Castor ricinoleic acid

The name ricinoleic acid is used in commerce for the mixture of fatty acids obtained by hydrolysing castor oil, and its salts are called ricinoleates. 

Castor oil (qv) contains a predominance of ricinoleic acid which has an unusual stmcture inasmuch as a double bond is present in the 9 position while a hydroxyl group occurs in the 12 position. The biochemical origin of ricinoleic acid [141-22-0] in the castor seed arises from enzymatic hydroxylation of oleoyl-CoA in the presence of molecular oxygen. The unusual stmcture of ricinoleic acid affects the solubiUty and physical properties of castor oil. 

Castor Oil. Castor oil [8001-79-4] (qv) is the fixed oil from the seeds of Picinus communis Linne. Pale yellowish or almost colorless, it is a transparent viscid Hquid with a faint, mild odor and a bland taste followed by a slightly acrid and usually nauseating taste. Its specific gravity is between 0.945 and 0.965. Castor oil is soluble in alcohol, and miscible with anhydrous alcohol, glacial acetic acid, chloroform, and diethyl ether. It consists chiefly of the glycerides of ricinoleic acid [141 -22-0], and isoricinoleic acid [73891-08-4], found in the small intestine. The seed contains a highly... 

Castor oil is a cathartic only after Hpolysis in the small intestine Hberating ricinoleic acid. Ricinoleic acid inhibits the absorption of water and electrolytes. It is commonly used for preparation of the large bowel for diagnostic procedures. 

Castor oil sulfation results largely in a sulfuric acid ester in which the hydroxyl group of ricinoleic acid has been esterified. However, other reactions can also take place. For example, the double bond can be attacked to produce an ester or the hydroxysulfonic acid (33). Hydrolysis of the sulfuric acid esters occurs during the reaction and subsequent treatment forming hydroxy acids and sulfuric acid. These hydroxy acids can be further sulfated. 

Pyrolytic Decomposition. The pyrolytic decomposition at 350—460°C of castor oil or the methyl ester of ricinoleic acid spHts the ricinoleate molecule at the hydroxyl group forming heptaldehyde and undecylenic acids. Heptaldehyde, used in the manufacture of synthetic flavors and fragrances (see Elavors and spices Perfumes) may also be converted to heptanoic acid by various oxidation techniques and to heptyl alcohol by catalytic hydrogenation. When heptaldehyde reacts with benzaldehyde, amyl cinnamic aldehyde is produced (see Cinnamic acid, cinnamaldehyde, and cinnamyl... 

Polymerization of castor od, chemical or oxidative, results in higher viscosity or bodied ods that are more usehd in urethane coatings than the untreated castor od (87). Other castor derivatives used to prepare urethanes are amides prepared by reaction of castor od and alkanolamines, amides of ricinoleic acid with long-chain di- and triamines, and butanediol diricinoleate (88,89). 

Castor esters have been found to be nonirritating and noncomedogenic to the skin. Cetyl ricinoleate was found to be an effective noncomedogenic moisturizer (118). Castor-based quaternaries prepared by reaction of a castor fatty acid and a tertiary diamine are used for hair care. The ricinoleic quaternium is incorporated into clear shampoo formulations for foam enhancement and conditioning (119,120). 

Sebacic Acid. This acid is produced commercially by Union Camp in Dover, Ohio, by Hokoku OU Company in Japan, and by a state enterprise in the People s RepubHc of China (57). The process used in each case is based on the caustic oxidation of castor oU or ricinoleic acid [141-22-0] in... 

Sebacic acid is normally made from castor oil, which is essentially glyceryl ricinoleate. The castor oil is treated with caustic soda at high temperature, e.g. 250°C, so that saponification, leading to the formation of ricinoleic acid is followed by a reaction giving sebacic acid and octan-2-ol Figure 18.5. 

The starting point for this amino acid, from which nylon 11 is obtained, is the vegetable product castor oil, composed largely of the triglyceride of ricinoleic acid. This is first subjected to treatment with methanol or ethanol to form the appropriate ricinoleic acid ester. 

Ricinus, m. castor-oil plant, -ijl, n. castor oil. -(ilsaure, /. ricinoleic acid. -Slseife, /. caator-soap, -olsulfosaure, /. castor-oil sulfonic acid, -samen, m. castor bean, -saure, /. ricinic (ricinoleic) acid, -seife, /. castor-oil soap. 

The important but unusual fatty acid ricinoleic acid, or 12-hydroxyoleic acid, is a major component of castor oil (>87%) and is also found in useful quantities in ergot. The metal salts of the acid find use in dry-cleaning soaps but the majority is converted to aminoundecanoic acid (Scheme 6.6) which is used to make nylon 11. Nylon 11 has very good chemical and shock-resistance properties, which have led to it being used in the automotive industry. Ricinoleic triglyceride is initially transesterified to the methyl ester. This is heated to 300 °C at which temperature it is... 

Nevertheless, there are some vegetable oils that have a very specific composition. For example, castor oil consists of large amounts (83 89%) of 12-hydroxy-(Z)-9-octadecenoic acid (ricinoleic acid) which is not found in other natural lipids [21]. Ricinoleic acid produces a very characteristic oxidation product, 9,12-dihydroxyoctadecanoic acid [43], and both of these compounds can be considered as specific biomarkers for castor oil and have been used to assess its presence in ceramic lamps [43] and mummification balms [23]. 

Hydroxyoctadecanoic (ricinoleic) acid, 9,12 dihydroxyoctadecanoic acid Castor oil [1 7,44]... 

Castor oil is metabolized in the GI tract to an active compound, ricinoleic acid, which stimulates secretory processes, decreases glucose absorption, and promotes intestinal motility, primarily in the small intestine. Castor oil usually results in a bowel movement within 1 to 3 hours of administration. Because the agent has such a strong purgative action, it should not be used for the routine treatment of constipation. 

It can be prepared by heating castor oil with NaOH at 250°C. During the reaction ricinoleic acid is produced which forms octane-2-ol and sebacic acid ... 

It can be obtained from castor oil. Methanolysis of castor oil yields methylester of ricinoleic acid. Pyrolysis at 500°C forms n-heotaldehyde and methyl-undecylenate. Hydrolysis of latter... 

Cassel green See barium manganate. kas-ol, gren castor oil acid See ricinoleic add. kas-tor 6il as-od ... 

Ricinoleic acid (18 1 with an hydroxyl group on Cl2) from Ricims communis, the castor oil plant. Castor oil, containing 90% of ricinoleic acid, is poorly digested (because of the hydroxyl group) and acts as a lubricant and a slight irritant to the intestines, hence its use to relieve constipation. 

Vndecylenic acid Undecylenic acid, 10-undecylenic acid (35.4.7), is synthesized by pyrolysis at 400°C and low pressure (50 mm) an oxyderivative of oleic acid— ricinoleic acid—the glyceride of which is the main ingredient of castor oil [59,60]. 

Castor oil is a triglyceride that is well suited for use in polyurethane applications. Unlike most other oil-producing plants, the castor plant produces a triglyceride containing >90% of a single fatty acid, that being ricinoleic acid. Ricinoleic acid contains secondary hydroxyl groups appended to the Cjg fatty acid backbone (Fig. 8). 

Much work has been done on the incorporation of castor oil into polyurethane formulations, including flexible foams [64], rigid foams [65], and elastomers [66]. Castor oil derivatives have also been investigated, by the isolation of methyl ricinoleate from castor oil, in a fashion similar to that used for the preparation of biodiesel. The methyl ricinoleate is then transesterified to a synthetic triol, and the chain simultaneously extended by homo-polymerization to provide polyols of 1,000, 000 molecular weight. Polyurethane elastomers were then prepared by reaction with MDl. It was determined that lower hardness and tensile/elongation properties could be related to the formation of cyclization products that are common to polyester polyols, or could be due to monomer dehydration, which is a known side reaction of ricinoleic acid [67]. Both side reactions limit the growth of polyol molecular weight. 

One of the more advanced technical offerings from castor oil is a line of polyester diols, triols, and higher functional polyols derived from 100% castor oil as products for the preparation of polyurethane prepolymers and elastomers [68]. The Polycin line of polyols are prepared by transesterification of ricinoleic acid and derivatives. The producers (Vertellus) offer diol and triol products, as well as a recently developed series of diol and triol glyceryl ricinoleate esters that are stated to be prepared from 100% castor oil, making them fully renewable in content. The products are recommended for coatings, sealants, and adhesive applications. 

The parallels to castor oil and ricinoleic acid are clear. Some important differences exist. The hydroxylated fatty acids (hydroxyeicosenoic acid and... 

One species of Euphorbia in Brazil (Bernardia pulchelld) has been determined to contain more than 90% vemolic acid in the triglyceride [120]. This level of single-component purity is equivalent to the level of ricinoleic acid typically found in castor oil. These different varieties of epoxidized oil plants will probably continue to be the subject of agricultural development in the coming years. 

Castor oil is a bland oil that is hydrolyzed in the gut to yield ricinoleic acid, the active purging agent. This hydrolysis requires bile, a fact that is sometimes overlooked when castor oil is given as a laxative before radiography in biliary obstruction. The ricinoleic acid acts on the ileum and colon to induce an increased fluid secretion and colonic contraction. 

Castor oil [CO Structure (4.3)] is a triglyceride of ricinoleic (12-hydroxyoleic) acid about 90% of the fatty acid portion of the molecule consists of ricinoleic acid and 10% in the form of non-hydroxy acids consisting largely of oleic and linoleic acids. Small amounts of stearic and dihydroxystearic acids are also found in some industrial grades. 

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