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monocrotaline
(13-alpha,14-alpha)-14,19-dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione

Supplier Sponsors

CAS Number: 315-22-0Picture of molecule3D/inchi
FDA UNII: 73077K8HYV
Nikkaji Web:J107.104A
Beilstein Number:0048732
MDL:MFCD00084656
XlogP3-AA:-0.70 (est)
Molecular Weight:325.36151000
Formula:C16 H23 N O6
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:colorless prisms (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 537.30 °C. @ 760.00 mm Hg (est)
Flash Point: 534.00 °F. TCC ( 278.70 °C. ) (est)
logP (o/w): -0.370 (est)
Soluble in:
 water, 9.019e+005 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Monocrotaline; Crotaline 98%
BOC Sciences
For experimental / research use only.
monoCROTALINE >98%
Odor: characteristic
Use: Crotaline a natural ligand exhibits dose-dependent cytotoxicity with potent antineoplastic activity.Crotaline produced a positive result in the liver at a non-hepatotoxic lower dose level anti-cancer
ExtraSynthese
For experimental / research use only.
monoCrotaline TLC ≥90%
Glentham Life Sciences
Crotaline
Santa Cruz Biotechnology
For experimental / research use only.
monoCrotaline ≥98%
Sigma-Aldrich
For experimental / research use only.
monoCrotaline analytical standard
Sigma-Aldrich: Sigma
For experimental / research use only.
Crotaline
sds
 
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:
unreported-mammal (species unspecified) LDLo 60 mg/kg
Pharmacological Reviews. Vol. 22, Pg. 429, 1970.

intraperitoneal-mouse LD50 259 mg/kg
Toxicology and Applied Pharmacology. Vol. 59, Pg. 424, 1981.

intravenous-mouse LD50 261 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 75, Pg. 78, 1942.

intravenous-rat LD50 92 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 83, Pg. 265, 1945.

oral-rat LD50 66 mg/kg
LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"
Toxicology and Applied Pharmacology. Vol. 18, Pg. 387, 1971.

intraperitoneal-rat LDLo 130 mg/kg
LIVER: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Chemico-Biological Interactions. Vol. 12, Pg. 299, 1976.

Dermal Toxicity:
subcutaneous-rat LD50 60 mg/kg
Toxicology and Applied Pharmacology. Vol. 23, Pg. 470, 1972.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for monocrotaline usage levels up to:
 not for fragrance use.
 
Recommendation for monocrotaline flavor usage levels up to:
 not for flavor use.
 
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
AIDS Citations: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 :9415
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0000315220
RTECS:QB3140000 for cas# 315-22-0
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):9415
Pubchem (sid):134974959
 
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
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10350
HMDB (The Human Metabolome Database):HMDB34363
FooDB:FDB012736
Export Tariff Code:2939.90.1000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 crotalaria spectabilis
Search Trop Picture
 
Synonyms:
monocrotalin
(13-alpha,14-alpha)-14,19-dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione
12-beta,13-beta-dihydroxy-12-alpha,13-alpha,14-alpha-trimethylcrotal-1-enine
20-norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13alpha,14alpha)-
(2,3,4-gh)pyrrolizine-2,6(3H)-dione, (4,5,8,10,12,13,13a,13b)-octahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-(1,6)dioxacycloundecino-
 

Articles:

PubMed:UPLC-MS/MS method for determination of selected pyrrolizidine alkaloids in feed.
PubMed:[Determination of five pyrrolizidine alkaloids in honey by liquid chromatography-tandem mass spectrometry].
PubMed:Development and validation of a rapid multiplex ELISA for pyrrolizidine alkaloids and their N-oxides in honey and feed.
PubMed:Diaphragm atrophy and contractile dysfunction in a murine model of pulmonary hypertension.
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:Dehydropyrrolizidine alkaloids, including monoesters with an unusual esterifying acid, from cultivated Crotalaria juncea (Sunn Hemp cv.'Tropic Sun').
PubMed:¹H NMR study of monocrotaline and its metabolites in human blood.
PubMed:Anti-TNF treatment reduces rat skeletal muscle wasting in monocrotaline-induced cardiac cachexia.
PubMed:Involvement of RhoA/Rho kinase signaling in protection against monocrotaline-induced pulmonary hypertension in pneumonectomized rats by dehydroepiandrosterone.
PubMed:Anticoagulation and inhibition of nitric oxide synthase influence hepatic hypoxia after monocrotaline exposure.
PubMed:Bosentan, sildenafil, and their combination in the monocrotaline model of pulmonary hypertension in rats.
PubMed:Acquired and partially de novo synthesized pyrrolizidine alkaloids in two polyphagous arctiids and the alkaloid profiles of their larval food-plants.
PubMed:Modes of cell death in rat liver after monocrotaline exposure.
PubMed:The coagulation system contributes to synergistic liver injury from exposure to monocrotaline and bacterial lipopolysaccharide.
PubMed:Endothelial cell injury and coagulation system activation during synergistic hepatotoxicity from monocrotaline and bacterial lipopolysaccharide coexposure.
PubMed:Role of neutrophils in the synergistic liver injury from monocrotaline and bacterial lipopolysaccharide exposure.
PubMed:The role of Kupffer cells and TNF-alpha in monocrotaline and bacterial lipopolysaccharide-induced liver injury.
PubMed:The temporal relationship between bacterial lipopolysaccharide and monocrotaline exposures influences toxicity: shift in response from hepatotoxicity to nitric oxide-dependent lethality.
PubMed:Temporal modulation of pyrrolizidine alkaloid intake and genetic variation in performance of Utetheisa ornatrix caterpillars.
PubMed:Lack of protective action of cysteine against the fetotoxic effect of monocrotaline.
PubMed:Synergistic hepatotoxicity from coexposure to bacterial endotoxin and the pyrrolizidine alkaloid monocrotaline.
PubMed:Fetotoxicity and reproductive effects of monocrotaline in pregnant rats.
PubMed:Effect of some indole derivatives on xenobiotic metabolism and xenobiotic-induced toxicity in cultured rat liver slices.
PubMed:Sexually transmitted chemical defense in a moth (Utetheisa ornatrix).
PubMed:Metabolic activation of pyrrolizidine alkaloids by human, rat and avocado microsomes.
PubMed:Dietary restriction, polyamines and monocrotaline-induced pulmonary hypertension.
PubMed:A potential kairomone stimulates pheromone-responsive receptor neurons inUtetheisa ornatrix (Lepidoptera: Arctiidae).
PubMed:Dual role of pyrrolizidine alkaloids in nectar.
PubMed:The in vivo erythrocyte micronucleus test: measurement at steady state increases assay efficiency and permits integration with toxicity studies.
PubMed:Bioactivation and detoxication of the pyrrolizidine alkaloid senecionine by cytochrome P-450 enzymes in rat liver.
PubMed:Evaluation of amino acids, B vitamins and butylated hydroxyanisole as protective agents against pyrrolizidine alkaloid toxicity in rats.
PubMed:Protective role of dietary butylated hydroxyanisole against chemical-induced acute liver damage in mice.
PubMed:Effect of dietary Senecio jacobaea and injected Senecio alkaloids and monocrotaline on guinea pigs.
PubMed:Effects of monocrotaline pretreatment of rats on removal of 5-hydroxytryptamine and noradrenaline by perfused lung.
 
Notes:
Hepatotoxin. Causative agent of much seneciosis, e.g. accidental poisoning by S. by weed residues in bread, and characterised by venoocculosive disease
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