Nandinine

Base Information

• Chemical Name: Nandinine
• CAS No.: 572-76-9
• Molecular Formula: C19H19NO4
• Molecular Weight: 325.3585
• UNII: 7T6VF792DB
• ChEMBL ID: CHEMBL2314732
• DSSTox Substance ID: DTXSID301024074
• Nikkaji Number: J6.546C
• Wikidata: Q27225637
• Mol file: 572-76-9.mol

Synonyms:Nandinine;(+)-Nandinin;S-Tetrahydroberberrubine;Nandinine [MI];(+)-Tetrahydroberberrubine;Nandinine, (+)-;(S)-nandinine;572-76-9;UNII-7T6VF792DB;10-Methoxy-2,3-(methylenedioxy)berbin-9-ol;7T6VF792DB;CHEMBL2314732;(13aS)-5,8,13,13a-Tetrahydro-10-methoxy-6H-benzo(g)-1,3-benzodioxolo(5,6-a)quinolizin-9-ol;6H-Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizin-9-ol, 5,8,13,13a-tetrahydro-10-methoxy-, (13aS)-;(+)-nandinine;SCHEMBL905060;CHEBI:132749;DTXSID301024074;BDBM50424073;PD119743;C21370;Q27225637;(13aS)-10-methoxy-5,8,13,13a-tetrahydro-2H,6H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-9-ol;(1S)-17-methoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaen-16-ol

Chemical Property of Nandinine

Chemical Property:

• Vapor Pressure: 9.49E-10mmHg at 25°C
• Melting Point: 195-196°
• Boiling Point: 477.7°Cat760mmHg
• Flash Point: 242.7°C
• PSA: 51.16000
• Density: 1.42g/cm³
• LogP: 2.72290
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 325.13140809
• Heavy Atom Count: 24
• Complexity: 474

Purity/Quality:

99% ^*data from raw suppliers

NANDININE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C(CC3C4=CC5=C(C=C4CCN3C2)OCO5)C=C1)O
• Isomeric SMILES: COC1=C(C2=C(C[C@H]3C4=CC5=C(C=C4CCN3C2)OCO5)C=C1)O
• Description: Eijkman obtained an amorphous compound from the root bark of Nandina domestica L. to which this name was given. It was subsequently obtained crystal_x0002_line by Iwakawa who was also able to separate it into three well-defined phenolic substances, Nandinine, Domesticine and Isodomesticine (q.v.). This alkaloid may be crystallized from EtOH as colourless leaflets which develop a pink colour on exposure to air. With CH2N2 the base yields (+)-Canadine (q.v.). The solution in H2S04 is initially yellow, changing through green to blue.

Technology Process of Nandinine

There total 46 articles about Nandinine 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: 85.0%

14-(S)-9-benzyloxy-2,3-methylenedioxy-10-methoxytetrahyrdooxyprotoberberine (1422431-64-8) → tetrahydroberberrubine (572-76-9)

Guidance literature:

With hydrogenchloride; In ethanol; water; for 2h; Reflux;

DOI:10.1016/j.bmc.2012.12.016

Reference yield: 84.0%

14-(R)-9-benzyloxy-2,3-methylenedioxy-10-methoxytetrahyrdooxyprotoberberine (1429118-98-8) → 5,6,13,14-tetrahydro-9-hydroxy-10-methoxy-2,3-(methylenedioxy)-8H-dibenzo[a,g]quinolizine (572-76-9,6724-39-6,6808-56-6,17388-17-9)

Guidance literature:

With hydrogenchloride; In ethanol; water; for 2h; Reflux;

DOI:10.1016/j.bmc.2012.12.016

Reference yield:

berberrubine chloride (15401-69-1) → 5,6,13,14-tetrahydro-9-hydroxy-10-methoxy-2,3-(methylenedioxy)-8H-dibenzo[a,g]quinolizine (572-76-9,6724-39-6,6808-56-6,17388-17-9)

Guidance literature:

With methanol; sodium tetrahydroborate; at 60 ℃; for 0.25h;

upstream raw materials:

berberrubine chloride

C₁₉H₁₉NO₇S

berberine chloride

(+/-)-nandinine