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Wikipedia

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
  • 24394-09-0 Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1257707 N
ChemSpider
  • 4444781 Y
ECHA InfoCard 100.042.004
  • 5281435
UNII
  • C998MWY30L Y
  • DTXSID90878518
  • 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 Y
    Key: ZTDFZLVUIVPZDU-QGNHJMHWSA-N Y
  • 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).
N verify (what is YN ?)

References edit

  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

External links edit

  •   Media related to Cnicin at Wikimedia Commons

cnicin, sesquiterpene, lactone, esterified, with, substituted, acrylic, acid, belonging, germacranolide, class, natural, products, mainly, found, cnicus, cnicus, benedictus, asteraceae, present, spotted, knapweed, plants, where, highest, lowest, concentrations. 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 NamesPreferred 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 methylidenebutanoateIdentifiersCAS Number 24394 09 0 Y3D model JSmol Interactive imageChEMBL ChEMBL1257707 NChemSpider 4444781 YECHA InfoCard 100 042 004PubChem CID 5281435UNII C998MWY30L YCompTox Dashboard EPA DTXSID90878518InChI 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 YKey ZTDFZLVUIVPZDU QGNHJMHWSA N YInChI 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 s1Key ZTDFZLVUIVPZDU QGNHJMHWBPSMILES 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 COPropertiesChemical formula C 20H 26O 7Molar mass 378 421 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesReferences edit 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 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 UniversityExternal links edit nbsp Media related to Cnicin at Wikimedia Commons Retrieved from https en wikipedia org w index php title Cnicin amp oldid 1107519004, wikipedia, wiki, book, books, library,

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