Ricinoleate oil

We have elucidated the biochemistry of castor oil biosynthesis, an essential step in generating effective transgenic sources of a high ricinoleate oil. Because this aspect of our research has been described recently (6), and is discussed further in this volume (7), this paper will focus mainly on our other fatty acid of interest, cw-vaccenate. 

The effectiveness of the simple CCD method was demonstrated for the isolation of [2], The hydroxyl group on the C-9 or C-12 position of the hydroxy fatty acid esters is an interesting tool for further chemical modifications of compounds [l]-[3]. In this section, a few chemical modifications and addition reaction of the hydrogenated methyl esters of the compounds [1],[2] are described. These methyl esters [4],[5] can be obtained from dimorphecolic and ricinolic oil after hydrogenation and transesterification of the compounds [1],[2]. The methyl esters [4],[5] were also pu-... 

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. 

The starting amino acid for nylon-11 is produced from methyl ricinoleate [141 -24-2] which is obtained from castor oil (qv). The methyl ricinoleate is pyrolized to methyl 10-undecylenate [25339-67-7] and heptanal [111-71-7]. The unsaturated ester is hydroly2ed and then converted to the amino acid by hydrobromination, followed by ammoniation and acidification. The CO-amino acid product is a soft paste containing water, which is dried in the first step of the polymeri2ation process. 

Sulfated Natural Oils and Fats. Sulfated natural triglycerides were the first nonsoap commercial surfactants introduced in the middle of the nineteenth century. Since then sulfates of many vegetable, animal, and fish oils have been investigated (see also Fats AND FATTY oils). With its hydroxyl group and a double bond, ricinoleic acid (12-hydroxy-9,10-octadecenoic acid) is an oil constituent particularly suited for sulfation. Its sulfate is known as turkey-red oil. Oleic acid is also suited for sulfation. Esters of these acids can be sulfated with a minimum of hydrolysis of the glyceride group. Polyunsaturated acids, with several double bonds, lead to dark-colored sulfation products. The reaction with sulfuric acid proceeds through either the hydroxyl or the double bond. The sulfuric acid half ester thus formed is neutralized with caustic soda ... 

PVB resins are also compatible with a limited number of plasticizers and resins. Plasticizers (qv) improve processibility, lower T, and increase flexibihty and resiUency over a broad temperature range. Usehil plasticizers include dibutyl and butyl benzyl phthalates, tricresyl and 2-ethylhexyl diphenyl phosphates, butyl ricinoleate, dibutyl sebacate, dihexyl adipate, triethylene glycol di-2-ethylbutyrate, tetraethylene glycol diheptanoate, castor oil, and others (64-73). 

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. 

Alkali Fusion. Tha alkaU fusion of castor oil using sodium or potassium hydroxide in the presence of catalysts to spHt the ricinoleate molecule, results in two different products depending on reaction conditions (37,38). At lower (180—200°C) reaction temperatures using one mole of alkah, methylhexyl ketone and 10-hydroxydecanoic acid are prepared. The 10-hydroxydecanoic acid is formed in good yield when either castor oil or methyl ricinoleate [141-24-2] is fused in the presence of a high boiling unhindered primary or secondary alcohol such as 1- or 2-octanol. An increase to two moles of alkali/mole ricinoleate and a temperature of 250—275°C produces capryl alcohol [123-96-6] CgH gO, and sebacic acid [111-20-6] C QH gO, (39—41). Sebacic acid is used in the manufacture of nylon-6,10. 

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... 

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. 

Ricinoleic acid carstor oil. Argot oil Meconic acid Papaveraceaa... 

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... 

Oil Palmitic acid Stearic acid Oleic acid Linoleic acid Linolenic Elaeostearic Ricinoleic Gondoic Erucic acid... 

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]... 

The GC-MS chromatogram obtained with the same substance after acid methanolysis and silylation is presented in Figure 10.10. The major compounds are fatty acid methyl esters corresponding to a mixture of an animal fat (attested by the presence of E15 0 and E17 0 with ante and iso isomers) and castor oil (attested by the presence of methyl ricinoleate E18 1,120H) [32]. Diterpenoid or triterpenoid resin components are not observed. 

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 ... 

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