112-80-1] ((Z)-9-octadecenoic acid) also are present. 

Eleostearic acid, Ci8H30O2( is a rare fatty acid found in the tung oil used for finishing furniture. On ozonolysis followed by treatment with zinc, eleostearic acid furnishes one part pentanal, two parts glyoxal (OHC—CHO), and one part 9-oxononanoic acid [0HC(CH2)7C02H]. What is the structure of eleostearic acid ... 

Polyunsaturated fatty acids are characterized by a large number of C = C double bonds in their hydrocarbon chain. Stearic acid has no C = C double bonds and therefore is not unsaturated, let alone polyunsaturated. But eleostearic acid has three C = C double bonds and thus is polyunsaturated. Polyunsaturated fatty acids are recommended in dietary programs since saturated fats are linked to a high incidence of heart disease. Of the lipids listed in Table 28-2, safflower oil has the highest percentage of unsaturated fatty acids, predominately linoleic acid, an unsaturated fatty acid with two C=C bonds. 

P-diketone chelates, 25 89-91 Beta distribution, 26 1020 P-eleostearic acid, physical properties,... 

Elemental uranium, crystal structures of, 25 409. See also Uranium (U) Elementary reaction, 21 336 Element/isotope ratios, in fine art examination/conservation, 11 419 Element mapping, in fine art examination/ conservation, 11 406 Element names/symbols, 17 386-387 transfermium, 17 387t Elements, in earth s crust, 26 23 a-Eleostearic acid, physical properties, 5 33t... 

Polyunsaturated fatty acids can also be prepared by Wittig reactions. Thus, Bergel-son and Shemyakin synthesized a-eleostearic acid [(9Z, 11ZT, 13 )-9,11,13-octadeca-trienoic acid 42] from (2 ,4 )-2,4-nonadienal 40 and phosphorane 4149). The intro-... 

A second double bond lowers the melting point further (linoleic acid, mp — 5 °C), and a third double bond lowers it still further (linolenic acid, mp —11 °C). The trans double bonds in eleostearic acid (mp 49 °C) have a smaller effect on the melting point than the cis double bonds of linolenic acid. The geometry of a trans double bond is similar to the zigzag conformation of a saturated acid, so it does not kink the chain as much as a cis double bond. 

Tsuzuki,T.,Tokuyama,Y., Igarashi, M., and Miyazawa,T. 2004. Tumor growth suppression by alpha-eleostearic acid, a linolenic acid isomer with conjugated triene system, via lipid peroxidation. Carcinogenesis, 25,1-9. 

Cholesterol esterase, 10000 U/l lipase 20000 U/l and phospholipase A2 (from Naja naja venom 10000 U/l Sigma Chemicals, U.K.). /J-Eleostearic acid (internal standard [18 3(9,11,13-cw)]) from Alltech Associates, U.K. 

The only conjugated dienoic fatty acid isolated from plant sources (the seed oil of Chilopsis linearis) is reported to be trans-lO, trans-12-octadecadienoic acid. In contrast, fatty acids with conjugated triene systems have been detected in various plant species. Tung oil is the commercial source of the most widespread fatty acid from this group, 9-cis, W-trans, I i-trans-octadecatrienoic (a-eleostearic) acid (1, 2). 

Oiticica (Licania rigida). The kernel oil obtained from this Brazilian tree is characterized by its high level ( 78%) of licanic acid (4-oxo-9cllfl3f-octadeca-trienoic acid)—a keto derivative of the more familiar eleostearic acid. The oil shows drying properties but does not dry as quickly as tung oil (156). 

The cherry tree Prunus avium L.) is a member of the Rosaceae family. Cherry seed contains about 18% oil on a dry weight basis (48). Significant levels of oleic acid were detected in the cherry seed oils prepared by hexane extraction using a Soxhlet apparatus. Oleic acid comprised 24—38% of the total fatty acids from three different varieties of cherry fruits (Table 7) (48). Linoleic acid was the major fatty acid in the cherry seed oil, and ranged 40 9% in the seed oil, along with ot-eleostearic (18 n-5), palmitic, stearic, arachidonic, and ot-linolenic acids (Table 7). alpha-eleostearic acid comprising 10-13% of cherry seed oil, is a conjugated... 

Among the oils that contain carbon-carbon double bonds as the functional groups, linseed, tung, corn, cottonseed, rapeseed, and soybean are more widely used as polymeric sources. Linseed oil is extracted from the seeds of the flax plant Linum usitatissimum). The major constituents of linseed oil are a-linolenic acid (60%), linoleic acid (29%), and oleic acid (27%). This composition varies with changes in climatic conditions. On the other hand, tung oil, also called china wood oil, is derived from the seeds or nuts of the trees aleurites fordii and A. montana. The major constituent of tung oil is eleostearic acid (77-82%), whereas the other important components of tung oil are oleic acid (3.5-12.7%) and linoleic acid (8-10%). It is known that the carbon-carbon double bond in oleic acid is at C9, in linoleic acid it is at C6 and C9, and in linolenic acid it is at C3, C6, and C9, whereas eleostearic acid has double bonds at positions C5, C7, and C9. 

Figure 9. Structures of oleic, linoleic, a-linolenic and eleostearic acid.

Induction This process begins by the autocatalysis of eleostearic acid, and the oxygen uptake starts increasing slowly. 

Initiation The film continues to absorb oxygen from the atmosphere and, as a result of this absorption, the mass of the film increases and the double bonds of eleostearic acid undergo a rearrangement process. On rearrangement, hydroxyl and hydroperoxy groups are formed in the film. 

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