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CAS No.: | 505-75-9 |
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Name: | cicutoxin |
Article Data: | 4 |
Molecular Structure: | |
Formula: | C17H22 O2 |
Molecular Weight: | 258.36 |
Synonyms: | 8,10,12-Heptadecatriene-4,6-diyne-1,14-diol,(E,E,E)-(-)-; Cicutoxin (6CI,7CI,8CI); (R)-(-)-Cicutoxin; NSC 606489 |
Density: | 1.025g/cm3 |
Melting Point: | 54° |
Boiling Point: | 467.2°Cat760mmHg |
Flash Point: | 218.3°C |
Safety: | Poison by ingestion, intravenous, and possibly other routes. When heated to decomposition it emits acrid smoke and irritating fumes. |
PSA: | 40.46000 |
LogP: | 2.59530 |
(4R,5E,7E,9E)‐17‐((tetrahydro‐2H‐pyran‐2‐yl)oxy)heptadeca‐5,7,9‐trien‐11,13‐diyn‐4‐ol
Cicutotoxin
Conditions | Yield |
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With toluene-4-sulfonic acid In methanol at 20℃; for 0.5h; Inert atmosphere; | 61% |
With toluene-4-sulfonic acid In methanol at 20℃; for 1.5h; Darkness; | 53% |
7-bromohepta-4,6-diyn-1-ol
(4R,5E,7E,9E)-10-(tributylstannyl)deca-5,7,9-trien-4-ol
Cicutotoxin
Conditions | Yield |
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With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium fluoride; copper(l) iodide; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol In 1-methyl-pyrrolidin-2-one at 45℃; for 3.5h; Stille coupling; Inert atmosphere; |
7-iodohepta-4,6-diyn-1-ol
(4R,5E,7E,9E)-10-(tributylstannyl)deca-5,7,9-trien-4-ol
Cicutotoxin
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; copper(l) iodide; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol In tetrahydrofuran at 20 - 45℃; for 5h; Stille coupling; Inert atmosphere; |
Conditions | Yield |
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Multi-step reaction with 4 steps 1: iodine; potassium hydroxide / methanol; water / 7 h / 20 °C 2: piperidine; copper(l) chloride / 1 h / 0 °C / Inert atmosphere; Neat (no solvent) 3: N-Bromosuccinimide; silver nitrate / acetone / 18 h / 20 °C / Inert atmosphere; Darkness 4: copper(l) iodide; potassium fluoride; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol / 1-methyl-pyrrolidin-2-one / 3.5 h / 45 °C / Inert atmosphere View Scheme |
7-(trimethylsilyl)hepta-4,6-diyn-1-ol
Cicutotoxin
Conditions | Yield |
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Multi-step reaction with 2 steps 1: N-Bromosuccinimide; silver nitrate / acetone / 18 h / 20 °C / Inert atmosphere; Darkness 2: copper(l) iodide; potassium fluoride; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol / 1-methyl-pyrrolidin-2-one / 3.5 h / 45 °C / Inert atmosphere View Scheme |
5-iodo-4-pentyn-1-ol
Cicutotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: piperidine; copper(l) chloride / 1 h / 0 °C / Inert atmosphere; Neat (no solvent) 2: N-Bromosuccinimide; silver nitrate / acetone / 18 h / 20 °C / Inert atmosphere; Darkness 3: copper(l) iodide; potassium fluoride; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol / 1-methyl-pyrrolidin-2-one / 3.5 h / 45 °C / Inert atmosphere View Scheme |
(E)-7-chlorohept-6-en-4-yn-1-ol
Cicutotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 3 h / -20 °C / Inert atmosphere 1.2: 0.5 h / Inert atmosphere 2.1: copper(l) iodide; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol / tetrahydrofuran / 5 h / 20 - 45 °C / Inert atmosphere View Scheme |
Cicutotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / -50 °C 2: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Darkness View Scheme |
Cicutotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 12 h / 20 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.5 h / 20 °C / Schlenk technique 2.2: 12 h 3.1: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 °C / Darkness; Schlenk technique 4.1: barium(II) hydroxide / tetrahydrofuran; water / 0.5 h / 20 °C / Schlenk technique; Darkness 5.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / -50 °C 6.1: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Darkness View Scheme |
Cicutotoxin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: barium(II) hydroxide / tetrahydrofuran; water / 0.5 h / 20 °C / Schlenk technique; Darkness 2: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / -50 °C 3: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Darkness View Scheme |
IUPAC Name: (8E,10E,12E)-Heptadeca-8,10,12-trien-4,6-diyne-1,14-diol
Synonyms of Cicutoxin (CAS NO.505-75-9) : (E,E,E)-(-)-8,10,12-Heptadecatriene-4,6-diyne-1,14-diol ; (8E,10E,12E)-Heptadeca-8,10,12-triene-4,6-diyne-1,14-diol ; 8,10,12-Heptadecatriene-4,6-diyne-1,14-diol, (E,E,E)-(-)- ; Cicutoxin ; trans-Heptadeca-8,10,12-triene-4,6-diyne-1,14-diol
CAS NO:505-75-9
Molecular Formula:C17H22O2
Molecular Weight :258.3554
Molecular Structure :
Index of Refraction: 1.547
Surface Tension: 46.2 dyne/cm
Density: 1.025 g/cm3
Flash Point: 218.4 °C
Enthalpy of Vaporization: 84.07 kJ/mol
Boiling Point: 467.2 °C at 760 mmHg
Vapour Pressure: 1.08E-10 mmHg at 25°C
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LDLo | intravenous | 5360ug/kg (5.36mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 52, Pg. 29S, 1956. | |
cat | LDLo | oral | 7mg/kg (7mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935. | |
frog | LDLo | unreported | 61mg/kg (61mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935. | |
mouse | LD50 | intraperitoneal | 48300ug/kg (48.3mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 52, Pg. 29S, 1956. |
Poison by ingestion, intravenous, and possibly other routes. When heated to decomposition it emits acrid smoke and irritating fumes.
Cicutoxin (CAS NO.505-75-9) is a poisonous polyyne and alcohol found in various plants, most notably water hemlock (Cicuta species). It is structurally related to the oenanthotoxin of hemlock water dropwort.
Cicutoxin (CAS NO.505-75-9) causes death by disruption of the central nervous system. It is a potent, noncompetitive gamma-aminobutyric acid (GABA) receptor antagonist. In humans, cicutoxin rapidly produces symptoms of nausea, emesis and abdominal pain, typically within 60 minutes of ingestion. This can lead to tremors, seizures, and death.