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Catharanthine

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Name

Catharanthine

EINECS 219-586-6
CAS No. 2468-21-5 Density 1.27 g/cm3
PSA 45.33000 LogP 3.11320
Solubility N/A Melting Point 138-140 °C
Formula C21H24N2O2 Boiling Point 491.5 °C at 760 mmHg
Molecular Weight 336.434 Flash Point 251.1 °C
Transport Information N/A Appearance off-white to pale beige solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 2468-21-5 (Catharanthine) Hazard Symbols N/A
Synonyms

Catharanthine(6CI,7CI,8CI);(+)-3,4-Didehydrocoronaridine;(+)-Catharanthine;Ibogamine-18-carboxylicacid, 3,4-didehydro-, methyl ester, (2a,5b,6a,18b)-;Catharanthine, (+)-;

Article Data 9

Catharanthine Synthetic route

105729-49-5

(16R)-5-oxo-catharanthine

2468-21-5

catharinthine

Conditions
ConditionsYield
With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran for 2h; Ambient temperature;96.2%
87-51-4

indole-3-acetic acid

2468-21-5

catharinthine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine / dimethylformamide / 0.33 h / -10 - -5 °C
2: triethylamine / dimethylformamide / 24 h
3: 29.5 percent / NaBH4, tributyltin chloride / methanol / Irradiation
4: 96.2 percent / NaBH4, boron trifluoride etherate / tetrahydrofuran / 2 h / Ambient temperature
View Scheme
125213-31-2

C15H17NO3

2468-21-5

catharinthine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / dimethylformamide / 24 h
2: 29.5 percent / NaBH4, tributyltin chloride / methanol / Irradiation
3: 96.2 percent / NaBH4, boron trifluoride etherate / tetrahydrofuran / 2 h / Ambient temperature
View Scheme
129030-48-4

(-)-2-(1-<2-(indol-3-yl)-1-oxo-ethyl>)-6-ethyl-7-exo-chloro-2-azabicyclo<2.2.2>oct-5-ene-7-endo-carboxylic acid methyl ester

2468-21-5

catharinthine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 29.5 percent / NaBH4, tributyltin chloride / methanol / Irradiation
2: 96.2 percent / NaBH4, boron trifluoride etherate / tetrahydrofuran / 2 h / Ambient temperature
View Scheme

stemmadenine acetate

2468-21-5

catharinthine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: T. iboga precondylocarpine acetate synthase 1; FAD / aq. buffer / 2 h / 37 °C / pH 9.5 / Enzymatic reaction
2: NADPH / aq. buffer / 1 h / 37 °C / pH 9.5 / Enzymatic reaction
3: NADPH / aq. buffer / pH 9.5 / Enzymatic reaction
View Scheme

C23H27N2O4(1+)

2468-21-5

catharinthine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NADPH / aq. buffer / 1 h / 37 °C / pH 9.5 / Enzymatic reaction
2: NADPH / aq. buffer / pH 9.5 / Enzymatic reaction
View Scheme

dehydrosecodine

2468-21-5

catharinthine

Conditions
ConditionsYield
With NADPH In aq. buffer pH=9.5; Enzymatic reaction;
2468-21-5

catharinthine

38542-83-5

(+)-dihydrocatharanthine

Conditions
ConditionsYield
With platinum(IV) oxide; hydrogen In methanol under 760.051 Torr; for 0.0833333h; Inert atmosphere;93%
Conditions
ConditionsYield
Stage #1: catharinthine; vindoline With iron(III) chloride hexahydrate at 25℃;
Stage #2: With sodium tetrahydroborate at 0℃;
90%
With sodium tetrahydroborate; iron(III) chloride 1.) buffer; Yield given. Multistep reaction;
With hydrogenchloride; iron(III) chloride In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere;
2468-21-5

catharinthine

79-22-1

methyl chloroformate

60706-87-8

N-(methoxycarbonyl)catharanthine

Conditions
ConditionsYield
Stage #1: catharinthine With potassium hydride In tetrahydrofuran at 0℃;
Stage #2: methyl chloroformate In tetrahydrofuran at 0 - 23℃; for 15h;
90%
Stage #1: catharinthine With potassium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Stage #2: methyl chloroformate In tetrahydrofuran at 0 - 20℃; for 19h; Inert atmosphere;
86%
Stage #1: catharinthine With potassium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Stage #2: methyl chloroformate In tetrahydrofuran at 0 - 20℃; for 19h; Inert atmosphere;
86%

Catharanthine Chemical Properties

Molecular Structure of Catharanthine (CAS NO.2468-21-5):

Product Name: (+)-Catharanthine
Molecular Formula: C21H24N2O2
Molecular Weight: 336.427460 g/mol
Appearance: off-white to pale beige solid
Melting Point: 138-1400 °C
Density: 1.27 g/cm3
Flash Point: 251.1 °C
Enthalpy of Vaporization: 75.83 kJ/mol
Boiling Point: 491.5 °C at 760 mmHg
Vapour Pressure: 8.33E-10 mmHg at 25 °C
Water Solubility: 72.28 mg/L at 25 °C
EINECS: 219-586-6
Synonyms of Catharanthine (CAS NO.2468-21-5): (+)-3,4-didehydrocoronaridine ; 18-beta)-lph ; Catharanthin ; Ibogamine-18-carboxylicacid,3,4-didehydro-,methylester,(2-alpha,5-beta,6-a ; Methyl(2-alpha,5-beta,6-alpha,18-beta)-3,4-didehydroibogamine-18-carboxylate ; Catharanthine;catharanthine base ; Methyl (2alpha,5beta,6alpha)-3,4-didehydroibogamine-18beta-carboxylate
Categories of Catharanthine (CAS NO.2468-21-5): Heterocycles ; Chiral Reagents ; Intermediates & Fine Chemicals ; Pharmaceuticals

Catharanthine Uses

 Catharanthine (CAS NO.2468-21-5) is used as a precursor of Vinblastine-type alkaloids.

Catharanthine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 800mg/kg (800mg/kg)   Biochemical Pharmacology. Vol. 26, Pg. 1213, 1977.

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