Decarine

Base Information

• Chemical Name: Decarine
• CAS No.: 54354-62-0
• Molecular Formula: C19H13NO4
• Molecular Weight: 319.317
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID90202738
• Nikkaji Number: J934.431D
• Wikidata: Q27134211
• Metabolomics Workbench ID: 135746
• ChEMBL ID: CHEMBL458702
• Mol file: 54354-62-0.mol

Synonyms:Decarine;54354-62-0;Rutaceline;Zanthoxyline;1-methoxy-[1,3]benzodioxolo[5,6-c]phenanthridin-2-ol;[1,3]Benzodioxolo[5,6-c]phenanthridin-2-ol, 1-methoxy-;CHEBI:65727;1-methoxy-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridin-2-ol;1-Methoxy[1,3]benzodioxolo[5,6-c]phenanthridin-2-ol;Zanthoxylin;(1,3)Benzodioxolo(5,6-c)phenanthridin-2-ol, 1-methoxy-;CHEMBL458702;SCHEMBL3855119;DTXSID90202738;AKOS028108611;Q27134211;1-methoxy-[1,3]benzodioxolo[6,5-c]phenanthridin-2-ol;B0005-190022

Chemical Property of Decarine

Chemical Property:

• Vapor Pressure: 2E-14mmHg at 25°C
• Melting Point: 243-244.5 °C
• Boiling Point: 588°C at 760 mmHg
• PKA: 8.72±0.20(Predicted)
• Flash Point: 309.4°C
• PSA: 60.81000
• Density: 1.46g/cm³
• LogP: 3.98410
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 319.08445790
• Heavy Atom Count: 24
• Complexity: 474

Purity/Quality:

98% ^*data from raw suppliers

Decarine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC2=C3C=CC4=CC5=C(C=C4C3=NC=C21)OCO5)O
• Description: The stem bark of Zanthoxylum decaryi yields this alkaloid which forms orange needles when purified by recrystallization from MeOH-CHC13. It gives a complex ultraviolet spectrum in EtOH having absorption maxima at 249, 257, 277, 326 and 382 nm with shoulders at 285 and 335 nm. The structure has been determined from chemical degradation and spectroscopic examination.
• Uses: Decarine can be used to crudely extract constituents of bark of Fagara tessmannii toward multi-factorial drug resistant cancer cells. It can also be used to create anti-mildew preservative paper with good barrier properties and solar water heater anti-freezing liquid,

Technology Process of Decarine

There total 36 articles about Decarine 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: 94.0%

2-(ethoxymethoxy)-1-methoxy-[1,3]dioxolo-[4',5':4,5]benzo[1,2-c]phenanthridine (1432677-52-5) → decarine (54354-62-0)

Guidance literature:

With hydrogenchloride; In ethanol; water; at -8 ℃; for 3h; Sealed tube;

DOI:10.1016/j.tet.2013.03.105

Reference yield: 84.0%

8-isopropoxy-7-methoxy-N-methoxymethyl-2,3-methylenedioxybenzo[c]phenanthridin-6(5H)-one (511545-62-3) → decarine (54354-62-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.3987/COM-02-S35

Reference yield: 83.0%

(4bR,10bS)-8,9-dimethyl-4b,10b-dihydrobenzo[c]phenanthridine → decarine (54354-62-0)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.joc.1c01612

upstream raw materials:

8-(benzyloxy)-7-methoxy-2,3-(methylenedioxy)benzophenanthridine

8-isopropoxy-7-methoxy-N-methoxymethyl-2,3-methylenedioxybenzo[c]phenanthridin-6(5H)-one

naphtho[2,3-d][1,3]dioxol-5-amine

3-isopropoxy-2-methoxybenzaldehyde

Downstream raw materials:

norchelerythrine

8-(benzyloxy)-7-methoxy-2,3-(methylenedioxy)benzophenanthridine

O-benzyl-N-methyl-5,6-dihydrodecarine