senkirkine
senecionanium, 8,12-dihydroxy-4-methyl-11,16-dioxo-
Identification
| Name | senkirkine |
| IUPAC | (4E,6R,7R,11Z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione |
| CAS Number | 2318-18-5 |
| FDA UNII | X65P7V4LVJ |
| Molecular Formula | C19 H27 N O6 |
| Molecular Weight | 365.42639000 |
| MDL Number | MFCD01684247 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 198.00 °C. @ 760.00 mm Hg (est) |
| Boiling Point | 604.90 °C. @ 760.00 mm Hg (est) |
| Flash Point | 607.00 °F. TCC ( 319.60 °C. ) (est) |
| logP (o/w) | 0.690 (est) |
| Soluble in | water, 8.591e+004 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | intraperitoneal-rat LD50 220 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 |
| Recommendation for senkirkine usage levels up to | not for fragrance use. |
| Recommendation for senkirkine flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
2,12-
dihydroxy-4-methyl-11,16-dioxosenecionanium
trans-15-
ethylidene-12-beta-hydroxy-4,12-alpha,13-beta-trimethyl 8-oxo-4,8 secosenec-1-enine
(4E,6R,7R,11Z)-4-
ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione
renardin
renardine
4,8-
secosenecionan-8,11,16-trione, 12-hydroxy-4-methyl-
senecionanium, 8,12-dihydroxy-4-methyl-11,16-dioxo-
senkarkane
senkirkin
senkirkine (neutral)
PubMed:
UPLC-MS/MS method for determination of selected pyrrolizidine alkaloids in feed.
PubMed:
Diversity of pyrrolizidine alkaloids in native and invasive Senecio pterophorus (Asteraceae): Implications for toxicity.
PubMed:
Three new monoterpene glucosides from Senecio solidagineus.
PubMed:
Toxicity of pyrrolizidine alkaloids to Spodoptera exigua using insect cell lines and injection bioassays.
PubMed:
[Determination of five pyrrolizidine alkaloids in honey by liquid chromatography-tandem mass spectrometry].
PubMed:
Structure-activity relationship in the passage of different pyrrolizidine alkaloids through the gastrointestinal barrier: ABCB1 excretes heliotrine and echimidine.
PubMed:
Pyrrolizidine alkaloid-derived DNA adducts as a common biological biomarker of pyrrolizidine alkaloid-induced tumorigenicity.
PubMed:
Analysis of pyrrolizidine alkaloids and evaluation of some biological activities of Algerian Senecio delphinifolius (Asteraceae).
PubMed:
Comparison of metabolism-mediated effects of pyrrolizidine alkaloids in a HepG2/C3A cell-S9 co-incubation system and quantification of their glutathione conjugates.
PubMed:
[Studies on the alkaloids of Senecio scandens growing in Guangdong].
PubMed:
Determination of senkirkine and senecionine in Tussilago farfara using microwave-assisted extraction and pressurized hot water extraction with liquid chromatography tandem mass spectrometry.
PubMed:
Identification of five hepatotoxic pyrrolizidine alkaloids in a commonly used traditional Chinese medicinal herb, Herba Senecionis scandentis (Qianliguang).
PubMed:
Pyrrolizidine alkaloids of the endemic Mexican genus Pittocaulon and assignment of stereoisomeric 1,2-saturated necine bases.
PubMed:
Dynamic pH junction-sweeping capillary electrophoresis for online preconcentration of toxic pyrrolizidine alkaloids in Chinese herbal medicine.
PubMed:
Differences in effects of pyrrolizidine alkaloids on five generalist insect herbivore species.
PubMed:
Acquisition, transformation and maintenance of plant pyrrolizidine alkaloids by the polyphagous arctiid Grammia geneura.
PubMed:
Separation and determination of toxic pyrrolizidine alkaloids in traditional Chinese herbal medicines by micellar electrokinetic chromatography with organic modifier.
PubMed:
Specific recognition, detoxification and metabolism of pyrrolizidine alkaloids by the polyphagous arctiid Estigmene acrea.
PubMed:
On-line structure characterization of pyrrolizidine alkaloids in Onosma stellulatum and Emilia coccinea by liquid chromatography-ion-trap mass spectrometry.
PubMed:
Pyrrolizidine alkaloids as oviposition stimulants for the cinnabar moth, Tyria jacobaeae.
PubMed:
Toxicity of Senecio vernalis to laying hens and evaluation of residues in eggs.
PubMed:
Structure-activity relationships of pyrrolizidine alkaloids in insect chemical defense against the orb-weaving spider Nephila clavipes.
PubMed:
Simultaneous determination of N-oxides and free bases of pyrrolizidine alkaloids by cation-exchange solid-phase extraction and ion-pair high-performance liquid chromatography.
PubMed:
Interplant alkaloid variation and Senecio vernalis toxicity in cattle.
PubMed:
SOS induction of selected naturally occurring substances in Escherichia coli (SOS chromotest).
PubMed:
Generation and characterization of monoclonal antibodies against the pyrrolizidine alkaloid retrorsine.
PubMed:
A competitive enzyme immunoassay for the pyrrolizidine alkaloids of the senecionine type.
PubMed:
Hepatotoxic pyrrolizidine alkaloids in the Mexican medicinal plant Packera candidissima (Asteraceae: Senecioneae).
PubMed:
Pyrrolizidine alkaloids from Senecio leucanthemifolius and Senecio rodriguezii.
PubMed:
Anonamine, C19H27NO7, neosenkirkine, C19H27NO6, and hydroxysenkirkine, C19H27NO7.CH3OH. Macrocyclic secopyrrolizidine alkaloids from Senecio anonymus Wood.
PubMed:
Macrocyclic pyrrolizidine alkaloids from Senecio anonymus. Separation of a complex alkaloid extract using droplet counter-current chromatography.
PubMed:
Alkaloid patterns and biosynthetic capacity of root cultures from some pyrrolizidine alkaloid producing Senecio species.
PubMed:
[Pyrrolizidine Alkaloids from Emilia sonchifolia.].
PubMed:
Genotoxicity of a variety of pyrrolizidine alkaloids in the hepatocyte primary culture-DNA repair test using rat, mouse, and hamster hepatocytes.
PubMed:
Induction of SCEs by some pyrrolizidine alkaloids in V79 Chinese hamster cells co-cultured with chick embryo hepatocytes.
PubMed:
Mutagenic activity of the pyrrolizidine alkaloids seneciphylline and senkirkine in Drosophila and their transfer into rat milk.
PubMed:
Senkirkine.
PubMed:
Neosenkirkine and Senkirkine from Senecio pierotii.
PubMed:
[On the gas-chromatographical determination of the pyrrolizidine alkaloids of some Senecio-species].
PubMed:
Chromosomal aberrations and mutation in cultured mammalian cells induced by pyrrolizidine alkaloids.
PubMed:
Mutagenicity of pyrrolizidine alkaloids in the Salmonella/mammalian-microsome test.
PubMed:
Induction of hepatic tumors in rats by senkirkine and symphytine.
PubMed:
Carcinogenic activity of coltsfoot, Tussilago farfara l.
PubMed:
Senkirkine.
PubMed:
The nature of intramolecular N--C equals O interactions. Crystal structure of the Senecio alkaloid senkirkine.
PubMed:
Hepatotoxic activity of retrorsine, senkirkine and hydroxysenkirkine in newborn rats, and the role of epoxides in carcinogenesis by pyrrolizidine alkaloids and aflatoxins.
PubMed:
ALKALOIDS OF NEW ZEALAND SENECIO SPECIES. II. SENKIRKINE.