# Cnicin

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> Markdown URL: https://mediated.wiki/source/Cnicin.md
> Source: https://en.wikipedia.org/wiki/Cnicin
> Source revision: 1305176021
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{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 =
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| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI =
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = 
}}
|Section2={{Chembox Properties
| C=20 | H=26 | O=7
| Appearance =
| Density = 
| MeltingPt = 
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| pKa = 
| pKb = }}
|Section7={{Chembox Hazards
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| NFPA-R = 
| NFPA-S =
| FlashPt = 
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| ExploLimits = 
| PEL = }}
}}

'''Cnicin''' is a [sesquiterpene lactone](/source/sesquiterpene_lactone), esterified with a substituted [acrylic acid](/source/acrylic_acid), and belonging to the [germacranolide](/source/germacranolide) class of natural products. It is mainly found in [Cnicus](/source/Cnicus) (''Centaurea--formerly Cnicus--benedictus'' L. (''[Asteraceae](/source/Asteraceae)'')), and is present in [spotted knapweed](/source/Centaurea_maculosa) 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

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Adapted from the Wikipedia article [Cnicin](https://en.wikipedia.org/wiki/Cnicin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Cnicin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.