Hydrocotarnine

Base Information

• Chemical Name: Hydrocotarnine
• CAS No.: 550-10-7
• Molecular Formula: C12H18ClNO4
• Molecular Weight: 221.256
• European Community (EC) Number: 208-978-2
• UNII: G22L6JNE61
• DSSTox Substance ID: DTXSID60203535
• Nikkaji Number: J6.709A
• Wikidata: Q27164371
• Metabolomics Workbench ID: 46163
• ChEMBL ID: CHEMBL1606295
• Mol file: 550-10-7.mol

Synonyms:hydrocotarnine;hydrocotarnine hydrobromide;hydrocotarnine hydrochloride;hydrocotarnine hydrochloride monohydrate

Chemical Property of Hydrocotarnine

Chemical Property:

• Vapor Pressure: 7.56E-05mmHg at 25°C
• Melting Point: 56°C
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 342.4°C at 760 mmHg
• PKA: 7.75±0.20(Predicted)
• Flash Point: 106.7°C
• PSA: 30.93000
• Density: 1.1514 (rough estimate)
• LogP: 1.34970
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 221.10519334
• Heavy Atom Count: 16
• Complexity: 261

Purity/Quality:

99%, ^*data from raw suppliers

4-Methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC3=C(C(=C2C1)OC)OCO3
• Uses: Hydrocotarnine Hydrochloride, is an oxidative degradation product of the drug Noscapine (128-62-1).

Technology Process of Hydrocotarnine

There total 37 articles about Hydrocotarnine 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: 98.0%

5,6,7,8-Tetrahydro-4-methoxy-6-methyl-1,3-dioxolo<4,5-g>isoquinolin-8-ol (108261-07-0) → hydrocotarnine (550-10-7)

Guidance literature:

With sodium tetrahydroborate; trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 25h;

DOI:10.3987/COM-13-12843

Reference yield: 95.0%

5,6,7,8-Tetrahydro-8-acetoxy-4-methoxy-6-methyl-1,3-dioxolo<4,5-g>isoquinoline (108434-79-3) → hydrocotarnine (550-10-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 50 ℃; for 7h;

DOI:10.1021/jo00299a016

Reference yield: 93.0%

N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluene-sulfonyl)aminoacetaldehyde diethylacetal (108261-03-6) → hydrocotarnine (550-10-7)

Guidance literature:

With sodium hydroxide; sulfuric acid; palladium; In dichloromethane; water; acetic acid;

upstream raw materials:

4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-ol

4-Methoxy-6-methyl-1,3-dioxolo<4,5-g>isochinolinium-methoiodid

methylmagnesium bromide

noscapine

Downstream raw materials:

4-methoxy-6-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide

N-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline

1,2,3,4-tetrahydro-2-methylisoquinolin-7-ol

(±)-α-noscapine

Refernces

• 1、 Mao, Yongjun,Song, Shuai,Zhao, Dongmei,Cheng, Maosheng. "A new total synthesis of (±)-α-noscapine". . p. 2633 - 2640. Retrieved 2014/01/06.
• 2、 Simig, Gy.,Schlosser, M.. "THE SYNTHESIS OF 6-METHOXY-7,8-METHYLENEDIOXYISOQUINOLINE DERIVATIVES". . p. 217 - 228. Retrieved 2007/10/02.