(+)-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
• Description: Matrine is extracted by organic solvents from the dry roots, plants, and fruits of kushen 苦参 (Sophora flavescens Ait) and also existed in S. alopecuroides L. and S. subprostrata Chun et T.?Chen.Chinese medicine Radix sophorae flavescentis have dampness eliminating insecticide and diuretic effects. Sophora flavescens is used for heat dysentery, hemafecia, jaundice and anuria, red leukorrhea, vulva pruritus, eczema, wet sores, skin itching, scabies, ringworm, and trichomonas vaginitis. Sophora flavescens is recorded in the ancient Materia Medica. “Southern Yunnan Materia Medica” also recorded the effects of Saphora flavescens .Sophora flavescens is a species of Sophora japonica and distributed in temperate and subtropical regions. Sophora flavescens is widely distributed in China, mainly in the north of Hebei, the west of Henan, and southwest of Shandong, Anhui, Hubei, and Guizhou. Matrine is extracted and isolated from the Chinese medicine Sophora flavescens
• Physical properties: Appearance: white, needle-like crystal or crystalline powder that becomes yellow and solid after long-time exposure in air. Solubility: soluble in water, benzene, chloroform, and methanol and slightly soluble in petroleum ether. Melting point: 76?°C (α-matrine), 87?°C (β-matrine), 223?°C (γ-matrine), and 84?°C (δ-matrine). Specific optical rotation: +31 to +36°.
• Uses: antifungal, nematocide (+)-Matrine is an alkaloid compound extracted from the roots of Sophora species which maintain anti-inflammatory, anti-cancer and a host of other positive pharmacological effects. Apoptotic agent.
• Indications: In clinical settings, matrine injection was used for chronic active hepatitis, and suppository was used for trichomoniasis or Candida vaginitis and chronic cervicitis and can also be used for senile vaginitis and pelvic inflammatory disease.
• Clinical Use: Matrine has multiple pharmacological effects and can treat a variety of diseases in clinical setting. At present, the researches on matrine are mainly focused on antiliver injury and liver fibrosis and anti-tumor and anti-cardiovascular diseases. It was worthy of attention that matrine has other pharmacological activities, such as leukocyte-elevating effects and anti-virus effects, and these effects were necessary for further development and utilization. The pharmacological effects of matrine stayed in the experimental phase, and they need further development and research to promote the development of clinical practice. Improvements in the modern formulation of matrine can improve their clinical application.

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

• 1、 Ding, Fangwei,Jiang, Yanqiu,Gan, Shaoyan,Bao, Robert Li-Yuan,Lin, Kaifeng,Shi, Lei. "B(C6F5)3-Catalyzed Deoxygenation of Sulfoxides and Amine N-Oxides with Hydrosilanes". . p. 3427 - 3430. Retrieved 2017/07/04.
• 2、 -. "PROCESS FOR THE PURIFICATION OF SOPHORA ALKALOIDS". Page/Page column 9-10. . Retrieved 2009/10/22.