Ricinic acid

CAS 141-22-0 EINECS/ELINCS 205-470-2 Synoryms Castor oil acid 12-Hydroxy-9-octadecenoic acid 12-Hydroxy-cis-9-octadecenoic acid cis-12-Hydroxyoctadec-9-enoic acid 12-Hydroxyoleic acid d-12-Hydroxyoleic acid 9-Octadecenoic acid, 12-hydroxy- Oleic acid, 12-hydroxy- Ricinic acid Ricinolic acid Classification Unsaturated fatty acid Empirical CisHsjOs... 

Rice wax. See Rice (Oryza sativa) wax Ricinic acid. See Ricinoleic acid Ricini oleum. See Castor (Ricinus communis) oil... 

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. 

Type 2 (Blender method) - Using acetone, dilute sulfuric acid, sodium hydroxide (lye), sodium carbonate (washing soda), sodium sulfate, and carbon tetrachloride. Uses more chemicals and equipment but produces an article of much greater purity. All chemi-lcals used are cheaply and readily available. Geared to the production of larger quantities than field grade, this method was actually developed to produce ricin ((or use by the Chemical Warfare Branch of the Army. 

Ricin is added to three times its weight of distilled water and brought to a pH of 3.8, using 5% sulfuric acid. 

Nicotinic acid (Figure 29) provides alkaloids with the pyridine nucleus in the synthesizing process. This nucleus appears in such alkaloids as anabasine, anatabine, nicotine, nornicotine, ricine and arecoline. Moreover, many alkaloids... 

Panopoulos P, Dresios J, Synetos D (2004) Biochemical evidence of translational infidelity and decreased peptidyltransferase activity by a sarcin/ricin domain mutation of yeast 25S rRNA. Nucleic Acids Res... 

N.A. Ricinoleic acid, ricin, ricinine, lectins.99 The seeds are toxic. Laxative, prompting a bowel movement. 

Alakhov, V., et al. 1990. Increasing cytostatic effects of ricin A chain and Staphylococcus aureus enterotoxin A through in vitro hydrophobization with fatty acid residues. Biotechnol Appl Biochem 12 94. 

Nicotinic acid undoubtedly provides the basic skeleton for some other alkaloids. Ricinine (Figure 6.35) is a 2-pyridone structure and contains a nitrile grouping, probably formed by dehydration of a nicotinamide derivative. This alkaloid is a toxic constituent of castor oil seeds (Ricinus communis Euphorbiaceae), though the toxicity of the seeds results mainly from the polypeptide ricin (see page 434). Arecoline (Figure 6.36) is found in Betel nuts (Areca catechu Palmae/Arecaceae) and is a tetrahydronicotinic acid derivative. Betel nuts are chewed in India and Asia for the stimulant effect of arecoline. 

Ricin is a type II toxin. The A chain (ricin A) contains 267 amino acid residues, and the B chain (ricin B) 262 residues. Ricin A is exceptionally toxic, and it has been estimated that a single molecule is sufficient to kill an individual cell. This peptide can be prepared by genetic engineering using Escherichia coli. The potent action of this material on eukaryotic cells has been investigated in anticancer therapy. Ricin A has been coupled to monoclonal antibodies and successfully delivered specifically to the tumour cells. However, in vitro toxicity of ricin A-based immunotoxins is enhanced significantly if ricin B is also present. 

The presence of the hydroxy group on ricinoleate (12-hydroxy oleate) underlies many industrial uses, such as the manufacture of lithium grease, plastics, paints, coatings, and cosmetics. Castor oil contains 90% of its fatty acids (FA) as ricinoleate (Achaya et al., 1964) and is the only commercial source of ricinoleate. Since the castor bean contains the toxin ricin and potent allergens, it... 

R/S domain, highly conserved ricin/a-sarcin-interacting domain of 28S rRNA RA-R, retinoic acid receptor RER, rough endoplasmic reticulum Rha, rhamnose, rhamnoside,... 

Shock-sensitive, detonable compounds (such as sodium azide, dry picric acid) or extremely poisonous materials (such as cyanides, osmium tetroxide, cacodylic acid, tetrodotoxin, picrotoxin, ricin) should be stored in locked cabinets. DEA-regulated substances (e.g., pentobarbital, phenobarbital)... 

Ricin can be made from the waste material left over from processing castor oil. It can be made in either powder, mist, or pellet form, or it can be dissolved in water or weak acid. Ricin is a stable substance under normal conditions, but can be inactivated by heat above 80°C. 

FIGURE 25.2. The effects of ricin on hepatic lipid peroxidation. Concentration of thioharituric acid reactive substances (TEARS) in the liver was compared between control (untreated) mice and mice treated with 25 pg ricin/kg. Values are the averages of 4-10 animals SD. p < 0.05 with respect to corresponding control group. 

Lipopeptldes emulsify with difficulty aromatic oils such as styrene or toluene. Furthermore they are not able to emulsify some oils such as vaseline, ricin, wheat germ and silicon oils. To emulsify such oils we have used a binary emulsifying system consisting of a mixture of a fatty alcohol (cetyl alcohol) and a ionic lipopeptide (liposarcosine chlorhydrate, lipolysine bromhydrate or llpoglutamic acid sodium salt). With concentrations of lipopeptide and cetyl alcohol of 1 to 3 % we have obtained miniemulsions similar to those obtained by El Aasser and al. with sodium lauryl sulfate and cetyl alcohol (10). 

---