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Cnicin



Cnicin
IUPAC name [(1R,2S,4E,8Z,10S)-8-(hydroxymethyl) -4-methyl-13-methylidene-12-oxo-11 -oxabicyclo[8.3.0]trideca-4,8-dien-2-yl] (3S)-3,4-dihydroxy-2-methylidene-butanoate
Identifiers
CAS number 24394-09-0
PubChem 5281435
SMILES OC/C1=C\[C@@H](OC(C2=C)=O)[C@H]2[C@@H] (OC(C([C@@H](O)CO)=C)=O)C\C(C)=C\CC1
Properties
Molecular formula C20H26O7
Molar mass 378.17 g/mol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

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 (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.[1][2] Cnicin is used as a bitter tonic and the bitterness value is approximately 1,500.


References

  1. ^ OLSON, B. E. AND KELSEY, R. G. 1997. Effect of Centaurea maculosa on sheep rumen microbial activity and mass in vitro. J. Chem. Ecol. 23:1131-1144.
  2. ^ CHEESEMAN, M. 2006. Providing Supplement, with or without PEG,to reduce the effects of cnicin and enhance grazing of spotted knapweed by sheep and cattle.[1]
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Cnicin". A list of authors is available in Wikipedia.
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