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Castor oil

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Castor beans.

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 (595 °F) 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]

Background

Structure of the major component of castor oil.

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 commands 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 U.S. 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.

Sulfonated castor oil, also called sulfated castor oil, or Turkey Red Oil, is the only oil that completely disperses in water. It is made by adding sulfuric acid to pure castor oil.[5] This allows easy use for making bath oil products. It was the first synthetic detergent after ordinary soap. It is used in formulating lubricants, softeners, and dyeing assistants.[6]

The castor seed contains ricin, a toxic protein removed by cold pressing and filtering.[7] However, harvesting castor beans is not without risk.[8] 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.[9] These health issues, in addition to concerns about the toxic byproduct (ricin) from castor oil production, have encouraged the quest for alternative sources for hydroxy fatty acids.[10][11] Alternatively, some researchers are trying to genetically modify the castor plant to prevent the synthesis of ricin.[12]

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,[13] flavorings, candy (e.g., chocolate),[14] as a mold inhibitor, and in packaging. Polyoxyethylated castor oil (e.g., Cremophor EL)[15] is also used in the foodstuff industries.[16]

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, with its major site of action the small intestine.[17] However, although it may be used for constipation, it is not a preferred treatment.[18] Undecylenic acid, a castor oil derivative, is also FDA-approved for over-the-counter use on skin disorders or skin problems.[19]

Castor oil penetrates deep into the skin thanks to its molecular weight, which is low enough to penetrate into the stratum corneum. Castor Isostearate Succinate is a polymeric mixture of esters with Isostearic Acid and Succinic Acid used for skin conditioning, such as in shampoo, lipstick and lip balm.[20]

Ricinoleic acid is the main component of castor oil and it exerts anti-inflammatory effects.[21]

One study has found that castor oil decreased pain more than ultrasound gel or Vaseline during extracorporeal shockwave application.[22]

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:

Traditional or folk medicines

The use of cold pressed castor oil in folk medicine predates government medical regulations. Cold pressed castor oil is tasteless and odorless when pure. Uses include skin problems, burns, sunburns, skin disorders, skin cuts, and abrasions. Castor oil has also been used to draw out styes in the eye by pouring a small amount into the eye and allowing it to circulate around the inside of the eyelid. Note that most bottles of castor oil indicate the oil is to be kept away from the eyes. 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 psychic Edgar Cayce, given in many healing readings in the early mid-1900s. Castor oil has also been noted for its acne-healing abilities.[32]

Castor oil has been used to induce childbirth in pregnant women, though it is not always effective in application. Castor oil, when ingested, triggers cramping in the bowel (making it an effective laxative). Thus, it is intended that such cramping extend to the uterus. In an overdue pregnancy in which the mother's cervix is already effacing and partially dilated, this cramping can lead to labor contractions. The irregular, painful contractions of castor-oil-induced labor can be stressful on the mother and fetus.[citation needed] It also leaves the laboring woman quite dehydrated as a result of the vomiting and diarrhea which result when the recommended dose of castor oil for labor induction is taken—2 oz, or about 8 tbsp. This leaves her without access to the energy she could otherwise derive from food or drink throughout her labor process. Using castor oil for induction is not recommended without consulting a medical practitioner and is not recommended in a complex pregnancy. [citation needed]. In south Egypt, women use a dose of full large spoon of castor oil to prevent pregnancy for one year.

Industrial castor oil

Castor oil has numerous applications in transportation, cosmetics and pharmaceutical, and manufacturing industries, for example: adhesives,[33] brake fluids,[34] caulks, dyes,[33] electrical liquid dielectrics, humectants,[33] hydraulic fluids, inks,[33] lacquers, leather treatments,[33] lubricating greases, machining oils, paints,[33] pigments, polyurethane adhesives,[35] refrigeration lubricants, rubbers,[33] sealants, textiles,[33] 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.[36] 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.[37] 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 race engines. Biodegradability results in decreased persistence in the environment (relative to petroleum-based lubricants[38]) 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.[39]

Castor oil is the preferred lubricant for bicycle pumps, most likely because it doesn't dissolve natural-rubber seals.[40]

Uses in early aviation and aeromodelling

Castor oil was the preferred lubricant for the early aviation powerplant design known as the rotary engine, such as the Gnome engines used in pre-World War I "pioneer aircraft", after that engine's widespread adoption for aviation in Europe in 1909, and was used almost universally by the rotary engines in World War I Allied aircraft.

The methanol-fuelled glow plug engines used for aeromodelling purposes, since their adoption in the model airplane hobby in 1948, have used castor oil as a dependable lubricant that is highly resistant to degradation when the engine has its fuel-air mixture "leaned out" for maximum engine speed. The aforementioned gummy residue problem can still be troublesome for aeromodelling powerplants lubricated with castor oil, however, usually resulting in eventual ball bearing replacement when the residue builds up too much within the engine's bearing races.

Castor biofuel farming started in 2008 in Ethiopia. Families in the Waletia and Goma Gofa regions of Ethiopia began by seeding castor beans for use in biodiesel. The initiative is run by energy company Global Energy Ethiopia, who are also conducting a research and development programme to create new varieties of castor with better yields. (Sub-Saharan Africa gateway, Science and Development Network website, 2008)

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.[41][42][43] 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 rarely died, though often had to bear the humiliation of the laxative effects resulting from excessive consumption of the oil.[44]

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. These words are still used to satirize patronizing politicians, or the authors of disliked legislation. They should be used with caution in common conversation. The terms Usare l'olio di ricino, ("to use castor oil") and usare il manganello ("use the bludgeon") mean "to coerce or abuse," and can be misunderstood in the absence of proper context.

See also

References

  1. ^ Aldrich Handbook of Fine Chemicals and Laboratory Equipment, Sigma-Aldrich, 2003.
  2. ^ NNFCC "Castor", The National Non-Food Crops Centre, Retrieved on 2009-02-23
  3. ^ "July 2007 commodity price for Indian castor oil". Retrieved 2008-08-10.
  4. ^ "Seed oil prices from US Dept. of Agriculture, see page 31" (PDF). Retrieved 2008-08-10.
  5. ^ Turkey Red Oil - A defoaming & wetting agent, manure, lubricant
  6. ^ CastorOil.in – Home of Castor Oil Online
  7. ^ "Castor Oil is non-toxic". ICOA. Retrieved 2006-12-28.
  8. ^ Auld, Dick L. (1999). "Selection of Castor for Divergent Concentrations of Ricin and Ricinus communis Agglutinin and references therein" (PDF). Crop Science. 39 (MARCH–APRIL): 353–357. Retrieved 2007-07-31. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  9. ^ "Hazards of harvesting castor plants". Retrieved 2007-07-31.
  10. ^ Dierig, David A. (1995). "Lesquerella". New Crop FactSHEET. Center for New Crops & Plant Products, at Purdue University. Retrieved 2007-08-01.
  11. ^ Dierig, David A. (2002). "Lesquerella" (PDF). The National Non-Food Crops Centre. Retrieved 2007-08-01.
  12. ^ Wood, M. (2001). "High-Tech Castor Plants May Open Door to Domestic Production". Agricultural Research Magazine. 49 (1). Retrieved 2007-08-02.
  13. ^ Castor Oil Facts
  14. ^ Wilson R, Van Schie BJ, Howes D (1998). "Overview of the preparation, use and biological studies on polyglycerol polyricinoleate (PGPR)". Food Chem. Toxicol. 36 (9–10): 711–8. doi:10.1016/S0278-6915(98)00057-X. PMID 9737417.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  15. ^ "BASF Technical data sheet on Cremophor EL" (PDF). Retrieved 2007-08-01.
  16. ^ Busso C, Castro-Prado MA (2004). "Cremophor EL stimulates mitotic recombination in uvsH//uvsH diploid strain of Aspergillus nidulans". An. Acad. Bras. Cienc. 76 (1): 49–55. PMID 15048194. {{cite journal}}: Unknown parameter |month= ignored (help)
  17. ^ "Ingredient List A-C" (PDF). FDA (see page 52 of this link). Retrieved 2006-12-28.
  18. ^ Castor Oil. DRUGDEX System. n.d. Thomson Micromedex. Retrieved February 19, 2007 [1]
  19. ^ "Ingredient List P-Z" (PDF). FDA (see page 65 of this link). Retrieved 2006-12-28.
  20. ^ Skin-Conditioning Agents by the Environmental Working Group
  21. ^ Vieira C, Evangelista S, Cirillo R, Lippi A, Maggi CA, Manzini S (2000). "Effect of ricinoleic acid in acute and subchronic experimental models of inflammation". Mediators Inflamm. 9 (5): 223–8. doi:10.1080/09629350020025737. PMC 1781768. PMID 11200362.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  22. ^ Maier M, Staupendahl D, Duerr HR, Refior HJ (1999). "Castor oil decreases pain during extracorporeal shock wave application". Arch Orthop Trauma Surg. 119 (7–8): 423–7. doi:10.1007/s004020050013. PMID 10613232.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  23. ^ Marmion LC, Desser KB, Lilly RB, Stevens DA (1976). "Reversible thrombocytosis and anemia due to miconazole therapy". Antimicrob. Agents Chemother. 10 (3): 447–9. doi:10.1128/AAC.. PMC 429768. PMID 984785. {{cite journal}}: Check |doi= value (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link) See page 1, Methods and Materials.
  24. ^ Fromtling RA (1988). "Overview of medically important antifungal azole derivatives". Clin. Microbiol. Rev. 1 (2): 187–217. PMC 358042. PMID 3069196. {{cite journal}}: Unknown parameter |day= ignored (help); Unknown parameter |month= ignored (help) See page 6, /192, Clinical studies
  25. ^ Micha JP, Goldstein BH, Birk CL, Rettenmaier MA, Brown JV (2006). "Abraxane in the treatment of ovarian cancer: the absence of hypersensitivity reactions". Gynecol. Oncol. 100 (2): 437–8. doi:10.1016/j.ygyno.2005.09.012. PMID 16226797. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  26. ^ "Sandimmune ingredients". DailyMed. Retrieved 2007-01-06.
  27. ^ Zhang KE, Wu E, Patick AK; et al. (2001). "Circulating metabolites of the human immunodeficiency virus protease inhibitor nelfinavir in humans: structural identification, levels in plasma, and antiviral activities". Antimicrob. Agents Chemother. 45 (4): 1086–93. doi:10.1128/AAC.45.4.1086-1093.2001. PMC 90428. PMID 11257019. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  28. ^ Sugar AM, Salibian M, Goldani LZ (1994). "Saperconazole therapy of murine disseminated candidiasis: efficacy and interactions with amphotericin B". Antimicrob. Agents Chemother. 38 (2): 371–3. doi:10.1128/AAC.. PMC 284460. PMID 8192469. {{cite journal}}: Check |doi= value (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  29. ^ "Product Information: Xendaderm topical ointment, balsam Peru, castor oil and trypsin topical ointment. Healthpoint,Ltd., San Antonio, TX, 2002". Retrieved 2007-10-11.
  30. ^ Beitz JM (2005). "Heparin-induced thrombocytopenia syndrome bullous lesions treated with trypsin-balsam of peru-castor oil ointment: a case study". Ostomy Wound Manage. 51 (6): 52–4, 56–8. PMID 16014993. {{cite journal}}: Unknown parameter |month= ignored (help)
  31. ^ "Aci-Jel (Vaginal Jelly) drug description - prescription drugs and medications at RxList". RxList. Retrieved 2007-10-26.
  32. ^ What is Castor Oil?. Edgar Cayce's Association for Research Enlightenment, Inc.
  33. ^ a b c d e f g h "Multiple uses of castor oil". Retrieved 2007-08-02.
  34. ^ "Castor oil as a component of brake fluid". Retrieved 2007-08-03.
  35. ^ Azambuja, Maximiliano dos Anjos (2006). "Use of castor oil-based polyurethane adhesive in the production of glued laminated timber beams". Mat. Res. [online]. 9 (3): 287–91. Retrieved 2007-08-02. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  36. ^ "Chemical modification to improve vegetable oil lubricants". Retrieved 2007-08-02.
  37. ^ McGuire, Nancy (2004). "Taming the Bean". The American Chemical Society. Retrieved 2007-08-02.
  38. ^ "Petroleum Oil and the Environment". DOE. Retrieved 2006-12-28.
  39. ^ Ogunniyi, D.S. (2006). "Castor oil: A vital industrial raw material". Bioresource Technology. 97 (9): 1086–91. doi:10.1016/j.biortech.2005.03.028. {{cite journal}}: Unknown parameter |month= ignored (help)
  40. ^ Older, Jules (2000). Backroad and offroad biking. Mechanicsburg, PA: Stackpole Books. p. 37. ISBN 0-8117-3150-2. 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 {{cite book}}: External link in |quote= (help)
  41. ^ "Italy The rise of Mussolini". Encyclopædia Britannica Online. Encyclopædia Britannica. 2007. Retrieved 2007-08-03.
  42. ^ "Benito's Birthday". Time, in partnership with CNN. August 6, 1923. Retrieved 2007-08-03.
  43. ^ Bosworth, R. J. B. (2002). Mussolini. New York: Arnold/Oxford Univ. Press. ISBN 0340731443. {{cite book}}: Cite has empty unknown parameter: |coauthors= (help)
  44. ^ The Straight Dope: Did Mussolini use castor oil as an instrument of torture?
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