แคปเซอิซิน

แคปเซอิซิน
ชื่อ
	IUPAC name 8-Methyl-N-vanillyl-trans-6-nonenamide
	ชื่ออื่น (E) -N- (4-Hydroxy-3-methoxybenzyl) ; -8-methylnon-6-enamide,; trans-8-Methyl-N-vanillylnon; -6-enamide, (E) -Capsaicin,; CPS, C
เลขทะเบียน
เลขทะเบียน CAS	404-86-4;
3D model (JSmol)	รูปภาพแบบโต้ตอบ;
เคมสไปเดอร์	1265957;
ECHA InfoCard	100.006.337
EC Number	206-969-8;
ผับเคม CID	1548943;
CompTox Dashboard (EPA)	DTXSID9020241 ;
	SMILES CC (C)/C=C/CCCCC (NCC1=CC (OC) =C (O) C=C1) =O;
คุณสมบัติ
สูตรเคมี	C18H27NO3
มวลโมเลกุล	305.41 g/mol
จุดหลอมเหลว	62–65 °C
จุดเดือด	210–220 °C @ 0.01 Torr
ความอันตราย
	อาชีวอนามัยและความปลอดภัย (OHS/OSH):
อันตรายหลัก	Toxic (T)
NFPA 704 (fire diamond)	2 1 0
	หากมิได้ระบุเป็นอื่น ข้อมูลข้างต้นนี้คือข้อมูลสาร ณ ภาวะมาตรฐานที่ 25 °C, 100 kPa อ้างอิงกล่องข้อมูล

แคปเซอิซิน (capsaicin) เป็นสารที่ให้ความเผ็ดในพริก แคปเซอิซินมีสูตรโมเลกุล C₁₈H₂₇NO₃ ชื่อตามระบบ IUPAC คือ 8-methyl-N-vanillyl-6-nonenamide เป็นส่วนประกอบที่ใช้งานของพริกซึ่งเป็นพืชที่อยู่ในสกุล แคปซิคัม (genus Capsicum)

ประวัติ

สารประกอบ^[1] นี้ถูกสกัดได้เป็นครั้งแรก (แม้ว่าจะอยู่ในรูปแบบที่ไม่บริสุทธิ์) ในปี ค.ศ. 1816 โดยคริสเตียน ฟรีดริช บูคอลซ์ (Christian Friedrich Bucholz; 1770-1818)^[2] เขาเรียกมันว่า "capsicin" ตามชื่อสกุลของพริกที่มีชื่อว่า แคปซิคัม (genus Capsicum) จากที่มันได้ถูกสกัดออกมา จอห์น คลัฟ เทรช (John Clough Thresh; 1850-1932) คือผู้ที่แยกสารแคปเซอิซินในรูปแบบที่เกือบจะบริสุทธิ์ออกมาได้สำเร็จ^[3]^[4] และให้ชื่อว่า "แคปเซอิซิน" ในปี ค.ศ. 1876 ^[5]

อ้างอิง

เชิงอรรถ

↑
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.
↑
See:
- C. F. Bucholz (1816) "Chemische Untersuchung der trockenen reifen spanischen Pfeffers" [Chemical investigation of dry, ripe Spanish peppers], Almanach oder Taschenbuch für Scheidekünstler und Apotheker (Weimar) [Almanac or Pocket-book for Analysts (Chemists) and Apothecaries], vol. 37, pages 1-30. [Note: 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:
1. 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).
2. 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 [constituent, component], and of that of plants of the family Ranunculus), Annales de Chemie et de Physique, vol. 6, pages 122- 131.
3. 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.
4. 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.
↑
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. [Note: This article is summarized in: "Capsaicin, the active principle in Capsicum fruits," The Analyst, vol. 1, no. 8, pages 148-149, (1876).]. 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).
↑ J King, H Wickes Felter, J Uri Lloyd (1905) A King's American Dispensatory. Eclectic Medical Publications (ISBN 1888483024)

อ้างอิงทั่วไป

Dray A (1992). "Mechanism of action of capsaicin-like molecules on sensory neurons". Life Sci. 51 (23): 1759–65. doi:10.1016/0024-3205(92)90045-Q. PMID 1331641.
Garnanez RJ, McKee LH (2001) "Temporal effectiveness of sugar solutions on mouth burn by capsaicin" IFT Annual Meeting 2001 เก็บถาวร 2009-12-10 ที่ เวย์แบ็กแมชชีน
Henkin R (November 1991). "Cooling the burn from hot peppers". JAMA. 266 (19): 2766. doi:10.1001/jama.266.19.2766b. PMID 1942431.
Nasrawi CW, Pangborn RM (April 1990). "Temporal effectiveness of mouth-rinsing on capsaicin mouth-burn". Physiol. Behav. 47 (4): 617–23. doi:10.1016/0031-9384(90)90067-E. PMID 2385629.
Tewksbury JJ, Nabhan GP (July 2001). "Seed dispersal. Directed deterrence by capsaicin in chilies". Nature. 412 (6845): 403–4. doi:10.1038/35086653. PMID 11473305.
Kirifides ML, Kurnellas MP, Clark L, Bryant BP (February 2004). "Calcium responses of chicken trigeminal ganglion neurons to methyl anthranilate and capsaicin". J. Exp. Biol. 207 (Pt 5): 715–22. doi:10.1242/jeb.00809. PMID 14747403.{{cite journal}}: CS1 maint: multiple names: authors list (ลิงก์)
Tarantula Venom, Chili Peppers Have Same "Bite," Study Finds http://news.nationalgeographic.com/news/2006/11/061108-tarantula-venom.html
Minna M. Hamalainen, Alberto Subieta, Christopher Arpey, Timothy J. Brennan, "Differential Effect of Capsaicin Treatment on Pain-Related Behaviors After Plantar Incision," The Journal of Pain, 10,6 (2009), 637-645.

บทความเคมีนี้ยังเป็นโครง คุณสามารถช่วยวิกิพีเดียได้โดยการเพิ่มเติมข้อมูล

[1] 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.

[2] 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.

[3] 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.

[2] See:
C. F. Bucholz (1816) "Chemische Untersuchung der trockenen reifen spanischen Pfeffers" [Chemical investigation of dry, ripe Spanish peppers], Almanach oder Taschenbuch für Scheidekünstler und Apotheker (Weimar) [Almanac or Pocket-book for Analysts (Chemists) and Apothecaries], vol. 37, pages 1-30. [Note: 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 [constituent, 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.

[5] C. F. Bucholz (1816) "Chemische Untersuchung der trockenen reifen spanischen Pfeffers" [Chemical investigation of dry, ripe Spanish peppers], Almanach oder Taschenbuch für Scheidekünstler und Apotheker (Weimar) [Almanac or Pocket-book for Analysts (Chemists) and Apothecaries], vol. 37, pages 1-30. [Note: Christian Friedrich Bucholz's surname has been variously spelled as "Bucholz", "Bucholtz", or "Buchholz".]

[6] 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.

[7] 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.

[8] Biographical information about C. F. Bucholz is also available (in German) on-line at: Allgemeine Deutsche Biographie.

[9] Some other early investigators who also extracted the active component of peppers:

[10] 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).

[11] 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 [constituent, component], and of that of plants of the family Ranunculus), Annales de Chemie et de Physique, vol. 6, pages 122- 131.

[12] 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.

[13] 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.

[3] 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. [Note: This article is summarized in: "Capsaicin, the active principle in Capsicum fruits," The Analyst, vol. 1, no. 8, pages 148-149, (1876).]. 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.

[15] J. C. Thresh (1876) "Isolation of capsaicin," The Pharmaceutical Journal and Transactions, 3rd series, vol. 6, pages 941-947;

[16] 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. [Note: This article is summarized in: "Capsaicin, the active principle in Capsicum fruits," The Analyst, vol. 1, no. 8, pages 148-149, (1876).]. In The Pharmaceutical Journal and Transactions, volume 7, see also pages 259ff and 473 ff and in vol. 8, see pages 187ff;

[17] Year Book of Pharmacy… (1876), pages 250 and 543;

[18] J. C. Thresh (1877) "Note on Capsaicin," Year Book of Pharmacy…, pages 24-25;

[19] J. C. Thresh (1877) "Report on the active principle of Cayenne pepper," Year Book of Pharmacy..., pages 485-488.

[4] 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).

[5] J King, H Wickes Felter, J Uri Lloyd (1905) A King's American Dispensatory. Eclectic Medical Publications (ISBN 1888483024)

[22] 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).

[23] 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 [constituent, component], and of that of plants of the family Ranunculus), Annales de Chemie et de Physique, vol. 6, pages 122- 131.

[24] 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.

[25] 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.

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