Cnicin

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.

Cnicin
Names
Preferred IUPAC name
(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
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.042.004
UNII
  • InChI=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 checkY
    Key: ZTDFZLVUIVPZDU-QGNHJMHWSA-N checkY
  • 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
    Key: ZTDFZLVUIVPZDU-QGNHJMHWBP
  • 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
Properties
C20H26O7
Molar mass 378.421 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Olson, B. E.; Kelsey, R. G. (1997). "Effect of Centaurea maculosa on sheep rumen microbial activity and mass in vitro". J. Chem. Ecol. 23 (4): 1131–1144. doi:10.1023/B:JOEC.0000006391.88098.12. S2CID 12499959.
  2. 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
  • Media related to Cnicin at Wikimedia Commons
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