Catharanthine

Base Information

• Chemical Name: Catharanthine
• CAS No.: 2468-21-5
• Molecular Formula: C21H24N2O2
• Molecular Weight: 336.434
• European Community (EC) Number: 219-586-6
• UNII: WT0YJV846J
• DSSTox Substance ID: DTXSID80947621
• Nikkaji Number: J15.154H,J2.996.318E
• Wikipedia: Catharanthine
• Wikidata: Q104964769
• Pharos Ligand ID: Z22ZDAHBMNTR
• ChEMBL ID: CHEMBL2163793
• Mol file: 2468-21-5.mol

Synonyms:catharanthine;catharanthine monohydrochloride, (2alpha,5beta,6alpha,18beta)-isomer;catharanthine sulfate, (2alpha,5beta,6alpha,18beta)-isomer

Chemical Property of Catharanthine

Chemical Property:

• Appearance/Colour: off-white to pale beige solid
• Vapor Pressure: 8.33E-10mmHg at 25°C
• Melting Point: 138-140 °C
• Refractive Index: 1.663
• Boiling Point: 491.5 °C at 760 mmHg
• PKA: 6.8(at 25℃)
• Flash Point: 251.1 °C
• PSA: 45.33000
• Density: 1.27 g/cm³
• LogP: 3.11320
• Storage Temp.: ?20°C
• Solubility.: DMSO: soluble5mg/mL (clear solution; warmed)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 336.183778013
• Heavy Atom Count: 25
• Complexity: 603

Purity/Quality:

99% ^*data from raw suppliers

Catharanthine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1=CC2CC3(C1N(C2)CCC4=C3NC5=CC=CC=C45)C(=O)OC
• Isomeric SMILES: CCC1=C[C@H]2C[C@]3([C@@H]1N(C2)CCC4=C3NC5=CC=CC=C45)C(=O)OC
• Uses: Precursor of Vinblastine-type alkaloids Anticancer Catharanthine is an indole alkaloid analog and an inhibitor of TRPM8.

Technology Process of Catharanthine

There total 16 articles about Catharanthine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(+)-3β-Cyanocatharanthine (300535-95-9) → (+)-Catharanthine (2468-21-5)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.25h;

DOI:10.1039/b001114m

Reference yield: 96.2%

(16R)-5-oxo-catharanthine (105729-49-5) → catharinthine (2468-21-5)

Guidance literature:

With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81977-3

Reference yield:

→ 3,4-didehydro-ibogamine-18-carboxylic acid methyl ester (2468-21-5,20395-98-6,67110-66-1,113158-99-9)

Guidance literature:

18β-Carbomethoxycleavamin XVIII, Hg-acetat;

DOI:10.1021/ja00709a050

upstream raw materials:

(16R)-5-oxo-catharanthine

indole-3-acetic acid

C₁₅H₁₇NO₃

(-)-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

Downstream raw materials:

anhydrovinblastine

vinleurosine

catharine

(+)-dihydrocatharanthine

Refernces

• 1、 Cocquet, Guillaume,Rool, Patrice,Ferroud, Clotilde. "Photosensitized oxidation, by single-electron transfer, of catharanthine and vindoline: A highly regio- And diastereoselective photocyanation reaction". . p. 2277 - 2281. Retrieved 2000.
• 2、 -. "NEW BIS-INDOLE ALKALOIDS AS ANTICANCER DRUGS". Page/Page column 17. . Retrieved 2014/12/12.