lasiocarpine

heliotridine ester with lasiocarpum and angelic acid

CAS: 303-34-4 C21 H33 N O7 MW: 411.49541000

Identification

Namelasiocarpine
IUPAC[(7S,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2R)-2,3-dihydroxy-2-[(1S)-1-methoxyethyl]-3-methylbutanoate
CAS Number303-34-4
FDA UNIIS770100Q96
Molecular FormulaC21 H33 N O7
Molecular Weight411.49541000
Nikkaji NumberJ4.477F

Regulatory

Physical Properties

Appearance beige crystalline solid (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 95.00 °C. @ 760.00 mm Hg
Boiling Point 519.80 °C. @ 760.00 mm Hg (est)
Flash Point 515.00 °F. TCC ( 268.10 °C. ) (est)
logP (o/w) 1.280
Soluble in water, 2136 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral Toxicityintravenous-guinea pig LDLo 50 mg/kg
Dermal ToxicityNot determined
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 lasiocarpine usage levels up tonot for fragrance use.
Recommendation for lasiocarpine flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

heliotrope european heliotrope

Synonyms

7- angelyl europine 7- angelyleuropine (7alpha- angelyloxy-5,6,7,8alpha-tetrahydro-3H-pyrrolizin-1-yl)methyl-2,3-dihydroxy-2-(1'-methoxyethyl)-3-methylbutyrate 2- butenoic acid, 2-methyl-, 7-((2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester, (1S-(1alpha(Z),7(2S*,3 europine 7-angelate heliotridine ester with lasiocarpum and angelic acid 2,3,5,7alphabeta-Tetrahydro-1- hydroxy-1H-pyrrolizine-7-methanol-1-angelate-7-(2,3-dihydroxy-2(1-methoxyethyl))-3-methyl-butyrate (-)- lasiocarpine [(7S,8R)-7-[(Z)-2- methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2R)-2,3-dihydroxy-2-[(1S)-1-methoxyethyl]-3-methylbutanoate (Z)-2- methylcrotonic acid, 2,3-dihydroxy-2-(1-methoxyethyl)-3-methylbutyrate (ester) PubMed: Identification of a New Reactive Metabolite of Pyrrolizidine Alkaloid Retrorsine: (3H-Pyrrolizin-7-yl)methanol. PubMed: Pyrrolizidine alkaloid-derived DNA adducts as a common biological biomarker of pyrrolizidine alkaloid-induced tumorigenicity. PubMed: Metabolism, genotoxicity, and carcinogenicity of comfrey. PubMed: Determination of pyrrolizidine alkaloids in comfrey by liquid chromatography-electrospray ionization mass spectrometry. PubMed: Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, heliotrine. PubMed: Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, lasiocarpine. PubMed: Evaporative light scattering detection of pyrrolizidine alkaloids. PubMed: Toxicity of dietary Heliotropium circinatum to rats. PubMed: Metabolism of pyrrolizidine alkaloids by Peptostreptococcus heliotrinreducens and a mixed culture derived from ovine ruminal fluid. PubMed: Toxicity of dietary Heliotropium dolosum seed to mice. PubMed: The efficacy and safety of comfrey. PubMed: Transplantation of normal hepatocytes modulates the development of chronic liver lesions induced by a pyrrolizidine alkaloid, lasiocarpine. PubMed: Detection of sulphur-conjugated pyrrolic metabolites in blood and fresh or fixed liver tissue from rats given a variety of toxic pyrrolizidine alkaloids. PubMed: Alterations of pancreatic hepatocytes in rats exposed to carcinogens. PubMed: Model systems for detecting the hepatic toxicity of pyrrolizidine alkaloids and pyrrolizidine alkaloid N-oxides. PubMed: Pyrrolizidine alkaloids from Heliotropium rotundifolium. PubMed: The fetal blood erythrocyte micronucleus assay: classification of RNA-positive erythrocytes into two age populations by RNA aggregation state. PubMed: Statistical analysis of a carcinogen mixture experiment. I. Liver carcinogens. PubMed: Human liver debrisoquine 4-hydroxylase: test for specificity toward various monooxygenase substrates and model of the active site. PubMed: Initiation and selection of resistant hepatocyte nodules in rats given the pyrrolizidine alkaloids lasiocarpine and senecionine. PubMed: Substrate specificity of human liver cytochrome P-450 debrisoquine 4-hydroxylase probed using immunochemical inhibition and chemical modeling. PubMed: Chemical mutagenesis testing in Drosophila. IV. Results of 45 coded compounds tested for the National Toxicology Program. PubMed: Poisonous plants contaminating edible ones and toxic substances in plant foods. Part 3. Pyrrolizidine alkaloids from Heliotropium digynum Forssk. (= H. luteum, Poir.). PubMed: Assay for gene mutation in a human lymphoblast line, AHH-1, competent for xenobiotic metabolism. PubMed: Peroxisome-associated enzymes and serum lipids in tumour-bearing rats treated with peroxisome-proliferating agents. PubMed: Influences of various xenobiotic inducers on cytocidal toxicity of lasiocarpine and senecionine in primary cultures of rat hepatocytes. PubMed: Mutagenic effects of aqueous extracts of Symphytum officinale L. and of its alkaloidal fractions. PubMed: Effect of calorie restriction on the fate of hyperplastic liver nodules induced by concurrent administration of lasiocarpine and thioacetamide. PubMed: [Electrolyte effect on heliotrine and lasiocarpine extraction with organic solvents]. PubMed: Rapid hepatoma induction in rats by dipentylnitrosamine and its modification by other carcinogens. 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: Poisoning of chickens and ducks by pyrrolizidine alkaloids of Heliotropium europaeum. PubMed: [Reactions for the detection of heliotrin and lasiocarpine in toxicological chemical studies]. PubMed: Malignant neoplasms in rats fed lasiocarpine. PubMed: Bioassay of lasiocarpine for possible carcinogenicity. PubMed: Rapid development of hyperplastic nodules and cirrhosis in the liver of rats treated concurrently with thioacetamide and the pyrrolizidine alkaloid lasiocarpine. PubMed: Lasiocarpine. PubMed: Experimental acute gastrointestinal disease caused by the pyrrolizidine alkaloid, lasiocarpine. PubMed: Localization in the cell cycle of the antimitotic action of the pyrrolizidine alkaloid, lasiocarpine and of its metabolite, dehydroheliotridine. PubMed: Decreased synthesis of hepatic satellite DNA in pyrrolizidine alkaloidosis of the sheep. PubMed: Spongy degeneration in the central nervous system of domestic animals. Part III: Occurrence and pathogenesis hepatocerebral disease caused by hyperammonaemia. PubMed: Spongy degeneration in the central nervous system of domestic animals. Part II: Chemical analysis and vascular permeability studies. PubMed: Dissociation of ribosomes produced by dimethylnitrosamine and lasiocarpine in mouse liver. PubMed: Malignant tumors in rats given lasiocarpine. PubMed: Induction of morphological changes in human embryo liver cells by the pyrrolizidine alkaloid lasiocarpine. PubMed: The effects of lasiocarpine, retrorsine and retronecine pyrrole on human embryo lung and liver cells in culture. PubMed: Different effects of pretreatment with 2-diethylaminoethyl-2,2-diphenylvalerate on the mouse liver polysomal disaggregation by dimethylnitrosamine and lasiocarpine. PubMed: Effect of lasiocarpine on aflatoxin B 1 carcinogenicity in rat liver. PubMed: Hepatic megalocytosis in chronic lasiocarpine poisoning. Some functional studies. PubMed: Effects of ethanol on mouse liver polysomal disaggregation by dimethylnitrosamine and lasiocarpine. PubMed: Effects of lasiocarpine on protein synthesis in rat liver. PubMed: Pyrrolizidine alkaloids: actions on muscarinic receptors in the guinea-pig ileum. PubMed: Lasiocarpine: factors influencing its toxicity and effects on liver cell division. PubMed: Lytic necrosis resembling peliosis hepatis produced by lasiocarpine in the mouse liver. A light and electron microscopic study. PubMed: [Persisting extranucleolar RNA synthesis in the liver of rats treated with lasiocarpine. A high resolution autoradiographic study]. PubMed: Effect of lasiocarpine on transcription in liver cells. PubMed: Polyribosome disaggregation in rat liver by lasiocarpine. PubMed: [Induction by aflatoxin and lasiocarpine of perichromatin grain clusters in rat liver]. PubMed: The influence of a low lipotrope diet on response of maternal and fetal rats to lasiocarpine. PubMed: Inhibition by lasiocarpine of RNA synthesis, RNA polymerase and induction of tryptophan pyrrolase activity. PubMed: Delayed hepatitis and cirrhosis in weanling rats following a single small dose of the senecio alkaloid, lasiocarpine. PubMed: EFFECTS OF THE PYRROLIZIDINE ALKALOID, LASIOCARPINE N-OXIDE, ON NUCLEAR AND CELL DIVISION IN THE LIVER RATS. PubMed: The chronic pathological effects on the liver of the rat of the pyrrolizidine alkaloids heliotrine, lasiocarpine, and their N-oxides. PubMed: Some pharmacological actions of supinine and lasiocarpine. PubMed: Liver lesions in young rats suckled by mothers treated with the pyrrolizidine (Senecio) alkaloids, lasiocarpine and retrorsine. PubMed: The acute toxic effects of heliotrine and lasiocarpine, and their N-oxides, on the rat.