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Cicutoxin
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Name

Cicutoxin

 EINECS N/A
CAS No. 505-75-9 Density 1.025g/cm3
PSA 40.46000 LogP 2.59530
Solubility N/A Melting Point 54°
Formula C17H22 O2 Boiling Point 467.2°Cat760mmHg
Molecular Weight 258.36 Flash Point 218.3°C
Transport Information N/A Appearance N/A
Safety Poison by ingestion, intravenous, and possibly other routes. When heated to decomposition it emits acrid smoke and irritating fumes. Risk Codes N/A
Molecular Structure Molecular Structure of 505-75-9 (cicutoxin) Hazard Symbols N/A
Synonyms

8,10,12-Heptadecatriene-4,6-diyne-1,14-diol,(E,E,E)-(-)-; Cicutoxin (6CI,7CI,8CI); (R)-(-)-Cicutoxin; NSC 606489

Article Data 4

Cicutoxin Synthetic route

1150616-77-5

(4R,5E,7E,9E)‐17‐((tetrahydro‐2H‐pyran‐2‐yl)oxy)heptadeca‐5,7,9‐trien‐11,13‐diyn‐4‐ol

505-75-9

Cicutotoxin

Conditions
ConditionsYield
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%
1001587-76-3

7-bromohepta-4,6-diyn-1-ol

1265526-17-7

(4R,5E,7E,9E)-10-(tributylstannyl)deca-5,7,9-trien-4-ol

505-75-9

Cicutotoxin

Conditions
ConditionsYield
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;
1265526-19-9

7-iodohepta-4,6-diyn-1-ol

1265526-17-7

(4R,5E,7E,9E)-10-(tributylstannyl)deca-5,7,9-trien-4-ol

505-75-9

Cicutotoxin

Conditions
ConditionsYield
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;
5390-04-5

pent-1-yn-5-ol

505-75-9

Cicutotoxin

Conditions
ConditionsYield
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
83670-22-8

7-(trimethylsilyl)hepta-4,6-diyn-1-ol

505-75-9

Cicutotoxin

Conditions
ConditionsYield
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
94230-39-4

5-iodo-4-pentyn-1-ol

505-75-9

Cicutotoxin

Conditions
ConditionsYield
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
646534-13-6

(E)-7-chlorohept-6-en-4-yn-1-ol

505-75-9

Cicutotoxin

Conditions
ConditionsYield
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

(5E,7E,9E)‐17‐((tetrahydro‐2H‐pyran‐2‐yl)oxy)heptadeca‐5,7,9‐trien‐11,13‐diyn‐4‐one

505-75-9

Cicutotoxin

Conditions
ConditionsYield
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

C17H20O4

505-75-9

Cicutotoxin

Conditions
ConditionsYield
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

C17H20O3

505-75-9

Cicutotoxin

Conditions
ConditionsYield
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

Cicutoxin Chemical Properties

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
 

Cicutoxin Toxicity Data With Reference

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.

Cicutoxin Safety Profile

Poison by ingestion, intravenous, and possibly other routes. When heated to decomposition it emits acrid smoke and irritating fumes.

Cicutoxin Specification

 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.

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