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capsaicin : ウィキペディア英語版
capsaicin

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Capsaicin ( (INN); 8-methyl-''N''-vanillyl-6-nonenamide) is an active component of chili peppers, which are plants belonging to the genus ''Capsicum''. It is an irritant for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related compounds are called capsaicinoids and are produced as secondary metabolites by chili peppers, probably as deterrents against certain mammals and fungi.〔(What Made Chili Peppers So Spicy? ) Talk of the Nation, 15 August 2008.〕 Pure capsaicin is a volatile, hydrophobic, colorless, odorless, crystalline to waxy compound.
==History==
The compound was first extracted in impure form in 1816 by Christian Friedrich Bucholz (1770–1818).〔History of early research on capsaicin:
* Harvey W. Felter and John U. Lloyd, ''King's American Dispensatory'' (Cincinnati, Ohio: Ohio Valley Co., 1898), vol. 1, page 435. Available on-line at: (Henriette's Herbal ).
* Andrew G. Du Mez, "A century of the United States pharmocopoeia 1820-1920. I. The galenical oleoresins" (Ph.D. dissertation, University of Wisconsin, 1917), pages 111-132. Available on-line at: ( Archive.org ).
* C. F. Bucholz (1816) "Chemische Untersuchung der trockenen reifen spanischen Pfeffers" (investigation of dry, ripe Spanish peppers ), ''Almanach oder Taschenbuch für Scheidekünstler und Apotheker'' (Weimar) (or Pocket-book for Analysts (Chemists) and Apothecaries ), vol. 37, pages 1-30. ( Christian Friedrich Bucholz's surname has been variously spelled as "Bucholz", "Bucholtz", or "Buchholz". )
* The results of Bucholz's and Braconnot's analyses of ''Capsicum annuum'' appear in: Jonathan Pereira, ''The Elements of Materia Medica and Therapeutics'', 3rd U.S. ed. (Philadelphia, Pennsylvania: Blanchard and Lea, 1854), vol. 2, (page 506 ).
* Biographical information about Christian Friedrich Bucholz is available in: Hugh J. Rose, Henry J. Rose, and Thomas Wright, ed.s, ''A New General Biographical Dictionary'' (London, England: 1857), vol. 5, (page 186 ).
* Biographical information about C. F. Bucholz is also available (in German) on-line at: (Allgemeine Deutsche Biographie ).
* Some other early investigators who also extracted the active component of peppers:
:# Benjamin Maurach (1816) "Pharmaceutisch-chemische Untersuchung des spanischen Pfeffers" (Pharmaceutical-chemical investigation of Spanish peppers), ''Berlinisches Jahrbuch für die Pharmacie'', vol. 17, pages 63-73. Abstracts of Maurach's paper appear in: (i) ''Repertorium für die Pharmacie'', vol. 6, (page 117-119 ) (1819); (ii) ''Allgemeine Literatur-Zeitung'', vol. 4, no. 18, (page 146 ) (Feb. 1821); (iii) "Spanischer oder indischer Pfeffer", ''System der Materia medica'' ... , vol. 6, (pages 381-386 ) (1821) (this reference also contains an abstract of Bucholz's analysis of peppers).
:# French chemist Henri Braconnot (1817) "Examen chemique du Piment, de son principe âcre, et de celui des plantes de la famille des renonculacées" (Chemical investigation of the chili pepper, of its pungent principle (component ), and of that of plants of the family ''Ranunculus''), ''Annales de Chemie et de Physique'', vol. 6, (pages 122- 131 ).
:# Danish geologist Johann Georg Forchhammer in: Hans C. Oersted (1820) "Sur la découverte de deux nouveaux alcalis végétaux" (On the discovery of two new plant alkalis), ''Journal de physique, de chemie, d'histoire naturelle et des arts'', vol. 90, (pages 173-174 ).
:# German apothecary Ernst Witting (1822) "Considerations sur les bases vegetales en general, sous le point de vue pharmaceutique et descriptif de deux substances, la capsicine et la nicotianine" (Thoughts on the plant bases in general from a pharmaceutical viewpoint, and description of two substances, capsicin and nicotine), ''Beiträge für die pharmaceutische und analytische Chemie'', vol. 3, pages 43ff.〕 He called it "capsicin", after the genus ''Capsicum'' from which it was extracted. John Clough Thresh (1850–1932), who had isolated capsaicin in almost pure form,〔In a series of articles, J. C. Thresh obtained capsaicin in almost pure form:
* J. C. Thresh (1876) "Isolation of capsaicin," ''The Pharmaceutical Journal and Transactions'', 3rd series, vol. 6, pages 941-947;
* J. C. Thresh (8 July 1876) "Capsaicin, the active principle in Capsicum fruits," ''The Pharmaceutical Journal and Transactions'', 3rd series, vol. 7, no. 315, pages 21 ff. . In ''The Pharmaceutical Journal and Transactions'', volume 7, see also pages 259ff and 473 ff and in vol. 8, see pages 187ff;
* ''Year Book of Pharmacy…'' (1876), pages 250 and 543;
* J. C. Thresh (1877) "Note on Capsaicin," (''Year Book of Pharmacy…'' ), pages 24-25;
* J. C. Thresh (1877) "Report on the active principle of Cayenne pepper," ''Year Book of Pharmacy...'', pages 485-488.〕〔Obituary notice of J. C. Thresh: ( "John Clough Thresh, M.D., D. Sc., and D.P.H.," ) ''The British Medical Journal'', vol. 1, no. 3726, pages 1057-1058 (4 June 1932).〕 gave it the name "capsaicin" in 1876.〔J King, H Wickes Felter, J Uri Lloyd (1905) A King's American Dispensatory. Eclectic Medical Publications (ISBN 1888483024)〕 Karl Micko isolated capsaicin in its pure form in 1898.〔Karl Micko (1898) ("Zur Kenntniss des Capsaïcins" ) (On our knowledge of capsaicin), ''Zeitschrift für Untersuchung der Nahrungs- und Genussmittel'' (Journal for the Investigation of Necessities and Luxuries), vol. 1, pages 818-829. See also: Karl Micko (1899) ("Über den wirksamen Bestandtheil des Cayennespfeffers" ) (On the active component of Cayenne pepper), ''Zeitschrift für Untersuchung der Nahrungs- und Genussmittel'', vol. 2, pages 411-412.〕 Capsaicin's chemical composition was first determined by E. K. Nelson in 1919, who also partially elucidated capsaicin's chemical structure.〔E. K. Nelson. ("The constitution of capsaicin, the pungent principle of capsicum". ) ''J. Am. Chem. Soc.'' 1919; 41: 1115–1121. doi 10.1021/ja02228a011〕 Capsaicin was first synthesized in 1930 by E. Spath and S. F. Darling.〔Ernst Späth, Stephen F. Darling. "Synthese des Capsaicins." ''Chem. Ber.'' 1930; 63B: 737–743.〕 In 1961, similar substances were isolated from chili peppers by the Japanese chemists S. Kosuge and Y. Inagaki, who named them capsaicinoids.〔S Kosuge, Y Inagaki, H Okumura (1961). Studies on the pungent principles of red pepper. Part VIII. On the chemical constitutions of the pungent principles. Nippon Nogei Kagaku Kaishi (J. Agric. Chem. Soc.), 35, 923–927; (en) ''Chem. Abstr.'' 1964, 60, 9827g.〕〔(ja) S Kosuge, Y Inagaki (1962) Studies on the pungent principles of red pepper. Part XI. Determination and contents of the two pungent principles. Nippon Nogei Kagaku Kaishi ''J. Agric. Chem. Soc.'', 36, pp. 251〕
In 1873 German pharmacologist Rudolf Buchheim〔Rudolf Buchheim (1873) "Über die 'scharfen' Stoffe" (On the "hot" substance), ''Archiv der Heilkunde'' (Archive of Medicine), vol. 14, pages 1ff. See also: R. Buchheim (1872) "Fructus Capsici," ''Vierteljahresschrift fur praktische Pharmazie'' (Quarterly Journal for Practical Pharmacy), vol. 4, pages 507ff.; reprinted (in English) in: ''Proceedings of the American Pharmaceutical Association'', vol. 22, pages 106ff (1873).〕 (1820–1879) and in 1878 the Hungarian doctor Endre Hőgyes〔Endre Hőgyes, "Adatok a paprika (Capsicum annuum) élettani hatásához" (on the physiological effects of the pepper (Capsicum annuum) ), ''Orvos-természettudumányi társulatot Értesítője'' (of the Medical Science Association ) (1877); reprinted in: ''Orvosi Hetilap'' (Journal ) (1878), 10 pages. Published in German as: "Beitrage zur physiologischen Wirkung der Bestandtheile des ''Capiscum annuum'' (Spanischer Pfeffer)" (on the physiological effects of components of ''Capsicum annuum'' (Spanish pepper) ), ''Archiv für Experimentelle Pathologie und Pharmakologie'', vol. 9, pages 117-130 (1878). See (springerlink.com )〕 stated that "capsicol" (partially purified capsaicin〔F.A. Flückiger, ''Pharmakognosie des Pflanzenreiches'' ( Berlin, Germany: Gaertner's Verlagsbuchhandlung, 1891).〕) caused the burning feeling when in contact with mucous membranes and increased secretion of gastric acid.

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