Fatty acids from castor oil

Derivation Sodium salt of the fatty acids from castor oil. 

Sodium salt, Soricin, Cotidosan. Sodium salts of the fatty acids from castor oil. White or slightly yellow, odorless or almost odorless powder. Sol in water or alcohol. The aq soln is alkaline. 

Po glycerol esters of interesterifed ricinoleic acid Polyglycetol esters of polycondensed fatty acids from castor oil. See Polyglyceryl polyricinoleate... 

Synonyms Glyceran esters of condensed castor oil fatty acids Glycerol esters of condensed castor oil fatty acids PGPR Polyglycerol esters of interesterified ricinoleic acid Polyglycerol esters of polycondensed fatty acids from castor oil Definition Polyglyceryl esters of interesterified ricinoleic acid... 

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). 

Traditional fermentation using microbial activity is commonly used for the production of nonvolatile flavor compounds such as acidulants, amino acids, and nucleotides. The formation of volatile flavor compounds via microbial fermentation on an industrial scale is still in its infancy. Although more than 100 aroma compounds may be generated microbially, only a few of them are produced on an industrial scale. The reason is probably due to the transformation efficiency, cost of the processes used, and our ignorance to their biosynthetic pathways. Nevertheless, the exploitation of microbial production of food flavors has proved to be successful in some cases. For example, the production of y-decalactone by microbial biosynthetic pathways lead to a price decrease from 20,000/kg to l,200/kg U.S. Generally, the production of lactone could be performed from a precursor of hydroxy fatty acids, followed by p-oxidation from yeast bioconversion (Benedetti et al., 2001). Most of the hydroxy fatty acids are found in very small amounts in natural sources, and the only inexpensive natural precursor is ricinoleic acid, the major fatty acid of castor oil. Due to the few natural sources of these fatty acid precursors, the most common processes have been developed from fatty acids by microbial biotransformation (Hou, 1995). Another way to obtain hydroxy fatty acid is from the action of LOX. However, there has been only limited research on using LOX to produce lactone (Gill and Valivety, 1997). 

Other modifications of vegetable oils in polymer chemistry include the introduction of alkenyl functions, the study of novel polyesters and polyethers and the synthesis of semi-interpenetrating networks based on castor oil (the triglyceride of ricinoleic acid) [42], and also the production of sebacic acid and 10-undecenoic acid from castor oil [44]. Additionally, the recent application of metathesis reactions to unsaturated fatty acids has opened a novel avenue of exploitation leading to a variety of interesting monomers and polymers, including aliphatic polyesters and polyamides previously derived from petrochemical sources [42, 45]. 

The regiospecific characterization of TAG as lithiated adducts by collisionally activated dissociation tandem mass spectrometry (CAD-MS ) has been reported by Hsu and Turk [9]. The ions were reported from the loss of fatty acids as a,p-unsaturated fatty acid specific at the sn-2 position of TAG of lithiated adducts. We have used these ions to quantitate six regiospecific diricinoleoylacylglycerols (RRAcs) containing ricinoleate (a hydroxyl fatty acid) in castor oil [10],... 

One of our major areas of development was the synthesis and study of the chromatographic (8-10), spectroscopic (11-14), and spectrometric properties of a large number of heteroaromatic fatty acid derivatives (each containing either a furan, pyrrole, thiophene, selenophene, or tellurophene nucleus). These fatty acid derivatives were obtained by total synthesis or by partial synthesis from polyunsaturated unsaturated fatty acids (12,13,15-18) and unsaturated hydroxylated fatty acids, such as ricinoleic acid (from castor oil) (19-24). In this range of heteroaromatic fatty acid derivatives, only fatty acids containing a furan nucleus are found in nature (lipid extracts of the pike and salmon and from the latex of the rubber plant) (25-29). A typical method for the preparation of a disub-... 

Fatty acids in castor oil have been determined in a like fashion [426]. They were reacted with radioactive diazomethane. The methyl esters of the ordinary fatty acids were separated from those of the monohydroxy- and dihydroxy acids, using adsorption TLC. AU three classes of methyl ester were eluted and the ratio of the amounts determined by measuring their radiation intensities. The mixture of esters of non-hydroxy-acids was then fractionated further by reversed phase PC and its composition quantitatively determined in the gas flow proportional counter. The ratio of monohydroxy- to dihydroxy- fatty acids may be more easily determined through the hot acetylated acids or esters. The small amount of dihydroxy fatty acids could then be labelled with two radioactive acetyl groups per molecule, which would double the specific activity and increase the accuracy of the result still further. 

ADMET has been used to take advantage of several natural polymer feedstocks, mainly plant oils and fatty acids (Figure 13.26) [190]. An initial study optimized the ADMET polymerization of a variety of plant oils, and yields of40—60% were obtained [191]. A set of polyamides were synthesized by ADMET polymerization of monomers ultimately derived from ricinoleic acid, the main fatty acid of castor oil [192]. Similarly, ADMET was utilized to polymerize 1,3-di-lO-undecenoxy-2-propanol, a castor oil-based diene, which was subsequently reacted with... 

Up until now, mostly pure substrates such as methyl oleate and its -isomer, methyl elaidate, have been tested as model substrates for hydroformylation, but in a few cases, linoleates, linolenates, and esters of ricinoleic acid have also been investigated (Figure 6.10). Oleic acid can be derived from new sunflower, linoleic acid from soybean, linolenic acid from linseed, and ricinoleic acid from castor oil. The long-chain mono-unsaturated fatty acid erucic acid (C22) can be extracted from old rapeseed oil. 

The reaction is also broadly used in industrial oleo-chemistry for h. of unsaturated - fatty acids. Starting materials are predominantly acid oils from the refining of oils for nutrition ( foots ), split (- hydrolysis) fatty acids, e. g., from tallow and the stearin fraction from the olein/stearin separation (- crystallization). H. is also applied for making - hydroxys-tearic acid from castor oil fatty acid, to eliminate unsaturation in coconut oil prior to - fractionation, to get - arachidic and - behenic acid from - fish and - rapeseed oil, to improve color in - dimer acid and to eliminate unsaturation in the starting material prior to separation by - crystallization of- stearic from - isostearic acid. 

Ibid 60, 185-6(1954) CA 48, 12422(1954) (Lacquers made of NC castor oil were only slightly yellowed when exposed to sunlight, but they did not pass the "fold test) i)K.Murai et al, JOilChemists Soc, Japan 3, 2-6(1954) CA 50, 250(1956)(Study of plasticizers for polyvinyl chloride obtained from castor-oil fatty acid, and lower fatty acids of coconut oil)... 

Other Cig-fatty acids have also a high potential in hydroformylation, such as ricinoleic acid, which contains an additional hydroxy group at position 12 of the fatty carbon chain and which is not food relevant [26], The hydroformylation of ethyl ricinoleate, derived from castor oil, shows selectivity for cyclization of the carbon chain because of the reaction of the hydroxyl group with the formyl group (Scheme 8). 

Fatty acids with trans or non-methylene-interrupted unsaturation occur naturally or are formed during processing for example, vaccenic acid (18 1 Hr) and the conjugated linoleic acid (CLA) rumenic acid (18 2 9tllc) are found in dairy fats. Hydroxy, epoxy, cyclopropane, cyclopropene acetylenic, and methyl branched fatty acids are known, but only ricinoleic acid (12(/f)-hydroxy-9Z-octadecenoic acid) (2) from castor oil is used for oleochemical production. OUs containing vernolic acid (12(5),13(/ )-epoxy-9Z-octadecenoic acid) (3) have potential for industrial use. 

Large supply of naturally derived lipids can be obtained from plants in which many oils and fatty acids can be readily extracted and purified. Animal sources (e.g., eggs or milkfats) are used to derive complex lipids such as phospholipids and cholesterol. Yield from natural sources is dependent on the weight-percent composition and the efficiency of the extraction procedure. The constitution of fatty acids in vegetable oils varies widely from different sources. For example, oleic acid is present at 64.6% by weight in olive oil but is present at only 0.7% in palm kernel oil. Similarly, castor oil triglyceride is comprised of almost entirely ricinoleic chains. There are numerous raw material suppliers of oils and oil fractions worldwide. As such, the relative cost of bulk purified... 

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