cnicin
germacra-1(10),4,11(13)-trien-12-oic acid, 6-alpha,8-alpha,15-trihydroxy-, 12,6-lactone, 8-(3,4-dihydroxy-2-methylenebutyrate)
Identification
| Name | cnicin |
| IUPAC | [(3aR,4S,6Z,10E,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (3R)-3,4-dihydroxy-2-methylidenebutanoate |
| CAS Number | 24394-09-0 |
| EINECS | 246-221-8 |
| FDA UNII | C998MWY30L |
| Molecular Formula | C20 H26 O7 |
| Molecular Weight | 378.42162000 |
| MDL Number | MFCD00075707 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 143.00 °C. @ 760.00 mm Hg |
| Boiling Point | 622.30 °C. @ 760.00 mm Hg (est) |
| Flash Point | 426.00 °F. TCC ( 219.10 °C. ) (est) |
| logP (o/w) | 2.320 (est) |
| Soluble in | water, 714.8 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | oral-mouse LD50 452 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
cnicine
germacra-1(10),4,11(13)-trien-12-oic acid, 6-alpha,8-alpha,15-trihydroxy-, 12,6-lactone, 8-(3,4-dihydroxy-2-methylenebutyrate)
[(3aR,4S,6Z,10E,11aR)-10-(
hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (3R)-3,4-dihydroxy-2-methylidenebutanoate
2,3,3a,4,5,8,9,11a-
octahydro-10-(hydroxymethyl)-6-methyl-3-methylene-2-oxocyclodeca(b)furan-4-yl 3,4-dihydroxy-2-methylenebutyrate
PubMed:
Sesquiterpene lactones from Centaurea zuccariniana and their antimicrobial activity.
PubMed:
Bioactivity-guided isolation of antiproliferative compounds from Centaurea jacea L.
PubMed:
Antimyeloma activity of the sesquiterpene lactone cnicin: impact on Pim-2 kinase as a novel therapeutic target.
PubMed:
Secondary metabolites of Centaurea calolepis and evaluation of cnicin for anti-inflammatory, antioxidant, and cytotoxic activities.
PubMed:
Antibacterial and cytotoxic activities of the sesquiterpene lactones cnicin and onopordopicrin.
PubMed:
Bioactivity-guided isolation of antiproliferative compounds from Centaurea arenaria.
PubMed:
Structure-activity relationships of tulipalines, tuliposides, and related compounds as inhibitors of MurA.
PubMed:
Acid rearrangment of epoxy-germacranolides and absolute configuration of 1beta,10alpha-epoxy-salonitenolide.
PubMed:
The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure-activity relationship.
PubMed:
The unusual binding mode of cnicin to the antibacterial target enzyme MurA revealed by X-ray crystallography.
PubMed:
Sesquiterpene lactones are potent and irreversible inhibitors of the antibacterial target enzyme MurA.
PubMed:
Plant-derived natural products exhibiting activity against formosan subterranean termites (Coptotermes formosanus).
PubMed:
Sesquiterpene lactones from Centaurea spinosa and their antibacterial and cytotoxic activities.
PubMed:
Antibacterial evaluation of cnicin and some natural and semisynthetic analogues.
PubMed:
New sources and antifungal activity of sesquiterpene lactones.
PubMed:
Microbial transformation of sesquiterpene lactones by the fungi cunninghamella echinulata and rhizopus oryzae
PubMed:
Biomimetic cyclization of cnicin to malacitanolide, a cytotoxic eudesmanolide from Centaurea malacitana.
PubMed:
Sesquiterpene lactones and other constituents of Centaurea napifolia.
PubMed:
Influence of cnicin, a sesquiterpene lactone ofCentaurea maculosa (Asteraceae), on specialist and generalist insect herbivores.
PubMed:
[Analysis and action of cnicin].
PubMed:
Phytotoxic properties of cnicin, a sesquiterpene lactone fromcentaurea maculosa (spotted knapweed).
PubMed:
[Further Compounds from Centaurea stoebe.].
PubMed:
Sesquiterpene Lactones from Aegialophila pumila.
PubMed:
[Antibiotic and cytotoxic activity of cnicin and of its hydrolysis products. Chemical structure - biological activity relationship (author's transl)].
PubMed:
[Antibiotic and cytotoxic activity of cnicin isolated from Cnicus benedictus L].