Castor oil

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Castor oil is a vegetable oil obtained from the castor bean (technically castor seed as the castor plant, Ricinus communis, is not a member of the bean family). Castor oil (CAS number 8001-79-4) is a colorless to very pale yellow liquid with mild or no odor or taste. Its boiling point is 313°C and its density is 961 kg·m-3.[1] It is a triglyceride in which approximately ninety percent of fatty acid chains are ricinoleic acid. Oleic and linoleic acids are the other significant components.[2]

The structure of the major component fo castor oil is shown below:

Background

Ricinoleic acid, a monounsaturated, 18-carbon fatty acid, is unusual in that it has a hydroxyl functional group on the twelfth carbon. This functional group causes ricinoleic acid (and castor oil) to be unusually polar, and also allows chemical derivatization that is not practical with most other seed oils. It is the hydroxyl group which makes castor oil and ricinoleic acid valuable as chemical feedstocks. Compared to other seed oils which lack the hydroxyl group, castor oil demands a higher price. As an example, in July 2007 Indian castor oil sold for about US$0.90 per kilogram (US$0.41 per pound)[3] while US soybean, sunflower and canola oil sold for about US$0.30 per kilogram (US$0.14 per pound)[4]

Castor oil and its derivatives have applications in the manufacturing of soaps, lubricants, hydraulic and brake fluids, paints, dyes, coatings, inks, cold resistant plastics, waxes and polishes, nylon, pharmaceuticals and perfumes.

The castor seed contains ricin, a toxic protein removed by cold pressing and filtering.[5] However, harvesting castor beans is not without risk, [6] allergenic compounds found on the plant surface can cause permanent nerve damage, making the harvest of castor beans a human health risk. India, Brazil and China are the major crop producers and the workers suffer harmful side effects from working with these plants.[7] These health issues, in addition to concerns about the toxic byproduct (ricin) from castor oil production, have encouraged the quest for alternative, domestic sources for hydroxy fatty acids.[8][9] Alternatively, some researchers are trying to genetically modify the castor plant to prevent the synthesis of ricin.[10]

Castor oil fatty acids

Average composition of Castor seed oil / fatty acid chains
Acid name Average Percentage Range
Ricinoleic acid 85 to 95%
Oleic acid 6 to 2%
Linoleic acid 5 to 1%
Linolenic acid 1 to 0.5%
Stearic acid 1 to 0.5%
Palmitic acid 1 to 0.5%
Dihydroxystearic acid 0.5 to 0.3%
Others 0.5 to 0.2%

Uses

Castor oil in food

In the food industry, castor oil (food grade) is used in food additives [3], flavorings, candy (i.e., chocolate) [11], as a mold inhibitor, and in packaging. Polyoxyethylated castor oil (eg. Cremophor EL)[12] is also used in the foodstuff industries.[13]

Medicinal use of castor oil

The United States Food and Drug Administration (FDA) has categorized castor oil as "generally recognized as safe and effective" (GRASE) for over-the-counter use as a laxative.[14] However, it is not a preferred treatment for constipation.[15]

Undecylenic acid, a castor oil derivative, is also FDA-approved for over-the-counter use on skin disorders or skin problems.[16]

Ricinoleic acid is the main component of castor oil and it exerts anti-inflammatory effects.[17]

One study has found that castor oil decreased pain more than ultrasound gel or Vaseline during extracorporeal shock wave application.[18]

Therapeutically, modern drugs are rarely given in a pure chemical state, so most active ingredients are combined with excipients or additives. Castor oil, or a castor oil derivative such as Cremophor EL (polyethoxylated castor oil, a nonionic surfactant), is added to many modern drugs, including:

  • Miconazole, an anti-fungal agent;[19][20]
  • Paclitaxel, a mitotic inhibitor used in cancer chemotherapy;[21]
  • Sandimmune (cyclosporine injection, USP), an immunosuppressant drug widely used in connection with organ transplant to reduce the activity of the patient's immune system;[22]
  • Nelfinavir mesylate, an HIV protease inhibitor;[23]
  • Saperconazole, a triazole antifungal agent (contains Emulphor EL -719P, a castor oil derivative);[24]
  • Prograf, an immunosuppressive drug (contains HCO-60, polyoxyl 60 hydrogenated Castor oil);[citation needed]
  • Balsam Peru - Castor oil - and Trypsin Topical (contains castor oil);[25]
  • Aci-Jel, a gel used to create or maintain the acidity of the vagina (comprises acetic acid/oxyquinoline/ricinoleic acid - vaginal);[citation needed]

Traditional or folk medicines

The use of cold pressed castor oil in folk medicine predates government regulations. Cold pressed castor oil is tasteless and odorless when pure. Uses include skin problems, burns, sunburns, skin disorders, skin cuts, abrasions, etc.

The oil is also used as a rub or pack for various ailments, including abdominal complaints, headaches, muscle pains, inflammatory conditions, skin eruptions, lesions, and sinusitis. A castor oil pack is made by soaking a piece of flannel in castor oil, then putting it on the area of complaint and placing a heat source, such as a hot water bottle, on top of it. This remedy was often suggested by the American Healing Psychic, Edgar Cayce, given in many healing readings in the early to mid-1900s.[26]

Industrial castor oil

Castor oil has numerous applications in transportation, cosmetics and pharmaceutical, and manufacturing industries, for example: adhesives[27], brake fluids [28], caulks, dyes[27], electrical liquid dielectrics, humectants,[27] hydraulic fluids, inks[27], lacquers, leather treatments,[27] lubricating greases, machining oils, paints[27], pigments, polyurethane adhesives [29] , refrigeration lubricants, rubbers[27], sealants, textiles[27], washing powders, and waxes.

Vegetable oils, due to their good lubricity and biodegradability are attractive alternatives to petroleum-derived lubricants, but oxidative stability and low temperature performance limit their widespread use.[30] Castor oil has better low temperature viscosity properties and high temperature lubrication than most vegetable oils, making it useful as a lubricant in jet, diesel, and race-car engines.[31] However, castor oil tends to form gums in a short time, and its use is therefore restricted to engines that are regularly rebuilt, such as motorcycle race engines. Biodegradability results in decreased persistance in the environment (relative to petroleum-based lubricants[32]) in case of an accidental release. The lubricants company Castrol took its name from castor oil.

Since it is has a relatively high dielectric constant (4.7), highly refined and dried castor oil is sometimes used as a dielectric fluid within high performance high voltage capacitors.

Castor oil is the raw material for the production of a number of chemicals, notably sebacic acid, undecylenic acid, nylon-11. A review listing numerous chemicals derived from castor oil is available.[33]

Castor oil is the preferred lubricant for bicycle pumps, most likely because it doesn't dissolve natural-rubber seals.[34]

Castor oil: Use as a means of intimidation in Fascist Italy

In Fascist Italy under the regime of Benito Mussolini, castor oil was one of the tools of the blackshirts[35] [36] [37] Political dissidents were force-fed large quantities of castor oil by Fascist paramilitary groups. This technique was said to have been originated by Gabriele D'Annunzio. Victims of this treatment would experience severe diarrhea and dehydration, often resulting in death [38]

Sometimes when the blackshirts wished to make sure that the victim would die rather than simply be badly disabled, they would mix gasoline with the castor oil.

It is said that Mussolini's power was backed by "the bludgeon and castor oil." In lesser quantities, castor oil was also used as an instrument of intimidation, for example to discourage civilians or soldiers who would call in sick either in the factory or in the military. Since its healing properties were widely exaggerated, abuse could be easily masked under pretense of a doctor's prescription. It took decades after Mussolini's death before the myth of castor oil as a panacea for a wide range of diseases and medical conditions was totally demystified, as it was also widely administered to pregnant women, elderly or mentally-ill patients in hospitals in the false belief that it had no negative side effects.

Linguistic connotations

Today the Italian terms manganello and olio di ricino, even used separately, still carry strong political connotations and if these words are still used to satirize patronizing politicians or the authors of unpopular legislation, they should be used with caution when engaging in a common conversation. Usare l'olio di ricino, ("to use castor oil") o usare il manganello ("use the bludgeon"), means to coerce or abuse and can be misunderstood in the absence of a proper context.

See also

References

  1. Aldrich Handbook of Fine Chemicals and Laboratory Equipment, Sigma-Aldrich, 2003.
  2. Castor. The National Non-Food Crops Centre. Retrieved on 2007-07-06.
  3. July 2007 commodity price for Indian castor oil. Retrieved on 2008-08-10.
  4. Seed oil prices from US Dept. of Agriculture, see page 31. Retrieved on 2008-08-10.
  5. Castor Oil is non-toxic. ICOA. Retrieved on 2006-12-28.
  6. Auld, Dick L.; Pinkerton,Scott D.; Rolfe, Rial; Ghetie, Victor and Lauterbach, Brenda F. (1999). "Selection of Castor for Divergent Concentrations of Ricin and Ricinus communis Agglutinin and references therein". CROP SCIENCE 39 (MARCH–APRIL): 353-357. Retrieved on 2007-07-31.
  7. Hazards of harvesting castor plants. Retrieved on 2007-07-31.
  8. Dierig, David A. (1995). Lesquerella. New Crop FactSHEET. Center for New Crops & Plant Products, at Purdue University. Retrieved on 2007-08-01.
  9. Dierig, David A. (2002). Lesquerella. The National Non-Food Crops Centre. Retrieved on 2007-08-01.
  10. Wood, M. (2001). "High-Tech Castor Plants May Open Door to Domestic Production". Agricultural Research Magazine 49 (1). Retrieved on 2007-08-02.
  11. Overview of the preparation, use and biological studies on polyglycerol polyricinoleate (PGPR). PubMed. Retrieved on 2007-01-26.
  12. BASF Technical data sheet on Cremophor EL®. Retrieved on 2007-08-01.
  13. Cremophor EL® stimulates mitotic recombination in uvsH//uvsH diploid strain of Aspergillus nidulans.. PubMed. Retrieved on 2007-01-26.
  14. Ingredient List A-C. FDA (see page 52 of this link). Retrieved on 2006-12-28.
  15. Castor Oil. DRUGDEX® System. n.d. Thomson Micromedex. Retrieved February 19, 2007 [1]
  16. Ingredient List P-Z. FDA (see page 65 of this link). Retrieved on 2006-12-28.
  17. Effect of ricinoleic acid in acute and subchronic experimental models of inflammation. PubMed. Retrieved on 2007-01-06.
  18. Castor oil decreases pain during extracorporeal shockwave application. PubMed. Retrieved on 2007-01-15.
  19. Reversible Thrombocytosis and Anemia Due to Miconazole Therapy (pdf). PubMed. Retrieved on 2007-01-06. See page 1, Methods and Materials.
  20. Overview of medically important antifungal azole derivatives (pdf). PubMed. Retrieved on 2007-01-06. See page 6, /192, Clinical studies
  21. Abraxane in the treatment of ovarian cancer: the absence of hypersensitivity reactions. PubMed. Retrieved on 2007-01-06.
  22. Sandimmune ingredients. DailyMed. Retrieved on 2007-01-06.
  23. Circulating Metabolites of the Human Immunodeficiency Virus Protease Inhibitor Nelfinavir in Humans: Structural Identification, Levels in Plasma, and Antiviral Activities. PubMed. Retrieved on 2007-01-06.
  24. Saperconazole Therapy of Murine Disseminated Candidiasis:. PubMed. Retrieved on 2007-01-06.
  25. Heparin - induced thrombocytopenia syndrome bullous lesions treated with trypsin - balsam of peru - castor oil ointment: a case study. PubMed. Retrieved on 2007-01-06.
  26. [2]
  27. 27.0 27.1 27.2 27.3 27.4 27.5 27.6 27.7 Multiple uses of castor oil. Retrieved on 2007-08-02.
  28. Castor oil as a component of brake fluid. Retrieved on 2007-08-03.
  29. Azambuja, Maximiliano dos Anjos; Dias, Antonio Alves (2006, vol. 9, no. 3). "Use of castor oil-based polyurethane adhesive in the production of glued laminated timber beams". Mat. Res. [online]: 287-291. Retrieved on 2007-08-02.
  30. Chemical modification to improve vegetable oil lubricants. Retrieved on 2007-08-02.
  31. McGuire, Nancy (2004). Taming the Bean. The American Chemical Society. Retrieved on 2007-08-02.
  32. Petroleum Oil and the Environment. DOE. Retrieved on 2006-12-28.
  33. Ogunniyi, D.S. (June 2006). "Castor oil: A vital industrial raw material". Bioresource Technology 97 (9): 1086-1091. Retrieved on 2008-08-10.
  34. "Here's a good tip: Instead of lubricating your pump with petroleum oil, which will rot the pump's rubber parts, use castor oil, available at your local drugstore." Jules Older, Backroad and Offroad Biking (Stackpole Books (August 2000)), ISBN 0811731502, ISBN 978-0811731508, at p. 37; viewable via Google Book Search here
  35. "Italy The rise of Mussolini". Encyclopædia Britannica Online. (2007). Encyclopædia Britannica. Retrieved on 2007-08-03. 
  36. "Benito's Birthday", Time, in partnership with CNN, Monday, Aug. 06, 1923. Retrieved on 2007-08-03. 
  37. Bosworth, R. J. B. (2002). Mussolini. New York: Arnold/Oxford Univ. Press. ISBN 0340731443. 
  38. http://www.straightdope.com/classics/a4_028.html
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de:Rizinusölid:Minyak jarak it:Olio di ricino nl:Wonderoliesu:Kastroli fi:Risiiniöljy


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