Cnicin: Difference between revisions

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Revision as of 14:23, 30 November 2010 editBeetstra (talk \| contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey.← Previous edit		Revision as of 14:33, 30 November 2010 edit undoCheMoBot (talk \| contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WiNext edit →
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	{{chembox		{{chembox
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	\| ImageFile = cnicin.png		\| ImageFile = cnicin.png
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	\| Section1 = {{Chembox Identifiers		\| Section1 = {{Chembox Identifiers
	\| Abbreviations =		\| Abbreviations =
			\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 4444781		\| ChemSpiderID = 4444781
	\| InChIKey = ZTDFZLVUIVPZDU-QGNHJMHWBP		\| 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		\| 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		\| StdInChIKey = ZTDFZLVUIVPZDU-QGNHJMHWSA-N
	\| CASNo = 24394-09-0		\| CASNo = 24394-09-0

Revision as of 14:33, 30 November 2010

Cnicin
Names
File:Cnicin.png
IUPAC name trideca-4,8-dien-2-yl] (3S)-3,4-dihydroxy-2-methylidene-butanoate
Identifiers
CAS Number	24394-09-0
3D model (JSmol)	Interactive image
ChemSpider	4444781
ECHA InfoCard	100.042.004
PubChem CID	5281435
CompTox Dashboard (EPA)	DTXSID90878518
InChI 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/s1Key: ZTDFZLVUIVPZDU-QGNHJMHWSA-N 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/s1Key: ZTDFZLVUIVPZDU-QGNHJMHWBP
SMILES O=C/1O2/C=C(/CC/C=C(/C(OC(=O)\C(=C)(O)CO)2C\1=C)C)CO
Properties
Chemical formula	C₂₀H₂₆O₇
Molar mass	378.17 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

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

References

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.
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.

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