monocrotaline

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

CAS: 315-22-0 C16 H23 N O6 MW: 325.36151000

Identification

Namemonocrotaline
CAS Number315-22-0
FDA UNII73077K8HYV
Molecular FormulaC16 H23 N O6
Molecular Weight325.36151000
MDL NumberMFCD00084656
Nikkaji NumberJ107.104A
Beilstein0048732

Regulatory

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)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityunreported-mammal (species unspecified) LDLo 60 mg/kg
Dermal Toxicitysubcutaneous-rat LD50 60 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for monocrotaline usage levels up tonot for fragrance use.
Recommendation for monocrotaline flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

crotalaria spectabilis

Synonyms

mono crotalin (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- 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.