Ricinus communis ricinoleic acid from

Ricinoleic acid (Figure 3.8) is the major fatty acid found in castor oil from seeds of the castor oil plant (Ricinus communis Euphorbiaceae), and is the 12-hydroxy derivative of oleic acid. It is formed by direct hydroxylation of oleic acid (usually esterified as part of a phospholipid) by the action of an 02- and NADPH-dependent mixed function oxidase, but this is not of the cytochrome P-450 type. Castor oil has a long history of use as a domestic purgative, but it is now mainly employed as a cream base. Undecenoic acid (A9-undecenoic acid) can be obtained from ricinoleic acid by thermal degradation, and as the zinc salt or in ester form is used in fungistatic preparations. 

Bafor, M., Smith, M. A., Jonsson, L., Stobart, K., and Stymne, S. 1991. Ricinoleic acid biosynthesis and triacylglycerol assembly in microsomal preparation from developing castor bean (Ricinus communis) endosperm. Biochem. J., 280, 507-514. 

Castor Oil occurs as a pale yellow or almost colorless, transparent, viscous liquid. It is the fixed oil obtained from the seed of Ricinus communis L. (Fam. Euphorbiaceae) and consists mainly of the triglyceride of ricinoleic acid. It is soluble in alcohol, and is miscible with absolute alcohol, with glacial acetic acid, with chloroform, and with ether. 

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). 

Castor oil is derived from the plant Ricinus communis grown mainly in India, Brazil, and China at a world production level of about 0.5 million tons of oil. This oil differs from all other commercial oils in being rich in ricinoleic acid ( 90%, 12-hydroxy oleic). Compared with the common vegetable oils, castor oil is more viscous, less soluble in hexane, and more soluble in ethanol, all as a consequence of the presence of the hydroxy acid. This hydroxy acid has several interesting properties by which it can be converted to useful products. 

Derivation From the seeds of the castor bean, Ricinus communis (Brazil, India, the former U.S.S.R., U.S.). They are cold-pressed for the first grade of medicinal oil and hot pressed for the common qualities, approximately 40% of the oil content of the bean being obtained. Residual oil in the cake is obtained by solvent extraction. Chief constituent Ricinolein (glyceride of ricinoleic acid). 

A unique vegetable oil is castor oil, extracted from the seeds of the plant Ricinus communis, which is a triglyceride of ricinoleic acid. Ricinoleic acid has 18 carbon atoms, a double bond (C9-C10) and a secondary hydroxyl group (C12) [29, 38, 41-43, 46]. The idealised structure of castor oil is shown in Figure 17.6. 

CASTOR OIL An age-old home remedy seldom recommended now, castor oil (purge, NEOLOID, others) is derived from the bean of the castor plant, Ricinus communis, which contains two well-known noxious ingredients an extremely toxic protein, ricin, and an oil composed chiefly of the triglyceride of ricinoleic acid. The triglyceride is hydrolyzed in the small bowel by the action of lipases into glycerol and the active agent, ricinoleic acid, which acts primarily in the small intestine to stimulate secretion of fluid and electrolytes and speed intestinal transit. When taken on an empty stomach, as little as 4 mL of castor oil may produce a laxative effect within 1-3 hours however, the usual dose for a cathartic effect is 15-60 mL for adults. 

The action of stimulant laxative herbs is, in most cases, due primarily to their content of anthraquinones. The one exception among the herbs listed in this category is castor oil (from Ricinus communis), the action of which is due to ricinoleic acid (Brunton et al. 2006). 

Castor oH (ricinus oil). The oil obtained from seeds of the castor-oil plant or castor beans (Ricinus communis, Euphorbiaceae), mp. -10 C. It contains about 80-85% ricinoleic acid as glycerol ester together with oleic (7%), linolic (3%), palmitic (2%), and stearic (1%) acids. The Ricinus seeds contain the highly poisonous constituents ricin, a mixture of proteins, and ricinine, a pyridone alkaloid. The presence of these substances leaves the oilcake remaining after pressing of C. unsuitable for use as animal fodder. 

Ricinoleic acid (Fig. 1) is the major component of castor oil, derived from the seed of Ricinus communis L., the castor plant. The oil is 90% ricinoleate and the presence of the hydroxy group imparts unique chemical and physical properties (1,2). Products derived from castor oil are listed in Table 1. In addition to these applications, there are many others that are promising but have not been implemented due to the limited supply of castor oil produced annually (1). 

Castor oil is ctirrently the most important natural source of hydroxy fatty acids. The oil is derived from the seed of Ricinus communis, which grows as a perennial or annual in tropical and subtropical areas. Castor oil is the main source and contains 90% ricinoleic acid (12-hydroxy-9-Z-octadecenoic acid) [1]. This is a Cjg fatty acid with a Z-double bond between C-9 and C-10 and a hydroxyl group on C-12 (Fig. 1 (1-3). Castoroilwasfirstusedformedicinalpurposes, but over time, a wide... 

Hydroxycarboxylic acids and 5-hydroxycarboxylic acids occur in the form of corresponding y- and 5-lactones in many fruits, especially apricots and peaches. Many other hydroxy fatty acids are also found in seed oils of plants. For example, (S)-jalapinolic acid (3-28) occurs in lipophilic ester-type dimers of acylated pentasaccharides derived from L-rhamnose in sweet potato Ipomoea batatas, Convolvulaceae), which are known as batatins. (9Z,12S)-12-Hydroxyoctadec-9-enoic (ricinoleic) acid (3-29) occurs in castor oil, where it represents about 90% of the total fatty acids. So-called castor oil is extracted from the seeds of the castor oil plant Ricinus communis) of the Euphorbiaceae family, and is used only for technical purposes as it has purgative properties. 

These hypotheses were examined by characterizing the selectivity of CPT and DAGAT in microsomal preparations from developing cotyledons of a series of oilseed plants towards different DAG species. Four different plants were used as model systems safflower (Carthamus tinctorius), a plant producing no unusual fatty acids rapeseed (Brassica napus), which stores erucic acid (22 1) in its TAG species Cuphea, a plant accumulating medium chain fatty acids (C8 - C12) in its seed triacylglycerols and castor bean (Ricinus communis) which stores up to 90% ricinoleic acid (18 1-OH) in its seed oils. 

This chapter focuses on the preparation of thermosets, polyesters, and other polymers from industrial oilseeds. Nature has provided a few examples of plant oils that possess multiple functional groups needed for polymer synthesis, such as castor (Ricinus communis), lesquerella (Lesquerella fendleri), and vemonia (Vernonia galamensis) oils, enriched in —OH and epoxide-functionalized fatty acids ricinoleic, lesquerolic, and vemolic acid, respectively (Table 3.1). Many common plant seed oils (eg, soybean, cottonseed, com, soybean, safQower, sunflower, canola, jatropha, and olive oils) are enriched in Ci6—Cig saturated and mono- and diunsaturated fatty acids, such as palmitic (16 0), oleic (18 l-9c), and linoleic (18 2-9c,12c) acids and lesser amounts of a-linolenic acid (18 3-9c,12c,15c) however, linseed (flaxseed), camelina (Camelina saliva). 

GaUiard, T., Stumpf, PK., 1966. Fat metabolism in higher plants XXX. Enzymatic synthesis of ricinoleic acid by a microsomal preparation from developing Ricinus communis seeds. J. Biol. Chem. 241,5806-5812. 

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