{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 399725332 | ImageFile = cnicin.svg | PIN = (3a''R'',4''S'',6''E'',10''Z'',11a''R'')-10-(Hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2,3,3a,4,5,8,9,11a-octahydrocyclodeca[''b'']furan-4-yl (3''R'')-3,4-dihydroxy-2-methylidenebutanoate | OtherNames = |Section1={{Chembox Identifiers | Abbreviations = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4444781 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 1257707 | InChIKey = ZTDFZLVUIVPZDU-QGNHJMHWBP | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C20H26O7/c1-11-5-4-6-14(9-21)8-17-18(13(3)20(25)27-17)16(7-11)26-19(24)12(2)15(23)10-22/h5,8,15-18,21-23H,2-4,6-7,9-10H2,1H3/b11-5+,14-8-/t15-,16-,17+,18+/m0/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = ZTDFZLVUIVPZDU-QGNHJMHWSA-N | CASNo_Ref = {{cascite|correct|??}} | CASNo = 24394-09-0 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = C998MWY30L | EINECS = | PubChem = 5281435 | SMILES = O=C/1O[C@@H]2/C=C(/CC/C=C(/C[C@H](OC(=O)\C(=C)[C@@H](O)CO)[C@H]2C\1=C)C)CO | InChI = 1/C20H26O7/c1-11-5-4-6-14(9-21)8-17-18(13(3)20(25)27-17)16(7-11)26-19(24)12(2)15(23)10-22/h5,8,15-18,21-23H,2-4,6-7,9-10H2,1H3/b11-5+,14-8-/t15-,16-,17+,18+/m0/s1 | RTECS = | MeSHName = | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = }} |Section2={{Chembox Properties | C=20 | H=26 | O=7 | Appearance = | Density = | MeltingPt = | MeltingPt_notes = | BoilingPt = | BoilingPt_notes = | Solubility = | SolubleOther = | Solvent = | pKa = | pKb = }} |Section7={{Chembox Hazards | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | FlashPt = | AutoignitionPt = | ExploLimits = | PEL = }} }}
'''Cnicin''' is a sesquiterpene lactone, esterified with a substituted acrylic acid, and belonging to the germacranolide class of natural products. It is mainly found in Cnicus (''Centaurea--formerly Cnicus--benedictus'' L. (''Asteraceae'')), and is present in spotted knapweed plants, where highest and lowest concentrations are found in the leaves (0.86-3.86% cnicin) and stems respectively.<ref>{{cite journal |author1=Olson, B. E. |author2=Kelsey, R. G. | year = 1997 | title = Effect of Centaurea maculosa on sheep rumen microbial activity and mass in vitro | journal = J. Chem. Ecol. | volume = 23 | pages = 1131–1144 | doi = 10.1023/B:JOEC.0000006391.88098.12 | issue = 4|s2cid=12499959 }}</ref><ref>[http://etd.lib.montana.edu/etd/2006/cheeseman/CheesemanM0506.pdf Providing Supplement, with or without PEG, to reduce the effects of cnicin and enhance grazing of spotted knapweed by sheep and cattle], Masters Thesis, M Cheeseman, Montana State University</ref> Cnicin is used as a bitter tonic and the bitterness value is approximately 1,500.
==References== {{Reflist}}
==External links== *{{Commons category-inline}}
Category:Sesquiterpene lactones Category:Triols Category:Carboxylate esters Category:Oxygen heterocycles Category:Primary alcohols Category:Vinylidene compounds