Cnicin

Last updated
Cnicin
Cnicin.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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 Yes check.svgY
    Key: ZTDFZLVUIVPZDU-QGNHJMHWSA-N Yes check.svgY
  • 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Related Research Articles

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<i>Centaurea diffusa</i> Species of flowering plant

Centaurea diffusa, also known as diffuse knapweed, white knapweed or tumble knapweed, is a member of the genus Centaurea in the family Asteraceae. This species is common throughout western North America but is not actually native to the North American continent, but to the eastern Mediterranean.

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<i>Agapeta zoegana</i> Species of moth

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<i>Bangasternus fausti</i> Species of beetle

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Chaetorellia acrolophi is a species of tephritid fruit fly known as the knapweed peacock fly. It is used as an agent of biological pest control against noxious knapweeds, especially spotted knapweed.

<i>Cyphocleonus achates</i> Species of beetle

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<i>Larinus obtusus</i> Species of beetle

Larinus obtusus is a species of true weevil known as the blunt knapweed flower weevil. It is used as an agent of biological pest control against noxious knapweeds, especially spotted knapweed.

<i>Metzneria paucipunctella</i> Species of moth

Metzneria paucipunctella is a species of moth known as the spotted knapweed seed head moth. It is used as an agent of biological pest control against noxious knapweeds, particularly spotted knapweed.

<i>Urophora affinis</i> Species of fly

Urophora affinis is a species of tephritid or fruit flies in the genus Urophora of the family Tephritidae. It has been released in the United States and Canada as a biocontrol agent to control spotted knapweed. U. affinis became established in Montana in 1973.

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<i>Centaurea stoebe</i> Species of flowering plant in the family Asteraceae

Centaurea stoebe, the spotted knapweed or panicled knapweed, is a species of Centaurea native to eastern Europe, although it has spread to North America, where it is considered an invasive species. It forms a tumbleweed, helping to increase the species' reach, and the seeds are also enabled by a feathery pappus.

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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