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heliotrine
butanoic acid, 2-hydroxy-3-methoxy-2-(1-methylethyl)-, [(1S,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl ester, (2S,3R)-

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CAS Number: 303-33-3Picture of molecule3D/inchi
FDA UNII: ZYB88Y4FUZ
Nikkaji Web:J4.476H
Beilstein Number:0292841
MDL:MFCD00213991
XlogP3-AA:0.10 (est)
Molecular Weight:313.39419000
Formula:C16 H27 N O5
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 4.635e+004 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Heliotrine 98 %. (TLC).
Odor: characteristic
Use: Extract from plants of the Heliotropum genus, an alkaloid used for obtaining models of hepatitis and cirrhosis of the liver. ADCs Cytotoxin
Santa Cruz Biotechnology
For experimental / research use only.
Heliotrine
Sigma-Aldrich: Sigma
For experimental / research use only.
Heliotrine ≥98% (TLC), solid
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:
intraperitoneal-mammal (species unspecified) LDLo 250 mg/kg
Pharmacological Reviews. Vol. 22, Pg. 429, 1970.

unreported-mammal (species unspecified) LDLo 260 mg/kg
Pharmacological Reviews. Vol. 22, Pg. 429, 1970.

intravenous-mouse LD50 251 mg/kg
LIVER: OTHER CHANGES
AMA Archives of Pathology. Vol. 64, Pg. 152, 1957.

intraperitoneal-rat LD50 296 mg/kg
GASTROINTESTINAL: OTHER CHANGES GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" KIDNEY, URETER, AND BLADDER: HEMATURIA
Journal of Pathology and Bacteriology. Vol. 75, Pg. 17, 1958.

intravenous-rat LD50 274 mg/kg
LIVER: OTHER CHANGES
AMA Archives of Pathology. Vol. 64, Pg. 152, 1957.

oral-rat LDLo 50 mg/kg
Nature. Vol. 179, Pg. 361, 1957.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for heliotrine usage levels up to:
 not for fragrance use.
 
Recommendation for heliotrine 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
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :906426
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
[(7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoate
Chemidplus:0000303333
 
References:
 [(7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):906426
Pubchem (sid):134973440
Pherobase:View
 
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):C10324
HMDB (The Human Metabolome Database):Search
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
 heliotrope european heliotrope
Search Trop Picture
 
Synonyms:
 butanoic acid, 2-hydroxy-3-methoxy-2-(1-methylethyl)-, [(1S,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl ester, (2S,3R)-
[(7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoate
 

Articles:

PubMed:Pyrrolizidine alkaloids in food and feed on the Belgian market.
PubMed:Utility of an appropriate reporter assay: Heliotrine interferes with GAL4/upstream activation sequence-driven reporter gene systems.
PubMed:Disturbance of gene expression in primary human hepatocytes by hepatotoxic pyrrolizidine alkaloids: A whole genome transcriptome analysis.
PubMed:Characterization and screening of pyrrolizidine alkaloids and N-oxides from botanicals and dietary supplements using UHPLC-high resolution mass spectrometry.
PubMed:An in vitro comparison of the cytotoxic potential of selected dehydropyrrolizidine alkaloids and some N-oxides.
PubMed:Heliotropium europaeum poisoning in cattle and analysis of its pyrrolizidine alkaloid profile.
PubMed:Reaction of dehydropyrrolizidine alkaloids with valine and hemoglobin.
PubMed:Structure-activity relationship in the passage of different pyrrolizidine alkaloids through the gastrointestinal barrier: ABCB1 excretes heliotrine and echimidine.
PubMed:Development and validation of a rapid multiplex ELISA for pyrrolizidine alkaloids and their N-oxides in honey and feed.
PubMed:Pyrrolizidine alkaloid-derived DNA adducts as a common biological biomarker of pyrrolizidine alkaloid-induced tumorigenicity.
PubMed:Pyrrolizidine alkaloids: their occurrence in Spanish honey collected from purple viper's bugloss (Echium spp.).
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:[Morphologic characteristic of chronic toxic hepatitis for treatment with Neoselen].
PubMed:Pyrrolizidine alkaloids in honey: risk analysis by gas chromatography-mass spectrometry.
PubMed:Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, heliotrine.
PubMed:Major components in the hairpencil secretion of a butterfly, Euploea mulciber (Lepidoptera, Danaidae): their origins and male behavioral responses to pyrrolizidine alkaloids.
PubMed:Final report of the safety assessment of niacinamide and niacin.
PubMed:Differential utilization of pyrrolizidine alkaloids by males of a danaid butterfly, Parantica sita, for the production of danaidone in the alar scent organ.
PubMed:[Effect of maternal toxic hepatitis on the functional characteristics of the lactation process].
PubMed:[Experimental and clinical evaluation of the efficacy of ecdysten in the treatment of hepatitis].
PubMed:Evaporative light scattering detection of pyrrolizidine alkaloids.
PubMed:[Morphological characteristics of chronic toxic hepatitis treated with neoselen].
PubMed:Taste receptors for pyrrolizidine alkaloids in a monophagous caterpillar.
PubMed:Pyrrolizidine alkaloids as oviposition stimulants for the cinnabar moth, Tyria jacobaeae.
PubMed:Toxicity of dietary Heliotropium circinatum to rats.
PubMed:Biochemical processing of plant acquired pyrrolizidine alkaloids by the neotropical leaf-beetle Platyphora boucardi.
PubMed:Metabolism of pyrrolizidine alkaloids by Peptostreptococcus heliotrinreducens and a mixed culture derived from ovine ruminal fluid.
PubMed:[Effects of maternal toxic hepatitis on the postnatal development of duodenal morphology of their offspring].
PubMed:[Correction of the lipid composition of the liver plasma membranes during heliotrine intoxication].
PubMed:[Some aspects of the formation of the immune system organs in newborn rats born to females with chronic hepatitis].
PubMed:Toxicity of dietary Heliotropium dolosum seed to mice.
PubMed:[The effect of perftoran on the biochemical detoxication parameters in rats with an acute toxic lesion of the liver].
PubMed:[Thymus changes in chronic heliotrine-induced hepatitis].
PubMed:The two facies of pyrrolizidine alkaloids: the role of the tertiary amine and its N-oxide in chemical defense of insects with acquired plant alkaloids.
PubMed:[Enzymatic activity of the pancreas and small intestinal mucosa in modelling of toxic hepatitis by administration of heliotrine].
PubMed:Sequestration of pyrrolizidine alkaloids in several arctiid moths (Lepidoptera: Arctiidae).
PubMed:Insect pheromone biosynthesis: stereochemical pathway of hydroxydanaidal production from alkaloidal precursors in Creatonotos transiens (Lepidoptera, Arctiidae).
PubMed:[Mechanism of the damaging effect of heliotrine on the functional and metabolic parameters of hepatocytes].
PubMed:Micronuclei in adult and foetal mice exposed in vivo to heliotrine, urethane, monocrotaline and benzidine.
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:A potential kairomone stimulates pheromone-responsive receptor neurons inUtetheisa ornatrix (Lepidoptera: Arctiidae).
PubMed:Chemistry of sulphur-bound pyrrolic metabolites in the blood of rats given different types of pyrrolizidine alkaloid.
PubMed:[Change in lipid peroxidation processes and level of individual gangliosides and phospholipids in the liver of rats with toxic experimental hepatitis].
PubMed:Identity of a biliary metabolite formed from monocrotaline in isolated, perfused rat liver.
PubMed:Disturbances in oxidative phosphorylation in the liver of rats with heliotrine-induced hepatitis and restoration by phosphatidylcholine and ATP.
PubMed:[Reparation of the hepatocyte plasma membrane using phosphatidylcholine liposomes].
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:[Features of protein secretion by the rat liver in various stages of carbon tetrachloride or heliotrine poisoning].
PubMed:Somatic mutation induced by heliotrine in Drosophila.
PubMed:[Phosphatidylcholine-induced repair of damaged hepatocyte membranes in heliotrine poisoning].
PubMed:[Phospholipid composition and oxidative phosphorylation in liver mitochondria in hepatitis].
PubMed:[Action of phytoecdysteroids on the bile-secretory function of the normal liver and in experimental hepatitis].
PubMed:[Causes of hyperinsulinemia and decreased sensitivity to insulin in liver damage].
PubMed:Pheromones of two arctiid moths (Creatonotos transiens andC. gangis) : Chiral components from both sexes and achiral female components.
PubMed:[Functional state of the hepatocyte cytoplasmic network in heliotrine injury of the rat liver].
PubMed:Induction of SCEs by some pyrrolizidine alkaloids in V79 Chinese hamster cells co-cultured with chick embryo hepatocytes.
PubMed:Poisonous plants contaminating edible ones and toxic substances in plant foods. Part 3. Pyrrolizidine alkaloids from Heliotropium digynum Forssk. (= H. luteum, Poir.).
PubMed:Stereochemical course of pheromone biosynthesis in the arctiid moth, Creatonotos transiens.
PubMed:A Note on "Isolation and Pharmacological Action of Heliotrine, the Major Alkaloid of Heliotropium indicum Seeds".
PubMed:[State of oxidizing processes in rat liver in chronic heliotrine hepatitis].
PubMed:[Influence of heliotrin on the rat liver microsomal oxidation system].
PubMed:Isolation and pharmacological action of heliotrine, the major alkaloid of Heliotropium indicum seeds.
PubMed:Somatic and teratogenic effects induced by heliotrine in Drosophila.
PubMed:[Characteristics of the course of viral hepatitis B in patients with concomitant diseases treated with glucocorticosteroids].
PubMed:Heliotrine poisoning of broiler chickens: an experimental clinicopathologic study of low dose intoxication.
PubMed:[Electrolyte effect on heliotrine and lasiocarpine extraction with organic solvents].
PubMed:[On the gas-chromatographical determination of the pyrrolizidine alkaloids of some Senecio-species].
PubMed:Anticancer drug testing in vitro: use of an activating system with the human tumor stem cell assay.
PubMed:Comparison of the toxic effects of dehydroheliotridine and heliotrine in pregnant rats and their embryos.
PubMed:Chromosomal aberrations and mutation in cultured mammalian cells induced by pyrrolizidine alkaloids.
PubMed:Direct quantitative analysis of indicine-N-oxide in cancer patient samples by gas chromatography using the internal standard heliotrine-N-oxide including a mass spectral comparison of their trimethylsilyl derivatives.
PubMed:Mutagenicity of pyrrolizidine alkaloids in the Salmonella/mammalian-microsome test.
PubMed:Poisoning of chickens and ducks by pyrrolizidine alkaloids of Heliotropium europaeum.
PubMed:Relationship of the reductive metabolism of indicine N-oxide to its antitumor activity.
PubMed:The gas chromatographic mass spectrometric analysis of the new antitumor drug indicine-N-oxide utilizing a novel reaction accompanying trimethylsilylation.
PubMed:An epidemic of veno-occlusive disease of the liver in Afghanistan. Pathologic features.
PubMed:Herbal medicines and veno-occlusive disease in India.
PubMed:The role of nicotinamide and of certain other modifying factors in diethylnitrosamine carcinogenesis: fusaria mycotoxins and "spontaneous" tumors in animals and man.
PubMed:[Interrelationship between the structure, microcirculation and tissue-vascular permeability of the liver after experimental toxic damage].
PubMed:The effects of the pyrrolizidine alkaloid, heliotrine, and nicotinamide on the concentration of plasma insulin and blood glucose in the rat.
PubMed:Pancreatic islet-cell and other tumors in rats given heliotrine, a monoester pyrrolizidine alkaloid, and nicotinamide.
PubMed:Use of repair-deficient strains of Escherichia coli and liver microsomes to detect and characterise DNA damage caused by pyrrolizidine alkaloids heliotrine and monocrotaline.
PubMed:Decreased synthesis of hepatic satellite DNA in pyrrolizidine alkaloidosis of the sheep.
PubMed:Proceedings: Pancreatic islet cell and other tumours induced in rats by heliotrine- a mono-ester pyrrolizidine alkaloid; the effects of additional treatment with nicotinamide.
PubMed:An analysis of chromosomal sensitivity of HPK1 cells from the marsupial Potorous tridactylus to x-rays and to heliotrine.
PubMed:Pyrrolizidine alkaloids: actions on muscarinic receptors in the guinea-pig ileum.
PubMed:[Study of the action of oxido-reductive enzymes in the liver of rats with chronic heliotrine poisoning].
PubMed:Comparison of the effects of LSD, heliotrine and x-irradiation on chromosome breakage, and the effects of LSD on the rate of cell division.
PubMed:The effect of heliotrine, a pyrrolizidine alkaloid, on human liver cells in culture.
PubMed:The mutagenic activity of the pyrrolizidine alkaloid heliotrine in Drosophila melanogaster. II. Chromosome rearrangements.
PubMed:Excretion of the pyrrolizidine alkaloid heliotrine in the urine and bile of sheep.
PubMed:An electron microscopic study of giant cytosegresomes in acute liver injury due to heliotrine.
PubMed:[Hematopoiesis in chronic heliotrine poisoning in Wistar albino rats].
PubMed:An electron-microscope study of liver cell necrosis due to heliotrine.
PubMed:[Morphologic signs of the participation of immunologic mechanisms in the pathogenesis of heliotrine liver cirrhosis (experimental-morphologic study)].
PubMed:[Morphologic and histochemical changes in the rat liver after administration of heliotrine].
PubMed:Reduction of heliotrine by a rumen microorganism.
PubMed:[Phagocytosis of erythroblasts by bone marrow reticular cells in rats with chronic heliotrine poisoning].
PubMed:Effects of the pyrrolizidine alkaloid heliotrine on cell division and chromosome breakage in cultures of leucocytes from the marsupial Potorous tridactylus.
PubMed:Lysosome changes in acute liver injury due to heliotrine.
PubMed:The mutagenic activity of heliotrine in Drosophila. I. Complete and mosaic sex-linked lethals.
PubMed:THE EFFECT OF CYANIDE AND AZIDE ON THE MUTAGENIC ACTIVITY OF THE PYRROLIZIDINE ALKALOID HELIOTRINE IN DROSOPHILA MELANOGASTER.
PubMed:Acute toxic liver injury. nicotinamide-adenine dinucleotide-pyrophosphorylase activity of nuclei isolated from rat liver in heliotrine and in dimethylnitrosamine poisoning.
PubMed:Liver damage in acute heliotrine poisoning. 1. The intracellular distribution of pyridine nucleotides.
PubMed:Liver damage in acute heliotrine poisioning. 2. The effect of nicotinamide on pyridine nucleotide concentrations.
PubMed:Malformations in foetal rats induced by the pyrrolizidine alkaloid, heliotrine.
PubMed:Pyridine nucleotide metabolism in heliotrine poisoning.
PubMed:The chronic pathological effects on the liver of the rat of the pyrrolizidine alkaloids heliotrine, lasiocarpine, and their N-oxides.
PubMed:Mutagenic activity of the alkaloid heliotrine in Drosophila.
PubMed:The acute toxic effects of heliotrine and lasiocarpine, and their N-oxides, on the rat.
PubMed:Hepatotoxic and pharmacologic properties of heliotrine.
 
Notes:
None found
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