Monocrotaline supplier | CasNO.315-22-0

Name
MONOCROTALINE
EINECS 628-506-2
CAS No. 315-22-0
Article Data5
CAS DataBase
Density 1.35 g/cm³
Solubility 11.86g/L(temperature not stated)
Melting Point 204 °C
Formula C₁₆H₂₃NO₆
Boiling Point 537.3 °C at 760 mmHg
Molecular Weight 325.362
Flash Point 278.7 °C
Transport Information UN 1544 6.1/PG 3
Appearance white to light tan powder
Safety 36/37/39-45
Risk Codes 25-40
Molecular Structure
Hazard Symbols T
Synonyms 20-Norcrotalanan-11,15-dione,14,19-dihydro-12,13-dihydroxy-, (13a,14a)-;Monocrotaline (6CI,7CI,8CI);(-)-Monocrotaline;2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione,4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-,[3R-(3R*,4R*,5R*,13aR*,13bR*)]-;Monocrotalin;NSC 28693;Monocrotaline;(13-alpha,14-alpha)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione;Crotaline;
PSA 96.30000
LogP -0.45470

Synthetic route

: 110121-56-7, 121719-98-0, 121720-00-1
monocrotaline methylene acetal

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
With trityl tetrafluoroborate In dichloromethane for 48h; Heating;	86%
With hydrogenchloride; trityl tetrafluoroborate 1.) CH2Cl2, reflux, 48 h, 2.) room temperature, 17.5 h; Yield given. Multistep reaction;

: 110121-56-7, 121719-98-0, 121720-00-1
C17H23NO6

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
With hydrogenchloride In ethylene glycol at 110℃; for 2h;	75%

: 35337-98-5
Monocrotaline N-oxide

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
With intestinal gut bacteria in a human fecal suspension at 37℃; for 5h; Enzymatic reaction;	38%

: 24583-56-0
grahamine

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
With hydrogenchloride

: 109391-24-4, 121787-06-2
(2R,3R,4R)-2,3,4-trimethyl-2,3-methylenedioxypentanedioic anhydride

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 2: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min 3: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 2: 64 percent / 4-(dimethylamino)pyridine, 4-(dimethylamino)pyridine hydrochloride, dicyclohexylcarbodiimide / CHCl3 / 85 h 3: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme

: 109494-78-2, 121787-04-0
(2R,3R,4R)-2,3,4-Trimethyl-2,3-(methylenedioxy)pentanedioic acid

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Ac2O / CH2Cl2 / 3.5 h / Heating 2: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 3: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min 4: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme
Multi-step reaction with 4 steps 1: Ac2O / CH2Cl2 / 3.5 h / Heating 2: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 3: 64 percent / 4-(dimethylamino)pyridine, 4-(dimethylamino)pyridine hydrochloride, dicyclohexylcarbodiimide / CHCl3 / 85 h 4: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme

: 121719-94-6
(2'R,3R,4S)-5-<2'-methoxy-2'-(trifluoromethyl)phenylacetoxy>-2,3,4-trimethyl-3,4-methylenedioxy-2-pentene

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 1) BH3THF, 2) 3 M NaOH, 30percent H2O2 / 1) THF, 0 deg C, 20 h, 2) THF, r.t., 3 h 2: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2 min, 2) CH2Cl2, -78 deg C, 1 h 3: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer 4: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature 5: Ac2O / CH2Cl2 / 3.5 h / Heating 6: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 7: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min 8: 86 percent / Ph3CBF4 / CH2Cl2 / 48 h / Heating View Scheme
Multi-step reaction with 8 steps 1: 1) BH3THF, 2) 3 M NaOH, 30percent H2O2 / 1) THF, 0 deg C, 20 h, 2) THF, r.t., 3 h 2: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2 min, 2) CH2Cl2, -78 deg C, 1 h 3: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer 4: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature 5: Ac2O / CH2Cl2 / 3.5 h / Heating 6: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 7: 64 percent / 4-(dimethylamino)pyridine, 4-(dimethylamino)pyridine hydrochloride, dicyclohexylcarbodiimide / CHCl3 / 85 h 8: 86 percent / Ph3CBF4 / CH2Cl2 / 48 h / Heating View Scheme

Yield

Multi-step reaction with 8 steps
1: 1) BH3*THF, 2) 3 M NaOH, 30percent H2O2 / 1) THF, 0 deg C, 20 h, 2) THF, r.t., 3 h
2: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2 min, 2) CH2Cl2, -78 deg C, 1 h
3: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer
4: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature
5: Ac2O / CH2Cl2 / 3.5 h / Heating
6: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t.
7: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min
8: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating
View Scheme

Multi-step reaction with 8 steps
1: 1) BH3*THF, 2) 3 M NaOH, 30percent H2O2 / 1) THF, 0 deg C, 20 h, 2) THF, r.t., 3 h
2: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2 min, 2) CH2Cl2, -78 deg C, 1 h
3: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer
4: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature
5: Ac2O / CH2Cl2 / 3.5 h / Heating
6: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t.
7: 64 percent / 4-(dimethylamino)pyridine, 4-(dimethylamino)pyridine hydrochloride, dicyclohexylcarbodiimide / CHCl3 / 85 h
8: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating
View Scheme

: 146070-68-0
(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (4S,5R)-4,5-dimethyl-5-((R)-1-methyl-2-oxo-ethyl)-[1,3]dioxolan-4-ylmethyl ester

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer 2: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature 3: Ac2O / CH2Cl2 / 3.5 h / Heating 4: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 5: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min 6: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme
Multi-step reaction with 6 steps 1: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer 2: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature 3: Ac2O / CH2Cl2 / 3.5 h / Heating 4: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 5: 64 percent / 4-(dimethylamino)pyridine, 4-(dimethylamino)pyridine hydrochloride, dicyclohexylcarbodiimide / CHCl3 / 85 h 6: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme

Yield

Multi-step reaction with 6 steps
1: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer
2: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature
3: Ac2O / CH2Cl2 / 3.5 h / Heating
4: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t.
5: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min
6: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating
View Scheme

Multi-step reaction with 6 steps
1: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer
2: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature
3: Ac2O / CH2Cl2 / 3.5 h / Heating
4: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t.
5: 64 percent / 4-(dimethylamino)pyridine, 4-(dimethylamino)pyridine hydrochloride, dicyclohexylcarbodiimide / CHCl3 / 85 h
6: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating
View Scheme

: 121719-96-8
(2'R,2S,3R,4S)-5-<2'-methoxy-2'-(trifluoromethyl)phenylacetoxy>-2,3,4-trimethyl-3,4-methylenedioxypentanoic acid

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature 2: Ac2O / CH2Cl2 / 3.5 h / Heating 3: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 4: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min 5: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme
Multi-step reaction with 5 steps 1: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature 2: Ac2O / CH2Cl2 / 3.5 h / Heating 3: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 4: 64 percent / 4-(dimethylamino)pyridine, 4-(dimethylamino)pyridine hydrochloride, dicyclohexylcarbodiimide / CHCl3 / 85 h 5: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme

Yield

Multi-step reaction with 5 steps
1: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature
2: Ac2O / CH2Cl2 / 3.5 h / Heating
3: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t.
4: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min
5: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating
View Scheme

Multi-step reaction with 5 steps
1: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature
2: Ac2O / CH2Cl2 / 3.5 h / Heating
3: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t.
4: 64 percent / 4-(dimethylamino)pyridine, 4-(dimethylamino)pyridine hydrochloride, dicyclohexylcarbodiimide / CHCl3 / 85 h
5: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating
View Scheme

: 121719-93-5, 121787-08-4
(2'R,3R,4S)-5-<2'-methoxy-2'-(trifluoromethyl)phenylacetoxy>-2,3,4-trimethyl-3,4-methylenedioxy-2-pentanol

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 83 percent / POCl3, pyridine / 17 h / 85 °C 2: 1) BH3THF, 2) 3 M NaOH, 30percent H2O2 / 1) THF, 0 deg C, 20 h, 2) THF, r.t., 3 h 3: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2 min, 2) CH2Cl2, -78 deg C, 1 h 4: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer 5: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature 6: Ac2O / CH2Cl2 / 3.5 h / Heating 7: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 8: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min 9: 86 percent / Ph3CBF4 / CH2Cl2 / 48 h / Heating View Scheme
Multi-step reaction with 9 steps 1: 83 percent / POCl3, pyridine / 17 h / 85 °C 2: 1) BH3THF, 2) 3 M NaOH, 30percent H2O2 / 1) THF, 0 deg C, 20 h, 2) THF, r.t., 3 h 3: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2 min, 2) CH2Cl2, -78 deg C, 1 h 4: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer 5: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature 6: Ac2O / CH2Cl2 / 3.5 h / Heating 7: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 8: 64 percent / 4-(dimethylamino)pyridine, 4-(dimethylamino)pyridine hydrochloride, dicyclohexylcarbodiimide / CHCl3 / 85 h 9: 86 percent / Ph3CBF4 / CH2Cl2 / 48 h / Heating View Scheme

Yield

Multi-step reaction with 9 steps
1: 83 percent / POCl3, pyridine / 17 h / 85 °C
2: 1) BH3*THF, 2) 3 M NaOH, 30percent H2O2 / 1) THF, 0 deg C, 20 h, 2) THF, r.t., 3 h
3: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2 min, 2) CH2Cl2, -78 deg C, 1 h
4: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer
5: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature
6: Ac2O / CH2Cl2 / 3.5 h / Heating
7: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t.
8: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min
9: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating
View Scheme

Multi-step reaction with 9 steps
1: 83 percent / POCl3, pyridine / 17 h / 85 °C
2: 1) BH3*THF, 2) 3 M NaOH, 30percent H2O2 / 1) THF, 0 deg C, 20 h, 2) THF, r.t., 3 h
3: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2 min, 2) CH2Cl2, -78 deg C, 1 h
4: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer
5: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature
6: Ac2O / CH2Cl2 / 3.5 h / Heating
7: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t.
8: 64 percent / 4-(dimethylamino)pyridine, 4-(dimethylamino)pyridine hydrochloride, dicyclohexylcarbodiimide / CHCl3 / 85 h
9: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating
View Scheme

: 121719-95-7, 121787-09-5
(2'R,2S,3R,4S)-5-<2'-methoxy-2'-(trifluoromethyl)phenylacetoxy>-2,3,4-trimethyl-3,4-methylenedioxy-1-pentanol

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2 min, 2) CH2Cl2, -78 deg C, 1 h 2: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer 3: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature 4: Ac2O / CH2Cl2 / 3.5 h / Heating 5: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 6: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min 7: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme
Multi-step reaction with 7 steps 1: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2 min, 2) CH2Cl2, -78 deg C, 1 h 2: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer 3: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature 4: Ac2O / CH2Cl2 / 3.5 h / Heating 5: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 6: 64 percent / 4-(dimethylamino)pyridine, 4-(dimethylamino)pyridine hydrochloride, dicyclohexylcarbodiimide / CHCl3 / 85 h 7: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme

Yield

Multi-step reaction with 7 steps
1: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2 min, 2) CH2Cl2, -78 deg C, 1 h
2: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer
3: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature
4: Ac2O / CH2Cl2 / 3.5 h / Heating
5: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t.
6: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min
7: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating
View Scheme

Multi-step reaction with 7 steps
1: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2 min, 2) CH2Cl2, -78 deg C, 1 h
2: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer
3: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature
4: Ac2O / CH2Cl2 / 3.5 h / Heating
5: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t.
6: 64 percent / 4-(dimethylamino)pyridine, 4-(dimethylamino)pyridine hydrochloride, dicyclohexylcarbodiimide / CHCl3 / 85 h
7: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating
View Scheme

: 121719-97-9
(4R,5R)-5-((R)-1-Carboxy-ethyl)-4,5-dimethyl-[1,3]dioxolane-4-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min 2: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 64 percent / 4-(dimethylamino)pyridine, 4-(dimethylamino)pyridine hydrochloride, dicyclohexylcarbodiimide / CHCl3 / 85 h 2: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme

: (4R,5S)-5-[(R)-2-(Diethoxy-phosphoryloxy)-1-methyl-2-oxo-ethyl]-4,5-dimethyl-[1,3]dioxolane-4-carboxylic acid 2-trimethylsilanyl-ethyl ester

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: tetrahydrofuran / Ambient temperature 2: 96 percent / 5percent aqueous HF / tetrahydrofuran 3: Et3N / CH2Cl2 4: 71 percent / Bu4N(1+)F(1-)*3H2O / acetonitrile / 34 °C 5: 75 percent / 38percent HCl / ethane-1,2-diol / 2 h / 110 °C View Scheme

: 109391-29-9
(4R,5S)-5-[(R)-1-((1R,7aR)-7-Hydroxymethyl-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yloxycarbonyl)-ethyl]-4,5-dimethyl-[1,3]dioxolane-4-carboxylic acid 2-trimethylsilanyl-ethyl ester

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N / CH2Cl2 2: 71 percent / Bu4N(1+)F(1-)*3H2O / acetonitrile / 34 °C 3: 75 percent / 38percent HCl / ethane-1,2-diol / 2 h / 110 °C View Scheme

: 109432-25-9
(4R,5S)-5-{(R)-1-[(1R,7aR)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yloxycarbonyl]-ethyl}-4,5-dimethyl-[1,3]dioxolane-4-carboxylic acid 2-trimethylsilanyl-ethyl ester

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 96 percent / 5percent aqueous HF / tetrahydrofuran 2: Et3N / CH2Cl2 3: 71 percent / Bu4N(1+)F(1-)*3H2O / acetonitrile / 34 °C 4: 75 percent / 38percent HCl / ethane-1,2-diol / 2 h / 110 °C View Scheme

: (4R,5S)-5-[(R)-1-((1R,7aR)-7-Methanesulfonyloxymethyl-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yloxycarbonyl)-ethyl]-4,5-dimethyl-[1,3]dioxolane-4-carboxylic acid 2-trimethylsilanyl-ethyl ester

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / Bu4N(1+)F(1-)*3H2O / acetonitrile / 34 °C 2: 75 percent / 38percent HCl / ethane-1,2-diol / 2 h / 110 °C View Scheme

: 89710-47-4
Lithium; (1R,7aR)-7-(tert-butyl-dimethyl-silanyloxymethyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-olate

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: tetrahydrofuran / Ambient temperature 2: 96 percent / 5percent aqueous HF / tetrahydrofuran 3: Et3N / CH2Cl2 4: 71 percent / Bu4N(1+)F(1-)*3H2O / acetonitrile / 34 °C 5: 75 percent / 38percent HCl / ethane-1,2-diol / 2 h / 110 °C View Scheme

: (4R,5R)-5-((R)-1-Carboxy-ethyl)-4,5-dimethyl-[1,3]dioxolane-4-carboxylic acid (7R,7aS)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-yl ester

: 315-22-0
monocrotaline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) 2,4,6-trichlorobenzoyl chloride, 2.) 4-dimethylaminopyridine / 1.) THF, room temperature, 3.5 h, 2.) toluene, reflux, 10 min 2: 1.) Ph3CBF4, 2.) 1M HCl / 1.) CH2Cl2, reflux, 48 h, 2.) room temperature, 17.5 h View Scheme

: 315-22-0
monocrotaline

: 480-85-3
retronecine

Conditions

Conditions	Yield
With methanol; potassium hydroxide at 100℃; for 0.0833333h; Microwave irradiation;	99%
With barium dihydroxide In water 1.) from 40 deg C to 50 deg C, 2 h, 2.) reflux, 2 h;	91%
With barium dihydroxide for 2h; heating;	81%

: 315-22-0
monocrotaline

: 567-39-5
retronecanol

Conditions

Conditions	Yield
With platinum(IV) oxide; hydrogen In water; isopropyl alcohol at 80℃; under 750.075 Torr; Solvent; Pressure; Temperature; Flow reactor;	61%

: 315-22-0
monocrotaline

: 26543-09-9
Monocrotalic acid

Conditions

Conditions	Yield
With ethanol; acetic acid; platinum Hydrogenation;
With ethanol; nickel Hydrogenation;

: 315-22-0
monocrotaline

: 6029-72-7
1,2-didehydro-7β-hydroxy-1-methyl-8α-pyrrolizidine

Conditions

Conditions	Yield
With quinoline; Pd/SrCO3; ethanol Hydrogenation;

: 315-22-0
monocrotaline

: 35337-98-5
Monocrotaline N-oxide

Conditions

Conditions	Yield
With ethanol; dihydrogen peroxide
With dihydrogen peroxide

: 315-22-0
monocrotaline

A: 520-55-8
spectabiline

B: 25490-68-0
12,13-diacetoxy-(13βH,14βH)-14,19-dihydro-20-nor-crotalanane-11,15-dione

Conditions

Conditions	Yield
With acetyl chloride

: 315-22-0
monocrotaline

: 77057-77-3
12,13-[(Ξ)-sulfinyldioxy-(13βH,14βH)-14,19-dihydro-20-nor-crotalanan-11,15-dione

Conditions

Conditions	Yield
With thionyl chloride

: 315-22-0
monocrotaline

: (7aR)-7t-methyl-(7ar)-hexahydro-pyrrolizin-1t-ol; salt with monocrotalic acid

Conditions

Conditions	Yield
With ethanol; acetic acid; platinum under 2206.5 Torr; Hydration;
With ethanol; nickel under 2206.5 Torr; Hydration;

: 315-22-0
monocrotaline

A: 526-79-4
2,3-dimethyl-4-oxo-valeric acid

B: 480-85-3
retronecine

Conditions

Conditions	Yield
With barium dihydroxide; water

: 108-24-7
acetic anhydride

: 315-22-0
monocrotaline

: 25490-68-0
12,13-diacetoxy-(13βH,14βH)-14,19-dihydro-20-nor-crotalanane-11,15-dione

Conditions

Conditions	Yield
With acetyl chloride

: 315-22-0
monocrotaline

: 2,3,4-trimethyl-L-2-deoxy-arabinitol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran

: 315-22-0
monocrotaline

: 109494-78-2, 121787-04-0
(2R,3R,4R)-2,3,4-Trimethyl-2,3-(methylenedioxy)pentanedioic acid

Conditions

Conditions	Yield
Multistep reaction;

: 315-22-0
monocrotaline

A: 520-55-8
spectabiline

B O,O'-diacetyl-monocrotaline: O,O'-diacetyl-monocrotaline

Conditions

Conditions	Yield
With acetyl chloride

: 463-51-4
Ketene

: 315-22-0
monocrotaline

A: 76971-16-9
12,13-carbonyldioxy-(13βH,14βH)-14,19-dihydro-20-nor-crotalanan-11,15-dione

B spectabiline: spectabiline

Conditions

Conditions	Yield
With chloroform

...Expand

: 315-22-0
monocrotaline

: 23107-12-2
Dehydroretronecine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / Ba(OH)2*8H2O / 2 h / heating 2: 40 percent / o-bromanil / CHCl3 / 0.03 h View Scheme

: 315-22-0
monocrotaline

: 103958-13-0
5'-monophosphate of 7-(deoxyguanosin-N2-yl)dehydrosupinidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / Ba(OH)2*8H2O / 2 h / heating 2: 40 percent / o-bromanil / CHCl3 / 0.03 h 3: 0.9 percent / aq. K2CO3 / 6 h / 60 °C / pH 7.4 View Scheme

: 315-22-0
monocrotaline

: hydroquinone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / Ba(OH)2*8H2O / 2 h / heating 2: o-bromanil / CHCl3 / 0.03 h View Scheme

: 315-22-0
monocrotaline

: 3'-monophosphate of 7-(deoxyadenosine-N6-yl)dehydrosupinidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / Ba(OH)2*8H2O / 2 h / heating 2: 40 percent / o-bromanil / CHCl3 / 0.03 h 3: aq. K2CO3 / 40 h / 60 °C / pH 8.0 View Scheme

: 315-22-0
monocrotaline

: 612490-81-0
3'-monophosphate of 7-(deoxyguanosin-N2-yl)dehydrosupinidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / Ba(OH)2*8H2O / 2 h / heating 2: 40 percent / o-bromanil / CHCl3 / 0.03 h 3: 2.5 percent / aq. K2CO3 / 6 h / 60 °C / pH 8.0 / stirred anaerobically View Scheme

: 315-22-0
monocrotaline

: 3',5'-bisphosphate of 7-(deoxyguanosin-N2-yl)dehydrosupinidine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 81 percent / Ba(OH)2*8H2O / 2 h / heating 2: 40 percent / o-bromanil / CHCl3 / 0.03 h 3: 2.5 percent / aq. K2CO3 / 6 h / 60 °C / pH 8.0 / stirred anaerobically 4: dithiotreitol; ATP; MgCl2 / cloned T4 polynucleotide kinase / H2O / 0.67 h / 37 °C / pH 9.5 View Scheme

: 315-22-0
monocrotaline

: 520-62-7
platynecine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Ba(OH)2 / H2O / 1 h / Heating 2: 20 mg / hydrogen / Pd/C / ethanol / 2 h View Scheme
Multi-step reaction with 2 steps 1: potassium hydroxide; methanol / 0.08 h / 100 °C / Microwave irradiation 2: hydrogen / ethanol / 50 °C / 750.08 Torr / Flow reactor View Scheme

: 315-22-0
monocrotaline

: 154922-76-6
(7R,7aR)-7-Hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizine-1-carbaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / Ba(OH)2*8H2O / H2O / 1.) from 40 deg C to 50 deg C, 2 h, 2.) reflux, 2 h 2: Dess-Martin periodinane, CF3COOH / CH2Cl2 / 1 h View Scheme

: 315-22-0
monocrotaline

: <9-2H>-retronecine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 91 percent / Ba(OH)2*8H2O / H2O / 1.) from 40 deg C to 50 deg C, 2 h, 2.) reflux, 2 h 2: Dess-Martin periodinane, CF3COOH / CH2Cl2 / 1 h 3: NaB(2)H4 / methanol / 0.5 h / 0 °C View Scheme

Monocrotaline Consensus Reports

IARC Cancer Review: Group 2B IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 10 ,1976,p. 291.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program.

Monocrotaline Specification

The systematic name of Monocrotaline is (3R,4R,5R,13aR,13bR)-4,5-dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione. With the CAS registry number 315-22-0, it is also named as (13-alpha,14-alpha)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione. The product's category is Miscellaneous Natural Products. Besides, it is white to light tan powder, which should be stored in sealed and dry place at 2-8 °C. This chemical is anticarcinoma drug that is used for biochemical research. In addition, its molecular formula is C₁₆H₂₃NO₆ and molecular weight is 325.35692.

Physical properties about Monocrotaline are: (1)ACD/LogP: -4.137; (2)ACD/LogD (pH 5.5): -4.76; (3)ACD/LogD (pH 7.4): -4.15; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 7; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.586; (12)Molar Refractivity: 80.3 cm³; (13)Molar Volume: 239.352 cm³; (14)Polarizability: 31.834 10-24cm³; (15)Surface Tension: 59.2760009765625 dyne/cm; (16)Density: 1.359 g/cm³; (17)Flash Point: 278.731 °C; (18)Enthalpy of Vaporization: 93.63 kJ/mol; (19)Boiling Point: 537.27 °C at 760 mmHg

When you are using this chemical, please be cautious about it as the following: it is toxic if swallowed. Limited evidence of a carcinogenic effect. You should wear suitable protective clothing, gloves and eye/face protection. Moreover, in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

You can still convert the following datas into molecular structure:
(1)InChI=1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-/m0/s1;
(2)InChIKey=QVCMHGGNRFRMAD-XFGHUUIASA-N;
(3)Smiles[C@@H]12[C@H]3CCN1CC=C2COC(=O)[C@]([C@]([C@H](C(=O)O3)C)(C)O)(C)O

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mammal (species unspecified)	LDLo	unreported	60mg/kg (60mg/kg)		Pharmacological Reviews. Vol. 22, Pg. 429, 1970.
mouse	LD50	intraperitoneal	259mg/kg (259mg/kg)		Toxicology and Applied Pharmacology. Vol. 59, Pg. 424, 1981.
mouse	LD50	intravenous	261mg/kg (261mg/kg)		Journal of Pharmacology and Experimental Therapeutics. Vol. 75, Pg. 78, 1942.
rat	LD50	intravenous	92mg/kg (92mg/kg)		Journal of Pharmacology and Experimental Therapeutics. Vol. 83, Pg. 265, 1945.
rat	LD50	oral	66mg/kg (66mg/kg)	LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"	Toxicology and Applied Pharmacology. Vol. 18, Pg. 387, 1971.
rat	LD50	subcutaneous	60mg/kg (60mg/kg)		Toxicology and Applied Pharmacology. Vol. 23, Pg. 470, 1972.
rat	LD50	unreported	60mg/kg (60mg/kg)		Cancer Research. Vol. 28, Pg. 2237, 1968.
rat	LDLo	intraperitoneal	130mg/kg (130mg/kg)	LIVER: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Chemico-Biological Interactions. Vol. 12, Pg. 299, 1976.

Product Name

MONOCROTALINE

Synthetic route

Monocrotaline Consensus Reports

Monocrotaline Specification

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