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Category: natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00 %
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| Food Chemicals Codex Listed: | No |
| Soluble in: |
| | water, 4.635e+004 mg/L @ 25 °C (est) |
Organoleptic Properties:
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| Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| 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.
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | natural substances and extractives |
| Recommendation for heliotrine usage levels up to: | | | not for fragrance use.
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| Recommendation for heliotrine 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 |
| 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:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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. |
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