EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

chelidonine
[5bR-(5ba,6b,12b4a)]-5b,6,7,12b,13,14-hexahydro-13-methyl[1,3]benzodioxolo[5,6-c]-1,3-di oxolo[4,5-i]phenanthridin-6-ol

Supplier Sponsors

CAS Number: 476-32-4Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-504-1
FDA UNII:8K7EK8446J
Nikkaji Web:J5.974I
Beilstein Number:4275089
MDL:MFCD00069660
XlogP3-AA:2.20 (est)
Molecular Weight:353.37443000
Formula:C20 H19 N O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:cosmetic agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:chocolate brown powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 135.50 °C. @ 760.00 mm Hg
Boiling Point: 507.39 °C. @ 760.00 mm Hg (est)
Flash Point: 501.00 °F. TCC ( 260.70 °C. ) (est)
logP (o/w): 2.899 (est)
Soluble in:
 water, 196.4 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: skin conditioning
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Chelidonine 98%
BOC Sciences
For experimental / research use only.
Chelidonine >98%
Coompo
For experimental / research use only.
Chelidonine from Plants ≥98%
ExtraSynthese
For experimental / research use only.
(+)-Chelidonine (HPLC) ≥95%
Santa Cruz Biotechnology
For experimental / research use only.
Chelidonine
Sigma-Aldrich: Sigma
For experimental / research use only.
Chelidonine ≥97.0% (HPLC)
 
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:
intravenous-mouse LD50 35 mg/kg
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 5, Pg. 163, 1946.

unreported-mouse LD50 2750 mg/kg
Herba Polonica. Vol. 25, Pg. 209, 1979.

Dermal Toxicity:
subcutaneous-cat LD50 140 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.

subcutaneous-dog LD50 500 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.

subcutaneous-frog LD50 160 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.

subcutaneous-mouse LD50 125 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.

subcutaneous-rabbit LD50 360 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 135, 1960.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
cosmetic agents
Recommendation for chelidonine usage levels up to:
 not for fragrance use.
 
Recommendation for chelidonine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :197810
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(1S,12S,13R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol
Chemidplus:0000476324
RTECS:FL9450000 for cas# 476-32-4
 
References:
 (1S,12S,13R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):197810
Pubchem (sid):134973497
 
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):C12242
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
 found in nature
 
Synonyms:
[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol, 5b,6,7,12b,13,14-hexahydro-13-methyl-, (5bR,6S,12bS)-
 chelidonin
 helidonine
[5bR-(5ba,6b,12b4a)]-5b,6,7,12b,13,14-hexahydro-13-methyl[1,3]benzodioxolo[5,6-c]-1,3-di oxolo[4,5-i]phenanthridin-6-ol
 khelidonin
(5bR,6S,12bS)-13-methyl-5b,6,7,12b,13,14-hexahydro[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol
(5bR,6S,12bS)-13-methyl-5b,6,7,12b,13,14-hexahydro[1,3]dioxolo[4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol
 stylophorin
 stylophorine
(1S,12S,13R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol
 

Articles:

PubMed:Poly (lactide-co-glycolide) nano-encapsulation of chelidonine, an active bioingredient of greater celandine (Chelidonium majus), enhances its ameliorative potential against cadmium induced oxidative stress and hepatic injury in mice.
PubMed:Cytotoxicity and apoptotic signalling cascade induced by chelidonine-loaded PLGA nanoparticles in HepG2 cells in vitro and bioavailability of nano-chelidonine in mice in vivo.
PubMed:[The reactivity of liver monoamine oxidase in the ringed seal Phoca hispida ladogensis].
PubMed:[Study on the separation process of pharmacological active total alkaloids from Chelidonium majus L. growing in Georgia].
PubMed:Capillary electrophoretic study of the synergistic biological effects of alkaloids from Chelidonium majus L. in normal and cancer cells.
PubMed:A sensitive and selective liquid chromatography-tandem mass spectrometry method for simultaneous determination of five isoquinoline alkaloids from Chelidonium majus L. in rat plasma and its application to a pharmacokinetic study.
PubMed:Modulation of multidrug resistance in cancer cells by chelidonine and Chelidonium majus alkaloids.
PubMed:Chelidonine isolated from ethanolic extract of Chelidonium majus promotes apoptosis in HeLa cells through p38-p53 and PI3K/AKT signalling pathways.
PubMed:Total syntheses of chelidonine and norchelidonine via an enamide-benzyne-[2 + 2] cycloaddition cascade.
PubMed:The in vivo effect of chelidonine on the stem cell system of planarians.
PubMed:Chelidonium majus leaves methanol extract and its chelidonine alkaloid ingredient reduce cadmium-induced nephrotoxicity in rats.
PubMed:Alkaloids from Chelidonium majus and their inhibitory effects on LPS-induced NO production in RAW264.7 cells.
PubMed:Capillary electrophoresis with LED-induced native fluorescence detection for determination of isoquinoline alkaloids and their cytotoxicity in extracts of Chelidonium majus L.
PubMed:In vivo anthelmintic activity of chelidonine from Chelidonium majus L. against Dactylogyrus intermedius in Carassius auratus.
PubMed:Benzo[c]phenanthridine alkaloids exhibit strong anti-proliferative activity in malignant melanoma cells regardless of their p53 status.
PubMed:Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Chelidonium majus (Papaveraceae).
PubMed:[Comparative substrate-inhibitor analysis of liver monoamine oxidases of minks].
PubMed:Simultaneous determination of seven main alkaloids of Chelidonium majus L. by ultra-performance LC with photodiode-array detection.
PubMed:Transcriptional down regulation of hTERT and senescence induction in HepG2 cells by chelidonine.
PubMed:A decisive role of mitochondria in defining rate and intensity of apoptosis induction by different alkaloids.
PubMed:Concise enantioselective total syntheses of (+)-homochelidonine, (+)-chelamidine, (+)-chelidonine, (+)-chelamine and (+)-norchelidonine by a Pd II-catalyzed ring-opening strategy.
PubMed:Differential effect of sanguinarine, chelerythrine and chelidonine on DNA damage and cell viability in primary mouse spleen cells and mouse leukemic cells.
PubMed:Apoptogenic activity of two benzophenanthridine alkaloids from Chelidonium majus L. does not correlate with their DNA damaging effects.
PubMed:Ukrain modulates glial fibrillary acidic protein, but not connexin 43 expression, and induces apoptosis in human cultured glioblastoma cells.
PubMed:[Effect of alkaloids from celandine on calcium accumulation and oxidative phosphorylation in mitochondria depending on their DNA intercalating properties].
PubMed:[Experimental study of the inhibitory effects of Chelidonium majus L. extractive on Streptococcus mutans in vitro].
PubMed:Intestinal spasmolytic effects of STW 5 (Iberogast) and its components.
PubMed:Effect of Ukrain on matrix metalloproteinase-2 and Secreted Protein Acidic and Rich in Cysteine (SPARC) expression in human glioblastoma cells.
PubMed:Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway.
PubMed:[Effect of some isoquinoline alkaloids on enzymatic activity of acetylcholinesterase and monoamine oxidase].
PubMed:Identification and quantification of isoquinoline alkaloids in the genus Sarcocapnos by GC-MS.
PubMed:Apoptotic response of uveal melanoma cells upon treatment with chelidonine, sanguinarine and chelerythrine.
PubMed:[Inhibition of liver mitochondrial monoamine oxidase activity by alkaloids isolated from Chelidonium and Macleaya and by their derivative drugs].
PubMed:Preliminary evaluation of CNS effects of 6-O-substituted chelidonine derivatives.
PubMed:Cytotoxic activity and quality control determinations on Chelidonium majus.
PubMed:Inhibitory activity on binding of specific ligands to the human angiotensin II AT(1) and endothelin 1 ET(A) receptors: bioactive benzo[c]phenanthridine alkaloids from the root of Bocconia frutescens.
PubMed:[Inhibition by various alkaloids of acetylcholinesterase and butyrylcholinesterase from human blood].
PubMed:NSC-631570 (Ukrain) in the palliative treatment of pancreatic cancer. Results of a phase II trial.
PubMed:[The inhibition enzymatic hydrolysis of acetylthiocholine by acetylcholinesterase using principal alkaloids isolated from celandine and macleya and their derivatives].
PubMed:Synthesis and biological activity of O-acyl and O-alkyl chelidonine derivatives.
PubMed:A method for determination of Ukrain in blood plasma for monitoring and pharmacokinetic study.
PubMed:Inhibitory effects of sanguinarine on monoamine oxidase activity in mouse brain.
PubMed:Synthesis of a [18F]labeled chelidonine derivative as a possible antitumor agent.
PubMed:The effects of chelidonine on tubulin polymerisation, cell cycle progression and selected signal transmission pathways.
PubMed:Chemical analyses of Ukrain, a semi-synthetic Chelidonium majus alkaloid derivative, fail to confirm its trimeric structure.
PubMed:[Minor alkaloids from the capsule of Papaver nudicaule L].
PubMed:Effect of sample handling on alkaloid and mineral content of aqueous extracts of greater celandine (Chelidonium majus L.).
PubMed:Inhibition of Candida rugosa lipase by berberine and structurally related alkaloids, evaluated by high-performance liquid chromatography.
PubMed:Antispasmodic and relaxant activity of chelidonine, protopine, coptisine, and Chelidonium majus extracts on isolated guinea-pig ileum.
PubMed:Benzophenanthridine alkaloids of Chelidonium majus; II. Potent inhibitory action against the growth of human keratinocytes.
PubMed:Benzophenanthridine alkaloids of Chelidonium majus; I. Inhibition of 5- and 12-lipoxygenase by a non-redox mechanism.
PubMed:Pharmacological activities of Chelidonium majus L. (Papaveraceae).
PubMed:Ukrain therapy in a frontal anaplastic grade III astrocytoma (case report).
PubMed:[The greater celandine (Chelidonium majus L.)--review of present knowledge].
PubMed:Antimicrotubule properties of benzophenanthridine alkaloids.
PubMed:[HPTLC separation and fluorodensitometric determination of isoquinoline alkaloids in Chelidonine majus L].
PubMed:Chelidonium majus L. (Ukrain) in the treatment of cancer patients.
PubMed:Stepwise gradient in thin-layer chromatography of Chelidonium alkaloids.
PubMed:Studies on the participation of the dopaminergic system in the central effects of chelidonine.
PubMed:Preliminary pharmacological evaluation of chelidonine in rodents.
PubMed:Separation and Quantification of Some Alkaloids from Fumaria parviflora by Capillary Isotachophoresis1.
PubMed:[Basic electron optical characteristics of chelidonine hydrochloride].
PubMed:THE ANTITUMOR FACTORS PRESENT IN CHELIDONIUM MAJUS L. I. CHELIDONINE AND PROTOPINE.
PubMed:[Partition of chelidonine and protopine by means of countercurrent cascade extraction].
PubMed:[On the pharmacology of chelidonine and sanguinarine].
PubMed:[Recent data on the pharmacology of chelidonine and sanguinarine].
PubMed:[The configurations of chelidonine and homchelidonine].
PubMed:Separation and determination of the dissociation constants of chelidonine and protopine by paper chromatography.
PubMed:[Chelidonine in liver and gallbladder diseases].
PubMed:[Studies on paper electrophoresis; paper electrophoresis of morphine and chelidonine in natural mixtures].
 
Notes:
benzophenanthridine derived from scoulerine from chelidonium majus.
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