Kapsaicin

IUPAC ime


8-Metil-N-vanilil-trans-6-nonenamid

Drugi nazivi

(E)-N-(4-Hidroksi-3-metoksibenzil)
-8-metilnon-6-enamid,
trans-8-Metil-N-vanililnon
-6-enamid, (E)-Kapsaicin,
CPS, C

Identifikacija

CAS registarski broj

404-86-4 ^Y

PubChem^[1]^[2]

1548943

ChemSpider^[3]

1265957

EINECS broj

206-969-8

MeSH

Capsaicin

ATC code

M02AB01

Jmol-3D slike

Slika 1

SMILES

O=C(NCc1cc(OC)c(O)cc1)CCCC/C=C/C(C)C

InChI

InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+^Y
Kod: YKPUWZUDDOIDPM-SOFGYWHQSA-N^Y

InChI=1/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13- 15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5, 7,9,13H2,1-3H3,(H,19,21)/b8-6+
Kod: YKPUWZUDDOIDPM-SOFGYWHQBQ

Svojstva

Molekulska formula

C₁₈H₂₇NO₃

Molarna masa

305,41 g/mol

Tačka topljenja

62–65 °C

Tačka ključanja

210–220 °C @ 0.01 Torr

Opasnost

Podaci o bezbednosti prilikom rukovanja (MSDS)

[1]

Opasnost u toku rada

Toxic (T)

NFPA 704

R-oznake

R24/25

S-oznake

S26, S36/37/39, S45

Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala

Infobox references

Kapsaicin (8-metil-N-vanilil-6-monenamid, (CH₃)₂CHCH=CH(CH₂)₄CONHCH₂C₆H₃-4-(OH)-3-(OCH₃)) je aktivna komponenta ljutih papričica, biljaka koje pripadaju rodu Capsicum.^[4] Kapsaicin deluje kao iritant na sisare, uključujući ljude, kod kojih izaziva osećaj pečenja na bilo kom tkivu sa kojim stupi u kontakt. Kapsaicin i nekoliko srodnih jedinjenja se nazivaju kapsaicinoidima a proizvode ih ljute papričice kao sekundarni metabolit, koji odbija određene biljojede i gljive^[5]. Čisti kapsaicin je hidrofobno, bezbojno, bezmirisno kristalasto do voskasto jedinjenje.^[6]^[7]^[8]

Istorija

Molekul je u kristalnom obliku prvi izolovao P. A. Buholc, a 30 godina kasnije i L. T. Treš, koji mu je dao ime kapsaicin.^[9] 1878, mađarski doktor Endre Hegjes ga je izolovao i dokazao da ne samo da izaziva osećaj pečenja u dodiru sa mukoznom membranom, već i povećano izlučivanje želudačnog soka. Strukturu kapsaicina je delimično razjasnio E. K. Nelson 1919. godine.^[10]

Kapsaicin su prvi izolovali E. Spat i F. S. Darling 1930. Slične supstance su iz ljutih papričica 1961. izolovali japanski hemičari S. Kosuge i J. Inagaki, koji su im dali ime kapsaicinoidi.^[11] ^[12]

Izvori

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Ruiz RS, Rhem MN, Prager TC (January 1989). „Effects of carbachol and acetylcholine on intraocular pressure after cataract extraction”. Am. J. Ophthalmol. 107 (1): 7–10. PMID 2912119.
↑ Od čega su ljute papričice toliko ljute? Razgovor nacije, 15. avgust 2008.
↑ Lide David R., ur. (2006). CRC Handbook of Chemistry and Physics (87th izd.). Boca Raton, FL: CRC Press. 0-8493-0487-3.
↑ Susan Budavari, ur. (2001). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (13th izd.). Merck Publishing. ISBN 0-911910-13-1.
↑ Keith Parker; Laurence Brunton; Goodman, Louis Sanford; Lazo, John S.; Gilman, Alfred (2006). „Chapter 62. Dermatological pharmacology; Miscellaneous agents”. Goodman & Gilman's The Pharmacological Basis of Therapeutics (11 izd.). New York: McGraw-Hill. ISBN 0-07-142280-3.
↑ J. King, H. Wickes Felter, J. Uri Lloyd (1905). A King's American Dispensatory. Eclectic Medical Publications. ISBN 1-888483-02-4.
↑ E. K. Nelson (1919). „The constitution of capsaicin, the pungent principle of capsicum”. J. Am. Chem. Soc. 41: 1115-1121. DOI:10.1021/ja02228a011.
↑ 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

Opšta literatura

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 Arhivirano 2009-12-10 na Wayback Machine-u
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.
Tarantula Venom, Chili Peppers Have Same "Bite," Study Finds http://news.nationalgeographic.com/news/2006/11/061108-tarantula-venom.html
J. King, H. Wickes Felter, J. Uri Lloyd (1905). A King's American Dispensatory. Eclectic Medical Publications. ISBN 1-888483-02-4.