(+)-Matrine

Base Information

• Chemical Name: (+)-Matrine
• CAS No.: 519-02-8
• Molecular Formula: C15H24N2O
• Molecular Weight: 248.368
• Hs Code.: 13021990
• NSC Number: 318810,143088
• DSSTox Substance ID: DTXSID20871734
• Nikkaji Number: J3.321.193G
• Wikidata: Q105382428
• Metabolomics Workbench ID: 124280
• ChEMBL ID: CHEMBL1733145
• Mol file: 519-02-8.mol

Synonyms:83148-91-8;Matridin-15-one;(+)-Matrine;(+)-Sophoridine;7,13-diazatetracyclo[7.7.1.02,7.013,17]heptadecan-6-one;Matridin-15-one, (6b,7b,11a)- (9CI);.alpha.-Matrine;Matrene, (+)-;d-Sophoridine;Matridin-15-one, (5.beta.,7.beta.,11.alpha.)-;Vegard;alpha-Matrine;6783-60-4;6-Allomatrine;6beta-Matrine;Tetrahydroisosophoramine;NSC-318810;regid845916;NEW BASE STRUCTURE;6.beta.,7.beta.-Matrine;Dodecahydro-3a,7a-diaza-benzo[de]anthracen-8-one;Oprea1_680866;Oprea1_860679;MLS000029265;SCHEMBL8260145;CHEMBL1733145;DTXSID20871734;ZSBXGIUJOOQZMP-UHFFFAOYSA-N;HMS1611N16;HMS2269A14;MFCD02735434;NSC143088;NSC318810;AKOS000591194;AKOS017259293;NSC-143088;1H,5H,10H-dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one, dodecahydro-;SMR000011610;FT-0603438;FT-0628171;FT-0696735;FT-0698746;AB00397099-11;A846751;SR-01000601144;Q-100583;Q6787831;SR-01000601144-3;(7aS,13aR,13bR)-dodecahydro-1H,5H,10H-dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one

Chemical Property of (+)-Matrine

Chemical Property:

• Vapor Pressure: 1.67E-06mmHg at 25°C
• Melting Point: 77 °C
• Refractive Index: 1,536
• Boiling Point: 396.7 °C at 760 mmHg
• PKA: 9.47±0.20(Predicted)
• Flash Point: 172.7 °C
• PSA: 23.55000
• Density: 1.16 g/cm³
• LogP: 1.74750
• Storage Temp.: 2-8°C
• Solubility.: Soluble in Water (up to 25 mg/ml)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 248.188863393
• Heavy Atom Count: 18
• Complexity: 356

Purity/Quality:

99% ^*data from raw suppliers

Matrine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-37/38-41-48-22
• Safety Statements: 22-26-36/37/39-45-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C3CCCN4C3C(CCC4)CN2C(=O)C1
• General Description: Matrine is a bioactive alkaloid derived primarily from the roots of *Sophora flavescens* and other *Sophora* species, known for its diverse pharmacological properties, including anti-inflammatory, antiviral, antitumor, and immunomodulatory effects. It exhibits a quinolizidine structure and has been studied for its potential therapeutic applications in treating conditions such as cancer, hepatitis, and skin disorders. Matrine's mechanisms of action involve modulation of signaling pathways, apoptosis induction, and inhibition of cell proliferation, making it a promising candidate for drug development. Its stereochemistry is defined as (7aS,13aR,13bR,13cS)-dodecahydro-1H,5H,10H-dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one.

Technology Process of (+)-Matrine

There total 4 articles about (+)-Matrine 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: 96.9%

(+)-oxymatrine (16837-52-8,54750-07-1,54809-73-3,54809-74-4,59091-53-1,75171-48-1) → (+)-matrine (519-02-8)

Guidance literature:

With ammonium sulfate; tin(ll) chloride; In water; at 50 ℃; for 4h; Reagent/catalyst; Solvent; Temperature;

Reference yield:

C15H26N2O2 → Matrin (519-02-8,641-39-4,4702-09-4,4979-18-4,6783-60-4,6838-36-4,6882-68-4,17801-36-4,20078-88-0,36284-98-7,68421-43-2,83148-91-8)

Guidance literature:

C₁₅H₂₆N₂O₂; With thionyl chloride; In 1,2-dichloro-ethane; at 0 - 70 ℃;

With 4-(2-hydroxyethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-N-oxide; dmap; dicyclohexyl-carbodiimide; In 1,2-dichloro-ethane;

With di-tert-butyl oxalate; sodium hydroxide; In water; 1,2-dichloro-ethane; tert-butyl alcohol;

DOI:10.1016/j.cclet.2009.11.033

Reference yield:

(+)-sophocarpine N-oxide (26904-64-3,64838-17-1) + (+)-oxymatrine (16837-52-8,54750-07-1,54809-73-3,54809-74-4,59091-53-1,75171-48-1) → (+)-matrine (519-02-8)

Guidance literature:

With hydrogen; nickel; In water; at 20 ℃; for 8h;

upstream raw materials:

(+)-sophocarpine N-oxide

(+)-oxymatrine

(3aS,6aR,11aR,11bR,11cS)-3a-Oxy-dodecahydro-3a,7a-diaza-benzo[de]anthracen-8-one

Downstream raw materials:

(+)-allomatridine

(+)-oxymatrine

sophocarpine

Refernces

A simple matrine derivative for the facile syntheses of mesoporous zeolites ITQ-37 and ITQ-43

10.1039/c8cc08196d

The research aims to develop a cost-effective and sustainable method for synthesizing mesoporous zeolites ITQ-37 and ITQ-43 using a simple matrine-derived organic structure-directing agent (OSDA). Matrine, a natural product extracted from Sophora flavescens, was modified to create N-methylmatrinium (MeMAS), which served as the OSDA. The study successfully synthesized highly crystalline MAS-ITQ-37 and MAS-ITQ-43 with record-high nitrogen adsorption BET surface areas (978.9 m2/g for MAS-ITQ-37 and 923.7 m2/g for MAS-ITQ-43). The researchers explored the influence of synthetic factors such as Si/Ge ratios, water content, and the presence of aluminum on the crystallization process. They found that a Si/Ge ratio of 2 and specific water content (H2O/T ratios of 1.5-3.0) were optimal for obtaining pure phases of these zeolites. The introduction of a small amount of aluminum facilitated the formation of pure MAS-ITQ-43. The study concluded that MeMAS is an efficient and sustainable OSDA for synthesizing these zeolites, offering a promising route for large-scale practical applications and potentially serving as a template for constructing other novel porous materials.