echimidine
[(7R,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-hydroxyethyl]-3-methylbutanoate
 
Notes:
None found
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CAS Number: 520-68-3Picture of molecule3D/inchi
FDA UNII: 31NEL09379
Nikkaji Web: J867.787E
XlogP3-AA: -0.10 (est)
Molecular Weight: 397.46847000
Formula: C20 H31 N O7
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 334.1 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Santa Cruz Biotechnology
For experimental / research use only.
Echimidine
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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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for echimidine usage levels up to:
 not for fragrance use.
 
Recommendation for echimidine 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
Cancer Citations: Search
Toxicology Citations: Search
EPA GENetic TOXicology: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5281729
National Institute of Allergy and Infectious Diseases: Data
 [(7R,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-hydroxyethyl]-3-methylbutanoate
Chemidplus: 0000520683
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References:
 [(7R,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-hydroxyethyl]-3-methylbutanoate
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5281729
Pubchem (sid): 134977025
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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): C10299
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 echium amoenum
Search Trop  Picture
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Synonyms:
[(7R,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-hydroxyethyl]-3-methylbutanoate
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Articles:
PubMed: Toxic pyrrolizidine alkaloids provide a warning sign to overuse of the ethnomedicine Arnebia benthamii.
PubMed: Development and validation of a QuEChERS method coupled to liquid chromatography and high resolution mass spectrometry to determine pyrrolizidine and tropane alkaloids in honey.
PubMed: A 28-day oral toxicity study of echimidine and lasiocarpine in Wistar rats.
PubMed: Acetylcholinesterase inhibitory activity of pyrrolizidine alkaloids from Echium confusum Coincy.
PubMed: Pyrrolizidine Alkaloids from Echium vulgare in Honey Originate Primarily from Floral Nectar.
PubMed: Metabolic Profiling of Pyrrolizidine Alkaloids in Foliage of Two Echium spp. Invaders in Australia--A Case of Novel Weapons?
PubMed: Quantification of pyrrolizidine alkaloids in North American plants and honey by LC-MS: single laboratory validation.
PubMed: Pyrrolizidine alkaloids in food and feed on the Belgian market.
PubMed: Disturbance of gene expression in primary human hepatocytes by hepatotoxic pyrrolizidine alkaloids: A whole genome transcriptome analysis.
PubMed: Development of a fast isocratic LC-MS/MS method for the high-throughput analysis of pyrrolizidine alkaloids in Australian honey.
PubMed: Structure-activity relationship in the passage of different pyrrolizidine alkaloids through the gastrointestinal barrier: ABCB1 excretes heliotrine and echimidine.
PubMed: Pyrrolizidine alkaloids: their occurrence in Spanish honey collected from purple viper's bugloss (Echium spp.).
PubMed: Dehydropyrrolizidine alkaloids in two Cryptantha species: including two new open chain diesters one of which is amphoteric.
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: Metabolism, genotoxicity, and carcinogenicity of comfrey.
PubMed: Pyrrolizidine alkaloids in honey: comparison of analytical methods.
PubMed: Determination of pyrrolizidine alkaloids in comfrey by liquid chromatography-electrospray ionization mass spectrometry.
PubMed: Metabolic activation of herbal and dietary constituents and its clinical and toxicological implications: an update.
PubMed: Pyrrolizidine alkaloids of Echium vulgare honey found in pure pollen.
PubMed: On-line structure characterization of pyrrolizidine alkaloids in Onosma stellulatum and Emilia coccinea by liquid chromatography-ion-trap mass spectrometry.
PubMed: Analysis of herbal teas made from the leaves of comfrey (Symphytum officinale): reduction of N-oxides results in order of magnitude increases in the measurable concentration of pyrrolizidine alkaloids.
PubMed: Isolation of symlandine from the roots of common comfrey (Symphytum officinale) using countercurrent chromatography.
PubMed: Toxicity of dietary Heliotropium dolosum seed to mice.
PubMed: Pyrrolizidine alkaloids from Echium rauwolfii and Echium horridum (Boraginaceae).
PubMed: [II1: TLC and HPLC-Analysis of Pyrrolizidine-N-oxid Alkaloids of Symphyti Radix].
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