CAS No.505-75-9,cicutoxin Suppliers

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Basic Information

Molecular Structure:
CAS No.:	505-75-9
Name:	cicutoxin
Article Data:	4

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

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

Conditions	Yield
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

Conditions	Yield
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

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;

: 5390-04-5
pent-1-yn-5-ol

: 505-75-9
Cicutotoxin

Conditions

Conditions	Yield
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

Yield

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

Conditions	Yield
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

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

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

: 646534-13-6
(E)-7-chlorohept-6-en-4-yn-1-ol

: 505-75-9
Cicutotoxin

Conditions

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

: (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

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

: C17H20O4

: 505-75-9
Cicutotoxin

Conditions

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

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

: C17H20O3

: 505-75-9
Cicutotoxin

Conditions

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

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Chemistry

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

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	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.

Safety Profile

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

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.