Cnicin

Cnicin

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Names
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 Y
ChEMBL	ChEMBL1257707 N
ChemSpider	4444781 Y
Jmol 3D model	Interactive image
PubChem	5281435
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/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
SMILES 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
Chemical formula	C20H26O7
Molar mass	378.42 g·mol−1
Vapor pressure	{{{value}}}
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 ?)
Infobox 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. Cnicin is used as a bitter tonic and the bitterness value is approximately 1,500.