Product Name

  • Name

    cicutoxin

  • EINECS
  • CAS No. 505-75-9
  • Article Data4
  • CAS DataBase
  • Density 1.025g/cm3
  • Solubility
  • Melting Point 54°
  • Formula C17H22 O2
  • Boiling Point 467.2°Cat760mmHg
  • Molecular Weight 258.36
  • Flash Point 218.3°C
  • Transport Information
  • Appearance
  • Safety Poison by ingestion, intravenous, and possibly other routes. When heated to decomposition it emits acrid smoke and irritating fumes.
  • Risk Codes
  • Molecular Structure Molecular Structure of 505-75-9 (cicutoxin)
  • Hazard Symbols
  • Synonyms 8,10,12-Heptadecatriene-4,6-diyne-1,14-diol,(E,E,E)-(-)-; Cicutoxin (6CI,7CI,8CI); (R)-(-)-Cicutoxin; NSC 606489
  • PSA 40.46000
  • LogP 2.59530

Synthetic route

(4R,5E,7E,9E)‐17‐((tetrahydro‐2H‐pyran‐2‐yl)oxy)heptadeca‐5,7,9‐trien‐11,13‐diyn‐4‐ol
1150616-77-5

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

Cicutotoxin
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%
7-bromohepta-4,6-diyn-1-ol
1001587-76-3

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

(4R,5E,7E,9E)-10-(tributylstannyl)deca-5,7,9-trien-4-ol
1265526-17-7

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

Cicutotoxin
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;
7-iodohepta-4,6-diyn-1-ol
1265526-19-9

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

(4R,5E,7E,9E)-10-(tributylstannyl)deca-5,7,9-trien-4-ol
1265526-17-7

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

Cicutotoxin
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;
pent-1-yn-5-ol
5390-04-5

pent-1-yn-5-ol

Cicutotoxin
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
7-(trimethylsilyl)hepta-4,6-diyn-1-ol
83670-22-8

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

Cicutotoxin
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
5-iodo-4-pentyn-1-ol
94230-39-4

5-iodo-4-pentyn-1-ol

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

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

Cicutotoxin
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

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

Cicutotoxin
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

C17H20O4

Cicutotoxin
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

C17H20O3

Cicutotoxin
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
2‐(hepta‐4,6‐diyn‐1‐yloxy)tetrahydro‐2H‐pyran
159646-46-5

2‐(hepta‐4,6‐diyn‐1‐yloxy)tetrahydro‐2H‐pyran

Cicutotoxin
505-75-9

Cicutotoxin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: methyllithium / tetrahydrofuran; diethyl ether / 0.5 h / Schlenk technique
1.2: 1 h / -78 °C
1.3: 4 h / -78 - 20 °C
2.1: 12 h / 20 °C
3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.5 h / 20 °C / Schlenk technique
3.2: 12 h
4.1: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 °C / Darkness; Schlenk technique
5.1: barium(II) hydroxide / tetrahydrofuran; water / 0.5 h / 20 °C / Schlenk technique; Darkness
6.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / -50 °C
7.1: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Darkness
View Scheme
(2E,4E)‐12‐((tetrahydro‐2H‐pyran‐2‐yl) oxy)dodeca‐2,4‐dien‐6,8‐diynoic acid

(2E,4E)‐12‐((tetrahydro‐2H‐pyran‐2‐yl) oxy)dodeca‐2,4‐dien‐6,8‐diynoic acid

Cicutotoxin
505-75-9

Cicutotoxin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.5 h / 20 °C / Schlenk technique
1.2: 12 h
2.1: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 °C / Darkness; Schlenk technique
3.1: barium(II) hydroxide / tetrahydrofuran; water / 0.5 h / 20 °C / Schlenk technique; Darkness
4.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / -50 °C
5.1: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Darkness
View Scheme
(2E,4E)‐N‐methoxy‐N‐methyl‐12-((tetrahydro‐2H‐pyran‐2‐yl)oxy)dodeca‐2,4‐dien‐6,8‐diyne amide

(2E,4E)‐N‐methoxy‐N‐methyl‐12-((tetrahydro‐2H‐pyran‐2‐yl)oxy)dodeca‐2,4‐dien‐6,8‐diyne amide

Cicutotoxin
505-75-9

Cicutotoxin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 °C / Darkness; Schlenk technique
2: barium(II) hydroxide / tetrahydrofuran; water / 0.5 h / 20 °C / Schlenk technique; Darkness
3: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / -50 °C
4: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Darkness
View Scheme
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Cicutotoxin
505-75-9

Cicutotoxin

(5E,7E,9E)-(R)-17-(tert-Butyl-dimethyl-silanyloxy)-heptadeca-5,7,9-triene-11,13-diyn-4-ol

(5E,7E,9E)-(R)-17-(tert-Butyl-dimethyl-silanyloxy)-heptadeca-5,7,9-triene-11,13-diyn-4-ol

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0℃; for 3h; Substitution;80%
(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride
39637-99-5, 20445-33-4

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride

Cicutotoxin
505-75-9

Cicutotoxin

(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (2E,4E,6E)-(R)-1-propyl-14-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-tetradeca-2,4,6-triene-8,10-diynyl ester

(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (2E,4E,6E)-(R)-1-propyl-14-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-tetradeca-2,4,6-triene-8,10-diynyl ester

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 5h; Esterification;76%
acetic anhydride
108-24-7

acetic anhydride

Cicutotoxin
505-75-9

Cicutotoxin

A

Acetic acid (8E,10E,12E)-(R)-14-hydroxy-heptadeca-8,10,12-triene-4,6-diynyl ester

Acetic acid (8E,10E,12E)-(R)-14-hydroxy-heptadeca-8,10,12-triene-4,6-diynyl ester

B

Acetic acid (2E,4E,6E)-(R)-14-acetoxy-1-propyl-tetradeca-2,4,6-triene-8,10-diynyl ester

Acetic acid (2E,4E,6E)-(R)-14-acetoxy-1-propyl-tetradeca-2,4,6-triene-8,10-diynyl ester

C

Acetic acid (2E,4E,6E)-(R)-14-hydroxy-1-propyl-tetradeca-2,4,6-triene-8,10-diynyl ester

Acetic acid (2E,4E,6E)-(R)-14-hydroxy-1-propyl-tetradeca-2,4,6-triene-8,10-diynyl ester

Conditions
ConditionsYield
With pyridine at 0℃; for 8.3h;A 55%
B 23%
C 10%
...Expand
Cicutotoxin
505-75-9

Cicutotoxin

methyl iodide
74-88-4

methyl iodide

A

(8E,10E,12E)-(R)-1,14-Dimethoxy-heptadeca-8,10,12-triene-4,6-diyne

(8E,10E,12E)-(R)-1,14-Dimethoxy-heptadeca-8,10,12-triene-4,6-diyne

B

(14R)-(8E,10E,12E)-14-methoxyheptadecatriene-4,6-diyn-1-ol

(14R)-(8E,10E,12E)-14-methoxyheptadecatriene-4,6-diyn-1-ol

C

(5E,7E,9E)-(R)-17-Methoxy-heptadeca-5,7,9-triene-11,13-diyn-4-ol

(5E,7E,9E)-(R)-17-Methoxy-heptadeca-5,7,9-triene-11,13-diyn-4-ol

Conditions
ConditionsYield
With potassium hydroxide In N,N-dimethyl-formamide at 0℃; for 0.166667h;A 27%
B 5%
C 24%
...Expand
Cicutotoxin
505-75-9

Cicutotoxin

A

17-hydroxy-heptadeca-5t,7t,9t-triene-11,13-diyn-4-one
25525-18-2

17-hydroxy-heptadeca-5t,7t,9t-triene-11,13-diyn-4-one

B

(8E,10E,12E)-14-oxoheptadecatriene-4,6-diyn-1-al

(8E,10E,12E)-14-oxoheptadecatriene-4,6-diyn-1-al

C

(8E,10E,12E)-(R)-14-Hydroxy-heptadeca-8,10,12-triene-4,6-diynal
321655-32-7

(8E,10E,12E)-(R)-14-Hydroxy-heptadeca-8,10,12-triene-4,6-diynal

Conditions
ConditionsYield
With pyridine-SO3 complex; dimethyl sulfoxide; triethylamine In dichloromethane at 0℃; for 4h;A 8%
B 16%
C 13%
...Expand
(R)-methoxytrifluoromethylphenylacetyl chloride
20445-33-4, 39637-99-5

(R)-methoxytrifluoromethylphenylacetyl chloride

Cicutotoxin
505-75-9

Cicutotoxin

(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (2E,4E,6E)-(R)-1-propyl-14-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-tetradeca-2,4,6-triene-8,10-diynyl ester

(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (2E,4E,6E)-(R)-1-propyl-14-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-tetradeca-2,4,6-triene-8,10-diynyl ester

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 5h; Esterification;
Cicutotoxin
505-75-9

Cicutotoxin

(8E,10E,12E)-(R)-14-Hydroxy-heptadeca-8,10,12-triene-4,6-diynoic acid
321655-37-2

(8E,10E,12E)-(R)-14-Hydroxy-heptadeca-8,10,12-triene-4,6-diynoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 13 percent / DMSO; SO3*pyridine; Et3N / CH2Cl2 / 4 h / 0 °C
2: 71 percent / KOH; I2 / 0.25 h / 0 °C
3: 75 percent / 1 N aq. NaOH / methanol / 9 h / 20 °C
View Scheme
Cicutotoxin
505-75-9

Cicutotoxin

(8E,10E,12E)-(R)-14-Hydroxy-heptadeca-8,10,12-triene-4,6-diynoic acid methyl ester
321655-36-1

(8E,10E,12E)-(R)-14-Hydroxy-heptadeca-8,10,12-triene-4,6-diynoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 13 percent / DMSO; SO3*pyridine; Et3N / CH2Cl2 / 4 h / 0 °C
2: 71 percent / KOH; I2 / 0.25 h / 0 °C
View Scheme
Cicutotoxin
505-75-9

Cicutotoxin

(8E,10E,12E)-(R)-14-Hydroxy-heptadeca-8,10,12-triene-4,6-diynoic acid amide

(8E,10E,12E)-(R)-14-Hydroxy-heptadeca-8,10,12-triene-4,6-diynoic acid amide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 13 percent / DMSO; SO3*pyridine; Et3N / CH2Cl2 / 4 h / 0 °C
2: 71 percent / KOH; I2 / 0.25 h / 0 °C
3: 75 percent / 1 N aq. NaOH / methanol / 9 h / 20 °C
4: 63 percent / NH4Cl; DPPA; Et3N / dimethylformamide / 8.5 h / 0 °C
View Scheme
Cicutotoxin
505-75-9

Cicutotoxin

(8E,10E,12E)-(R)-14-Hydroxy-heptadeca-8,10,12-triene-4,6-diynoic acid butylamide

(8E,10E,12E)-(R)-14-Hydroxy-heptadeca-8,10,12-triene-4,6-diynoic acid butylamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 13 percent / DMSO; SO3*pyridine; Et3N / CH2Cl2 / 4 h / 0 °C
2: 71 percent / KOH; I2 / 0.25 h / 0 °C
3: 75 percent / 1 N aq. NaOH / methanol / 9 h / 20 °C
4: 70 percent / DPPA; Et3N / dimethylformamide / 9.5 h / 0 °C
View Scheme
Cicutotoxin
505-75-9

Cicutotoxin

4-Methoxy-benzoic acid (2E,4E,6E)-(R)-14-(tert-butyl-dimethyl-silanyloxy)-1-propyl-tetradeca-2,4,6-triene-8,10-diynyl ester

4-Methoxy-benzoic acid (2E,4E,6E)-(R)-14-(tert-butyl-dimethyl-silanyloxy)-1-propyl-tetradeca-2,4,6-triene-8,10-diynyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / Et3N, DMAP / CH2Cl2 / 3 h / 0 °C
2: 94 percent / Et3N, DMAP / CH2Cl2 / 3 h / 0 °C
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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