Croton oil

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Croton oil, croton oil
Raw material plant (noun)

Croton tiglium L.

origin

Seeds

colour

clear, amber to brownish yellow

ingredients
Oleic acid 37-56%
Linoleic acid 19-29%
Palmitic acid <1%
Lauric acid <0.5%
Myristic acid up to 7.5%
More fatty acids 1.5% arachidic acid , 0.5% stearic acid , tiglic acid , caproic acid in traces
Other ingredients 1% formic acid , crotonic acid , 1% acetic acid , isobutyric acid , isovaleric acid
properties
density 0.94-0.95 kg / l (at 15 ° C)
Melting point −16 ° C
Iodine number approx. 102-110
Saponification number 200-215
Manufacturing and Consumption
use Pharmacy, medicine

Croton oil , also known as garnet oil (Oleum Crotonis, Oleum Tiglii), is made from the seeds of the croton oil tree ( Croton tiglium ), a Southeast Asian tree or bush from the milkweed family . Croton oil originally comes from India and the Malay Archipelago and is also grown there. It has a strong irritating effect on the skin and mucous membranes and is classified as a questionable prescription drug due to its tumor-increasing effect.

Another type of croton from which fatty oil can be extracted is Croton penduliflorus . But the composition is different.

Extraction and properties

Croton oil is extracted from the seeds of the Krotonölbaums Croton tiglium won

Croton oil is obtained from the peeled seeds of the croton oil tree by cold pressing or by pressing the ripe and lightly roasted seeds with a slight supply of heat. It is also pressed from unpeeled seeds. The seeds contain about 30-45% unpeeled, or about 45-60% croton oil when peeled and about 18-20% protein (contains crotin I and II). The somewhat thick and semi-solid oil is one of the heaviest vegetable oils, its color is clear and amber to brown-yellow. The weak smell is “peculiar” and “unpleasant”, the taste is initially mild, then sharp in the finish and persistently scratchy and painfully burning.

General chemical structure of oils, such as croton oil. R 1 , R 2 and R 3 therein are alkyl radicals (56%) or alkenyl radicals (44%) with a mostly uneven number of carbon atoms. Like other oils, croton oil is a mixture of tri esters of glycerine .

The melting point of croton oil is around −16 ° C, which is why it is liquid at room temperature. The triglycerides in croton oil have a particularly high proportion of oleic acid . It also contains other triglycerides that are derived from various fatty acids. In addition, other partly volatile organic acids such as formic acid and the like are found in croton oil. a. as well as several phorbol esters, including the tumor-promoting phorbol-12-myristate-13-acetate (PMA; also 12- O- tetradecanoylphorbol-13-acetate (TPA)).

Toxicology and other effects

The croton oil works in different ways due to its composition. In particular, the tumor-promoting effects of phorbol-12-myristate-13-acetate (PMA) and other diterpene esters in croton resin have been confirmed in animal experiments. Tumor promoters are substances that, without being carcinogenic themselves , increase the incidence of cancer after exposure to carcinogenic (initiating) substances.

The inflammatory effect of croton oil on skin cells has been confirmed in animal experiments. Even the application of a 0.25% solution to the ears of laboratory mice leads to the formation of edema with epidermal hyperplasia and a concentration of granulocytes in the epidermis. The effect could be increased and was strongest with a single use of 4% solution. Edema formation reached a maximum after 6 to 7 hours and then decreased again within 30 hours.

In another study, the direct damaging effect of croton oil on human intestinal mucous membrane cells could be demonstrated. A comparatively high dose of 80 mg / l results in retarded cell growth and cell death, while low doses of 4 mg / l have no measurable effect. Administration over a longer period of time with increasing dose can increase cell proliferation (multiplication of cells) and the content of heteroploid genomes as well as induce conversion into malignant cells. The release of cyclooxygenase-2 (COX-2) was significantly reduced and the expression of the gene for COX-2 was significantly increased, and the expression of other genes was also changed.

use

Medicine and medicine

Recipes containing croton oil are - also because of the possible cancer risk - classified as questionable and may no longer be marketed as medicinal products. Croton oil is also prohibited for use in cosmetics.

In the past, croton oil was used as a strong laxative (drastic). It is one of the most powerful laxatives together with physic nut and castor oil and was therefore only used in extremely urgent cases. The maximum single dose is given as 0.05 grams, the maximum daily dose with 0.15 grams and the lethal dose with 4–20 gtt (guttae, drops) of oil. When applied to the skin, even small amounts are sufficient to trigger severe local inflammation with pustules and a risk of infection. As part of the “croton oil test”, the oil is used to trigger skin edema in order to determine the effectiveness of anti-inflammatory substances. In plastic surgery it is used in an emulsion with phenol to peel the skin.

Croton oil (diluted with olive oil) has long been used in construction therapy as a skin irritant for derivation ( revulsion ) in pleurisy , pleural effusion , neuralgia and rheumatism .

history

Croton tiglium . C. Acosta 1578
Croton tiglium . Hull 1743

Croton tiglium is one of the five poisons listed in the mythical Chinese herbal book Shennong ben cao jing . Old Chinese pharmacopoeias already know the poisonous and laxative croton seeds as "Pa-tou" 巴豆. In Arabic medicine they were used at the latest since the 13th century.

The first mention of croton seeds in Europe is attributed to Cristóbal Acosta (1578). He called them "Pinones de Maluco." In his Pinax theatri botanici (1623) Caspar Bauhin called the drug "Pinus Indica nucleo purgante" and "Pinei nuclei Malucani". The Europeans only got more detailed knowledge of the plant itself through Rheede (1678) and Rumpf (1743). According to Rumpf, Indian surgeons used the oil with wine as a laxative to stimulate stool excretion and as a urine-inducing agent .

After the therapeutic use of croton seed oil in Holland and England had serious side effects, the agent was initially banned from the drug lists. It was not until the 1820s that croton oil became officinell again . William Eugène Edward Conwell (1825), Henry Rutledge Frost (1843) a. a. made it better known and promoted its use as a Drasticum (i.e., a powerful laxative ) for persistent stool constipation and tapeworm infestation, and as a urine-enhancing agent for ascites . The standard dose given for internal intake was half to one full to two drops of the oil. After the oil has been rubbed into the skin of the abdomen, it should be absorbed and thus exert its effect on the increased excretion of faeces and urine, a procedure that has been used in children in particular. Forthergill's facial pain was treated in England by rubbing a drop or two of the oil onto the tongue (Gerson / Julius 1822). Externally diluted with substances other than rubbing in, the oil served as an irritant for the skin and as a drainage agent ( derivation or revulsion ) in chronic inflammation of the airways, chronic rheumatic and gouty diseases, inflammation of the auditory organ, the eyes etc. (Ainslie 1813, Frost 1843, Clarus 1852).

swell

Individual evidence

  1. ↑ a b c d e f g h i j k S. Krist, G. Buchbauer and C. Klausberger: Lexicon of vegetable fats and oils. Springer Verlag, Vienna 2008, pp. 221-224, ISBN 978-3-211-75606-5 .
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  5. ^ A b Jan CJ Bart, N. Palmeri, Stefano Cavallaro: Biodiesel science and technology. Woodhead, 2010, ISBN 978-1-84569-591-0 , p. 192.
  6. ↑ Ojo, Ayomipo Martins, Amoo, Isiaka Adekunle u. a .: Physicochemical Properties, Fatty Acid Composition and Antimicrobial Potential of Turk's Cap (Croton penduliflorus) Seed Oil. In: CSIJ. 20 (4), 2017, pp. 1–7, Article no.CSIJ.3583, doi: 10.9734 / CSJI / 2017/35835 (PDF; 1 MB).
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  11. ↑ X. Wang, M. Lan, HP Wu et al. a .: Direct effect of croton oil on intestinal epithelial cells and colonic smooth muscle cells. In: World Journal of Gastroenterology. 8 (1), 2002; Pp. 103-7, PMID 11833082 .
  12. ↑ Drugs Commission of the German Pharmacists: Questionable prescription drugs . Status: February 2011 (PDF; 423 kB) Retrieved on November 29, 2011.
  13. ↑ Prussian Pharmacopoeia . Fifth edition (1827). Translation of the Latin original. CF Plahn, Berlin 1829, p. 276: Croton oil (digitized version)
  14. ↑ George Arthur Stuart. Chinese Materia Medica. Vegetable Kindom. Shanghai 1911, pp. 132-133 (digitized version )
  15. ^ Whitelaw Ainslie (1767-1837). Materia indica or, some account of those articles which are employed by the Hindoos, and other eastern nations, in their medicine, arts, and agricutlure comprising also formulas, with practical observations, names of diseases in various eastern languages, and a copious list of oriental books… Longman, Rees, Orme, Brown and Green, London 1826, Volume I, pp. 101–108 Croton tiglium (digitized) pp. 596–599 (digitized) Volume II, p. 398 Croton plicatum… as a decoction with something Mustard against leprosy (digitized version)
  16. ^ Joseph Sontheimer (translator). Ibn al-Baitar . Large compilation of the powers of the well-known simple healing and foodstuffs (Kitāb al-jāmiʿ li-mufradāt al-adwiya wa al-aghdhiya) . Hallberg, Stuttgart 1842, Volume I, pp. 427-429 (digitized version )
  17. ↑ Cristóbal Acosta : Tractado de las drogas, y medicinas de las Indias orientales , Burgos 1578, pp. 313-315: Pinones de Maluco (digitized version )
  18. ↑ Caspar Bauhin . Pinax theatri botanici. Basel 1623, p. 492: XI. Pinus Indica nucleo purgante ... (digitized version )
  19. ↑ Hendrik Adriaan van Rheede dead Draakenstein . Hortus Indicus Malabaricus: continens regni Malabarici apud Indos cereberrimi onmis generis plantas rariores, Latinas, Malabaricis, Arabicis, Brachmanum charactareibus hominibusque expressas… / adornatus per Henricum van Rheede, van Draakenstein,… et Johannem Casearium…; notis adauxit, & commentariis illustravit Arnoldus Syen… Amsterdam 1678–1703, Volume II, Figure 33: Cadel-Avanacu (digitized version ) ( A review (1839) of the references to the Hortus Malabaricus , p. 7 (digitized version ) )
  20. ↑ Georg Eberhard Rumpf . Herbarium Amboinense Volume 4 Amsterdam 1743 (Book 6, Chapter 48) P. 100 (digitized version)
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  26. ↑ With reference to: James Johnson (1777-1845) (Editor). The Medico-Surgical Review and Journal of Medical Science . Volume II for 1821-2, London, September 1821, pp. 428–429: Oil of Croton (digitized version )
  27. ^ William Eugène Edward Conwell (1785–1836): Recherches sur les propriétés médicinales et l'emploi en médicine de l'huile de Croton tiglium… Thèse, Paris 1824 (digitized)
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  32. ^ Henry Rutledge Frost (1790-1866): Elements of the materia medica and therapeutics . Burges & James, Charleston 1843, Volume I, pp. 127–129 (digitized version )
  33. ↑ Julius Clarus : Handbook of the special medicament theory after physiological-chemical basics for the medical practice . Otto Wigand, Leipzig 1852, pp. 429–432 (digitized version )
  34. ↑ Georg Friedrich Krich: Experimenta quaedam pharmacologica de oleis ricini, crotonis et euphorbiae lathyridis . Dorpat 1857 (digitized version)
  35. ↑ Joret: De l'huile de croton-tiglium, de ses propriétés et de ses usages . In: Bulletin général de thérapeutique médicale et chirurgicale . 1861, No 61, pp. 385–391 (digitized version ) and p. 441–450 (digitized version )
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  40. ↑ G. Pabst (editor): Köhler's medicinal plants in lifelike illustrations with brief explanatory texts . Eugen Köhler, Gera 1887, Volume II, No 182 (text digitized) , (illustration digitized)
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