senkirkine
senecionanium, 8,12-dihydroxy-4-methyl-11,16-dioxo-
 
Notes:
macrocyclic secopyrrolizidine alkaloid from senecio.
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      Product(s):
      2318-18-5 SENKIRKIN
       
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CAS Number: 2318-18-5Picture of molecule3D/inchi
FDA UNII: X65P7V4LVJ
MDL: MFCD01684247
XlogP3-AA: 1.40 (est)
Molecular Weight: 365.42639000
Formula: C19 H27 N O6
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
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US Patents: Search
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PubMed: Search
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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)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
BOC Sciences
For experimental / research use only.
SENKIRKIN
ExtraSynthese
For experimental / research use only.
Senkirkine
Santa Cruz Biotechnology
For experimental / research use only.
Senkirkine
Sigma-Aldrich
For experimental / research use only.
Senkirkine
analytical standard
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-rat LD50  220 mg/kg
JNCI, Journal of the National Cancer Institute. Vol. 63, Pg. 469, 1979.

oral-rat LDLo  200 mg/kg
LIVER: OTHER CHANGES
Nature. Vol. 227, Pg. 401, 1970.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
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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Safety References:
European Food Safety Authority (EFSA) reference(s):
Dietary exposure assessment to pyrrolizidine alkaloids in the European population
View page or View pdf
EPI System: View
Chemical Carcinogenesis Research Information System: Search
Cancer Citations: Search
Toxicology Citations: Search
Carcinogenic Potency Database: Search
EPA GENetic TOXicology: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 6433332
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (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
Chemidplus: 0002318185
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References:
 (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
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 6433332
Pubchem (sid): 134983033
Pherobase: View
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 brachyglottis huntii
Search Trop  Picture
 brachyglottis kirkii
Search Trop  Picture
 brachyglottis sciadophila
Search Trop  Picture
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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)
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Articles:
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.
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