Cnicin

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title: "Cnicin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["sesquiterpene-lactones", "triols", "carboxylate-esters", "oxygen-heterocycles", "primary-alcohols", "vinylidene-compounds"] topic_path: "general/sesquiterpene-lactones" source: "https://en.wikipedia.org/wiki/Cnicin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 399725332 | ImageFile = cnicin.svg | PIN = (3aR,4S,6E,10Z,11aR)-10-(Hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2,3,3a,4,5,8,9,11a-octahydrocyclodeca[b]furan-4-yl (3R)-3,4-dihydroxy-2-methylidenebutanoate | OtherNames = |Section1={{Chembox Identifiers | Abbreviations = | ChemSpiderID_Ref = | ChemSpiderID = 4444781 | ChEMBL_Ref = | ChEMBL = 1257707 | InChIKey = ZTDFZLVUIVPZDU-QGNHJMHWBP | StdInChI_Ref = | 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 = | StdInChIKey = ZTDFZLVUIVPZDU-QGNHJMHWSA-N | CASNo_Ref = | CASNo = 24394-09-0 | UNII_Ref = | UNII = C998MWY30L | EINECS = | PubChem = 5281435 | SMILES = O=C/1O[C@@H]2/C=C(/CC/C=C(/CC@H[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 = | ChEBI = | KEGG_Ref = | 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. Cnicin is used as a bitter tonic and the bitterness value is approximately 1,500.

References

References

  1. (1997). "Effect of Centaurea maculosa on sheep rumen microbial activity and mass in vitro". J. Chem. Ecol..
  2. [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

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sesquiterpene-lactonestriolscarboxylate-estersoxygen-heterocyclesprimary-alcoholsvinylidene-compounds