Croton oil

Last updated

Croton oil (Crotonis oleum) is an oil prepared from the seeds of Croton tiglium , [1] a tree belonging to the order Euphorbiales and family Euphorbiaceae, and native or cultivated in India and the Malay Archipelago. Small doses taken internally cause diarrhea. [1] Externally, the oil can cause irritation and swelling. Croton oil is used in Phenol-croton oil chemical peels [2] for its caustic exfoliating effects it has on the skin. [3] Used in conjunction with phenol solutions, it results in an intense reaction that leads to initial skin sloughing. Since croton oil is very irritating and painful, it is used in laboratory animals to study how pain works, pain-relieving and anti-inflammatory drugs, and immunology. [4]

Contents

Because croton tiglium oil is cocarcinogenic, it has been used in tumor research. [5] Berenblum and Shubik saw croton oil as a “promoting” agent: [6] a kind of carcinogen that acted through an inflammatory response. Mice painted only with croton oil hadn’t developed tumors. Croton oil is the source of the chemical compound phorbol. [7] Tumor promotion activity was traced to phorbol esters present in croton oil. [8] Pure phorbol 12-myristate 13-acetate, which is found in croton oil, is widely used in laboratory research to induce tumor development.

History of use

During World War II, the United States Navy added a small amount of croton oil to the neutral grain spirits that powered torpedoes. The oil was intended to prevent sailors from drinking the alcohol fuel. Sailors devised crude stills to separate the alcohol from the croton oil, as alcohol evaporates at a lower temperature than croton oil. [9]

Norwegian partisans among workers at a factory, ordered by the Quisling government to turn over a catch of sardines to the Nazi German government for shipment to Saint-Nazaire (a U-boat base of operations) arranged with the British for a large shipment of croton oil to covertly poison the sardines, whose fishy taste was expected to conceal the tampering. [10]

In "The Bulletin" (9 Dowry Square, Hot Wells, May 29, 1845,) the Reverend Richard Harris Barham wrote a medically inspired poem to relieve the anxiety of a very dear friend a month before his own death on June 17, 1845. The attending doctor advises his patient, among other treatments for a sore throat that is producing barely a sound: "... Please put out your tongue again! / Now the blister! / Ay, the blister! / Let your son, or else his sister, / Warm it well, then clap it here, sir, / All across from ear to ear, sir; / That suffices, / When it rises, / Snip it, sir, and then your throat on / Rub a little oil of Croton: / Never mind a little pain! / Please put out your tongue again! ..." The patient was Barham, who had accidentally swallowed a piece of pear core that got into his windpipe on October 28, 1844. Despite the "professional" advice and the very painful and "highest quality" treatments of the time being given freely to him by Doctors Roberts and Scott, and by the eminent surgeon Mr. Coulson, for "violent vomiting", "inflamed throat", and catching "a cold" in April 1845, Barham died.

"Medicinal" croton oil was supplied in the California Genocide to dying Indian groups. [11]

In Thomas Wolfe's 1929 novel Look Homeward Angel , 18-year-old Steve Gant and a friend sneak into neighbors' barn. In the barn, Steve and his friend find a liquor bottle that the husband hid from the wife; they drink the entire bottle. For revenge, the husband refills the bottle with croton oil. When Steve and his friend return to the barn and find the bottle refilled, they drink from it. This time they get very sick.

In John Steinbeck's novel East of Eden , published in 1952, Kate uses it to murder Faye and inherit her whorehouse. Faye is poisoned with a combination of first strychnine (unsuccessfully) and then two drops of croton oil, on a salad of home-canned beans, mimicking accidental botulism poisoning. To allay suspicion, Kate also poisons herself with cáscara sagrada which gives the same cathartic symptoms, but to a non-fatal degree. [12] [13] Steinbeck also alludes to croton oil in In Dubious Battle , chapter 7. [14]

In the movie They Rode West , released in 1954 and starring Robert Francis, an Army post's previous physician was widely disliked because he frequently prescribed croton oil for the troops.

In the 1966 movie El Dorado starring John Wayne, cayenne pepper, hot mustard, ipecac, asafoetida, croton oil, and gunpowder are the ingredients in an emetic administered to the drunken sheriff J. P. Harrah (Robert Mitchum) to sober him up and prevent him from drinking for the foreseeable future. Arthur Hunnicutt's character Bull expresses great surprise that the extract's use will be risked.

In Bernard Cornwell's 1994 historical fiction Copperhead, the second book of The Starbuck Chronicles, Nate Starbuck is force fed croton oil over a number of days whilst being interrogated by the Confederate authorities after he is accused of being involved in the attempted passing of sensitive military information to the Union. [15]

Related Research Articles

<span class="mw-page-title-main">Mouthwash</span> Liquid rinse for oral hygiene

Mouthwash, mouth rinse, oral rinse, or mouth bath is a liquid which is held in the mouth passively or swirled around the mouth by contraction of the perioral muscles and/or movement of the head, and may be gargled, where the head is tilted back and the liquid bubbled at the back of the mouth.

<span class="mw-page-title-main">Phenol</span> Organic compound (C6H5OH)

Phenol is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.

Cresols are a group of aromatic organic compounds. They are widely-occurring phenols which may be either natural or manufactured. They are also categorized as methyl phenols. Cresols commonly occur as either solids or liquids because their melting points are generally close to room temperature. Like other types of phenols, they are slowly oxidized by exposure to air, and the resulting impurities often give the samples a yellow to brownish red tint. Cresols have an odor characteristic to that of other simple phenols, reminiscent to some of a "coal tar" smell. The name "cresol" is an adduct of phenol and their traditional source, creosote.

<span class="mw-page-title-main">Rubbing alcohol</span> Alcohol used for germ protection

Rubbing alcohol, also known as surgical spirit in some regions, refers to a group of denatured alcohols commonly used as topical antiseptics. These solutions are primarily composed of either isopropyl alcohol (isopropanol) or ethanol, with isopropyl alcohol being the more widely available formulation. Rubbing alcohol is rendered undrinkable by the addition of bitterants or other denaturants.

<span class="mw-page-title-main">Disinfectant</span> Antimicrobial agent that inactivates or destroys microbes

A disinfectant is a chemical substance or compound used to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than sterilization, which is an extreme physical or chemical process that kills all types of life. Disinfectants are generally distinguished from other antimicrobial agents such as antibiotics, which destroy microorganisms within the body, and antiseptics, which destroy microorganisms on living tissue. Disinfectants are also different from biocides—the latter are intended to destroy all forms of life, not just microorganisms. Disinfectants work by destroying the cell wall of microbes or interfering with their metabolism. It is also a form of decontamination, and can be defined as the process whereby physical or chemical methods are used to reduce the amount of pathogenic microorganisms on a surface.

<span class="mw-page-title-main">Methyl salicylate</span> Chemical compound

Methyl salicylate (oil of wintergreen or wintergreen oil) is an organic compound with the formula C8H8O3. It is the methyl ester of salicylic acid. It is a colorless, viscous liquid with a sweet, fruity odor reminiscent of root beer (in which it is used as a flavoring), but often associatively called "minty", as it is an ingredient in mint candies. It is produced by many species of plants, particularly wintergreens. It is also produced synthetically, used as a fragrance and as a flavoring agent.

<span class="mw-page-title-main">Brucine</span> Poisonous alkaloid similar to strychnine

Brucine is an alkaloid closely related to strychnine, most commonly found in the Strychnos nux-vomica tree. Brucine poisoning is rare, since it is usually ingested with strychnine, and strychnine is more toxic than brucine. In chemical synthesis, it can be used as a tool for stereospecific chemical syntheses.

<span class="mw-page-title-main">Health effects of wine</span> Potential health effects resulting from drinking wine

The health effects of wine are mainly determined by its active ingredient – alcohol. Preliminary studies found that drinking small quantities of wine, particularly of red wine, may be associated with a decreased risk of cardiovascular diseases, cognitive decline, stroke, diabetes mellitus, metabolic syndrome, and early death. Other studies found no such effects.

Guaiacol is an organic compound with the formula C6H4(OH)(OCH3). It is a phenolic compound containing a methoxy functional group. Guaiacol appears as a viscous colorless oil, although aged or impure samples are often yellowish. It occurs widely in nature and is a common product of the pyrolysis of wood.

Neurolysis is the application of physical or chemical agents to a nerve in order to cause a temporary degeneration of targeted nerve fibers. When the nerve fibers degenerate, it causes an interruption in the transmission of nerve signals. In the medical field, this is most commonly and advantageously used to alleviate pain in cancer patients.

<span class="mw-page-title-main">Phorbol</span> Chemical compound

Phorbol is a natural, plant-derived organic compound. It is a member of the tigliane family of diterpenes. Phorbol was first isolated in 1934 as the hydrolysis product of croton oil, which is derived from the seeds of the purging croton, Croton tiglium. The structure of phorbol was determined in 1967. Various esters of phorbol have important biological properties, the most notable of which is the capacity to act as tumor promoters through activation of protein kinase C. They mimic diacylglycerols, glycerol derivatives in which two hydroxyl groups have reacted with fatty acids to form esters. The most common and potent phorbol ester is 12-O-tetradecanoylphorbol-13-acetate (TPA), also called phorbol-12-myristate-13-acetate (PMA), which is used as a biomedical research tool in contexts such as models of carcinogenesis.

A chemical peel is a treatment used to improve and smooth the texture of the skin. The skin on the face is most commonly treated, but peels can also be performed on the body. Chemical peels are intended to remove the outermost layers of the skin. To accomplish this task, the chosen peel solution induces a controlled injury to the skin, which causes the skin to peel. This process leads to smoother skin can improve fine lines, acne scars, and pigment. Medium depth peels must be performed by a medical provider.

<span class="mw-page-title-main">Tiglic acid</span> Chemical compound

Tiglic acid is a monocarboxylic unsaturated organic acid. It is found in croton oil and in several other natural products. It has also been also isolated from the defensive secretion of certain beetles.

<span class="mw-page-title-main">Absinthe</span> Alcoholic drink

Absinthe is an anise-flavored spirit derived from several plants, including the flowers and leaves of Artemisia absinthium, together with green anise, sweet fennel, and other medicinal and culinary herbs. Historically described as a highly alcoholic spirit, it is 45–74% ABV or 90–148 proof in the US. Absinthe traditionally has a natural green color but may also be colorless. It is commonly referred to in historical literature as la fée verte'the green fairy'. While sometimes casually referred to as a liqueur, absinthe is not traditionally bottled with sugar or sweeteners. Absinthe is traditionally bottled at a high level of alcohol by volume, but it is normally diluted with water before being consumed.

<span class="mw-page-title-main">Aplysiatoxin</span> Chemical compound

Aplysiatoxin is a cyanotoxin produced by certain cyanobacteria species. It is used as a defensive secretion to protect these cyanobacteria from predation by fish, being a potent irritant and carcinogen, by acting as a powerful activator of protein kinase C. While this action has a tumour-promoting effect, protein kinase C activation can be medically beneficial for some other applications, and synthetic analogues of aplysiatoxin have been researched for anti-cancer effects.

<span class="mw-page-title-main">Phorbol 12,13-dibutyrate</span> Chemical compound

Phorbol 12,13-dibutyrate (PDBu) is a phorbol ester which is one of the constituents of croton oil. As an activator of protein kinase C, it is a weak tumor promoter compared to 12-O-tetradecanoylphorbol-13-acetate.

<span class="mw-page-title-main">Syringic acid</span> Chemical compound

Syringic acid is a naturally occurring phenolic compound and dimethoxybenzene that is commonly found as a plant metabolite.

<span class="mw-page-title-main">Cathy Ames</span> Fictional character of John Steinbeck

Catherine "Cathy" Ames, later known as Kate Trask or Kate Albey, is a fictional character and the main antagonist in John Steinbeck's novel East of Eden. She is married to the main protagonist Adam Trask, and the mother of his twin sons, Caleb and Aron. Beneath her charming, attractive facade, she is an evil woman who manipulates and destroys people for her own amusement and profit. Steinbeck characterizes her as a "psychic monster" with a "malformed soul".

<span class="mw-page-title-main">Mezerein</span> Chemical compound

Mezerein is a toxic diterpene ester found in the sap of Daphne mezereum and related plants. Plants of the genera Euphorbiaceae and Thymelaeaceae possess a wide variety of different phorbol esters, which share the capacity of mimicking diacylglycerol (DAG) and thus activating different isoforms of protein kinase C. Mezerein was first isolated in 1975. It has antileukemic properties in mice, but it is also defined as a weak promoter of skin cancers in the same species. All parts of the plants contain an acrid and irritant sap that contains mezerein, thought to be the principal poison. The sap is especially prevalent in the bark and berries.

In December 2016, over 70 people died of methanol poisoning in the Russian city of Irkutsk. Precipitated by the consumption of adulterated surrogate alcohol, it was the deadliest such incident in Russia's post-Soviet history.

References

  1. 1 2 Chisholm, Hugh, ed. (1911). "Croton Oil"  . Encyclopædia Britannica . Vol. 7 (11th ed.). Cambridge University Press. p. 511.
  2. ↑ Wambier, CG; Lee, KC; Soon, SL; Sterling, JB; Rullan, PP; Landau, M; Brody, HJ; International Peeling, Society. (August 2019). "Advanced chemical peels: Phenol-croton oil peel". Journal of the American Academy of Dermatology. 81 (2): 327–336. doi:10.1016/j.jaad.2018.11.060. PMID   30550827. S2CID   54631945.
  3. ↑ Orra, S; Waltzman, J. T.; Mlynek, K; Duraes, E. F.; Kundu, N; Zins, J. E. (2015). "Periorbital Phenol-Croton Oil Chemical Peel in Conjunction with Blepharoplasty: An Evolving Technique for Periorbital Facial Rejuvenation". Plastic and Reconstructive Surgery. 136 (4 Suppl): 99–100. doi: 10.1097/01.prs.0000472401.26529.67 . PMID   26397611.
  4. ↑ Lawrence Kruger, ed. (2001). Methods in Pain Research. CRC Press.
  5. ↑ Berenblum, I; Shubik, P (1947). "The Role of Croton Oil Applications, Associated with a Single Painting of a Carcinogen, in Tumour Induction of the Mouse's Skin". British Journal of Cancer. 1 (4): 379–382. doi:10.1038/bjc.1947.35. PMC   2007538 . PMID   18906315.
  6. ↑ Preston, R. D.; Nicolai, E.; Reed, R.; Millard, A. (October 1948). "An Electron Microscope Study of Cellulose in the Wall of Valonia Ventricosa". Nature. 162 (4121): 665–667. Bibcode:1948Natur.162..665P. doi:10.1038/162665a0. PMID   18888170. S2CID   4007842.
  7. ↑ Meyer-Bertenrath, JG (1969). "150 Years of croton oil research". Experientia. 25 (1): 1–5. doi:10.1007/BF01903855. PMID   4885798. S2CID   26826980.
  8. ↑ E. Hecker (1967-01-31). "Phorbol esters from croton oil: Chemical nature and biological activities". Naturwissenschaften. 54 (11): 282–4. Bibcode:1967NW.....54..282H. doi:10.1007/BF00620887. PMID   5589922. S2CID   27775957.
  9. ↑ Ostlund, Mike. Find 'em, chase 'em, sink 'em, Globe Pequot, 2006, p. 88. ISBN   1-59228-862-6
  10. ↑ William B. Breuer (2002). Deceptions of World War II. Wiley & Sons. ISBN   9780471207474.
  11. ↑ The California Indians, a clever satire on the government's dealings with its Indian wards. From his Crusoe's island ... 1864, p. 284-308, Publication date 1919? John Ross Browne, 1821-1875 https://archive.org/details/californiaindians00browrich/page/8/mode/2up accessed 30 March 2023
  12. ↑ Jeffrey D. Schultz; Luchen Li (2005). "East of Eden". Critical Companion to John Steinbeck. Infobase Publishing. p. 68. ISBN   1438108508.
  13. ↑ Steinbeck, John (1986). "21:4". East of Eden . Penguin Books. ISBN   978-0-14-004997-8.
  14. ↑ Steinbeck, John (2006) [1936]. In Dubious Battle. Introduction and notes by Warren French. New York, New York: Penguin Books. p. 99. ISBN   0-14-30-3963-6. LCCN   92-10702.
  15. ↑ Bernard., Cornwell (1994). Copperhead (1st ed.). New York, NY: HarperCollinsPublishers. ISBN   0060177667. OCLC   28584240.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.